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10 Best Weekend Getaways From Chicago

Waterfalls, wildlife, and lots of small-town charm await.

Elizabeth Rhodes is a special projects editor at Travel + Leisure , covering everything from luxury hotels to theme parks to must-pack travel products. Originally from South Carolina, Elizabeth moved to New York City from London, where she started her career as a travel blogger and writer.

With fascinating architecture, great museums, and plenty of delicious local eateries (deep dish pizza, anyone?), Chicago has a lot to offer tourists and residents alike. That said, we could all use some respite from the urban hustle and bustle every so often. We've rounded up the best destinations within easy reach of the Windy City, from lakeside escapes to state and national parks. Whether you're looking for beautiful landscapes or small-town charm, these quick trips are sure to please every type of traveler. Here are our top 10 weekend getaways from Chicago.

Starved Rock State Park, Illinois

Wander among towering trees to find waterfalls and wildlife at Starved Rock State Park , located on the Illinois River about an hour and a half from Chicago. It's the perfect choice when you want to trade skyscrapers for the great outdoors. In the spring, heavy rains make the waterfalls especially active, and in the fall, the leaves turn beautiful shades of orange, red, and yellow. Stay within the state park at the Starved Rock Lodge , or opt to spend the night in nearby Ottawa, a charming little town with eclectic restaurants, independent shops, and more.

Indianapolis, Indiana

Just a three-hour drive from Chicago, "Indy," as the locals know it, offers plenty to do. Kids will love The Children's Museum of Indianapolis and the Indianapolis Zoo , while sports fans will want to check out the iconic Indianapolis Motor Speedway . The hip Broad Ripple neighborhood has nightlife, dining, shopping, and more, and the Massachusetts Avenue Arts District offers theaters, galleries, and independent boutiques. History lovers can book a stay in one of the 1920s Pullman train car rooms at the Crowne Plaza Indianapolis Downtown-Union Station .

Saugatuck, Michigan

Summer is the perfect time to visit this lakeside town, located just under two and a half hours from Chicago. Lounge on the sandy shores of Oval Beach or Saugatuck Dunes State Park , rent a boat and explore Lake Michigan, browse the art galleries, or check out the local breweries. After a day enjoying some of Lake Michigan's most pristine beaches , rest your head at one of the adorable inns or bed-and-breakfasts in town.

Lake Geneva, Wisconsin

For another nearby waterfront escape, head an hour and a half from Chicago to beautiful Lake Geneva . During the summer, you can get out on the lake, sunbathe on its beaches, or go zip lining, among other outdoor activities. During the winter, check out the Ice Castles , an awe-inspiring display of illuminated, human-made icicles that you can walk through.

Milwaukee, Wisconsin

An hour and a half north of Chicago on Lake Michigan, Milwaukee is teeming with great museums and even better beer. Pabst Brewing Company and Miller Brewing Company call this city home. Today, you can toast to the city's beer heritage by trying these classics or visiting one of the many local craft breweries. The Milwaukee Public Museum is a must-visit — it has fossils, a European village, a full-size display recreating the streets of Milwaukee in the late 19th and early 20th centuries, a butterfly garden, and more. Other sites worth visiting include the Milwaukee Art Museum , the Harley-Davidson Museum , and the Mitchell Park Horticultural Conservatory, also known as The Domes .

Indiana Dunes National Park, Indiana

Just under an hour's drive from the city, Indiana Dunes National Park is perfect for a quick getaway. You can even make it a day trip if you're short on time (it's accessible from the South Shore Line, so you don't even have to drive). This national park covers 15 miles of Lake Michigan's shoreline, making it ideal for a relaxing weekend away from Chicago. Go for a hike along the dunes, fly a kite on the beach, enjoy horseback riding, or check out the historic 1933 World's Fair Century of Progress Homes .

Madison, Wisconsin

Wisconsin's capital city is just over two and a half hours from Chicago, and it offers something for every type of traveler. Food lovers will want to visit the National Mustard Museum and try fresh ice cream at the Sassy Cow Creamery , located 20 miles from Madison. Meanwhile, outdoorsy types will love kayaking or taking a cruise around the lake during the summer, or snowshoeing in the winter. Families can check out the Madison Children's Museum and the Children's Theater of Madison for kid-friendly entertainment.

Holland, Michigan

Holland is a unique destination about two and a half hours from Chicago. The city's Dutch heritage is evident in its famous attractions like the Windmill Island Gardens , De Klomp Wooden Shoe and Delftware Factory , and Nelis' Dutch Village . The yearly Tulip Time Festival is another great reason to head to this quaint Michigan town — millions of tulips are planted across Holland, so visit in spring to see the beautiful flowers in bloom.

Wisconsin Dells, Wisconsin

For a family-friendly getaway, opt for a weekend trip to Wisconsin Dells, a three-hour drive from Chicago. This area, known as the "water park capital of the world," is packed with attractions kids will love. One of them, Noah's Ark Water Park , is the largest water park in the United States. For the ultimate relaxation, take a scenic boat ride through the Dells or visit one of the local wineries or breweries.

Geneva, Illinois

Just an hour outside of Chicago, you'll find Geneva, an ideal destination if you're looking for a small-town getaway. Wander the quaint downtown, check out the murals and outdoor sculptures, and browse independent shops selling antiques, jewelry, chocolate, ice cream, and more. The Fabyan Forest Preserve , with its mid-19th-century windmill, is just a few minutes' drive away.

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25 Weekend Getaways Near Chicago

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When you need a day trip from Chicago or a weekend getaway from the big city, you don't have to go far. These escapes—including Amish Country, Indiana; Galena, Illinois; and Lake Geneva, Wisconsin—are within a one- to three-hour drive and offer a variety of activities that will recharge your life.

Indiana Dunes: 54 miles southeast of Chicago

This stretch of Lake Michigan coastline offers wide sandy beaches, towering dunes, great birding, easy bike trails and interesting history. Head to neighboring Chesterton for creative burgers at the Octave Grill and a pleasant night at Dunes Walk Inn, a restored 1881 mansion.

Lake Geneva, Wisconsin: 80 miles northwest of Chicago

This resort town of 7,600 has draws for summer and winter. Hotels, resorts and restaurants hug the lakeshore. Most visitors loll on the beach or cruise the lake during summer, but you can also experience the warmth of its winter in January and February during the annual Winterfest .

Michigan's southwest shore: 70 to 150 miles east of Chicago

Towns like New Buffalo, St. Joseph, Benton Harbor, Holland, Saugatuck and Grand Haven provide pristine beaches, great shopping, lakeside restaurants and front-row view of sunsets over Lake Michigan. The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. How far you drive is up to you – each town has its own personality. Take a spin on the carousel at St. Joe, tour a working windmill in Holland or just stretch out on a beach - preferably with a view of a lighthouse.

Galena, Illinois: 163 miles west of Chicago

Shops and restaurants in century-old buildings have long attracted visitors to this town of 3,500. But take time to hike, cruise the river or ski the slopes, sip local wines, taste beer and ... do some shopping.

Mount Morris, Illinois: 100 miles northwest of Chicago

With its rolling terrain, state parks and preserves traversed by the mighty Rick and Mississippi rivers, plus biking and hiking trails crisscrossing the area, the Blackhawk Waterways region of northwest Illinois promises outdoor recreation bliss. The region also helped shape the childhood of our 40th president, whose boyhood home opens its doors to visitors.

Cedarburg, Wisconsin: 113 miles north of Chicago

A great weekend destination for both shoppers and history buffs, Cedarburg has a Main Street that's on the National Register of Historic Places and dozens of limestone buildings housing more than 70 boutiques, chocolate shops and restaurants. Explore the town's history at the General Store Museum and Kuhefuss House Museum, and admire handiwork at the Wisconsin Museum of Quilts and Fiber Arts .

Bloomington-Normal, Illinois: 130 miles southwest of Chicago

For theater-lovers, summertime means outdoor Shakespeare. But in downstate Illinois, that takes on a fresh new form. Want improv Shakespeare? Sing-along Shakespeare? Or just a performance of his classics? Starting in June, and running through mid-August, the Illinois Shakespeare Festival in Bloomington-Normal reveals its ode to the Bard. Other draws to the area: Bloomington's restored 1800s buildings house farm-to-table restaurants, shops and live-music venues. Inside the three-story courthouse, a museum highlights the area's historical treasures.

Madison, Wisconsin: 147 miles northwest of Chicago

This town embraces the quirky and classy in its arts, museums, shops, dining venues and outdoor activities. Even its farmers market is a Bohemian rhapsody of local produce, entertainment, art and political activism on the state capitol square. Wander the paths and trails at Olbrich Botanical Gardens or the University of Wisconsin Arboretum ; admire the art at Chazen Museum of Art or the Madison Museum of Contemporary Art ; take a leisurely cruise around Lake Mendota or Menona; and be sure to work up an appetite-Madison's 600-plus restaurants offer something for every taste.

Rockford, Illinois: 90 miles west of Chicago

Illinois' third-largest city spent years watching travelers whiz by on Interstate-90 on their way east to Chicago. Now, thanks to a revitalized downtown, an emerging foodie scene, new cultural attractions and beautiful public gardens, word is getting out: You'd be crazy not to stop. The tranquil Anderson Japanese Gardens is just one of the draws to the area.

Fox River Valley, Illinois: 60 miles west of Chicago

An hour west of Chicago's Loop, the Fox River provides a soothing backdrop to towns brimming with indulgent eats, stores housed in historical homes and posh places to stay. Three towns along the winding river offer restful diversions with a nod to history: Catch a household name playing at St. Charles' historical Arcada Theater, or just 3 miles south, explore Geneva's shopping district, where boutiques fill preserved storefronts. And just minutes from Oswego's charming Main Street-with brick-paved sidewalks-is a family-run winery.

Milwaukee: 93 miles north of Chicago

Art, music and food festivals fill the calendar, and the compact downtown has just as diverse offerings. Watch the Milwaukee Art Museum's striking Quadracci Pavilion open and close its "wings"; catch the Milwaukee Brewers in Miller Park ; tour the Pabst Mansion ; or take a simulated motorcycle ride at the Harley-Davidson Museum .

Amish Country, Indiana: 110 miles east of Chicago

In tiny Nappanee, an Amish man parks his buggy by a gas pump, a living metaphor for the way new and old coexist in northern Indiana. Some people come here for classic Amish Country : 31 kinds of pie at Das Dutchman Essenhaus , hand-sewn gifts and homemade jellies at Little Helpers Quilt Shop , treasure-hunting at the Shipshewana Flea Market . But towns like Goshen, Middlebury and Elkhart also are modern communities.

Champaign-Urbana: 140 miles south of Chicago

Great outdoors, grown-up eats and classic clubs make these two cultured cities especially appealing in the summer when University of Illinois students head home. Grab a cheesy bite of nostalgia at Papa Del's Pizza or enjoy more upscale fare at Miga ; take time to admire the works at Krannert Art Museum and Spurlock Museum ; go for a stroll at the University of Illinois arboretum or Allerton Park and Retreat Center .

Starved Rock State Park, Illinois: 100 miles southwest of Chicago

Starved Rock State Park is a remarkable pocket of land along the Illinois River that includes 18 sandstone canyons, 14 waterfalls; abundant wildlife and birds; Belle of the Rock paddleboat excursions; and guided hikes, special events and interpretive programs. Spend the night in rooms or cabins (and enjoy a hearty meal) at Starved Rock Lodge , built in the 1930s by the Civilian Conservation Corps. If you're up for more exploration, also visit neighboring Matthiessen State Park , where 5 miles of trails carve into the mile-long canyon, passing rocks, waterfalls and beautiful, sometimes dizzying, vantage points.

Zion, Illinois: 50 miles north of Chicago

Zion is located in Lake County , which bridges the gap between Chicago's Cook County and the Wisconsin border with family attractions and nature trails. The area is home to Illinois Beach State Park , Volo Auto Museum and The Chocolate Sanctuary . For more fun, be sure to visit Six Flags Great America .

South Bend, Indiana: 95 miles east of Chicago

Though it's home to the Fighting Irish, it's not all football in South Bend. The St. Joseph River provides a great place for water sports and serves as a sparkling backdrop for a weekend of shopping and dining in the hometown of the University of Notre Dame.

Turkey Run Inn, Indiana: 150 miles south of Chicago

Sitting on a rocking chair on a veranda at Indiana's Turkey Run State Park inn feels surprisingly like taking refuge deep in the forest. The only sounds? Wind rustling through the trees. Owls hooting. Squirrels chattering. Brooks babbling. Maybe that's why quiet types flock here-bird-watchers, hikers and history buffs eager to explore Parke County and its covered bridges.

Grand Rapids, Michigan: 175 miles northeast of Chicago

Inspiration flows on both sides of the Grand River, particularly near downtown . Grand Rapids' ArtPrize extravaganza every other fall is part art walk, part city tour and and entirely vacation-worthy. But there's plenty to see at other times of the year, too, including the Frederik Meijer Gardens and Sculpture Park , Frank Lloyd Wright's Meyer May House and the Gerald R. Ford Presidential Library and Museum .

Elkhart Lake, Wisconsin: 150 miles north of Chicago

Sun, sand and...race cars? Most people come here for quiet weekends of swimming, sunning, boating and water-skiing in the crystal-clear lake , but the legendary Road America course is popular with amateur racers and their fans. Nearby Kettle Moraine State Forest also offers outdoor rec of another type with trails for biking, hiking and running. Round out the weekend with a stay in one of the area resorts such as the Osthoff.

Lake Mills, Wisconsin: 125 miles northwest of Chicago

Famous for The Ephraim Pottery Studio and Gallery , a getaway to Lake Mills also offers plenty of outdoor recreation on Rock Lake, the Zeloski Marsh and the Glacial Drumlin Bike Trail, as well as a cozy Arts and Crafts style B&B. Snack on crackers and sip wine at Lewis Station Winery, and don't miss the old-fashioned James J. Chocolate Shop.

Glencoe, Illinois: 15 miles north of Chicago

Glencoe is one of the few cities bordering Chicago along Lake Michigan. The communities of the North Shore seem farther from the bustle of downtown, thanks to abundant green spaces, including the Chicago Botanic Garden . Make sure to visit to Grosse Point Lighthouse during sunset in Evanston and take a walk along the Green Bay Trail between Winnetka and Highland Park.

Apple River Canyon State Park, Illinois: 146 miles west of Chicago

Every day, hundreds of drivers speed past the turnoff on US-20 for Apple River Canyon State Park , bound for getaways in Galena. Those travelers admire the view from the car, not realizing that if they wanted a peek at one of the area's few remaining secrets, they should turn north on Canyon Park Road west of Stockton and drive for just 7 miles. The 297-acre Apple River Canyon State Park offers quiet amid the woods along Apple River. Hike the bluffs. Look for fossils. Listen for wildlife. Fish the river—and let the others head to Galena.

Beloit, Wisconsin: 96 miles northwest of Chicago

This area is famous for its supper clubs that serve nostalgia and hearty portions. It all goes down easily with an old-fashioned drink.

Midewin National Tallgrass Prairie: 60 miles southwest of Chicago

Experience landscape that once rolled across the Midwest like an ocean at this restored prairie. Spot birds, hear frogs, hike and bike, see wildflowers and unwind among the 19,000 acres at Midewin National Tallgrass Prairie.

Woodstock, Illinois: 60 miles northwest of Chicago

It's just a train ride from Chicago, but Woodstock feels anything but suburban. The historic town square (famously featured in Groundhog Day ) is adorable, with great home decor shops and a cozy bookstore. Come for the summer activities or the annual Groundhog Day Festival in early February.

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24 Top Weekend Getaways From Chicago

From beaches to ballparks and trails to rails, explore top breaks from the Windy City.

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Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago.

Known as the birthplace of the skyscraper, Chicago is home to award-winning restaurants , top sports teams and prized cultural treasures. But when you need a break from the excitement of the nation's third largest city, there are countless getaways within easy driving distance. You can explore rural Illinois or enjoy neighboring Indiana, Wisconsin, Iowa or Michigan all within a weekend. Whether you're planning a romantic getaway to a small-town bed-and-breakfast or a family-friendly trip to a water park resort, these nearby Midwest destinations will relieve the stress of big city life.

(Note: Some of the following activities, attractions and locations may be affected by the COVID-19 pandemic. New policies may be in place, including capacity restrictions, reservation requirements or mask mandates. Check with the Centers for Disease Control and Prevention, the U.S. Department of State and local tourism boards before traveling.)

Best Weekend Getaways from Chicago:

About two hours or less:, fox river valley, illinois, harbor country, michigan, st. joseph, michigan, milwaukee, wisconsin, south haven, michigan, starved rock state park, illinois, gurnee, illinois, wilmot mountain, wisconsin, lake geneva, wisconsin, grand geneva resort & spa, wisconsin, about three hours or less:, turkey run state park, indiana, the american club resort hotel, kohler, wisconsin, whistling straits golf course, sheboygan, wisconsin, saugatuck, michigan, wisconsin dells, wisconsin, about four hours or less:, parke county, indiana, galena, illinois, dubuque, iowa, and the field of dreams, ann arbor, michigan, madison, wisconsin, about five hours or less:, traverse city, michigan, louisville, kentucky, st. louis, missouri, a quick flight:, minneapolis – st. paul, minnesota.

Located along the picturesque Fox River on the western outskirts of Chicago lie the small towns that make up Illinois' Fox River Valley. Stretching from the village of Antioch in the north to Ottawa – the gateway to Starved Rock State Park – in the south, this area is an ideal daytrip from the Windy City. Go biking, hiking and cross-country skiing along the 32-mile Fox River Trail or rent a kayak for paddling on the Fox River. In addition to outdoor pursuits, unique cultural attractions abound, including Broadway productions and musical events in Aurora's historic and beautifully restored Paramount Theatre. Visitors rave about its exquisite decor and top-notch performances, applauding the Paramount for offering Broadway-caliber performances at Main Street prices. If you choose to overnight in the Fox River Valley, the Herrington Inn & Spa , which overlooks the Fox River in the small town of Geneva, would make for a romantic getaway.

New York has the Hamptons; Boston has Cape Cod . The summer playground for Chicagoans consists of eight glistening lakeshore towns dotting the coastline of southwest Michigan, collectively known as Harbor Country. Here you'll find beaches, orchards and plenty of outdoor activities. At the southern end of Harbor Country, just over the Michigan-Indiana state line and about 70 miles from Chicago's downtown loop, New Buffalo lures Chicagoans with its casual beach vibe and proximity. Families line up for burgers at The Stray Dog, but only adults can head up to the rooftop bar and patio. Patrons praise The Neighborhood Hotel Grand Beach for its modern design combined with cozy common areas, fire pits, ping pong tables and board games; they also appreciate the short walk to the beach and the heated pool.

[Read: The Top Things to Do in Michigan .]

Families will want to make the scenic 25-mile drive from New Buffalo north through the Harbor Country towns of Union Pier and Lakeside, past grand lakefront estates and bucolic farms, to St. Joseph, commonly called St. Joe's. The family-friendly Silver Beach Pizza is housed in St. Joe's former train depot, with diners saying it's well worth what can be a half hour wait for the amazing pizza. Across the street is the restored 1910 Silver Beach Carousel, a great option for passing the time while waiting for your table if you've got kids along. St. Joe's offers visitors the chance to step back in time with a beach, pedestrian-friendly downtown, boutiques and old-fashioned chocolate shops. One of St. Joe's more unique shops is Third Coast Surf, where you can rent a surfboard and sign up for surfing or sandboarding lessons. Not expecting a surf shop in the Midwest? Visitors are often surprised when they first see Lake Michigan, known to Midwesterners as the Third Coast: It resembles an ocean more than a lake.

Located about 80 miles north of Chicago on Lake Michigan is the Brew City of Milwaukee , which boasts more than 200 breweries, museums, festivals and the Harley-Davidson Museum . As this city is home of the Milwaukee Brewers baseball team, no trip is complete without getting a taste for Milwaukee's beer heritage. Visitors give Lakefront Brewery tours high marks for entertaining guides, extensive selection, riverfront views and its popular Beer Hall restaurant with live music on Fridays. Families will enjoy the lakefront museum campus, which includes the Discovery World science museum and Betty Brinn Children's Museum, while culture lovers can visit the architecturally stunning Milwaukee Art Museum when the building's "wings" open and close several times a day. Motorcycle enthusiasts will be in hog heaven at the modern steel-and-glass Harley Davidson Museum, which celebrates the machine invented in Milwaukee that's come to symbolize the freedom of America and the open road.

Winters are harsh, so summer is one endless celebration, with a multitude of neighborhood festivals, outdoor concerts and ethnic celebrations – check out German Fest at the end of July, honoring the city's largest immigrant group. Summer excitement reaches a crescendo at the end of June with Summerfest, the world's largest music festival. After a day of sightseeing or revelry, a top lodging choice is Milwaukee's stately grand dame, the historic Pfister Hotel , offering Gilded Age elegance alongside 21st-century amenities like a pool with panoramic city views and a popular top-floor cocktail bar.

[See more of Milwaukee:  Things to Do  | Hotels  |  Photos ]

South Haven is a fun-loving beach town with a population that swells in the summer – especially in August for the National Blueberry Festival, since this Michigan destination claims to be the blueberry capital of the U.S. About 110 miles from Chicago, you'll hear a lot of Jimmy Buffett playing in the bars and restaurants of this laid-back boating town where the harbors take center stage. Kick off your visit by learning about the area's rich Great Lakes boating history at the Michigan Maritime Museum.

Along with its seven public beaches – some of the best beaches in Michigan – and iconic red lighthouse, South Haven also has a pedestrian-friendly downtown filled with unique shops and restaurants. Climb aboard the stationary Idler Riverboat, where casual dining combines with world-class waterfront views. Clementine's is another local favorite, as is Captain Lou's, which serves fresh perch and live music on the weekends. For a romantic getaway, consider Inn at the Park, a bed-and-breakfast one block from Lake Michigan: Guests praise the beautiful decor and sumptuous breakfasts, using locally grown blueberries. Travelers also love Yelton Manor Boutique Hotel for its manicured gardens, spectacular sunset views of Lake Michigan and proximity to town.

Looking for an active adventure? Only about 100 miles southwest of Chicago, this wilderness known for its deep sandstone canyons and waterfalls is perfect for daytrips – though with 18 canyons to hike, there's plenty to keep you busy for a whole weekend. Walking along bluffs that lead to scenic lookouts over the Illinois River makes visitors feel immediately transported out of the flat Midwest heartland. Starved Rock State Park can be a weekend escape any time of year, but spectacular fall foliage makes it a favorite getaway for autumn in particular.

Starved Rock State Park has its own historic lodge with top-notch cabins , but kids may prefer going across the street to the family-friendly Grizzly Jack's Grand Bear Resort, with its massive water park, mini-golf, indoor arcade and Northwoods decor. Camp Aramoni is a great choice for a romantic getaway, with luxury glamping in safari tents outfitted with hardwood floors, air conditioning and heating, and full bathrooms with showers. Nightly stays include chef-prepared farm-to-table dinner and breakfast using produce grown in on-site gardens that guests are welcome to visit. End your day at Camp Aramoni's repurposed Airstream trailer that's been turned into a bar.

Looking for high-adrenaline family fun? About 35 miles north of Chicago, just south of the Wisconsin border, lies the village of Gurnee, home to the Six Flags Great America amusement park . Thrill-seekers will love the 17 heart-stopping roller coasters, but dozens of other rides mean you'll also find plenty for younger kids. Reluctant riders who want to steer away from high-speed coasters and intense drop rides can also enjoy the park's shows and other entertainment. On a hot day, plunge down steep waterslides or splash around the wave pool at Six Flags' 20-acre Hurricane Harbor water park. When it gets cold, a favorite local pastime is a stroll around Gurnee Mills, an outlet mall housing more than 170 stores.

Continue your Gurnee adventure with a stay at the Northwoods-themed Great Wolf Lodge, the most family-friendly hotel option in this destination. Guests say this water park resort makes even adults feel like kids again and rave about the endless family-friendly amenities, which include bowling, mini-golf, a ropes course and arcade – and, of course, the massive water park.

Since 1938 Wilmot Mountain has drawn visitors seeking wintertime leisure in the Midwest. About 25 miles northwest of Gurnee, just over Wisconsin's state line, Wilmot Mountain Ski Resort makes for a great cold-weather attraction when Six Flags is closed. The big-name Vail Resorts purchased Wisconsin's little ski hill in 2016 and rolled out plenty of upgrades, from improving terrain parks and snowmaking to adding chairlifts and elevating the dining experience. Enjoy winter sports over a variety of terrain at this alpine destination, whether you're looking to ski, snowboard or snow tube. There's no on-site lodging, but Gurnee's Great Wolf Lodge is still a relatively short drive away.

[Read: The Top Things to Do in Wisconsin .]

This Wisconsin resort city makes for an idyllic weekend or daytrip. About 70 miles northwest of Chicago, Lake Geneva is described as the " Newport of the Midwest" because of its opulent lakefront mansions. You can come surprisingly close to these impressive residences by ambling along the Geneva Lakeshore Path, a rustic 25-mile walkway that encircles the lake, cutting right through the backyards of magnificent mansions and second homes. Amazingly, there aren't any "No Trespassing" signs to scare away walkers; just beware the path is not intended for strollers, roller blades or bikes, since you'll have to maneuver past steps and other obstructions. When you've finished your stroll, a lakefront cruise is another fun way to enjoy this city. Visitors give Lake Geneva Cruise Line excellent reviews for being informative and entertaining. A variety of daily cruises are offered, but one of the most unique is the mail delivery cruise. As Lake Geneva is one of the few remaining places in the U.S. where mail is still delivered by boat, about 75 lakefront homes receive their U.S. mail service via boat – and passengers are invited to come along for the ride.

Consider a stay at the Abbey Resort, the only full-service resort directly on the shores of Lake Geneva, during a summer visit. This lodging option offers complimentary adult and kids bikes, ideal for use on the Lake Geneva Bike Path, which connects many of the resort town's amenities. The trail has five unique, color-coded segments, making it easy to find your way around. Things quiet down a bit in the fall, when the vibrant autumn colors set a serene scene.

[Read: The Best Midwest Vacations for Families .]

Tourists descend on Lake Geneva's charming downtown shops and restaurants in the summer, but the town has plenty to do year-round. One of the best winter attractions in this city is the Grand Geneva Resort & Spa , whose modest ski hill has three chair lifts, 20 runs and a terrain park. Grand Geneva Resort also has access to 5 miles of wooded trails for cross-country skiing and offers a limited number of ski rentals. Kids will love overnighting at Grand Geneva's family-friendly Timber Ridge Lodge and Waterpark for indoor aquatic fun while adults relax at the spa. Time your winter visit to coincide with Lake Geneva's Winterfest so you can observe one of the country's biggest snow sculpting competitions.

Turkey Run State Park is the crown jewel of Parke County and one of the Hoosier State's oldest and most popular state parks. Eleven trails ranging from a half-mile to 2 miles wind through rugged ravines surrounded by the park's signature sandstone cliffs – providing Midwest hiking at its best. Turkey Run Inn, a popular lodging option situated within the park, is appreciated by guests for its friendly staff and cozy atmosphere. There's an indoor pool and plenty of public sitting areas with fireplaces, whether you want to play a board game or read a book. Choose from rooms within the historic lodge or the adjacent cabins. Even if you don't stay at Turkey Run Inn, you can still enjoy its restaurant, The Narrows, which diners recommend for the catfish dinners as well as the fried biscuits and hot apple butter.

Most have never heard of this tiny town 140 miles north of Chicago, but Kohler is home to Wisconsin's only hotel to receive AAA's highest five diamond rating. The American Club Resort Hotel – part of the Destination Kohler Resort – is still owned by the family who built it: The Kohlers are best known for high-end plumbing and bathroom fixtures. The American Club's luxurious Kohler Waters Spa specializes in hydrotherapy, giving guests a chance to experience all the legendary bath and shower products Kohler is known for. Should you want to recreate that luxury spa experience in your own bathroom at home, a few steps away from the spa is the sleek, multistory Kohler Design Center, filled with model bathrooms and design ideas sure to give most of us bathroom envy. Amid your self-care ventures in Kohler, enjoy plenty of outdoor activities. Fall brings a boisterous bounty of color to this rural area, while winter experiences at The American Club include ice skating, curling, snowshoeing and cross-country skiing across miles of trails that wind through woodlands and meadows.

Ten miles from American Club Resort Hotel sits the Kohler-owned Whistling Straits Golf Course, which some golfers describe as reminiscent of the legendary Pebble Beach . Whistling Straits ranks among the top public courses in the country and has hosted 2021's Ryder Cup and three PGA championships. The two Pete Dye-designed courses at Whistling Straits offer stunning views of Lake Michigan or rolling green hills. Golfers will feel transported to Ireland's tranquil grassland or its rugged coastline as this course winds its way along the bluffs and dunes overlooking Lake Michigan.

It's easy to see why Saugatuck is one of the best places to visit in Michigan . Nicknamed the Art Coast of Michigan, this hip resort town about 130 miles from Chicago is stocked with galleries, boutiques, excellent dining and beaches. Perhaps surprisingly for a town of less than a thousand people, Saugatuck is also known for its lively nightlife and for being an LGBTQ-friendly destination. Take a seat at the counter of the century-old Saugatuck Drug Store and you'll get a taste of the town's more traditional side, served up via a classic malt or ice cream soda. Visitors are in for another nostalgia trip when you board the chain ferry: Operating since 1838, it claims to be the only remaining chain-driven ferry in the U.S., transporting passengers across the Kalamazoo River between downtown and Oval Beach. After disembarking on Oval Beach, active beachgoers love climbing the 302 steps to the top of Mount Baldhead – known as Mt. Baldy – and getting a bird's eye view of the area. Overlooking Lake Michigan, Saugatuck's Lake Shore Resort is applauded by patrons for its breathtaking views and many complimentary amenities, including bikes, kayaks, yoga and a heated pool.

About 190 miles northwest of Chicago is the ultimate Midwest family getaway: the "Waterpark Capital of the World." If traveling with kids to Wisconsin Dells, stay at one of the immensely popular water park resorts , such as the flagship property of Great Wolf Lodge. Guests appreciate the original Great Wolf Lodge for its signature Northwoods decor, endless amenities and the feeling of being in a tropical paradise year-round.

Beyond its myriad indoor and outdoor water parks, Wisconsin Dells boasts a wide variety of kid-friendly entertainment options, from zip lines to animal parks. Catch a performance at the Palace Theater, which offers everything from concerts to comedy shows to children's plays and Broadway-style productions; some theatergoers swear there isn't a bad seat in the house. More fun for the whole family can be found at the Rick Wilcox Magic Theater shows, which wow audiences with both humor and illusions that keep you guessing. Want to escape the indoor attractions for a natural one? Head over to Mirror Lake State Park for a scenic hike along a tranquil, no-wake lake set among sandstone bluffs. Pontoon boats, kayaks and stand-up paddleboards are available to rent here.

[Read: The Top Things to Do in Wisconsin Dells .]

Billing itself as the covered bridge capital of the world, Parke County, Indiana – about 160 miles south of Chicago – maintains 31 of these Instagram-worthy symbols of a bygone era. Visitors descend on the area every October for the Parke County Covered Bridges Festival, Indiana's largest annual festival. The popular biker bar Thirty Six Saloon is a family-friendly roadhouse in Rockville, the town where the popular fall festival is headquartered. Kids may be mesmerized by Thirty Six Saloon's vast collection of taxidermy, with animals from the region mounted throughout the restaurant. Diners compliment everything from the burgers and ribs to the fish sandwiches and unique decor. Another popular culinary option is the tenderloin sandwich at the Mecca Tavern in Mecca. Parke County's oldest tavern overlooks Mecca's historic schoolhouse and covered bridge. Locals and visitors alike say stopping by Wheelhouse Donuts is another must: This adorable bakery lets you design your own doughnut.

About 150 miles west of Chicago, in the northwest corner of Illinois, the charming Mississippi River town of Galena regularly makes national lists of best small towns . Its elegant dining, historic sites, quaint shops and bounty of bed-and-breakfasts make Galena an excellent choice for a romantic getaway. Because the glaciers that flattened most of the Midwest didn't reach here, the pastoral farmland is hillier, perfect for a Sunday drive. The 19th-century buildings in this old mining town have been painstakingly preserved, with 85% on the National Register of Historic Places – including the Ulysses S. Grant Home State Historic Site, a residence gifted to the nation's soon-to-be 18th president in 1865 by Galena citizens.

One memorable overnight option would be a stay at the former county jailhouse – now the luxurious Jail Hill Inn. For a more romantic atmosphere, the Goldmoor Inn is beloved by guests for its stunning views of the Mississippi River, in-room fireplaces and two-person hot tubs. Galena is gorgeous any time of year, with plenty of travelers drawn here during harvest time for apple and pumpkin picking amid the abundance of fall colors. Winter brings its own charm with shops along Main Street resembling something out of a Norman Rockwell painting. The small town also houses a popular old-school ski resort: Guests say Chestnut Mountain Resort's decor and amenities are a bit dated, but its 19 ski runs provide scenic views of the river below.

Head 170 hundred miles west of Chicago, cross the Mississippi River, and you'll be in Dubuque, Iowa. Get a feel for how important the river is here by visiting the National Mississippi River Museum and Aquarium, or take a ride on a riverboat for another scenic way to experience the Mississippi. Visitors give the Celebration Belle river cruise high marks for being fun, informative and affordable. Another must-see attraction is Fenelon Place Elevator, a steep funicular railway providing fabulous views of the surrounding area. History lives on at the elegant Hotel Julien Dubuque, which guests compliment for its charm and friendly service. Baseball fans will want to make the additional 25-mile drive west to the town of Dyersville to explore the Field of Dreams, one of the best tourist attractions in the U.S. Play on the baseball diamond and tour the home where the movie "Field of Dreams" was filmed.

About 230 miles northeast of Chicago, Ann Arbor is a quintessential college town, filled with independent bookstores and great live music. University of Michigan alumni are a proud bunch – and not just on game days, when they march clad in blue and yellow to what's known as The Big House, the largest sports stadium in the country. Ann Arbor also scores an A when it comes to food and culture. The world-class University of Michigan Museum of Art displays works by Picasso, Monet and Warhol. A few blocks away on Liberty Street is the edgier public art canvas known as Graffiti Alley, just steps from the historic Michigan Theater and State Theatre, which delight visitors with film screenings, festivals and live music throughout the year (as long as you follow the theaters' COVID-19 regulations ). A pastrami sandwich at Zingerman's Deli is a 40-year tradition, but if you're hungry for a more budget-friendly option head to Frita Batidos and take a seat at one of the communal tables for Cuban-inspired street food. Hit the books at Literati, a beloved independent bookstore. A fun hotel choice is Graduate Ann Arbor with its University of Michigan-themed decor.

[See more of Ann Arbor: Things to Do | Hotels | When to Visit | Photos ]

About 140 miles northwest of Chicago, Madison is more than just a cool college town: It's also the capital of Wisconsin. No trip here is complete without visiting the beautiful, white-domed Wisconsin state Capitol building; free tours are given throughout the day. Madison's isthmus location on a narrow strip of land between two lakes means waterfront biking and hiking trails abound. Foodies will also get their fill at Fromagination, a cheese lover's paradise popular with Wisconsin cheeseheads as well as out-of-town visitors. Located across from the Capitol, this delightful cheese shop features dozens of one-of-a-kind artisanal Wisconsin varieties. If visiting Madison between April and November, head to Capitol Square on Saturday morning for the Dane County Farmers' Market, the country's largest producer-only farmers market. The 72-room, collegiate-themed Graduate Madison hotel is an easy walk to campus, dining, shopping and nightlife. Decorated in the University of Wisconsin colors of red and white, the hotel gets high marks from guests for its nostalgic decor and artwork, including collages of political buttons, a nod to the town's legacy of social activism.

[See more of Madison: Things to Do | Hotels | When to Visit | Photos ]

Those who have more time could leave the bright lights of Chicago for the serenity of Michigan's Traverse City to visit Sleeping Bear Dunes National Lakeshore and its 64 miles of pristine coastline and mountains of sand dunes. Traverse City is about 300 miles from Chicago, but you'll be rewarded with breathtaking beaches, peaceful hikes, top-notch cuisine and the added perk of what's considered the " Napa Valley of the Midwest": the 24 wineries of the Leelanau Peninsula Wine Trail. When the temperatures drop and the snow arrives, a great winter weekend getaway involves cross-country skiing in Pere Marquette State Forest or the Leelanau Trail, which runs from Traverse City to Suttons Bay. Traverse City and northern Michigan are also filled with summer lake resorts: Top options include Lake Leelanau's Fountain Point Resort, the upscale Homestead Resort and the all-inclusive White Birch Lodge in nearby Elk Rapids. With White Birch known for its water sports program, teens and tweens will love water-skiing, tubing and ending the day swapping adventures with new friends around a beach bonfire.

[See more of Traverse City: Things to Do | Hotels | Tours | When to Visit | Photos ]

Best known as the location of the Kentucky Derby, Louisville sits 300 miles south of Chicago and has a whole lot more going on than just horse racing. About 95 percent of the world's bourbon is made in Kentucky ; for a taste of the state's signature liquor, head to downtown Louisville's historic Whiskey Row. Here you'll find distilleries, unique restaurants and live music. Topping any sports lover's itinerary should be a visit to the Louisville Slugger Museum and the Muhammad Ali Center , which visitors applaud for honoring the boxer's life, faith and humanitarian service. Art lovers would enjoy staying at the 21C Museum Hotel Louisville , which houses its own contemporary art museum.

[See more of Louisville: Things to Do | Hotels | Photos ]

About 300 miles southwest of Chicago, just over the Illinois border along the Mississippi River, sits this Missouri city. St. Louis is well worth a weekend trip for its plethora of restaurants, breweries and cultural treasures. Nicknamed the Gateway City for its iconic Gateway Arch , St. Louis gives travelers the chance to take a tram ride to the top of this engineering marvel. After getting a bird's-eye view of the surrounding area, head over to the nearly 1,300-acre Forest Park , site of the 1904 World's Fair, now home to the Saint Louis Zoo and several museums. Music lovers can't miss the National Blues Museum, which sings the praises of that melancholy American music form. If you find yourself in need of more music lessons, make your way to the Scott Joplin House State Historic Site, where the king of Ragtime lived. After a busy day sightseeing, Drury Plaza Hotel St. Louis at the Arch makes a good place to rest. Guests rave about the unbeatable value of the hotel's free breakfast and happy hour with complimentary hot food and drinks.

[See more of St. Louis: Things to Do | Hotels | When to Visit | Photos ]

The Twin Cities of Minneapolis − St. Paul straddle the Mississippi River, about 450 miles northwest of Chicago, with Minneapolis as Minnesota's most populous city and St. Paul as the state capital. Minneapolis is known as a city of lakes, but visitors also like to walk along the riverfront, taking in the magnificent Mississippi. Groundbreaking pop musician Prince was born in Minneapolis; now his legacy lives on at Paisley Park, a sprawling complex in the nearby town of Chanhassen that was once the artist's studio and home. Millions more travel here to visit the largest mall in the Western hemisphere, Mall of America , located in the nearby suburb of Bloomington. As much an entertainment complex as a retail center, this mall houses the indoor amusement park Nickelodeon Universe, a highlight for kids. Guests give Minneapolis' Hewing Hotel stellar reviews for its character, charm and stunning views from the rooftop lounge.

[See more of Minneapolis − St. Paul: Things to Do | Hotels | When to Visit | Photos ]

You might also be interested in:

• The Best Weekend Getaways
• The Top Romantic Getaways in Illinois
• The Top Romantic Getaways in Wisconsin
• The Top Romantic Getaways in Michigan
• The Top Romantic Getaways in Ohio
• The Top Fall Weekend Getaways
• The Top Travel Neck Pillows
• The Top Travel Backpacks
• The Top Duffel Bags

Tags: Travel , Midwest Vacations , US Vacations

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

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10 Easy Weekend Getaways from Chicago—No Flights Required

Escape chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in chicago..

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Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Photo by Bailey Berg

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location : With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a drivable trip. There are several weekend getaways from Chicago, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Read on for ten easy weekend getaway ideas from Chicago.

What cities are under three hours from Chicago by car?

• Milwaukee, Wisconsin (1 hour, 30 minutes)
• Madison, Wisconsin (2 hours, 25 minutes)
• Grand Rapids, Michigan (2 hours, 47 minutes)
• Peoria, Illinois (2 hours, 41 minutes)
• South Bend, Indiana (1 hour, 39 minutes)
• Indianapolis, Indiana (2 hours, 56 minutes)

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

Photo by MarynaG/Shutterstock

Geneva, Illinois

• Distance: An hour by car
• Best for: Singular art and great shopping

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa , located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district).

Michigan City is a breath of fresh air not far away.

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

• Distance: An hour and a quarter by car
• Best for: Hiking (and swimming for the brave)

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park ; in Michigan City proper, attractions include the 19th-century Barker Mansion —listed on the National Register of Historic Places—and family-friendly Washington Park Zoo .

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

• Best for: A beach and wine combo trip

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery , in nearby Baroda.

Milwaukee is home to one of the largest German populations in the U.S.

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

• Distance: An hour and a half by car
• Best for: Brats and brews

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront .

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

• Distance: An hour and forty minutes by car
• Best for: Whitewater rafting

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway , North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen . Play arcade games—for free!—at the Garage Arcade and Bar , which has all the classics, Galaga and Ms. Pac-Man included.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

• Distance: Around three hours by car
• Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail , a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market , which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park : here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

• Distance: Three hours by car
• Best for: Museums, both traditional and quirky

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art , don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library . Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the select Saturdays, May through October, between 10 a.m. and 3.15 p.m. (Private tours can be booked with Indiana Landmarks .)

Ann Arbor is known for its university, but a host of delights awaits all visitors.

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

• Distance: Around three hours and 45 minutes by car
• Best for: Adventures on the river

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum . Be sure to make time for the city’s Kerrytown Market and Shops , a picturesque neighborhood full of independent boutiques and restaurants. ( Zingerman’s Deli , one of the best spots in Ann Arbor for a sandwich, is here.)

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

• Distance: Four and a half hours by car
• Best for: Exploring rugged coastline

A 70-mile-long peninsula, Door County is often called the “ Cape Cod of the Midwest” —and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve , and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village .

Traverse City might be a bit further away, but it’s worth the drive—especially in the fall.

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

• Distance: Five hours by car
• Best for: Exploring shops and galleries in a justifiably popular small town

No wonder Traverse City was named one of the sweetest small towns to visit in summer : a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore .

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks:

• Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park )
• Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
• Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
• Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the U.S. for 2023 , after all, thanks to its top restaurants , world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica , California.

Happy weekending.

This article originally appeared online in 2020; it was most recently updated on August 31, 2023, to include current information.

30 Delightful Road Trips from Chicago

If you’re looking to get away from the city, here are the best destinations for day trips and weekend road trips from Chicago.

Chicago’s location makes it an ideal place to get in the car and go, whether you live in the city or you make it your home base for some Midwestern exploration.

I’ve lived in Chicago and its suburbs for twenty years, and in the Midwest my entire life (except for a brief four years in my early twenties).

Let’s just say I’ve been to a LOT of towns, villages, cities, parks, etc., that are within easy driving distance from the Windy City.

And while I love Chicago (I even wrote a book about it ) and The Local Tourist began as a guide to the city’s River North neighborhood, sometimes even I just need to get away.

I’ve hand-picked some of my favorite Midwest road trips from Chicago. If you’re looking for delightful towns with delicious food and drink, boutiques and artisan shops, intriguing history, outdoor adventures, natural beauty, and so much more, you’re sure to find your perfect road trip from Chicago.

Road trips are the equivalent of human wings. Ask me to go on one, anywhere. We’ll stop in every small town and learn the history and stories, feel the ground and capture the spirit. Then we’ll turn it into our own story that will live inside our history. Victoria Erickson

Love travel quotes? Here you go!

There may be affiliate links in this post, which means we may get a small commission if you make a purchase. It’s at no extra cost to you and helps keep TLT free. Everybody wins!

Road Trips from Chicago

How to choose the best road trips from chicago.

How far will you drive for a weekend trip?

I asked that question of members of The Local Tourist Facebook group and their answers surprised me. The winning time was five hours, and second place was four hours.

Several of these road trippers would even drive eight hours for a weekend vacation!

Based on their input, and my own obsession with road trips, I’ve included some destinations that require a few hours behind the wheel.

I’ve also included places that are much closer. In fact, there are a few towns and cities that are technically suburbs of Chicago. Depending on your starting point, these destinations may provide more of a staycation than a vacation.

But hey – that’s what being a Local Tourist is all about, right?

I’m only including destinations that I’ve personally visited and enjoyed. Clearly, I need to spend more time in Ohio and Michigan.

For each road trip destination, I’ve included driving time. This assumes you’ll be driving interstates and won’t be avoiding toll roads. It also assumes no traffic.

Depending on when you leave for your weekend road trips from Chicago, traffic could increase times by at least an hour, so check Google maps or Waze before you go.

I’ve also included suggestions for places to stay, as well as links to each destination’s official Convention and Visitors Bureau, or CVB. These local resources are my travel planning not-so-secret weapon .

Ready to plan your road trips from Chicago? Let’s go!

Related: before you go, check out all my tips for planning a road trip .

10 Day Trips from Chicago

If you’re looking for a quick getaway or even a day trip, these locations are short road trips from Chicago and all within two hours of the Windy City.

Elgin, Illinois

Driving time: 1 hour

Known as the City in the Suburbs, Elgin, Illinois, is a relatively quick drive or an easy train ride from downtown Chicago. Its proximity makes it perfect for a day trip, but there’s enough to do that you’ll want to make a weekend of it.

A good place to start is downtown Elgin. Located right on the Fox River, it’s filled with public art and historic buildings.

Get the history of the area at the Elgin History Museum (pictured above).

You can also take a free self-guided walking tour of the Elgin Historic District.

Since that walking will make you hungry, grab a sandwich at Blue Box Café or head up to West Dundee for a burger and a pint at Emmett’s Brewing Co., an award-winning brewery.

Another one of the great things to do in Elgin is visit Lords Park and Zoo. On its grounds is the Elgin Public Museum, the only natural history museum in the Fox Valley.

Where to stay in Elgin, Illinois: Most of the hotels in Elgin are along the I-90 corridor. The Holiday Inn & Suites is one of the most highly rated accommodations near Elgin.

CVB: Explore Elgin Area, exploreelginarea.com

Indiana Dunes National Park, Indiana

One of our newest national parks is a short drive or train ride from Chicago. Established in 2019 , Indiana Dunes National Park is 15,000 acres along the southern shores of Lake Michigan.

There are over fifty miles of trails, making hiking Indiana Dunes National Park one of its top attractions. Hikers can traverse dunes, wetlands, prairies, rivers, and forests, all in one park.

There’s a fee to access the park: $15 per person (up to $25 per family group) and $25 per carload.

You could spend the entire weekend at the park. However, if you want a break, drive a little further east to Michigan City.

While the town is known for Lighthouse Place Premium Outlets, it’s also home to several museums, including the Old Lighthouse Museum.

Where to stay near Indiana Dunes State Park: Camping is available within the park itself, and there are several hotel chains in Michigan City .

CVA: South Shore Indiana, southshorecva.com

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Just across the border from Michigan City, Indiana, is Harbor Country.

The Red Arrow Highway takes you through eight small towns, each unique, each charming in its own away. Think boutique instead of big box, locally owned versus chain.

Outdoor enthusiasts will find everything from kayaking and paddle boating to fishing, surfing, and golf. Of course, you can also spend the day at the beach.

One of the biggest attractions is the number of Southwest Michigan wineries and breweries. The climate is very similar to Napa Valley, and the area’s known for its award-winning wines.

Where to stay in Harbor Country: You can find inexpensive hotels as well as private homes in New Buffalo, Michigan .

CVB: Harbor Country Chamber of Commerce, harborcountry.org

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha is the fourth largest metro area in Wisconsin, as well as the fourth-largest city on the shores of Lake Michigan, and there are TONS of things to do.

It’s the home of the oldest operating velodrome in the country, a free dinosaur museum, historic restaurants, not one but two lighthouses, and you can still ride an electric trolley.

Start your visit at the Kenosha History Center for an overview of the area’s past. Then don’t miss the Dinosaur Discovery Museum or Kenosha Public Museum, both of which are free.

The Civil War Museum is an impressive look at Wisconsin’s role in the war.

A must-visit restaurant is House of Gerhard, featuring traditional German specialties. Another favorite is Franks Diner. Guy Fieri featured it on  Diners, Drive-ins, and Dives and it serves up tasty American cuisine with a side of sass.

Check out more reasons you should visit Kenosha, Wisconsin .

Where to stay in Kenosha: you can stay in Kenosha hotels that are conveniently located off I-94, or you can choose an historic inn like The Stella Hotel and Ballroom. For a great view, check out Wyndham Garden Kenosha, right on the harbor.

CVB: Visit Kenosha Wisconsin, visitkenosha.com

McHenry County, Illinois

Driving time: 1 hour 30 minutes

I lived in McHenry County, whose northern border is shared with Wisconsin, for five years and still found new things to do.

One of the most surprising aspects of the area is the sheer number of parks. The McHenry County Conservation District manages more than thirty conservation areas, and most of them have hiking trails.

There are also city and village parks, as well as two state parks within the county.

Another great thing about the area is the food. Oh, the food! There’s farm-to-table at 1776 Restaurant and Duke’s Alehouse and Kitchen, incredible Italian at 750° Cucina Rustica, rich encased meats at Richmond Brathaus, and the best custard anywhere at Julie Ann’s Frozen Custard.

All are local; all are family-owned; all are delicious.

McHenry County’s county seat is Woodstock, which you might recognize. It’s where Groundhog Day was filmed, and the town celebrates with their very own groundhog, Woodstock Willie.

You can even stay in the same bed and breakfast where Bill Murray’s character woke up again, and again, and again.

With the mouthwatering breakfasts served each morning at Cherry Tree Inn Bed and Breakfast, though, you won’t mind if the same thing happens to you.

Read more about why I love being a Local Tourist in McHenry County , and you will, too!

Where to stay in McHenry County: Cherry Tree Inn Bed and Breakfast , of course! Since there are only four rooms, if they’re full, you can find hotels in Crystal Lake , the largest town in the county.

CVB: Visit McHenry County, visitmchenrycounty.com

Starved Rock State Park

Head to Starved Rock State Park for a day of fresh air, physical fun, and outdoor adventure.

Located just 94 miles southwest of Chicago, the landscape is an unexpected tableau of bluffs, steep trails, and waterfalls. Since it’s on the Illinois River, there’s also fishing and boating.

You can bring a lunch to enjoy at the waterfront picnic area, or grab a bite to eat at the historic lodge.

Nearby Ottawa is a charming town with lots of creative chefs, so you can have the best of both worlds.

Where to stay in Starved Rock State Park: There’s a lodge at the park itself, but I personally prefer camping. Starved Rock has one of the best campgrounds in the Midwest .

Janesville, Wisconsin

Driving time: 1 hour 45 minutes

Located right off I-90, Janesville is an ideal weekend road trip from Chicago, especially if you like the great outdoors, art, and history.

The town’s tagline is “Wisconsin’s Great Outside,” and there are thirty miles of trails in Janesville, including a portion of Wisconsin’s Ice Age Trail. One of the most scenic treks is the mile and a half hike to Devil’s Staircase.

The Rotary Botanical Gardens is a non-profit garden covering twenty acres. You won’t want to miss their Holiday Light Show.

From Thanksgiving weekend through December, the gardens become a magical winter wonderland strewn with hundreds of thousands of lights.

History buffs will get a kick out of exploring Janesville’s thirteen historic districts. One of the highlights of any visit to Janesville would be the Lincoln-Tallman House.

Built in 1857, it’s been a museum since 1951. Eighty-five percent of the furnishings in the house are original, including the bed that Lincoln slept in when he was a guest.

Janesville’s dining scene is relatively new, but with restaurants like Genisa Wine Bar and the Sandwich Bar, it’s gaining steam and there are enough unique spots to keep your palate happy.

I definitely recommend bellying up to the 1933 Art Deco bar at O’Riley and Conway’s Irish Pub for some Scotch eggs.

Combine history and beer at Gray Brewing Co. They’ve been brewing beer since 1856, except during that pesky Prohibition when they turned to sodas. It’s one of the oldest family-owned breweries, not just in Wisconsin, but in the United States.

When you visit Janesville, make sure you’ve got your walking shoes and plenty of room on your SD card, because the town is filled with vibrant and colorful murals.

Where to stay in Janesville, Wisconsin: Renovated in 2019, the Hampton Inn provides comfortable rooms with modern décor. Breakfast is included, and it’s one of the better spreads I’ve seen.

When I stayed, the hot items were frequently replenished and there were several options including both waffles and mini-waffles.

CVB: Janesville Area Convention and Visitors Bureau, janesvillecvb.com

Lake Geneva, Wisconsin

Located just 75 miles northwest of Chicago on the other side of the Wisconsin border, Lake Geneva provides a year-round escape from hectic city life and is a short day trip from Chicago or great weekend destination.

One attraction with a direct tie to Chicago is the Yerkes Observatory (pictured above).

Yerkes is considered the birthplace of modern astrophysics and was funded by Charles Yerkes, who had a huge role in developing Chicago’s public transportation.

Lake Geneva has long been a playground for Chicagoans. In the late 1800s and early 1900s, it seemed that every wealthy Chicagoan built a mansion on the shores of the lake. Today, many of those mansions still stand.

The best way to see them is to take a boat tour, especially if you can ride along when they’re delivering the mail. Lake Geneva is one of the few places left in the country where mail is delivered by boat.

Another way to see the mansions is to walk the path that surrounds the lake. Like Chicago’s lakefront with its public beaches, Geneva Lake is surrounded by a trail that’s open to everyone.

The lakefront path is one of the most popular things to do in Lake Geneva .

One place you can only visit from a boat, unless you have physical limitations and can’t climb the many stairs from the dock, is Black Point Estate. This historic mansion has many ties to Chicago, including Jane Addams .

For something completely different, feed an ostrich. Safari Lake Geneva is a drive-through experience that allows you to feed giraffes, alpacas, elands, and emus.

An experience that’s both fun and tasty is taking a class at Lake Geneva Cooking School. Chef John teaches you how to make dishes you might never attempt on your own, and he pairs them with stellar wines.

Like many, during lockdowns he pivoted and fulfilled his dream of publishing a cookbook . I’ve made several recipes from it, and highly recommend it.

Golf is one of Lake Geneva’s biggest draws. During the winter months, you can ski, snowboard, snowshoe, and ice fish.

Where to stay in Lake Geneva: Technically located in Fontana on the west side of Geneva Lake, The Abbey Resort is a sprawling complex with beautiful rooms overlooking a marina.

They also have multiple pools and there’s often live music, either in the bar or outside during the summer.

CVB: Visit Lake Geneva, visitlakegeneva.com

Milwaukee, Wisconsin

Milwaukee, Wisconsin, is an urban getaway filled with culture and outdoor fun.

The instantly recognizable Milwaukee Art Museum is definitely worth visiting, and after you’ve browsed its collections you can take a walk along the lakefront.

For more art, book a room at Saint Kate The Arts Hotel . This astounding hotel is like staying in a work of art – because you are. It’s right downtown, providing easy access to the river walk.

Beer lovers will have a blast exploring Milwaukee’s breweries. Lakefront Brewery is known for its fun tours. Milwaukee Brewing Company and Mobcraft are also great places to visit.

There’s no beer at the Pabst Mansion, but you’ll still want to see Captain Frederick Pabst’s house, built in 1892. It’s a gorgeous Flemish Renaissance Revival mansion that’s on the National Register of Historic Places.

Fun fact: Captain Pabst earned his stripes with the Goodrich Line of steamships, which was based out of Chicago.

Another nautical stop is North Point Lighthouse. Built in 1888 high on a bluff, Frederick Law Olmsted himself designed the grounds. Chicagoans will recognize the famous landscaper’s name from the 1893 World’s Columbian Exposition and the University of Chicago, among others.

Olmsted also landscaped Lake Geneva’s Yerkes Observatory, which was part of the University until recently.

The Harley-Davidson Museum is another must-stop and be sure to dine at Motor, the on-site restaurant.

During the summer there are festivals just about every weekend, so check Visit Milwaukee’s events calendar to find out what’s happening.

And of course, make sure you have some cheese curds, brats, and beer.

Where to stay in Milwaukee: Saint Kate The Arts Hotel for a modern art experience, The Pfister Hotel for a dose of history, and Iron Horse for more industrial décor and easy access to the Harley-Davidson Museum.

CVB: Visit Milwaukee, visitmilwaukee.org

Lafayette, Indiana

Driving time: 2 hours

My grandparents lived in West Lafayette, Indiana, so I grew up visiting. However, it wasn’t until a few years ago that I actually explored the town. Boy, had I been missing out on a lot.

Known as the home of Purdue University, West Lafayette, and its sister city Lafayette, have history, art, culture, delicious food and drink, and a vital sense of community.

There are several places that make this a great place for a road trip from Chicago. One is the Haan Mansion Museum of American Art.

The mansion was originally built for the 1904 World’s Fair in Saint Louis. Now it’s in West Lafayette and is filled with impressionist paintings and historic furniture.

Another is SAMARA. Designed inside and out by Frank Lloyd Wright for Dr. John and Catherine Christian, it’s a nearly perfectly preserved example of Wright’s Usonian architecture.

Another fascinating spot is Prophetstown State Park, combining a landscape that’s distinctly Indiana with the history of the Native Americans who fought the settlers’ encroachment, and the farmers who eventually tilled the land. While there, visit the nearby Tippecanoe Battlefield.

I’ve got even more places to visit in Lafayette. These include not only places I’ve been, but also spots recommended by students at Purdue University. I’ve partnered with a 400-level travel-writing class since 2018, and many of their submissions are local to the college town.

See why you should visit Lafayette and West Lafayette Indiana

Where to stay in Lafayette, Indiana: Mr. TLT and I loved the cozy intimacy of Black Blanket Farms Bed and Breakfast . If they’re booked, Lafayette has a gazillion hotel options since it’s a college town.

CVB: Visit Lafayette-West Lafayette, homeofpurdue.com

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

If you’re looking for a slower pace, yet still want plenty to do, add Shipshewana to your weekend adventures.

Shipshewana is in LaGrange County, also known as Indiana Amish Country. You’ll know when you get close because you’ll start seeing horse-drawn buggies and bicyclists everywhere.

With the third largest Amish population in the world, this area is a definite departure from the hustle and bustle of city life. Instead, it’s antiques and hand-crafted furniture, delicious food, and fun entertainment.

One of Shipshewana’s most well-known attractions is the Shipshewana Flea Market . Begun in 1922 with a livestock auction, this family-owned business is the largest flea market in the Midwest.

Learn what it’s like to attend the Shipshewana Misc & Antique Auction .

You also don’t want to miss the Davis Mercantile . Another family affair, it’s a destination for dining, shopping, and riding the carousel.

If you plan your trip in advance, you might be able to dine in an Amish home, which is a real treat (and the best mashed potatoes ever). If it’s a last-minute getaway, The Blue Gate Restaurant is always a favorite. After dinner, head upstairs for a show at the theater.

Other fun things to do in Shipshewana include touring Cook’s Bison Ranch, exploring one of the many county parks, having dinner in an Amish home , canoeing or kayaking on the Pigeon River, and taking a driving tour on a hunt for barn quilts.

Where to stay in Shipshewana: The Blue Gate Garden Inn is a comfortable hotel that’s filled with amenities, including outdoor fire pits and an ice cream shop.

CVB: Visit Shipshewana, visitshipshewana.com

Sheboygan, Wisconsin

Driving time: 2 hours 30 minutes

When people ask me the destination that surprised me the most, Sheboygan, Wisconsin, tops the list.

I visited in August 2021, and it was my first press trip post-cancer. It was exactly the experience I needed: waves, beaches, amazing food, brilliant art, and a community that preserves its past.

Your first stop should be the Sheboygan Visitor Center. It is absolutely the coolest visitor center I’ve ever seen – and I’ve been to a lot.

Sheboygan’s known as the Malibu of the Midwest, so of course I had to get out on the water. One of my favorite things to do was take a first sailing lesson in Lake Michigan. That’s right – you can learn how to sail on a weekend trip to Sheboygan.

The Kohler name is prominent in the area. In addition to the manufacturing company and a nearby resort, there’s also the Kohler Arts Center and the Kohler Art Preserve, which opened in 2021.

Kohler also manages the James Tellen Woodland Sculpture Garden, one of several artist-built environments throughout the state.

History geeks will want to stop at Sheboygan Indian Mound Park and the Sheboygan County Historical Society and Museum.

For dining, don’t miss Black Pig, Il Ritrovo, and BoMallies. Breakfast should absolutely begin at Paradigm Coffee and Music. Best. bagel. sandwich. ever.

Check out my piece about this surprising place, and I’ve even included the perfect 3-day Sheboygan itinerary .

Where to stay in Sheboygan: Blue Harbor Resort offers gorgeous rooms and an even better view. They’ve also got a whole water park, on-site dining, and easy access to the beach.

CVB: Visit Sheboygan, visitsheboygan.com

Elkhart Lake, Wisconsin

About twenty minutes from Sheboygan is another delightful road trip from Chicago.

Elkhart Lake has all the feelings of a resort town. There are historic accommodations, unique boutiques, and delicious dining.

The eponymous lake is gorgeous, with crystal clear water. You can take a pontoon boat ride, or go kayaking or paddle boarding.

The village is also right by the Ice Age Scenic Trail and Kettle Moraine State Forest – Northern Unit, providing lots of opportunity for outdoor activities.

Racing fans won’t want to miss Road America. This four-mile road course is considered the best in the United States and one of the top in the world.

Not only can you watch racing, you can also take a spin around the track yourself. They offer both motorcycle and automobile driving schools.

Where to stay in Elkhart Lake, Wisconsin: Osthoff Resort is an historic inn that offers a variety of room options, including suites and villas, and features amenities such as an indoor and outdoor pool, spa, and fitness center.

The resort also has several dining options on-site, including a fine-dining restaurant and a casual bistro.

CVB: Elkhart Lake, visit website

Galena, Illinois

Driving time: 3 hours

Galena, Illinois, is located near the Mississippi River on the opposite side of the state from Chicago. Surrounded by the rolling hills and bluffs of the Driftless Region, it’s an area dotted with wineries and golf courses.

There are many reasons nearly a million people visit the former mining mecca each year. From shopping along its historic main street to the many wineries in the area, it’s a great spot for a romantic weekend or a girls getaway.

A stroll down Main Street feels like a step back in time. Be sure to stop into Galena Canning Company for a taste of salsas and jams, and Galena Brewing Company offers a lineup of tasty beers.

Thrill-seekers will love a visit to Long Hollow Canopy Tours , a zipline adventure through the woods.

Nature lovers can explore trails along the nearby Mississippi River, and golfers will love a few rounds at Eagle Ridge Resort & Spa.

There are also several historic buildings, and the Ulysses S. Grant Home is one of the most popular places to visit for a look into the past.

Where to stay in Galena, Illinois: While there are hotels that are closer to Galena’s historic Main Street, two of my favorites are a short drive from downtown. Goldmoor Inn Bed and Breakfast is an elegant getaway overlooking the Mississippi River.

Eagle Ridge Resort and Spa is my home away from home when I’m in Galena. I’ve stayed there at least five times. I love the variety of accommodations, activities, and the delicious food.

CVB: Visit Galena, visitgalena.org

Hendricks County, Indiana

My first visit to Hendricks County, Indiana, was in 2017, and since then I’ve returned four? five? times. You might say I like it. I even taught the first writing workshop for Midwest Travel Network (I’ve now taught three) at Natural Valley Ranch, a cabin with that private pond out its back door.

There are also horses, that you can ride. Squeee!

It’s a large county comprised of several towns. Some are large, like Plainfield and Avon, and others are small, like the tiny Lizton, which is home to the best barbecue – and pecan pie – in Indiana (and possibly the Midwest).

Race fans not only have easy access to the Indianapolis Motor Speedway, they can also see the NHRA Finals at the Lucas Oil Raceway within Hendricks County.

The only Doctor Who Museum and Store is in Hendricks County, as is the Tie-Dye Lab, where you can make your own tie-dye apparel. Beasley’s Orchard has the best apple cider. Oasis Diner is the only diner on the National Road and it’s got one of the best pork tenderloin sandwiches anywhere.

Basically, go to Hendricks County . There’s so much to do I bet you’ll want to go back again and again, just like I do.

Where to stay in Hendricks County: Natural Valley Ranch is great if there’s a big group of you exploring the area. If not, then I’m a fan of Staybridge Suites . Each room includes a kitchenette, plus they offer free breakfast and weekday happy hours.

CVB: Visit Hendricks County, visithendrickscounty.com

More Road Trips from Chicago between 2 and 3 hours

• Madison, Wisconsin; 2 hours 45 minutes
• New Glarus, Wisconsin; 2 hours 45 minutes
• Indianapolis, Indiana; 3 hours
• Quad Cities, Illinois/Iowa; 3 hours

11 Weekend Road Trips from Chicago between 3 and 5 hours

Fort wayne, indiana.

Driving time: 3 hours 10 minutes

When you go to Fort Wayne, go hungry. And thirsty. This northeastern Indiana town has a thriving food and beer scene that will have you coming back for more.

This All-American City is located at the confluence of three rivers, and that riparian location has fed its personality since it was founded when General “Mad” Anthony Wayne built a fort there in 1794. That fort didn’t last long, and by 1815 the town was on its third fort, built by Major John Whistler.

Chicagoans might recognize that name: he built Fort Dearborn when he was a Captain. You can visit a replica of Whistler’s fort, and they often have events.

One of the best things to do in Fort Wayne is visit the YLNI Farmers Market. This bustling marketplace features everything from handmade chocolates to hot sauces that’ll blow your top off to candles that smell like Fort Wayne (and Montana, Chicago, and everywhere else Simple Nature‘s creative creator has been). 

But what about that food, you ask? A few favorites include Club Soda, for white tablecloth dining with a side of live music, Birdie’s for shared plates in an airy rooftop, and Hall’s Prime Rib for down-home diner cooking.

Beer fans will want to belly up at Junk Ditch, The Hoppy Gnome, and Hop River Brewing Company.

Where to stay in Fort Wayne, Indiana: Courtyard Fort Wayne Downtown at Grand Wayne Convention Center is in a great location; across from the convention center and in between Parkview Field and Embassy Theatre.

CVB: Visit Fort Wayne, visitfortwayne.com

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

While it may seem blasphemous to some to suggest driving to the home of the Packers from the home of the Bears, I guarantee there’s a lot more going on than gridiron battles.

Auto enthusiasts will love The Automobile Gallery. Opened in 2016, this collection of pristine vehicles span over a century of automotive history.

From the iconic 1908 Cadillac Model T to the sleek 1960 Chevrolet Corvette, every car enthusiast will find something to admire.

The museum also features a rotating selection of vehicles, ensuring that there is always something new and exciting to discover.

For transportation of another kind, visit the National Railroad Museum. The museum began in 1956 and now covers a sprawling 33-acre campus.

Not only can you see locomotives like the iconic “Big Boy” No. 4017, you can step inside a Pullman sleeper car and learn about the porters who worked America’s rail lines.

Ready for a drink? From Captain’s Walk Winery to Zambaldi Beer, you’ll find something to whet your whistle.

And if you’re hungry, Green Bay will keep you fat and happy. (Speaking from experience here.) Don’t miss the authentic kringles at Uncle Mike’s Bake Shoppe or a cup of Booyah, a hearty Belgium chicken stew.

Where to stay in Green Bay, Wisconsin: Stay in the heart of Green Bay at the historic Hotel Northland . The hotel’s especially great for a romantic getaway.

CVB: Discover Green Bay, website

Dubuque, Iowa

Driving time: 3 hours 20 minutes

You’ll be glad Dubuque Iowa is one of these easy road trips from Chicago, because there’s so much to do you’ll want to return again and again.

Dubuque’s location on the Mississippi means it’s filled with river lore. Begin your visit at the Mines of Spain, a National Historic Landmark and Iowa State Recreation Area. It’s named for the mines that Julien Dubuque, the town’s founder, worked with permission from first the Mesquakie and then the Spanish. The Julien Dubuque Monument resembles a rook and overlooks the Mississippi; Dubuque is buried on the site.

Get an in-depth introduction to the river and the region at the National Mississippi River Museum and Aquarium, then go on the river itself. You can take a steamboat tour or an American Lady River Cruise aboard a yacht.

Like Janesville, Dubuque’s downtown is also covered with murals, and it’s a fun afternoon to walk the streets and find your favorite.

Dubuque’s most unusual attraction is the Fenelon Place Elevator. It’s the shortest, steepest railroad and a ride to the top provides some of the best views in the city.

Another spot for great views is Eagle Point Park. You’ll get a birds eye view of Lock and Dam #11 and can see into both Wisconsin and Illinois.

One of the most famous attractions is in nearby Dyer. The Field of Dreams Movie Site is surprisingly moving, especially now that you can tour the house. Inside you’ll discover stories behind the filming of this beloved classic.

I think the food scene in Dubuque will surprise you. It certainly surprised me to discover several innovative chefs serving quality cuisine. Make reservations for both Brazen Open Kitchen and Pepper Sprout and you’ll be one happy diner.

Where to stay in Dubuque, Iowa: since it’s right downtown, you can’t get much more convenient than Hotel Julien Dubuque . Plus, it’s a gorgeous hotel with oodles of history, including stories about Mr. and Mrs. Lincoln and a certain gangster from Chicago.

CVB: Travel Dubuque, traveldubuque.com

Brown County, Indiana

Driving time: 4 hours

Brown County, Indiana, is known for its beauty when the leaves change colors, but that doesn’t mean you can only visit in the fall. The rolling hills are beautiful year round.

While the area is easy to get to now, that wasn’t always the case. Its relative isolation fostered a vibrant artists community, which thrives to this day.

Visit Brown County and you can see the home and studio of one of the founding artists T.C. Steele. He was one of the five members of the acclaimed Hoosier Group. In the late 1800s, that group put Indiana’s art scene on the map, and Brown County in particular.

Browse the galleries of Nashville, Indiana, and you’ll see works of art from those early painters as well as artists of today.

Get a two-for-one cultural experience at Country Heritage Winery. Not only can you taste wines, when you take a weekend road trip from Chicago, you can do so while listening to live music.

Another favorite is Hard Truth Hills. Inspired by Sierra Nevada’s set-up in Asheville, North Carolina, this is a multi-purpose destination with a brewery, a distillery, a restaurant, and an outdoor stage. Pro tip: get the to-die-for pulled pork nachos.

Brown County is one of those places where you can choose to go-go-go, or you can kick back and relax. Either way, it’s definitely worth the drive.

Learn more about Brown County and how it became the tourist destination it is today.

Where to stay in Brown County: Abe Martin Lodge is located within Brown County State Park. Bring the kids and your swimsuits; they’ve got an indoors water park. Want something more secluded? There are cabins, too.

CVB: Brown County, browncounty.com

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Sandusky is most famous for being the home of Cedar Point amusement park, but this city on the shores of Lake Erie is much more than roller coasters and funnel cakes.

A fun way to get an overview is to take a Segway tour. Sandusky Segwave offers guided tours through the historic downtown. Perched atop your personal transporter, you’ll glide past historic sites, through city parks, along the lakefront, and past the Merry-Go-Round Museum. You’ll learn about the town’s very beginnings, as well as its role in the Underground Railroad.

Another reason to visit Sandusky is Kelleys Island. Take a high-speed ferry to the largest American island in Lake Erie for a day of art, shopping, and wine.

While you’re on the island, don’t miss Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Before you go back to Sandusky, get a scoop of Lake Erie Cookie Island Monster. It’s the official ice cream of Ohio’s Lake Erie Shores and Islands , Sandusky’s visitors bureau.

Warning: it will turn your tongue blue!

Check out my guide to see many more things to do on Kelleys Island .

Where to stay in Sandusky, Ohio: Hotel Kilbourne . This place puts the boutique in boutique hotel. In addition to being the only Sandusky hotel that’s on the water, it’s also got a rooftop bar and an on-site restaurant.

CVB: Ohio’s Lake Erie Shores and Islands, shoresandislands.com

Driving time: 5 hours, or as long as you’d like!

Route 66 epitomizes the freedom of the open road, and it begins in Chicago. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.

This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.

Some of the most popular roadside attractions include Buckingham Fountain (not technically on Route 66, but you’re so close!), the Gemini Giant, Bunyon’s Statue, and Carlinville’s Million Dollar Courthouse.

Route 66 in Illinois is only 301 miles, but it’s nearly a century of Illinois history, so take your time.

More road trips from Chicago between 3 and 5 hours:

• Iowa City, Iowa; 3 hours 45 minutes
• Door County, Wisconsin ; 3 hours 50 minutes
• Bloomington, Indiana ; 4 hours
• Spencer, Indiana : 4 hours
• Collinsville, Illinois and Cahokia Mounds State Historic Site : 4 hours 45 minutes
• Traverse City, Michigan; 4 hours 55 minutes

Want an epic trip from Chicago but don’t feel like driving? Consider a train to Seattle – here’s what it’s really like to ride the Amtrak Empire Builder !

Map of Road Trips from Chicago

I hope these delightful road trips from Chicago will help you find someplace wonderful to visit for your weekend getaways. Each place is special and offers unique experiences. When you go, I’d love it if you’d share your photos in our Facebook group .

Oh, and be sure to bookmark this page, because I’ve got more destinations to add!

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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• Planning a Road Trip in the USA: 13 Best Routes!
• 57 Coolest Things to Do in Chicago for 2023
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip
• 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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Best Weekend Getaways From Chicago

By Nina Kokotas Hahn

Chicagoans itching to travel right now should not underestimate the power of a great winter road trip, and not just because it may feel like the only safe option at the moment. In a break from the norm, we’ve found exciting places offering something fresh and surprising for the Midwest, making them well worth the drive. A fun, elegant cocktail experience, lakefront retreats that offer stunning views, snowy ski trips with plenty more to do off the slopes—it’s all available. Here are the best weekend getaways from Chicago .

(Editors note: Given the changing nature of the COVID-19 pandemic , the hours and accessibility of many venues are fluid and subject to change. Make sure to contact them before visiting.)

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

LAKE FOREST, ILLINOIS

Distance from Chicago 33 miles

The Deer Path Inn

In less than 60 minutes by Metra or just over 30 minutes by car, find yourself feeling far from the city in this pretty Northshore town off of Lake Michigan. No doubt Lake Forest is fancy with its sprawling estates, Market Square, and upscale shops (check out the all-women-run Lake Forest Bookstore and Valentina boutique), and coveted waterfront views. Being here also puts you 20 minutes closer to the 385-acre Chicago Botanic Gardens , where the Japanese and dwarf confider gardens are especially sublime in winter.

Where to Stay

The main reason to go to Lake Forest now is a weekend away at the 57-room Deer Path Inn ( from $329 per night ), a fabulous, little-known gem that puts you in arm's reach of the shops and lake, and offers many experiences available only to guests. Opened in 1929 with the style of an authentic manor house, the elegant inn feels as storied and local as it does far-flung and English. Spacious, modern, and sophisticated rooms offer upscale amenities (think Frette linens and bathtubs that fill from the ceiling); recently, the inn began in-room delivery of its popular Afternoon Tea service, complete with a tower of tea sandwiches, petit fours, and tartelettes. Patio dining in the English Garden at Deer Path is scenic and doable in winter with heaters. Guests at the hotel can also reserve the inn’s hidden cellar for a new, private, and totally custom cocktail or wine tasting paired with dinner that's led by Deer Path’s fun and expert chief spirits officer, Jorge Centeno.

INDIANA DUNES NATIONAL PARK, IN

Distance from Chicago 49 miles

The dunes overlooking Lake Michigan at Indiana Dunes National Park

Drive just 60 minutes and find yourself surrounded by beauty in the 15,000-acre Indiana Dunes National Park , which packs in an astounding amount of botanical diversity thanks to its variety of lowlands, highlands, prairies, wetlands, forests, and Lake Michigan shoreline. Time your visit with cool winter conditions, when snow cloaks the park in white, and there’s a chance to see spectacular shelf ice formations on the water, not to mention you’ll get a far more secluded experience. Venture out on cross-country skis or snowshoes—the latter of which can be borrowed for free at the park’s Paul H. Douglas Center for Environmental Education. All of the park’s 50 miles of trails are available for winter activities, but opt for a one-mile loop or three-mile route on the Paul H. Douglas Trail, which takes you to the beach through a rolling black savannah, one of the rarest habitats in the country. Often confused with the national park, the two-acre Indiana Dunes State Park , immediately next door, is also open and admission is waived on weekdays in winter.

Nearby Chesterton offers a good location central to both parks, and interesting B&B’s are the way to go. Within walking distance to restaurants and shopping, Riley's Railhouse Bed & Breakfast ( from $140 a night ) is housed in a former New York Central style freight station and has rooms in real rail cars. The family-friendly DunesWalk Inn at the Furness Mansion ( from $125 a night—you can also rent the entire place out on Airbnb ) is another historic option that balances digs in an 1881 mansion with modern comfort, just a few minutes from the beach.

HARBOR COUNTRY, MI

Distance from Chicago 75 miles

A view of Lake Michigan from the Water's Edge house

Didn’t score a Michigan beach house last summer? Winter isn’t hot, but it’s a gorgeous and secluded time to experience the dramatic Lake Michigan coast from the comfort of a luxury beach home, most of which can be had now at low season rates. Take your pick of towns on the state’s south coast like Union Pier, New Buffalo, and little-known Harbert. Sans summer crowds, this is the time to stop at the harborside Stray Dog Bar & Grill . Even better, book an igloo for outdoor dining at small-batch Beer Church Brewing , try alfresco wine tastings at Round Barn Estate , or get takeout from Red Arrow Roadhouse (try the buffalo cauliflower and nachos) and locally made whiskey from the Journeyman Distillery to bring back home. As everyone does, give into the pull of the lovely Lake Michigan coast, where dune walks and sledding at Warren Dunes State Park should be high on your list.

Bluefish Vacation Rentals (from $100 a night ) is your best option for a well-curated assortment of homes throughout Harbor Country, plus the bonus concierge-like guidance of the local husband-and-wife team who run it, Jason and Erika Milovich. In winter, most of their homes can be had at low season rates and don’t require summer’s usual full week stay. The scenery can’t be beat in Harbert at three-bedroom Water’s Edge , a splurge-worthy find tucked into a forested bluff overlooking a private stretch of Lake Michigan shoreline; spend $750 a night in winter verses the nearly double rate of $1,429 a night in summer. Walk the beach and watch glacier-like ice form with the waves, warm up in the hot tub, and light a bonfire under starry winter skies framed by trees. Other notable options include the three-bedroom Harbor Time , new five-bedroom Darby Cottage with its massive showroom-worthy open kitchen, and new four-bedroom Lake Life that puts spectacular lake views right in your lap.

KOHLER, WISCONSIN

Distance from Chicago 149 miles

By Jessica Puckett

By Madison Flager

By Melissa Liebling-Goldberg

By Julia Eskins

One of the Kohler luxury Cabins

On a drive of just over two hours, cruise past Mars Cheese Castle in Kenosha (hit the brakes to load up on Wisconsin gold), and lakefront Milwaukee, on your way to Kohler. Popular in temperate months for its jaw-dropping golf courses, which regularly feature on the PGA Tour, Destination Kohler is a find in winter with fewer visitors, killer spa treatments at its Kohler Waters Spa, and invigorating outdoor adventures at its lesser-known River Wildlife preserve. Like Kohler’s golf courses, the 500-acre wilderness playground showcases the natural beauty of the landscape here. Try hikes and horseback rides through rolling trails, ice skating and curling at Winter Wonderland, guided trap shooting in a forest canyon, and brunch or hot toddies at River Wildlife Lodge, the preserve’s atmospheric log cabin outpost.

Options at the resort include classic hotel rooms at the 241-room American Club ( from $189 ), but four chic and splurge-worthy cabins (f rom $842 a night ) are the way to go, especially if you want privacy and space wrapped in some gorgeous nature. The two-bedroom Lake Cabin ( from $1009 a night )—one of two opened just last summer—positions you on a staggering bluff just above Lake Michigan. The beach is inaccessible from this rugged perch, but you won’t care with endless, ocean-like views from the back porch and firepit, and the sprawling evergreen forest at the front of the house that doubles as a wildlife crossing (watch for deer and wild turkeys). It’s all the more magical with a dusting of snow on the beach grass, a warm fire, and dinners inside your own beautiful kitchen—everything from tenderloin and ricotta gnocchi takeout from the new Taverne on Woodlake to whiskey pairings, curated Wisconsin cheese boards, and gourmet groceries delivered from Woodlake Market .

Distance from Chicago 164 miles

Downtown Galena

With rolling forested landscapes, an historic downtown on the Mississippi River, and the best (one of the only!) ski mountain in Illinois, Galena is as charming as ever in winter. Even the two-hour-and-45-minute drive sets the mood as flat highways turn to one-lane roads that climb gentle hills and weave through farmlands and woods, eventually dropping you into this once-thriving river port town. Stroll the downtown’s Main Street for a superb array of local shops and studios; new options include Galena Book & Paper , the Galena Spoon Company for handcrafted spoons and carving classes, and Scent Workshop , where you can learn French perfuming techniques. There are loads of restaurants and boozy options here, too; go for especially good take-home dining and cocktail kits from French-meets-German Fritz and Frites , Miss Kitty’s Grape Escape , and the drive-thru Galena Brewing Co . Downhill skiers won’t want to miss Chestnut Mountain Resort, just 15 minutes from the downtown, with 19 runs that race to a halt at the bank of the Mississippi River.

It’s a-okay to vape in the new guest-only “potting shed” outside the pretty five-bedroom Aldrich House , Illinois’ only cannabis-friendly bed and breakfast ( from $145 a night ). For something upscale and romantic, it’s hard to do better than the luxury six-suite Jail Hill Inn , set in a former jailhouse at the end of Main Street and serving a three-course breakfast ( from $345 a night ). Families settle in nicely at the stylish, condo-like Ulysses Suites ( from $214 a night ), while south of downtown on 6,800 acres of Galena Territory, Eagle Ridge Resort & Spa offers a robust nordic activities program and everything from simple hotel rooms to full homes ( from $99 a night ).

INDIANAPOLIS, IN

Distance from Chicago 185 miles

The Bottleworks Hotel in Indianapolis' Bottleworks District

Every worthwhile weekend getaway from Chicago isn’t a charming small town or lakeside retreat. For those who want some city culture that isn’t their own, Indy’s Bottlework’s District is calling. Stop in Merrillville for proper road trip junk food—fresh Indiana-made gummy bears—at Alabanese Confectionery Group on the three-hour drive south to Indy. Once there, head to the new 12-acre, mixed-use neighborhood that spans the north side of Mass Ave in downtown Indianapolis and brims with local indie shops in historic industrial buildings. Explore the mix of offerings at Circle City Industrial Complex , a 500,000 square-foot warehouse opened in the old Schwitzer car manufacturing facility, where you should check out newly opened SoChatti dairy-free chocolate tasting room and a class at Indy Fused Glass. Other new places worth a visit are Good Neighbor for fresh duds and the Living Room movie theater. For dinner, head out of the district for romantic outdoor dining in the new fireside greenhouse huts at Public Greens , a modern, community-driven restaurant that shares its profits to feed nearly 2,000 of Indy’s less fortunate youth every week.

Opened in December in what was formerly the world’s largest Coca Cola bottling plant, the 139-room Bottleworks Hotel ( from $249 a night ) is the stylish new anchor for the Bottleworks District. The industrial, art-deco-inspired hotel occupies the top two floors of the historic building, showing off a white terra-cotta exterior and brass-patterned doors. High-style rooms have velvet couches, loft ceilings, and terrazzo-tiled floors. Adjacent to the hotel, find more dining options at Garage Food Hall , Indy’s first food hall opened this month in the factory’s former garages, with nearly two dozen vendors serving everything from lobster rolls and poke to Pakistani-Indian fare and Brazilian steak.

BOYNE, MICHIGAN

Distance from Chicago 346 miles

A look down Boyne Mountain

Make your winter ski trip happen at Boyne Mountain Resort , one of the most exciting ski mountains within a reasonable drive of Chicago—five and a half hours, plus a one-hour time change. Rising up from the northern part of Michigan’s lower peninsula, the mountain offers 500 feet of vertical with 60 downhill trails for a range of skiers and riders, though the biggest perk of a visit here is the abundance of high-quality outdoor adventures that go beyond skiing. Rent a new sno-go ski bike and shred downhill runs, fat-tire bike on forest trails, zipline 50 feet in the air across the mountain, cross country ski or snowshoe on dedicated trails, ice skate or snow tube, and even dine outdoors in one of five igloos serving at Forty Acres Tavern. If you have a little extra time you can also tack on the 40-minute drive north to Boyne Highlands , the mountain’s sister resort, for even more challenging ski terrain plus the new “Enchanted Trail,” an illuminated two-mile trail for nighttime winter walks and snowshoeing. NOTE: Like other ski resorts around the country, both mountains are limiting capacity during the pandemic and booking lift tickets and gear rental in advance is recommended.

Spread out in one of the fully-equipped three- and four-bedroom Mountain Cabins that are part of the resort (f rom $607 per night ). Each is set in the woods with a hot tub on the deck, fully equipped for cooking your own meals, and offers ski-in/ski-out access. Some of the cozy one- and two-bedroom condos at the Village at Disciples Ridge also offer ski-in/ski-out access ( from $488 per night ). Pro tip: the best way to guarantee access to the slopes this season along with your accommodations is to book a “ Ski & Stay Package ,” which bundles lodging and lift together and lets you ski both resorts.

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Learn how to easily plan your dream trip to the Midwest!

15 Best Day Trips From Chicago Worth The Effort

August 13, 2022 by //  by  Midwest Explored 1 Comment

Are you looking for the best day trips from Chicago that are actually worth the effort? Then this list is for you!

Maybe you want a break from the city, or maybe you just want to explore a new city.

Planning your trip to Chicago last minute?

Make sure to book ahead. Hotels and tours often sell out the closer you get to your trip. Here are our top pics for Chicago!

Top Experiences And Tours In Chicago:

• Chicago River Architecture Cruise (Skip the Ticket Office!)
• Willis TowerSkydeck & The Ledge Ticket (Elevator express entry!)
• Navy Pier Centennial Wheel Ticket (Panoramic views of Chicago!)
• Big Bus Hop on Hop Off Sightseeing Tours (24, 48, or 72-hour options available.)

Hop Hotels In Chicago:

• Eurostars Magnificent Mile (In the heart of Chicago!)
• The Peninsula Chicago (Near museums)
• Club Quarter Hotels Wacker (Overlooking the Chicago River!)
• Hotel Blake (Close to Millennium Park.)

No matter your interests you’ll find a great day trip option on this list.

I’ve found some of the most unique, fun, and adventurous day trips to make from Chicago.

There are beautiful state parks, metropolitan cities, unique and charming small towns, and so much more.

So, lets take a look at the 15 Best Day Trips from Chicago Worth The Effort!

Cedarburg, Wisconsin

In just under 2 hours, you can find yourself in the charming small town in Wisconsin called Cedarburg.

Cedarburg is an excellent day trip from Chicago for those looking for small-town charm, but with plenty of activities.

Because Cedarburg is know for its small town atmosphere, you’ll find some really unique shops and resturants.

There is a Candy Kitchen, an Amish Craftsmen Guild, stores full of items made by local artisans, and even a shop where you can search for unique gemstones.

Cedarburg also has a wide variety of unique museums.

There is a local art museum, a local history museum, a woolen mill and textile museum, and even a museum depicting early life in Cedarburg.

No matter your interests, Cedarburg is guaranteed to have something fun for you to do, and you’ll find it was worth the drive.

Rockford, Illinois

If you drive for about an hour and a half West of Chicago, you’ll find yourself in Rockford Illinois.

The best way to describe Rockford is to call it a big-little city. It’s the fourth largest city in Illinois, but still feels welcoming in a small-town sort of way.

Rockford is also bursting with things to do.

Music lovers will enjoy checking out one of the many spots home town band Cheap Trick helped make famous.

If museums are more your thing, don’t worry, Rockford has those too. Stop by the Burpee Museum of Natural History or the Discovery Center Museum.

If none of that sounds interesting, then maybe you’ll like the Anderson Japanese Garden. It is consistently rated as one of the best Japanese Gardens in North America.

There is so much to do that you may want to turn your day trip into a Midwest weekend getaway . With the endless list of activities in Rockford, it absolutely makes it worth the hour and a half drive from Chicago.

Grand Rapids, Michigan

Grand Rapids Michigan is one of the perfect day trips from Chicago for lovers of art, food, and beer.

In fact, Grand Rapids is known as Beer City USA.

For those who want to take full advantage of all Beer City USA has to offer, you’ll want to download the Brewsader App.

The App gives you a full map of all the breweries in Grand Rapids, and after you check in at 8 of them, you’ll earn a fun Brewsader shirt to commemorate your trip.

If beer isn’t your thing, not to worry.

There are still some absolutely amazing and unique restaurants in Grand Rapids you can check out. Or you can stop into one of the cities popular art galleries.

There really are so many cool things to do in Grand Rapids .

Oak Park, Illinois Is One Of The Best Day Trips From Chicago

Oak Park Illinois is the shortest distance you’ll have to travel for a day trip on this list as it’s just under 20 minutes outside of Chicago.

Despite that, many people in Chicago, or even visiting Chicago, don’t think to explore Oak Park.

Admirers of Frank Lloyd Wright, one of America’s most prominent architects will know Oak Park though.

Wright called Oak Park home, and left his mark on many of the cities most popular homes and buildings.

Oak Park was also home to another famous architect, George W. Maher, who also designed many of the cities most prominent homes and buildings.

Ernest Hemingway was also born in Oak Park, and you can visit his childhood home that has now been turned into a Hemingway Museum.

Book Tickets Here: Ernest Hemingway Boyhood Tour

Because of Oak Park’s proximity to Chicago, many gangsters in the early 20th century called the area home, and you can now take a Gangster tour.

Oak Park is a tremendously unique option for a day trip from Chicago and you don’t even have to travel far!

Michigan City, Indiana

Michigan City Indiana is about an hour away from Chicago, and you’ll spend the whole trip driving along Lake Michigan.

So it’s no surprise that Michigan City also has its fair share of lighthouse history.

In Michigan City you’ll be able to explore the Old Lighthouse Museum and even take a tour of the Michigan City Lighthouse and Pier.

Stroll along the beach or maybe head over to the Washington Park Zoo, which is full of more interesting architecture, and of course animals.

Travelers also enjoy touring the Barker Mansion and sipping on local wines at some of the best wineries in Indiana

Monroe, Wisconsin

Monroe Wisconsin is the Swiss Cheese Capital of the USA, and just over 2 hours away from Chicago.

Cheese lovers will delight in the many, many, cheese related activities that abound in Monroe.

Monroe is a cute small town that takes cheese very seriously, and for good reason. The city has thrived for over 100 years because of it’s cheese industry.

You can pair some locally made cheeses with local beers or just explore the numerous cheese shops.

Or watch a movie at the local drive-in theater while munching on cheese curds.

The small town even holds a yearly Cheese Days Festival where you can sample all of the local cheeses while sipping a cold local beer.

Monroe is perfect for your next day trip from Chicago the next time you’ve got a serious craving for all things cheese.

This cool town is one of the best places to visit in Wisconsin.

Kankakee, Illinois

Kankakee Illinois is a cute town in Illinois just over an hour south of Chicago.

It’s full of small town charm but it still has a lot of interesting things to do, making it perfect if you’re looking to escape the city for a day.

One of visitors favorite things to do in Kankakee is taking a tour of the B. Harley Bradley House, a famous house designed by Frank Lloyd Wright.

Kankakee is also amazing for those looking for a little outdoor adventure.

The entire Kankakee County and parts of the city of Kankakee are bursting with outdoor activities.

You can enjoy some of the best hiking in Illinois , along with canoeing, kayaking, and even scuba diving in the Haigh Quarry.

Kankakee is one of the best day trips from Chicago Illinois if you’re looking for fresh air, beautiful views of nature, and plenty of small-town charm.

New Glarus, Wisconsin

America’s Little Switzerland is in New Glarus Wisconsin, just 2 and half hours outside of Chicago.

New Glarus is a small town that loves beer, cheese, and festivals. In the warmer months, they may have 3-4 festivals a month.

Typical New Glarus festivals include Polkafest, The Beer, Bacon, & Cheese Festival, The Heidi Folk Festival, Blues Brews & Food Trucks Festival, Maxwell Street Days, and so many more.

New Glarus is also known for having a selection of brews that you can only buy in Wisconsin, and some of them you can only buy in New Glarus.

If you are a beer connoisseur, you’ll love checking out one of the local beer gardens. And if you decide to stay longer here are some epic Wisconsin Airbnbs to look into.

Foodies will love checking out one of the many restaurants that serves up Swiss and Swiss inspired fare.

New Glarus is a cute romantic getaway in Wisconsin!

Holland, Michigan

Holland Michigan is a little over 2 hours away from Chicago and is one of the best day trips from Chicago that is definitely worth it.

Named after the home country of it’s original settlers, Holland is bursting with Dutch charm.

In the Spring it’s host to the Tulip Time Festival where you will get to see a riot of colorful tulips with a windmill that is straight from Holland.

Even if you can’t make it to the Tulip Time Festival, you’ll love exploring this cozy small town.

There are plenty of unique shops, restaurants, breweries, and unique Dutch gardens.

Holland is also home to one of the coolest lighthouses in Michigan , The Big Red Lighthouse.

Visitors love to view the iconic lighthouse standing proudly on it’s pier, with the bright red façade making a striking contrast against Lake Michigan.

Holland is a small town in Michigan full of charm that is definitely worth the effort to visit, any time of year.

Milwaukee, Wisconsin

If you are looking to explore a city, but you want a break from Chicago, then I suggest driving the hour and half to Wisconsin’s largest city, Milwaukee.

Because Milwaukee is Wisconsin’s biggest city, it is full of unique things to do making it one of the best day trips from Chicago!

And there are so many things to do in Milwaukee!

If you’re on a budget, take a stroll down the streets and admire the many murals on the sides of buildings. Or go window shopping and one of the many boutique stores.

You can also check out a play or musical, go on a boat tour of Milwaukee, or explore one of the amazing restaurants in Milwaukee.

If you’re a sports fan, you may want to check out one of Milwaukee’s home teams. Afterwards, you can talk about the game at one of the cities awesome bars or resturants.

Milwaukee is an amazing city that often gets overlooked, but you won’t regret making the trip out there.

Oglesby, Illinois

In just under two hours you can be in beautiful Oglesby Illinois.

Oglesby is perfect for day trippers looking for a break from the city as it is home to two beautiful State Parks.

If you’re looking for some outdoor adventure and clear air, then you’ll find that this is one day trip that is worth the effort.

At Starved Rock State Park you’ll find trails that lead you along the Illinois River and into steep sandstone canyons.

It is Illinois’ most popular State Park and for good reason. It’s accessible for all skill levels and you get to experience some beautiful views.

The other state park near Oglesby is Matthiessen State Park. The entrance for this park is just a few miles South of Starved Rock State Park.

Matthiessen State Park has similar views, but it is often far less crowded.

It is a great choice to experience fall in Illinois.

You’ll still be able to hike beautiful trails, see gorgeous Illinois waterfalls, and enjoy nature, but you’ll be far less crowded.

If you have plenty of time on one of your day trips from Chicago Illinois, you should definitely check out both state parks.

Lake Geneva, Wisconsin

Lake Geneva is a Wisconsin town about an hour and a half outside of Chicago.

It has a history of being the go-to spot for Chicago’s wealthy families during the summer.

Lake Geneva is a beautiful small town that thrives because of the large Lake Geneva, and it’s a budget-friendly day trip option.

There are so many things to do in Lake Geneva all year long that include lake activities.

But you’ll also find a charming town full of unique boutiques, restaurants, and even outdoor activities like hiking and snow sports in the winter.

In early February the town holds a Winter Fest which features the only snow sculpting championship in the United States.

Visitors get to experience massive snow sculptures, food from local restaurants, and so much more – and it’s free to attend!

In the summer, enjoy boating, swimming, and kayaking on Lake Geneva before having a meal at one of the amazing local restaurants in Lake Geneva .

No matter what time of year you visit, Lake Geneva is a Chicago day trip that is worth the effort.

Highwood, Illinois

Highwood Illinois is another small town that goes big when it comes to festivals.

Just 35 minutes North of Chicago, this charming small town is the perfect day trip from Chicago Illinois for festival lovers

There’s almost a festival every month, and they all have different themes.

For foodies, there is a Taco Festival, a Bloody Mary Festival, and a Garlic Festival.

There are also smaller music festivals, fun runs, and a Pride Festival.

One of Highwood’s most iconic festivals though is probably The Great Highwood Pumpkin Festival every October.

It is one of the coolest things to do in Illinois .

The Festival benefits the Make-A-Wish Foundation and attendees get to check out rows and rows of carved pumpkins.

Attendess of Pumpkin Fest can even bring their own pumpkins and carve them before adding them to the walls of carved pumpkins.

Highwood is a truly unique town, full of really cool festivals that are sure to make the trip out there worth the effort, no matter what time of year you go.

Indiana Dunes National Park, Indiana Is One Of The Best Day Trips From Chicago

Just under an hour outside of Chicago, the Indiana Dunes National Park is one of the coolest national parks in the Midwest.

The Indiana Dunes National Park is on 15 miles of beach on Lake Michigan’s South shore.

It is a nature lover’s dream with over 15,000 acres of preserved land full of unique hiking trails, wetlands, prairies, woodlands, and of course beaches.

From Memorial Day to Labor Day, there is a $6 entrance fee to enter the park. During the ‘off season’ though, it’s free to enter.

The Indiana Dunes is full of fun things to do, and you could spend days exploring the park making it a fun weekend getaway in Indiana!

It’s a beautiful spot, and it is definitely one of the day trips from Chicago that is worth the effort.

Madison, Wisconsin Is One Of The Cool Day Trips From Chicago

In just over two hours you can find yourself in Madison Wisconsin.

If you’re looking for a fun Chicago day trip in the summer, Madison is perfect for you.

With five lakes, spanning over 15,000 acres, in summertime there are so many things to do in Madison.

There are water sports, festivals, water front dining, and so much more.

But Madison isn’t just a fun place to visit in the summer.

You’re sure to find fun no matter what time of year you go.

There are dinner theaters, breweries, delicious restaurants, and unique boutiques. Put treating yourself at some of the restaurants in Madison on your list!

You’ll find that Madison Wisconsin is one of the most entertaining day trips from Chicago that is definitely worth the effort.

Packing List For Daytrips From Chicago

Here are some  tips on how to pack lightly

A  concealed travel pouch  may be one of the most important items you bring along when on one of your Chicago day trips! 

It is  always   important  to protect your personal information. Identity thieves are everywhere.

This  unisex RFID blocking concealed travel pouch is  lightweight and comes in several colors. It has lots of organization to give you peace of mind.

You can place it under your clothes next to your body to carry your ID safely.

If you have a pouch already that does not come with the RFID protection, as I do, these  RFID  sleeves  are the perfect solution.

This configuration comes with enough credit card sleeves that the entire family would be protected. They are slim too, so they will easily fit into your pouch or wallet. 

If you are planning on taking a lot of pictures with your phone you will definitely want to consider an  external charging battery .

This  Anker high-speed phone charging battery  is  the exact one  I carry with me on all of my trips.

It can be used on a variety of phones, not just an iPhone like I have. And wow is it fast!

I like that it holds its charging capabilities for several uses so I do not have to worry about it while out and about, and if I forget to recharge it at night, it will still be good to go the next day.

My daughter gifted me with this  FugeTek selfie stick and tripod   setup for my birthday. I absolutely love it!

It is made of lightweight aluminum and so easy to use.

It has Bluetooth connectivity and is a breeze to use for taking selfies with all those nature shots while on your Chicago day trips..

Hydration is so important when hiking. You want to remain hydrated throughout your hikes to support your immune system which in turn will be stronger to fight off any germs you will encounter during your travels. 

You will want to bring your own  refillable water bottle  with you. 

I never leave home on a trip without my  Bobble filtration bottle .  The 18.5-ounce size is perfect for hiking and it fits nicely in the pocket of a backpack.

When filled with water, it is not too heavy to carry. And the charcoal filter ensures fresh clean water whenever you fill the Bobble.

Perhaps you are traveling a long distance to Chicago Illinois and packing space is a premium in your suitcase, or in your car.

Then this  set of collapsible silicone foldable water bottles  would work well for you. Would not take up much space at all. 

You will want a  backpack or daypack  with you to store snacks, your water bottle, phone, extra clothes, etc.. when on one of your day trips from Chicago Illinois. No matter the time of day or evening.

This   foldable water-resistant backpack   would be great

It is very affordable and is available in many color options for you to choose from. The fact that it folds down into a zippered pouch will make it easy to pack!

I hope you enjoyed this list of the 15 Best Day Trips From Chicago Worth the Effort! There are so many great big cities and little towns outside of Chicago just waiting to be explored.

If you are spending a weekend in Chicago , one of these trips from Chicago would def be fun!

If you take a trip to one of these awesome places, I’d love to hear about it in the comments!

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• Destinations

20 Best Weekend Getaways from Chicago

Last Updated By VI on June 17, 2024

Grand Geneva Resort - 1 hour 30 minutes from Chicago

Grand traverse resort - 5 hours from chicago, the abbey resort - 1 hour 40 minutes.

• Complete List & Map

Midwest Vacation Ideas: From Minneapolis , Ohio , MN , Iowa , From Detroit , Michigan --->

100 Grand Traverse Resort Village Blvd, Acme, MI 49610

269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125

Egg Harbor - The Newport Resort - 4 hours 30 minutes

7888 Church St, Egg Harbor , WI 54209

The Knickerbocker on the Lake - 1 hour 30 minute

Browse Best Beaches Near Milwaukee

The Green Tree Inn - 4 hours 25 min

15 Mill St., Elsah IL, 618-374-2821

The American Club, Kohler - 2 hours 30 minutes

East Coast Vacations: North Carolina Vacations , SC Getaways , From Atlanta , Connecticut , Rhode Island

Washington House Inn - 2 hours

More to Explore: Getaways from NYC , Maine Getaways , New Hampshire , From Boston , East Coast

Sweethaven Resort - 1 hour 20 minutes from Chicago

9517 Union Pier Rd, Union Pier, MI 49129

Hawk Valley Retreat & Cottages - 2 hours and 45 minutes

2752 W. Cording Rd., Galena IL, 888-777-6016

Mansion Hill Inn for Couples - 2 hours 30 minutes

424 N Pinckney St, Madison, WI 53703, 608-255-0172

Vrooman Mansion - 2 hours

701 East Taylor St., Bloomington IL, 309-828-8816

Oakwood Resort, Syracuse, IN

Oakwood Resort, 702 E. Lake View Road, Syracuse, IN 46567, 574-457-7100

Farmers Guest House - 2 hours 45 minutes

344 Spring St., Galena IL, 815-777-3456

Foodies can visit Crane Orchards and Cider Mill, Fenn Valley Vineyards and Winery. There are also some historic attractions you can visit including the Felt Mansion, the Old Schoolhouse History Center and the Saugatuck/Douglas History Museum. --->

Elkhart Lake

Elkhart Lake in Wisconsin is an ideal getaway destination for all nature lovers and water sport enthusiasts, boasting crystal clear lake water and an abundance of activities suitable for all ages. You can choose from a variety of accommodation options which vary from up-market resorts and vacation rentals to getting back to nature at the Broughton March Park campground, where you can pitch a tent or park your RV.

Water sports are the most popular summer activity and if you do not have your own equipment you can hire everything you need to enjoy the lake from Osthoff Resort Water Recreation Rentals or at Victorian Village Resort. You can try your hand at canoeing, kayaking, water skiing or simply enjoying the beautiful lake-side scenery on a pontoon cruise. Ecology Outfitters Guided Silent Water Tours provide equipment and lessons for beginners. The lake is famous for great fishing - Inland Waters Fishing Guide Service or Jay's Guide Service will lead the way.

Back on dry land you can explore the shores by horseback with Camp Anokjig Trailrides, do a Backroads Bike Tour (or simply rent a cycle at the Osthoff Resort) or go hiking along an abundance of trails. Speed enthusiasts can watch motorsports or enjoy various adventure programs at Road America. In winter the emphasis changes to cross-country skiing, snowshoeing and snowmobiling.

Door County

Door County in Wisconsin is situated on a peninsula which juts out into Lake Michigan and boasts over 300 miles of shoreline with beaches, bays and inlets waiting to be explored. Sun worshippers have an astounding 53 public beaches to choose from and if you would like to go boating there are 12 marinas where you can launch your own craft or charter one. Conclusion

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• Jun 21, 2022

26 Best Weekend Getaways from Chicago (within a 4-hour flight)

Updated: Jan 21

Deep dish pizza, sports, great bars, and awesome summers. Chicago has it all (except the ocean and nice winters). If you're looking to take a break from the norm in Chicago or escape the brutal winter, read on for some ideas about where to go for a quick weekend.

With a vast array of short domestic destinations, there are also many international destinations within reach. Here are some weekend getaway ideas for locals in the Chicago area within a non-stop 4-hour flight. More importantly, these trips are all possible without having to request PTO (for you M-F 9-5'ers), it just depends on what you want to do at your destination.

Miami, Florida (MIA, FLL) - Just Over a 3 Hour Flight

Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.

When to go?

Any time of the year, but best is October - February for perfect weather. Avoid the spring break crowd in late Feb/early March the best you can.

Who can fly you there?

AA from ORD - See flight deals

Spirit Airways from ORD - See flight deals

Southwest from ORD, MDW - See flight deals

United from ORD - See flight deals

How much will it cost to get there?

Airfare: $100+

Where can you stay?

See hotels in Miami

See hotels in Miami Beach

Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.

Orlando, Florida (MCO) - Just Under a 3 Hour Flight

Disney & Universal Studios. Bring bug spray and an umbrella if you go during the summer.

Frontier from ORD - See flight deals

Airfare: $150+

See hotels in Orlando

New York, New York (JFK, LGA, EWR, ISP, HPN) - 2 Hour Flight

It might not be the same city it was a few years ago, but it'll always make for a great weekend getaway.

Summer for the best weather, but peak rates for solid hotels.

Winter for Christmas festivities!

Delta from ORD - See flight deals

JetBlue from ORD - See flight deals

Airfare: $50+

See hotels in New York

Toronto, Ontario (YYZ, YTZ) - Just Under a 2 Hour Flight

Food, people, cleanliness, Hockey Hall of Fame.

Air Canada from ORD - See flight deals

WestJet from ORD - See flight deals

Swoop from ORD - See flight deals

Porter Airlines from MDW - See flight deals

See hotels in Toronto

Philadelphia, Pennsylvania (PHL) - 2 Hour Flight

History, sports, cheesesteaks

Summer and Fall

United Airlines from ORD - See flight deals

Airfare: $200+

See hotels in Philadelphia

Washington, DC (IAD, DCA, BWI) - Just Under a 2 Hour Flight

Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.

Year-round (spring season for cherry blossoms)

See hotels in Washington DC

For avid runners, pack your running shoes and go for daily runs around the White House, Washington Monument, Lincoln and Jefferson memorials.

Discover the ease of weekend escapes from Chicago with ING Chauffeured Transportation , your trusted choice for dependable ground transportation.

Kansas City, Missouri (MCI) - 1.5 Hour Flight

BBQ! BBQ! BBQ!

Southwest from MDW - See flight deals

See hotels in Kansas City

Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.

Nashville, Tennessee (BNA) - 1.5 Hour Flight

Music (not just country), endless bars, brewpubs, hot chicken.

Spring, Summer and Fall

See hotels in Nashville

Stay in the Gulch or near printer's alley.

New Orleans, Louisiana (MSY) - 2.5 Hour Flight

Jazz music, other music, culture, architecture, partying, passionate football fans.

Spring, Summer, Fall

See hotels in New Orleans

Check out Bourbon Street for a little bit, but don't get sucked in. It's absolutely disgusting. Chartres Street is better for those looking to maintain their cleanliness.

Atlanta, Georgia (ATL) - 2 Hour Flight

Brew pubs, art, nightlife, Mexican food.

Delta from ORD, MDW - See flight deals

Frontier from MDW - See flight deals

See hotels in Atlanta

Walk some of the BeltLine and stop at stores, bars, and restaurants.

Raleigh, North Carolina (RDU) - 2 Hour Flight

Outdoors activities, restaurants, college sports, booming tech sector.

See hotels in Raleigh

Glacier National Park, Montana (FCA) - Just Over a 4 Hour Flight

Glacier National Park and the great town of Whitefish. I recommend camping, but you can get a boutique hotel in Whitefish or Kalispell.

SkyWest from ORD - See flight deals

Airfare: $350+

See hotels in Whitefish

Austin, Texas (AUS) - Just Under a 3 Hour Flight

Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!

See hotels in Austin

Cancun, Mexico (CUN) - Just Under a 4 Hour Flight

Your money goes a long way: all-inclusive hotels, nightlife, and activities.

December to April for the best weather.

Avoid March Spring Break travel if you want to be at peace.

See hotels in Cancun

Jackson Hole, Wyoming (JAC) - Just Over a 3 Hour Flight

Bears, Yellowstone National Park, Grand Teton National Park, skiing, golfing, horseback riding, rustic boutique hotels, cool people.

Airfare: $400+

See hotels in Jackson Hole

Make sure you have time to visit both Yellowstone and Grand Teton. Jenny Lake is a must.

Aspen, Colorado (ASE) - Just Over a 3 Hour Flight

Skiing, great scenery, luxury.

See hotels in Aspen

It's very expensive, but worth a shot. 3.5 hour drive if you wish to save some $$.

Boston, Massachusetts (BOS) - Just Over a 2 Hour Flight

History and cool summertime temps!

Intercontinental Boston

See hotels in Boston

Las Vegas, Nevada (LAS) - 4 Hour Flight

Gambling, Hoover Dam, Death Valley National Park, Valley of Fire State Park, Partying, more Gambling.

See hotels in Las Vegas

Denver, Colorado (DEN) - Just Under a 3 Hour Flight

Mountains, beer, National Parks, hiking, clean city, nice people.

Year-round. Ski in the winter. Hike in the summer.

Airfare: $250+

See hotels in Denver

Salt Lake City, Utah (SLC) - 3.5 Hour Flight

Skiing, Salt Flats, Mormons, and great National Parks within a moderate drive.

See hotels in Salt Lake City

Nassau, Bahamas (NAS) - 3.5 Hour Flight

Turquoise waters, friendly people, and close proximity to Florida make the Bahamas a popular destination.

December to July to avoid hurricanes and tropical storms.

May to August to avoid crowds and surcharges.

November to February to avoid the summer heat.

Airfare: $500+

See hotels in Nassau

Rent a car ! Be prepared to drive on the left side of the road.

Charleston, South Carolina (CHS) - 2 Hour Flight

History, culture, family-friendly attractions, and watersports.

See hotels in Charleston

Asheville, North Carolina (AVL) - Just Under a 2 Hour Flight

Art, craft beer, and the Smoky Mountains. I'd recommend driving instead of flying, but it's your call!

Allegiant from MDW - See flight deals

See hotels in Asheville

Montreal, Quebec (YUL) - 2 Hour Flight

More restaurants per capita than any other North American city.

See hotels in Montreal

Bozeman, Montana (BZN) - 3.5 Hour Flight

Skiing, Hiking, Waterfalls, Museums, Rivers, and of course Yellowstone National Park (1.5-hour drive). It's possible to do the park in one day from Bozeman, but if going to the park is your goal, I'd recommend staying closer to the park in West Yellowstone.

See hotels in Bozeman

See hotels in West Yellowstone

Rapid City, South Dakota (RAP) - 2.5 Hour Flight

You'll find nature and parks galore in one of the most unique areas of the country. Mt. Rushmore National Monument, Custer State Park, Black Hills National Forest -- all within a 35 min drive from Rapid City, in the same direction. Do all 3 in one day and be sure to visit Sylvan Lake in Custer. Just incredible. Badlands National Park is 1 hour away and that's doable in a separate day. Devils Tower National Monument is just under 2 hours in the opposite direction across the Wyoming border.

See hotels in Rapid City

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Your Family Will Love These 30 Road Trips Near Chicago

• Updated: 04/03/2024

Chicago and US Midwest families, we feel you. Airplane tickets are pricier than ever. Though, your need for a getaway has never been greater. 

You want to get out of town with minimal effort and do not want to spend a small fortune to do it. 

To help, I share my favorite short to medium-distance driving destinations and those recommended by regional experts—other travel bloggers and planners passionate about places in the Midwest. 

Together, we came up with this list of the 30 best road trip destinations for the summer and the fall, from big cities to small charming towns to blow-you-away natural wonders, all within a five-hour drive of Chicago.

Table Of Contents

Check out our destination recommendations by state below. 

• Michigan & Ontario

Or view all 30+ places we recommend going in the map below.

How to use this map:  In the map header, click the square tab to the left of my logo or click the enlarge frame to the right to view detail. You can save the map to “Your Places” on Google Maps by clicking the star next to the map name. Or you can share it by clicking the share icon.

Wisconsin: Top Road Trips Within 5 Hours of Chicago

Welcome to Wisconsin, or the “Dairyland State,” loved by visitors for its rich dairy heritage, delicious cheeses, and beautiful landscapes, including miles upon miles of lakeshore coastline.

Check out these six Wisconsin destinations shared in more detail below.

• Madison, WI
• Milwaukee, WI
• Sheboygan, WI
• Door County, WI
• Wisconsin Dells, WI
• Lake Geneva, WI

Also, consider adding Green Bay (a 4-hour drive) and the lake-perfect Northwoods towns of Manitowish Waters and Boulder Junction (a 5.5-hour drive) to your driving trip wishlists.

Madison, Wisconsin

Approximate drive time from Chicago: 2.5 to 3 hours

Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com

At just two and a half hours from Chicago, Madison is the perfect destination for a quick day trip or a weekend away . This sustainability-focused college town offers families tons of outdoor activities, diverse dining, and art and culture.

If you’re a family that loves the outdoors, visiting Madison during the summer is best. This is the prime time to enjoy the city’s prized lake life (five lakes surround it) and over 200 miles of paved bike trails. Madisonians love to bike (even in the winter), which is one of the best ways to see the city.

Another great activity to see Madison’s unique and eco-friendly side is to explore the independent boutiques that line Willy Street. You’ll find plenty of vintage shops, locally created art, zero-waste products, and clothing that’s been ethically produced and sourced.

While you’re in the area, don’t miss an iconic Madison treat, Nutkrack — this sweet and salty snack was actually created by accident! And, around the corner from Nutkrack is Madison’s oldest vegetarian restaurant , Green Owl Café — don’t miss their loaded vegan cheese fries.

When deciding where to stay in the city, the best place is downtown. This will put you within easy walking distance of many shops, restaurants, and events.

The Hyatt Madison/Downtown offers spacious rooms and suites, perfect for families, along with continental breakfast, and has multiple sustainability initiatives to reduce its and its guest’s carbon footprint. Or search for more Madison lodging options here .

Sign up for my monthly Discovery Newsletter & get a free Trip Budget Calculator !

Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of WavesandCobblestones.com

Milwaukee, Wisconsin , is the perfect city to visit on a family road trip from Chicago. Milwaukee is an easy 1.5-hour drive from Chicago, located to the north along the banks of Lake Michigan.

There are plenty of great things to do in Milwaukee to keep your family entertained! Rent kayaks and paddle along the Milwaukee Riverfront for some fresh air and exercise. Or show some team spirit and take the family to a ball game and watch the Brewers play baseball at the American Family Field or the Bucks on the basketball court at the Fiserv Forum.

There are many fun museums to visit in Milwaukee with your family, such as the Milwaukee Art Museum , a top-notch fine arts museum, where admission is free for children 12 years and younger. Or Discovery World , Milwaukee’s science museum, and Reiman Aquarium. Or the National Bobblehead Hall of Fame and Museum—a one-of-a-kind museum with over 10,000 bobbleheads from across the globe!

Stay at the Plaza Hotel , centrally located in Milwaukee’s historic Lower East Side, with suites that include a pull-out sofa and accommodate up to four people. The Plaza rooms have full kitchens, and with a large grocery store just a block away, you can save money on meals and snacks during your stay.

Or search for more Milwaukee lodging options here .

Sheboygan, Wisconsin

Approximate drive time from Chicago: 2.5 hours

Recommended by: Theresa Goodrich of TheLocalTourist.com

Sheboygan, Wisconsin, is a surprising destination only two and a half hours away from Chicago and a great road trip for families because of the variety of things to do. Begin your visit at the Visit Sheboygan Visitors Center and see Science on a Sphere , a suspended globe that acts as a projector screen displaying programs provided by the National Oceanic and Atmospheric Administration. You can also get tips for places to visit and pick up brochures and souvenirs.

One of the best things to do in Sheboygan for families is Bookworm Gardens. This whimsical garden is a haven for book lovers and children alike, where literature comes to life through vibrant displays and interactive exhibits. Another must-stop for families is the Above and Beyond Children’s Museum . You can’t miss it—there is a ship’s hull sticking out of the building! While downtown, stroll 8th Street for delicious pizza at Il Ritrovo , and don’t miss the Victorian Chocolate Shoppe . Since Sheboygan is on the shores of Lake Michigan, it is also a great summer vacation spot, with sandy beaches and lakefront parks .

Make Blue Harbor Resort your base camp. With its own waterpark, an arcade, mini-golf, a beach, and outdoor games—the kids will love staying at this resort. Or search for more Sheboygan lodging options here . 

Door County, Wisconsin

Approximate drive time from Chicago: 4 to 5 hours

Recommended by: Janice Moskoff of GatherandGoTravel.com

This Wisconsin peninsula just north of Green Bay, surrounded by Lake Michigan, boasts beautiful beaches, scenic hiking trails, and family-friendly activities that will keep everyone pleased for days. 

We visited Door County in the fall , and it was gorgeous. The leaves had not quite fully changed, though we took full advantage of the pretty outdoors to bike and hike at several of the peninsula’s five state parks . 

We even visited Cave Point County Park , one of the Door’s nearly 20 county parks, and were treated to an easy-to-access spectacular scene of Lake Michigan waves crashing against a stunning rocky coastline on a windy day. The beauty of this experience blew us away. Expect the Door to do the same to you.

In the summer, the Door truly shines. Families flock here for the beaches, events, and the abundance of outdoor activities. 

With over 300 miles of shoreline , you can swim, kayak, and fish in the crystal-clear waters of Lake Michigan, especially gorgeous on a sunny day.  Plus, the towns dotting the peninsula are charming, full of shops, galleries, and many restaurants.

Visit or stay on the west or bayside of the peninsula, where you can catch sunsets in towns like Fish Creek or Sister Bay . Or opt for the eastside—where we stayed—and catch the sunrises in or around Bailey’s Harbor . Top family-friendly resorts include Newport Resort , Ephraim Shores Resort , and Scandinavian Lodge . Though, know that the Door books early. So, if you plan your trip last minute, grab the best lodging you can get from Sturgeon Bay or further north and use it as a base to drive around and explore the Door. 

Search all family-friendly Door County lodging options on VRBO or Booking.com .

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com

The Wisconsin Dells is the ideal road trip destination from Chicago as it is known as the Waterpark Capital of the World . The driving distance from Chicago to Wisconsin Dells is just under three hours, making it the perfect length for a weekend getaway . Kids love to splash and play in the water, so why not visit multiple waterparks in one road trip?

The Wisconsin Dells is home to the first-ever indoor waterpark and currently has the largest concentration of waterparks in the world. No matter if you are visiting in the summer or the winter, you will find an amazing waterpark for your family to visit and enjoy, as the area is home to 12 different indoor water parks and over 20 water parks in total.

The best place to stay in Wisconsin Dells is one of the Waterpark Hotels . Our favorite waterpark hotel is Great Wolf Lodge as not only does it have a fantastic waterpark with a 6000 ft outdoor pool, 1000 gallon tipping bucket, a wave pool with three-foot-tall waves, a toddler pool, and a variety of slides for kids of all ages.

The Great Wolf Lodge has unique themed rooms and fun activities, including magi-quest, live shows, and an arcade, making it a kid paradise!

Lake Geneva, Wisconsin

Approximate drive time from Chicago: 2 hours

Recommended by: Diana of TravelsinPoland.com

With an approximate driving time of 2 hours, Lake Geneva is a short drive from Chicago and one of the best cities to visit in Wisconsin. The small-town atmosphere combined with a variety of activities make it a perfect choice for families with children of all ages.

Families can enjoy a day on the water, renting boats, kayaks, or paddle boards, or opt for a scenic boat tour around the lake. Or walk along a portion of the Lake Geneva Shore Path , a 21-mile trail that offers stunning views of grand estates and natural beauty. Spending time on the lake is the best way to experience the area, particularly during warmer months. Shopping in downtown Lake Geneva can keep families occupied for hours. The shops along the main roads have unique items such as art and handcrafted goods. There are also mom-and-pop cafes, ice cream, and candy shops in town.

For accommodation, The Abbey Resort , located in the heart of town, offers a great choice. It is a full-service family-friendly resort offering spacious rooms, indoor and outdoor pools, a game room for the kids, and a full-service spa for the adults. Or search for more Lake Geneva lodging options here .

Michigan & Ontario: Top Road Trips Within 5 Hours of Chicago

Experience the best of the Mitten State , a northern gem and a truly ideal destination for vacationing families. The Michigan coastlines—particularly to the west, with sandy beaches, spectacular sunsets, and towering dunes —will wow you with their beauty. Plus, the vibrant cities and small towns in Michigan will offer enough activities and culinary delights to keep you busy and satisfied for days.

Check out these four Michigan & Ontario destinations shared in more detail below.

• Saugatuck, MI
• Ann Arbor, MI
• Detroit, MI, into Ontario, Canada (a loop driving trip)
• Traverse City, MI (with a day trip to Sleeping Bear Dunes National Lakeshore)

To expand your options—consider adding these Michigan Southwest coastal towns to your road-trip-and-relax lists, like New Buffalo, St. Joseph/Benton Harbor, South Haven, Holland, and Grand Haven. Or spend time exploring more urban centers like Detroit or Grand Rapids .

Saugatuck, Michigan

Approximate drive time from Chicago: 3 hours

We love Saugatuck. We have visited for weekend trips several times in the fall and keep returning for more.  What draws us? The unbelievably beautiful beaches and dunes, the quaint downtown area filled with art galleries and boutiques, and the concentration of seriously elevated cuisine.

Our favorite beaches are Oval Beach , which consistently ranks as one of the top beaches in the country, and offers soft sand, clear water, and stunning views of Lake Michigan.  Additionally, we love the nearby and dog-friendly Saugatuck Dunes State Park , which is perfect for hiking and exploring, with over 1,000 acres of dunes, forests, and beaches.

When not visiting the beaches or getting ice cream, or shopping the galleries on Butler Street, Saugatuck’s main thoroughfare, we spend our time apple picking (in the fall), boating on the Kalamazoo River, or dining at one of the truly fantastic eateries in and around town. I share more things we love to do in Fall Trip: 10 Wonderful Family Things to Do in Saugatuck, MI “

Visiting families also love going on Saugatuck Dune Rides . This thrilling ride takes you on a tour of the dunes, with steep climbs and drops, which the kids will love. And bonus! The knowledgeable guides will share the history and ecology of the area, making it both fun and educational. 

For meals, you cannot go wrong nearly anywhere you choose to eat, but our favorites include The Southerner , where the biscuits alone are worth repeat visits, Pennyroyal Cafe & Provisions , and a short 15-minute drive to enjoy drinks and snacks at Virtue Cider .

Booking a stay in Saugatuck can be surprisingly pricey, so I share helpful information on where you can stay in the surrounding areas for less in “ Saugatuck, MI: 8 Amazing Areas to Search for Lodging .” Then, and especially because many local inns do not allow children as guests, I detail my top choices for family lodging in “ Roundup of the Best Family-Friendly Places to Stay in Saugatuck .”

Ann Arbor, Michigan

Approximate drive time from Chicago: 4 hours

Whether you’re a University of Michigan sports enthusiast or just looking for a hip town surrounded by gorgeous natural beauty, Ann Arbor is the ideal Michigan town to visit!  From Chicago, the trip via car or train (Amtrak offers service from Chicago’s Union Station to Ann Arbor) is just under four hours , making it a perfect road trip for a few days away!

Ann Arbor is well known for its thriving arts and culture scene . Year-round, it hosts a variety of art, music, and film festivals, including one of the largest outdoor art fairs in the nation, The Ann Arbor Art Fair . The Art Fair takes over Ann Arbor every July and spans 30 city blocks with over 1,000 artists! You’ll also find food and music throughout the fair.

For families who enjoy outdoor activities, you’re in luck! Ann Arbor is surrounded by natural beauty, with parks, nature reserves, and the Huron River flowing through it. Head to the Argo Livery during the summer and rent a canoe, kayak, or stand-up paddle board. You can go out on your own, or Argo offers multiple group river trips that range in time and distance from just under 4 miles and 1.5 hours to almost 6 miles and 2.5 hours.

When it comes to dining, you’re in for a treat — the city is well-known for its eclectic mix of cafes and restaurants. From the famous and funky sandwiches at Zingerman’s Delicatessen to the veggie eats at Ann Arbor’s best vegan restaurant, Detroit Street Filling Station.

When choosing a place to stay, it’s best to stay right in the heart of the city (especially if it’s your first visit). Two terrific family options include the Residence Inn by Marriott Ann Arbor Downtown and The Graduate Ann Arbor . Or search for more Ann Arbor lodging options here .

Detroit to Southwestern Ontario Loop Trip (a 5 Day, 4 Night Itinerary)

Approximate drive time from Chicago to Detroit: 4.5 hours

Recommended by: Erie Conners of EverywhereOntario.com

For a unique road trip that takes you into another country, consider making the trip from Chicago to Southwestern Ontario , Canada.  This southernmost region of Canada is filled with quaint small towns, sandy beaches , an abundance of fruit farms and wineries , and incredible historic sites that tell important stories from the Underground Railroad that delivered many slaves to freedom in the 1800s. 

From Chicago, you’ll drive 4 hours to the Detroit-Windsor border. In Detroit, you’ll cross the Ambassador Bridge or take the Detroit-Windsor Tunnel to get into Canada. 

Depending on how long you’ll be staying in Canada, here are the sites I recommend according to a path that takes you from the Detroit-Windsor border to the Sarnia-Port Huron border , where you’ll loop back to Chicago:

• Optional overnight at Caesar’s Windsor Hotel , or search for other Windsor lodging .
• Or, Pelee Island : Take the ferry to Canada’s southernmost landmass, Pelee Island. Visit Pelee Island Winery and bike around the island before taking the ferry home. Overnight in Leamington at a beautiful B&B , or other lodging . 
• Grand Bend Beach : Visit one of Ontario’s top beaches in the summer months. Lounge on the beach, participate in water sports, or walk along the Grand Bend Strip for boutique shopping.
• Sarnia: Walk along the waterfront to see Port Huron from the Canadian side. Overnight at The Insignia Hotel , in Sarnia . Or stay search for other nearby lodging .
• Cross the Bluewater Bridge back to Port Huron and drive 5 hours back to Chicago.

Traverse City, Michigan

Approximate drive time from Chicago: 5 to 5.5 hours

We visited vibrant Traverse City, MI , picturesquely nestled at the southern u-shaped end of Grand Traverse Bay , for five days in the heart of summer with our family dog and loved every minute of our trip. 

In addition to enjoying the lakeshore views that front the length of the town and strolling the shops and restaurants of bustling Front Street, our favorite activities were biking along the wooded TART trails—especially the Leelanau Trail, and hiking. 

We walked the paths in Grand Traverse Commons Natural Area , located behind the outdoor shopping plaza, making our way to the Hippie Tree, a massive old willow tree at the center of the trail network. Painted in bright colors by locals representing living artwork, the tree is rumored to have a haunted history that we only learned about after our visit. 

On another day, we drove out to the Old Mission Point Peninsula to spend the day enjoying the sweeping lake views from the lighthouse, hiking the trails in the adjacent Old Mision Point Park , stopping to buy fresh farmstand cherries, picking blueberries with the kids, and to enjoy a late al fresco lakeside lunch at the Jolly Pumpkin Restaurant & Brewery .

Another highlight was taking a day to visit the Sleeping Dunes National Lakeshore (a 40-minute drive), where we climbed dunes, hiked the Empire Bluff Trail , one of many in the area , and relaxed and picnicked on dog-friendly Esch beach. 

In addition to the outdoor activities, which could also include boat trips on Lake Michigan or kayaking on local lakes or rivers, your family will love the varied collection of breweries and wineries with outdoor dining areas ideal for families. When visiting, you can stay at a centrally located and family-friendly hotel, like the Bayshore Resort . Or search for a rental in the area. Find more available Traverse City hotels and lodging here . 

Indiana: Top Road Trips Within 5-Hours of Chicago

Hang out in the Hoosier State in one of these two top destinations:

• Indiana Dunes National Park, IN
• Indianapolis, IN

Additionally, consider staying in French Lick, IN, at the French Lick Resort  (a 5-hour drive), located in the hills of Indiana’s Hoosier National Forest. It is a classic family-friendly Americana resort offering loads of activities including, golf, biking, hiking, spa treatments, and supervised drop-off kid activities.

Indiana Dunes National Park, Indiana

Approximate drive time from Chicago: 45 minutes

Recommended by: Caitlin Dismore of TwinFamilyTravels.com

If you are in the Chicago area and looking for a family-friendly trip nearby, definitely consider visiting Indiana Dunes National Park and the surrounding area. Just 45 minutes outside of the city, the park offers a beautiful setting with plenty of beach access points and hiking trails.

In addition to the fabulous activities within the park, the surrounding towns offer a variety of attractions, shopping, and dining to keep the whole family entertained. West Beach is the perfect place for a family outing. It’s the largest beach in Indiana Dunes National Park and is great for swimming, sunbathing, or just relaxing. The Lake Michigan water is clean and clear, and there’s plenty of sand for kids to play with.

Hiking is another popular activity while in the park. Explore Indiana Dune’s biodiversity by hiking along the boardwalks, past historic homes, and even through marsh areas. If you are up for it, complete the 3 Dune Challenge at the nearby Indiana Dunes State Park .

If you are traveling with young children, consider staying at the Country Inn & Suites By Carlson Portage . The hotel has both a standard indoor pool and a shallow pool specifically designed for children, complete with a frog slide. Or search for other lodging options in the nearby Portage, Indiana area.

Indianapolis, Indiana

Approximate drive time from Chicago: 3 to 3.5 hours

This lively Midwestern city offers a wide range of activities and attractions ideal for families. From world-class museums to racetracks , expect a visit to Indy will be a memory-making trip your kids will love.

Top spots include the Indianapolis Children’s Museum , which has 472,900 square feet and five halls of exhibit space, making it the largest children’s museum in the world!  While there, kids can explore science, history, and art exhibits. Or they can ride a carousel, board a train, or climb a giant treehouse.

Prefer outdoor activities?  Be sure to visit the Indianapolis Zoo and White River Gardens , where the kids can roam, see amazing things, and do fun activities. In addition to seeing tigers, dolphins, and orangutans, the kids can visit the petting zoo, ride trains, join for animal feedings, or watch cheetah racing. 

For families who love cars and racing, include a visit to the Indianapolis Motor Speedway . Known as the “Racing Capital of the World,” the speedway is home to the famous Indianapolis 500 race and offers tours of the track and museum. When in the area, stop for burgers and root beers at the Mug ‘n Bun, a nearby vintage drive-in.

On where to stay, consider booking a room at the five-star Conrad Indianapolis tops the list with its spacious rooms and prime downtown location. Prefer something less splurgy? The more budget-friendly Homewood Suites by Hilton Downtown Indianapolis , with a complimentary breakfast, makes for an excellent alternative. Or search for other lodging options in the Indy area here .

Illinois: Top Road Trips Within 5-Hours of Chicago

Check out these top locations in the Land of Lincoln: 

• Starved Rock State Park, IL
• Shawnee National Forest, IL

Also, consider a visit to Galena (a 2.5 to 3-hour drive) with a historic downtown full of shops and restaurants, nearby outdoor activities like walking and biking along the Galena River, and lots of family-friendly lodging , some with pools.

Starved Rock State Park, Illinois

Recommended by: Alyssa of AnAppleaPlane.com

Only 1.5 hours by car outside the bustling city of Chicago, Starved Rock State Park transports visitors into another world. Dramatic canyons and cascading waterfalls are not the first things you picture when you think of the Midwest!  

If you do not plan to drive your own car, renting one will be most effective for your time and budget. Or, you can get to the area by taking a train from Chicago’s Union Station to Mendota Amtrak Station and hailing a 30-minute cab to the park. A huge draw to Starved Rock is its easy-to-access features . Many of Starved Rock’s most famous waterfalls provide drive-up parking lots, so the walk to the waterfall is only a couple of minutes.

Alternatively, consider parking at the main visitor center lot and hiking to your waterfalls of choice. Waterfalls at Starved Rock flow after rainfall or snow melt, so be mindful that these will not be here year-round. The longest-lasting waterfalls are at St. Louis Canyon and La Salle Canyon.

Other top features of the park include hiking, boat tours, and camping . And perhaps the park’s biggest draw—the entrance is free !

Consider staying in the highly-rated Starved Rock Lodge for either cabin or hotel room options. Or search for other nearby family-friendly lodging options here .

Shawnee National Forest, Illinois

Approximate drive time from Chicago: 5 hours

Recommended by: Melissa of HelloWanderlustFamily.com

Located in southern Illinois, Shawnee National Forest is about a 5-hour drive from Chicago, making it an easy and accessible destination for families. 

One of the best things about Shawnee National Forest is its variety of activities , such as hiking, fishing, ziplining, or just relaxing in nature—it offers something for everyone.  Two must-see attractions are Cave in Rock and Little Grand Canyon Trail. Cave in Rock is a 55-foot-wide cave formed over thousands of years by the forces of the Ohio River and the wind, and a highlight of Little Grand Canyon Trail is you get to hike in and around a series of waterfalls that cascade down the rocky cliffs. 

When looking for a place to stay, consider the location of your planned activities . Shawnee National Forest is huge, with some attractions only 15 minutes away, while others may take an hour to reach. Because of this, choose accommodation closer to the area where most of your activities will be. One excellent lodging option for families is Home2 Suites in Carbondale , which not only provides larger room sizes and access to a pool but is in a city that offers plenty of amenities. Or search for more Carbondale lodging options here . Alternatively, for a more unique and memorable experience, consider staying at the Timber Ridge Outpost & Cabins , which offers cozy treehouses perfect for families seeking a one-of-a-kind stay.

Gurnee, Illinois

Approximate drive time from Chicago: 45 minutes to 1 hour

Recommended by: Lisa of PlanningAway.com

If you are looking for a fun short road trip from Chicago, Gurnee Illinois is just the place! There are lots of fun things to do in Gurnee, Illinois !  Gurnee is about 45 minutes north of the city. Home to Six Flags Great America and Great Wolf Lodge , it is the perfect place to spend a fun weekend.   

Six Flags Great America is the highlight of a trip to Gurnee. There are over 30 roller coasters and rides to explore. There is also a water park inside Six Flags called Hurricane Harbor. Six Flags has great shows and entertainment options for all ages.  

To relax after a fun day at Six Flags, stay nearby at Great Wolf Lodge , where you can enjoy many activities, including an indoor water park, Magiquest game, rock climbing, ropes course, arcade, bowling, and mini golf.  Kids will also love character meet and greets, dance parties, and many other fun activities by Great Wolf Lodge, and included in your stay. The lodge is perfect for kids under the age of 12 . 

There are some places to eat inside Great Wolf Lodge, but if you want to really experience Gurnee, you will want to venture out and try some local favorites. Kaiser Pizza is delicious, and Oberweis Ice Cream is a must. Gurnee Mills shopping and outlet mall is a good stop for families too. Shop at the Bass Pro, eat at the Rainforest Cafe, and enjoy many more fun shopping options. If you do not want to stay overnight—Gurnee also makes for a great day trip from Chicago.

Missouri: Top Road Trips Within 5-Hours of Chicago

Saint louis, missouri.

Approximate drive time from Chicago: 4 hours 30 minutes

Recommended by: Lynli Roman of Wanderbig.com

With less than five hours between cities, Saint Louis is a family getaway that feels far away but is easy to drive from Chicago in a half-day! Book a room at the railroad depot turned hotel , Union Station , and spend your time exploring the many family-focused activities that Saint Louis offers.  First, take your family to explore the City Museum . Described as “weirdly wonderful,” the City Museum is the crown jewel of family-friendly fun in St Louis. Housed in an old shoe factory, the City Museum boasts a huge network of slides, tunnels, and caves for all ages. All ages love the rooftop, where you can ride the Ferris wheel or climb a giant praying mantis for perfect views of the St Louis skyline. 

Next, wander through Soulard Farmers Market and taste your way through the city. The Soulard Farmers Market is one of the oldest markets in the United States, with roots dating back to 1779! Most alive during the weekends, you’ll find 147 stalls filled with unique vendors selling everything from local Missouri produce to handmade gifts. Nearby grounds include a playground and plenty of space for an impromptu picnic with your market spoils. 

No family road trip to St Louis is complete without a trip to Forest Park— one of the nation’s largest and most-visited urban parks. The park is home to the Saint Louis Art Museum , the Saint Louis Science Center , the Missouri History Museum , an outdoor theater, and the Saint Louis Zoo . Entrance fees vary, but many amenities, including general admission to the zoo, are free!

Want to see more St. Louis lodging options ? Search for other family-friendly accommodation options here .

Ohio: Top Road Trips Within 5-Hours of Chicago

From city trips to world-class amusement parks to under-the-radar natural gems, Ohio regularly delights visitors , and especially families, with all it offers as a vacation destination.

Four Buckeye State destinations to consider for your next road trip include:

• Cincinnati, OH
• Cleveland, OH
• Cuyahoga Valley National Park, OH
• Cedar Point Amusement Park, OH

Cincinnati, Ohio

Approximate drive time from Chicago: 4.5 to 4.75 hours

Recommended by: Linda of MidwestExplored.com

If you’re looking for one of the best family road trips near Chicago—you can’t beat Cincinnati, Ohio.  After all, this underrated city is located just four and a half hours, or 297 miles, away from Chicago and is a well-priced, family-friendly destination brimming over with fun Cincinnati things to do that everyone will love.

So, start your visit with a trip to The Cincinnati Art Museum , founded in 1881, and in the Eden Park area.  Not only is the museum free to visit, but there are over 67,000 works that cover 6,000 years, ensuring there is something for everyone at this incredible institution. 

Next, grab a picnic lunch and explore Ault Park , which spans an impressive 220 acres of land and is the city’s fourth-largest park, and features a wealth of picnic areas, playgrounds, and walking trails that will help keep energetic kids busy. Finally, learn more about the Underground Railroad at the National Underground Railroad Freedom Center before taking in the electric hue of the cool signs on display at the American Sign Museum.

Then, when you’re ready to call it a day, return to your room at the Hyatt Regency Cincinnati , where you can take advantage of their family-friendly suites, indoor pool and catch up on laundry at their on-site facility. Or search for more Cincinnati lodging options here .

Cleveland, Ohio

A visit to Cleveland truly offers the best of all worlds—thrills at nearby Cedar Point Amusement Park (1-hour drive), cultural chills, and hills made for hiking at Cuyahoga Valley National Park (30-minute drive).  Stay in town at a place like centrally located and highly-rated Roost Cleveland , which offers fully furnished apartments with hotel-like perks,  and use it as a base to explore the area. 

The city, on the shores of Lake Erie, is home to the Rock and Roll Hall of Fame, the Cleveland Museum of Art, and the Cleveland Orchestra—great destinations and cultural institutions for families to experience and explore.  And when your crew gets hungry, head to the historic West Side Market to grab a bite from local food vendors and souvenir shop for artisanal products.

For families with outdoor enthusiasts, pair a visit to Cleveland with a day trip to Cuyahoga Valley National Park , a 30-minute drive away, where you can hike one of many highly rated wooded or waterfall trails.

Want to see more Cleveland lodging options ? Search for other family-friendly accommodation options here .

Cuyahoga Valley National Park, Ohio

Another must-see destination for families visiting Ohio is Cuyahoga Valley National Park .  Located just outside Cleveland (a 30-minute drive), this park offers over 33,000 acres of natural beauty and outdoor activities. 

Families can explore the park’s hiking trails , go fishing or kayaking on the Cuyahoga River, or even take a scenic train ride.  With its pretty waterfalls, wooded paths, and diverse wildlife, Cuyahoga Valley National Park is a perfect destination for families looking to get outside, get moving, and enjoy the best of what nature and national parks offer.  

If you do not plan on staying in Cleveland, consider booking rental lodging in tiny and historic Peninsula Village , a private island of town surrounded by Cuyahoga Valley National Park.  Top rental picks in Peninsula, OH, for families include a few three and four-bedroom homes that can sleep up to ten. Search “Peninsula, OH” on VRBO  to find them.

Cedar Point Amusement Park, Ohio

Approximate drive time from Chicago: 4.5 hours

Cedar Point Amusement Park , located on a peninsula extending into Lake Erie near Sandusky, Ohio, is surrounded by water and overflowing with family-style fun. 

Known as the “ Roller Coaster Capital of the World ” with over 70 rides, including 18 roller coasters—thrill-seeking families will love it. The park also features a water park, live entertainment, and plenty of family-friendly dining.  Take at least two days to enjoy all it has to offer.

Stay on-site at one of the Cedar Point resorts like the beachfront Hotel Breakers , Lighthouse Point offering cottages and campgrounds, Castaway Bay with an indoor water park, or the budget-friendly Cedar Points Express Hotel .

Kentucky: Top Road Trips Within 5-Hours of Chicago

Louisville, ky.

Need a reason to visit Louisville, KY? How about six? Your family will love visiting the Louisville Zoo or strolling along Waterfront Park facing the Ohio River and adjacent to downtown Louisville, stopping to play in playgrounds or cool down in hot summers at the splash park. 

While in the area, catch a ride on a riverboat like the Belle of Louisville , which offers several different types of cruises, including historic narrated ones to picnic lunch cruises . Or your whole crew might love the Hometown Music Kids Cruise , designed especially for families.

Kids and parents who love baseball—or love to see how things how are made—will enjoy a visit to the Louisville Slugger Museum & Factory , conveniently located downtown. Your tickets give you access to the museum and a tour of the factory—kids even get a free mini-bat at the end of the tour.

Need an indoor day activity? Explore the Mega Cavern , a former limestone quarry, now an underground adventure park offering ziplining, ropes courses, and a bike park, just a 15-minute drive from downtown and near the Zoo.  Or visit the downtown Kentucky Science Center , where your kids can engage with exhibits about the human body and outer space.

For places to stay, The Grady Hotel and Homewood Suites by Hilton Louisville Downtown are great choices. Both hotels are centrally located downtown and highly rated. Or search for more Louisville lodging options here . 

Related Reading

For traveling families, check out my related articles below for more trip ideas and tips that will help smooth your travels and get out the door with less hassle.

• Need An Itinerary For A Spring Trip To Europe? Here Are 25 Amazing Ideas
• 31 Warm Winter Break Vacation Ideas Your Family Will Love
• Enjoy the Ride: 12 Tips for Better Family Road Trips
• 15 Tips on How to Raise the Bar on Rental Cars
• Pack Faster & Better With This Universal Printable Packing List
• 25 Expert Packing Tips to Help You Travel Better
• Pre-Trip: A Practical Checklist to Close the House & Pack

Additional Trip Planning Resources

To further help you with travel planning, I share my go-to resources for every trip below. 

Google Flights. My first research stop for affordable flights for every trip. Learn why here . 

Google Hotels . Use its “ Where to stay ” button to discover the best neighborhoods to base your visit.

Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.

Viator , Get Your Guide , & Airbnb Experiences . Quickly find and book highly-rated tours and activities on these sites.

Google Travel Things to Do & Google Maps . Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list. 

AllTrails . Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.

Guide Along . 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour .

Insure My Trip. I never travel internationally without trip insurance. Learn why here . My preferred place to shop and compare policies is InsureMyTrip.com . 

Plus, check out the 15 travel apps I use on trips, my preferred guidebooks , and my free customizable travel itinerary template , downloadable in four file formats.

About the author:  Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog,  Gather and Go Travel . Check out  her bio , learn how she became  a blogger , and discover how to  work with her . Sign up for her monthly  Discovery Newsletter  to get her latest travel recommendations and  how-to’s .

Love to travel? Sign up for m y monthly Gather & Go Travel Discovery Newsletter and get a free trip budget calculator .

Affiliate Disclosure: Some of the links on this page may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I only recommend products and companies I use. And the income goes to keeping the site community-supported and ads minimal.

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Welcome to Gather and Go Travel , a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, an experienced traveler to over 50 countries and a travel writer, book lover, and blogger. Learn more about me , read our story , and how to work with me .

Need an Itinerary for a Spring Trip to Europe? Here are 25 Amazing Ideas

49 Things You Need to Do to Plan Your Best Trip (Free Travel Research & Planning Checklist)

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The best weekend getaways from Chicago for families

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

Photograph: Hamilton County Tourism

Chicago boasts plenty of kid-friendly activities  and restaurants , but if you're planning a family vacation, there are many approachable, fun and memorable destinations close by for a weekend away. Cities, state parks and lakes across the region are full of hiking for all ages and engaging, hands-on ways to learn about history, ecology and wildlife. Along the way, discover quirky shops, longstanding eateries with decadent desserts and recreational activities that children of all ages will enjoy. From wacky and weird to active and relaxing, here are the best  weekend getaways from Chicago for families.

RECOMMENDED:  The best day trips from Chicago  RECOMMENDED:   The most unique day trips from Chicago

Been there, done that? Think again, my friend.

Family weekend getaways from Chicago

1.  wisconsin dells, wi.

Driving time from Chicago: Three hours The waterpark capital of the world—what's not to love? It doesn't matter if the weather is sunny or rainy, though, because this Wisconsin town offers both indoor and outdoor parks. Mt. Olympus is one of the biggest and most popular, with both water and theme park attractions (and rides for the really little ones as well). Those looking to do something a little different can visit MagiQuest in the Great Wolf Lodge to participate in a live-action role-playing game. If the little ones come up for air long enough to eat, head to Buffalo Phil's , where kids get their food delivered on a train before spending some coinage in a giant arcade. Paul Bunyan's is a fun, themed spot for an all-you-can-eat breakfast.

If you're looking for animals, look no farther than Timbavati Wildlife Park for behind-the-scenes tours with exotic animals. Or let the kids feed gentle deer at Wisconsin Deer Park .

2.  Hamilton County, IN

Driving time from Chicago: Three hours Take a trip back in time at the Conner Prairie Interactive History Park  and explore 1836 Prairietown, see a Civil War reenactment or stroll along the nature walk. There’s also a large Swiss Family Robinson–esque tree house called Treetop Outpost for the whole family to enjoy. Then, of course, there's Conner Prairie’s tethered helium balloon, which elevates guests 377 feet above the prairie for unbeatable views over Indiana.

Nearby, you can take to the more than 300 miles of trails in the county, including paved paths that lead to shopping, dining and sightseeing. Bring your bike or rent one during your stay.

3.  Lake Geneva, WI

Driving time from Chicago: One and a half hours At a sprawling resort like the Grand Geneva , you can count on plenty of activities to keep the family busy. Explore the Dan Patch Stables , where the kids can go on pony rides and feed the animals in the free petting zoo. Waterpark lovers will clamor for Moose Mountain Falls , a 50,000-square-foot waterpark. For dinner, check out Popeye's (not the chain with an amazing fried chicken sandwich): It's super family-friendly with great views of the water and a large menu.

4.  Door County, WI

Driving time from Chicago: Four hours

A longtime favorite of Chicagoans seeking a bit of R&R, Door County has more to do than your family will be able to fit into just one weekend. Kids will make some amazing memories with the host of experiential activities, like feeding a baby goat at The Farm ,  making their own crafts at Hands On  or ziplining, gem mining or go-karting at Egg Harbor Fun Park . More active families will love exploring the stunning Cave Point County Park — you can even get kayak cave tours or stand-up paddleboards through Gravity Trails . 

The region isn't short on kid-friendly restaurants either—go for highly cutomizable wood-fired pizzas at Wild Tomato or watch goats graze on the roof at Al Johnson's Swedish Restaurant and Butik . And don't forget to stop at Door County Creamery for some indulgent gelato. 

5.  Indianapolis, IN

Driving time from Chicago: Three hours Indianapolis has enough indoor and outdoor activities for a fun-filled weekend. Head to  The Children's Museum of Indianapolis  for top-notch exhibits like the planetarium and the Dinosphere, where kids can dig for dinosaur bones. It also has a great play area for toddlers. For some fresh air, walk or bike along the Monon Trail, a 10.5-mile path that runs through most of Indy. Stop in the Broad Ripple neighborhood to browse some shops and grab a scoop of ice cream at Brics .

Rest your weary heads at the Crowne Plaza Downtown Indianapolis Union Station , and be sure to call ahead to check for family packages that may include lodging plus tickets to attractions like the Children's Museum and  Indianapolis Zoo .

6.  Holland, MI

Driving time from Chicago: Two and a half hours Since the mid-19th century, the small city of Holland has been home to wooden shoes and tulips. Whether you're there in time for the Tulip Time Festival in May or want to visit the Windmill Island Gardens , the family will have a blast. Check out a working 250-year-old Dutch windmill—”De Zwaan,”—or stroll 36 acres of pristine lawns; bring your picnic blanket and a camera for a vibrant family photo op. During the day, catch a tour of the 125-foot windmill from a guide in traditional plaid Dutch garb. Need even more flowers? See more than five million in bloom in April and May at Veldheer Tulip Gardens . To take home a piece of Holland, though, you must not miss De Klomp Wooden Shoe and Delft Factory , where you can also enjoy a free tour of the famous, centuries-old pottery maker from the Netherlands. Once you've worked up an appetite, take the kids out for an authentic Dutch dessert like sugar bread from deBoer Bakkerij . If you need to burn off some energy, a 20-minute drive takes you to Saugatuck Dunes State Park . Surrounded by 300 acres of nature and dunes that rise up to more than 200 feet tall, you won’t have a care in the world running and playing along this long, sandy shore.

7.  St. Louis, MO

Diving time from Chicago:  Five hours

Brimming with attractions, St. Louis is perfect for families. The iconic Gateway Arch is an absolute must—you’ll understand why when you reach the top of the 630-foot-tall monument—but don’t miss the interactive, immersive City Museum , an educational playground with slides, sculptures you can play on and even vintage pinball machines. If nature’s your thing, the Missouri Botanical Garden has one of the largest Japanese gardens in North America, the Saint Louis Zoo is free and home to more than 600 species of animals and the St. Louis Aquarium features a 250,000-gallon shark habitat.

8.  Peoria, IL

Driving time from Chicago: Two and a half hours

There’s plenty of family-friendly history, recreation and adventure in Illinois’s oldest European settlement. Enjoy the scenic views and watch the barges go by along the RiverFront District before making a stop at the The Peoria Riverfront Museum to immerse yourself in space shuttle launches, solar systems and eclipses in the domed planetarium. Then fill up on smoked meats and burgers at The Blue Duck Barbecue Tavern , housed in a repurposed train depot utilized from 1899 to 1978. Sleep close to the activities at the Mark Twain Hotel , a quaint and understated 111-room accommodation 10 minutes walking from the RiverFront.

You’ll also find lots of greenery and wildlife to experience, even within city limits. Spend time at the 60 square miles of parks—the oldest park district in Illinois. Wander around the 5-acre Luthy Botanical Garden for year-round floral beauty or hike through seven miles of trails in Forest Park .

9.  Harbor Country, MI

Driving time from Chicago: One hour and 15 minutes With a population of less than 2,000 permanent residents, the small lakefront city of New Buffalo is charming for all ages. If traveling by train, Amtrak will drop you off near The Harbor Grand , where a stay feels like home but cozier, with an in-room fireplace and harbor view (or glimpse of a frozen lake). During warm months, you can hop on one of the hotel's bikes for a quick ride around town. And kids will always get a kick out of the nearby Hesston Steam Museum and Captain Mike's Fun Park . For lunch, Redamak’s is the popular burger joint in the area, filled with fun activities for kids, including a mini firetruck. And what would a visit to a beach town be without ice cream? Don’t miss funky Oink's Dutch Treat Ice Cream & Yogurt Shop . For dinner, visit the hotel’s Terrace Room  for a comforting Italian dish like spaghetti and meatballs (described as Grandma’s family recipe with sweet marinara) that everyone will love. Or pop over to Bentwood Tavern for wood-fired pizza.

10.  Gurnee, IL

Driving time from Chicago:  45 minutes

If you’re taking the family up north for a day of fun and games at Six Flags Great America , why not make a weekend out of it? Aside from the amusement park, the village of Gurnee is also home to Great Wolf Lodge —a resort with an 80,000-square-foot indoor water park. Once you’ve dried off, shop ‘til you drop at outlet mall Gurnee Mills .

For even more activities, make the short drive across the border to Kenosha for America's Action Territory Fun Park , where you'll find everything from bumper boats and cars to laser tag and batting cages. The youngins’ can gaze at dinosaur fossils and learn about the link between the prehistoric reptiles and birds at the Dinosaur Discovery Museum , or climb to the top of Southport Lighthouse for sweeping views. There are also a ton of adventures to be had at the Bristol Renaissance Faire during the summertime, when fairgoers dressed in costumes converge on a recreated 16th century port city.

11.  Ottawa, IL

Driving time from Chicago: One and a half hours In just an hour and a half, you'll be transported to a beautiful setting filled with both water and land activities to keep your family entertained. Hike at nearby Starved Rock State Park  or Buffalo Rock State Park ; bike along the I&M Canal State Trail that runs for more than 60 miles; take a dip in the on-site pool or build sandcastles and pack a picnic at the aptly named Picnic Grove. You can also rent a variety of boats, kayaks, water skis and canoes at a nearby private beach. Renting a cottage is the way to go, and you can find a lovely place to rest your head at Heritage Harbor .

12.  Battle Creek, MI

There are no picturesque tree-lined streets or Michelin-starred restaurants in the manufacturing hub nicknamed “Cereal City,” but it’s full of wacky family adventures. The home of Kellogg’s and Post Consumer Brands honors its origins with an annual CerealFest each June. If you miss it, venerate America’s favorite breakfast any time of year with a visit to The Calhoun County Visitors Bureau’s  "Cereal History" exhibit to journey through the history, manufacturing, and culture significance of Battle Creek native John Harvey Kellogg’s invention.

After some cereal nostalgia, meet rescued gators at the Critchlow Alligator Sanctuary twenty minutes south of Battle Creek. There are more than 180 alligators on site, including the 11-foot "Godzilla." (Don’t worry—staff only let the kids touch the small ones.)

Grab dinner a turkey buffet dinner at Cornwell’s Turkeyville USA and then stay for one of the venue’s rotating musicals or theatre performances. For those who prefer more traditional animal encounters, you can glimpse lions, zebras and giraffes at Binder Park Zoo .

As the sun sets over Goguac Lake, you can pretend you’re miles away from Southwestern Michigan at the ostentatious McMansion Paradise Island the Fantasy of the Nouveau Riche . Filled with regionally inappropriate nautical decor, this rental on the lake’s Clark Island sleeps 12, is only accessible by boat and features big windows that offer lake views.

13.  Northern Indiana

Driving time from Chicago: One hour and 40 minutes

With the charming university town South Bend as your home base, spend time exploring Northern Indiana’s outdoor expanses and Amish culture. Start with a visit to St. Patrick’s County Park , a 398-acre preserve with activities for any season. The park features year-round bird watching opportunities and hiking along the numerous trails of varying lengths, canoeing and kayaking along St. Joseph River in the summer and cross country skiing in the winter.

During summer visits, make time to browse outdoor markets running May through September. The South Bend Farmers Market and the Mishawaka Market  are both go-to spots for sampling local produce and artisanal cheeses and meats.

You can easily spend an entire day at Shipshewana Auction & Flea Market —the largest in the Midwest—located an hour drive east from South Bend. The size of more than 30 football fields, you’ll find antiques and vintage furniture, decor, apparel, food stalls, and even plants. On your way back to South Bend, make a stop in Middlebury, a town of around 3,500 with a strong Amish presence. Visit the original Rise ‘n Roll Bakery and Deli and grab a box of the notoriously addictive cinnamon caramel doughnuts.

14.  Springfield, IL

Driving time from Chicago: Three hours and 15 minutes

The capital of Illinois is full of history and things to do with the family. Tour the Old State Capitol —the spot where Abraham Lincoln announced his candidacy for the presidency—or visit the Abraham Lincoln Presidential Library and Museum to learn more about the nation’s 16th president and the American Civil War. Hit up sporting goods store SCHEELS for much more than just athletic apparel—the popular attraction also houses a Ferris wheel, 16,000-gallon aquarium, arcade and cafe. For some outdoor activities, the Henson Robinson Zoo is home to over 300 animals while Knight’s Action Park is a 62-acre water park with a mini golf course. 

15.  Walworth County, WI

If you’re looking for an off-the-beaten track destination to unplug and reconnect with nature, the Walworth County lakes within thirty five minutes of Lake Geneva are a no-brainer. At Delavan Lake, Whitewater Lake, Rice Lake, Lauderdale Lakes (comprised of three interconnected lakes) and nearby Lake Wandawega to the south and Pleasant Lake to the north, visitors can canoe, kayak, fish, swim and hike. Head south to the 12-mile White River Trail  for hiking, biking and horseback riding.

Whitewater Lake’s Scenic Ridge Campground  offers wooded or grassy campsites along the water, access to volleyball nets, horseshoe pits and hiking trails, plus an extensive calendar of sports, entertainment and activities for folks of all ages.

16.  Columbus, IN

Driving time from Chicago : Four hours

You might be thinking, “Why would any kid enjoy a hub of modernist architecture?” However, this ode to inventive constructions can be appreciated by all ages. The vibrant pavement in the city center and colorful bridges are just enough to keep young ones captivated, and if that’s not enough, the kidscommons Columbus’ Community Children's Museum  is always an option. 

A must visit in this eccentric town is Zaharakos Ice Cream Parlor and Museum , an authentic ice cream shop that opened in 1900. For dinner, family-friendly ZwanzigZ Pizzeria and Brewery has something for everyone. 

17.  Brown County, IN

Brown County State Park is famous for its vibrant fall colors, but this nature oasis 30 minutes northeast of Bloomington is fun during any time of the year. Indiana’s largest state park, often referred to as the “Little Smokies,” has 11 hiking and 14 mountain biking trails of varying lengths and difficulty levels—plus, 20 miles of roads for when your legs get tired—you can mix and match for your desired adventure, whether it's to see stunning views of rolling tree-covered hills and waterfalls or to feel immersed in the backcountry. If you need to rent two-wheeled transport, stop by Q’s Bikes .

There are plenty of campsites around the park, but for indoor stays head just outside the park boundaries to Nashville, a small town full of mom-and-pop craft stores, fudge shops, ice cream and restaurants with live entertainment. Cornerstone Inn has a campus of 41 affordable accommodations around town and a cabin in the woods. The delicious pizzas and craft beer at Big Woods are much needed fuel after an active day—and don’t skip the sizzling skillet cookie topped with ice cream.

18.  Galena, IL

Driving time from Chicago: Three hours

Words people use regularly to describe Galena include “quaint,” “charming” and “historic,” but none of those have to also mean “boring.” One of the best all-ages options for more active families is the Chestnut Mountain Resort , a 100-room lodge featuring skiing and snowboarding in the winter and ziplining and a 2,050-foot alpine slide in the summer. 

If you don’t want to go the resort route, there’s still plenty to do in the great outdoors with the whole family, from kayaking or canoeing down the Galena River with a rented vessel from Nuts Outdoors to a scenic trail ride with the Shenandoah Riding Center to strawberry picking at Terrapin Orchards . For a fun, family-friendly evening activity, catch some thrilling illusions at the P.T. Murphy Magic Theater or get your nostalgia on with a drive-in movie at the Midway Drive-In in nearby Sterling. And if you’re browsing through downtown Galena, don’t forget a stop for some sweets at Galena Kandy Kitchen . 

19.  Ann Arbor, MI

There are plenty of reasons to take a family road trip to Ann Arbor, even when it isn’t Michigan football or basketball season. Kids can spend hours at the interactive Ann Arbor  Hands-On Museum or the Leslie Science and Nature Center, where they can run around the Nature Playspace and get up close with birds of prey in the raptor enclosure, or snakes and frogs in the Critter House. The whole family will find something to love exploring the shops and restaurants on colorful Main Street—the little ones will be particularly drawn to the nostalgic soda and sweet shop Rocket Fizz and the countless shelves of books, comics, toys and games at Vault of Midnight .

As for going out to eat with your whole crew, even the breweries here cater to craft beer enthusiasts with kiddos— Blue Tractor BBQ & Brewery and Jolly Pumpkin offer award-winning brews and hearty, creative food for the parents, with solid kids menu options and crowd-pleasing desserts. Speaking of dessert, a trip to Zingerman’s Deli for their decadent brownies is also a must.

20.  Casey, IL

Just under a four hour drive from Chicago, the small town of Casey is home to some giant public sculptures. From a 28-foot Chevy truck key to a 46,000-pound rocking chair, 12 of the  world’s largest items can be seen here. It’s a great day whenever kids feel like they’ve been shrunken down to the size of an ant.

Stay at the quaint and comfy Eighteen-Ninety Sleepover Hotel   while planning your sightseeing around the city. Locals love the Wildflower Bakery and Candy Company and it’s a great treat to keep the kids happy. For any java-dependent parents running on fumes, the Casey Coffee Company is conveniently located right between the World’s Largest Rocking Chair and the World’s Largest Mailbox.

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23 Best Family Road Trips from Chicago

Chicago's got it all - from its towering skyline and delicious deep-dish pizza to a cultural scene that's second to none. The city also boasts an amazing location and if you're on the hunt for your next family getaway, you're in luck. The Midwest is full of places that are just a drive away from Chicago.

On our list of 23 best family road trips from Chicago, you will find everything from amusement parks and peaceful nature retreats to fascinating historical sites and hands-on museums. There's something out there for families of all shapes and sizes.

That's exactly why we've put together a go-to list of the best family road trips from Chicago. So get your car games ready, and pack your books and keep reading to discover our top picks for family road trips, including how far you'll need to travel and what exciting attractions await at each destination.

Below, you will find our shortlist of amazing adventures on the road for all the family members, young in age or young at heart!

Best family road trips from Chicago: a quick overview

But that's not all; there are many other road trips you can enjoy from Chicago. If you are traveling during spring break, you can refer to our best spring break road trips from Chicago . Alternatively, for the colder months, you can check out our guide to the best winter road trips from Chicago .

Not sure when you want to travel and want to be inspired? You can find amazing ideas in our guide to the best road trips from Chicago .

Family-friendly day trips from Chicago (under 3 hours each way)

Day trips are perfect getaways, especially if you are traveling with younger children, and there are so many amazing places to visit with family near Chicago. From amusement parks to interesting museums, you will be spoilt for choice!

45 minutes from Chicago (40 miles)

Why visit Gurnee with family? The shortest drive on our list, which is perfect for a day trip, Gurnee is home to numerous theme parks, water parks and shopping centers.

Even though Gurnee is not exactly a city on its own but a suburb of the Chicago metropolitan area, there was no way we could not include this amazing location on our list of family road trips.

The town is also known for lovely beaches, hiking and biking. With these attractions, Gurnee is truly a premier family destination on Lake Michigan.

Driving to Gurnee from Chicago: The drive from Chicago city center to Gurnee is quite straightforward. Just follow Interstate 94 (I-94) north and then take US-41 to reach your destination.

Our highlights: Six Flags Great America is a wonderful theme park for travelers of any age. Here, you can enjoy a double-decker carousel, an atmospheric County Fair section or the themed Yukon Territory Section, or take a ride on the thrilling roller coasters.

Great Wolf Lodge's indoor water park is a fabulous family destination. It is a whole world of play, with various slides, pools, adventurous attractions, and a children's play area.

Once you have had your fill of thrills, Gurnee Mills is a large shopping center with over 200 stores and plenty of restaurants and cafés to enjoy.

If you are in the mood for a more serene afternoon with your family, you can pack a picnic and enjoy the waters and scenery of Lake Michigan at Illinois Beach State Park.

Did you know? On average, 23 million visitors find their way to Gurnee every year, showing the popularity of this Chicago suburb on Lake Michigan!

Things to note: Gurnee is close to Chicago and a popular destination, so traffic is often fairly busy on this stretch. Be vigilant on the road, especially if you're going to Gurnee in winter and snowy conditions.

Six Flags Great America is temporarily closed, but it is set to reopen this year. Please check before traveling to avoid any disappointment.

2. Harbor Country

Via indiana dunes national park.

1 hour 25 minutes from Chicago (75 miles)

Why visit Harbor County with family? Harbor Country, on the southwestern shore of Lake Michigan, is a great day trip destination for the entire family. It is just a short drive away from Chicago, and what draws people here are the lovely beaches, bed and breakfasts, and vineyards.

The area is also known for beautiful hiking, birding, swimming, and other lake-based activities. For families, there are also amazing farmers' markets, family-owned farms, and more to enjoy.

Driving to Harbor County from Chicago: Head south on I-90 out of Chicago and follow the shore until you reach Indiana Dunes National Park. From here, you will switch to I-94, heading east to reach Harbor County.

Our highlights: Indiana Dunes National Park is a top lakeside destination on the way to Harbor Country. On top of swimming and exploring the dunes, you can do bird watching and learn about the various vegetation types found in the area, from shorelines to wetlands, prairies and oak savannahs.

Hesston Steam Museum is a great place for the entire family to visit. You can take a ride on a real steam-powered train through the countryside, learn about the history of steam engines that enabled much of the development in these regions, and enjoy refreshments at a restaurant.

Three Oaks Market, in downtown Three Oaks, takes place every Friday afternoon, and it offers the freshest food, produce, and artisanal goods the region has to offer.

Captain Mike's Fun Park in Lake Charter Township is open during summer. This five-acre park offers go-karts, bumper boats, putt-putt courses, snacks, and more.

Fernwood Botanical Garden, slightly inland close to Buchanan, offers wonder, beauty and family fun. On top of a regular arboretum, there is also an adventure garden, nature trails, an education center, and more to enjoy at this beautiful venue.

Did you know? This area is known for its beautiful beaches along Lake Michigan, making it a popular spot for finding Petoskey stones, Michigan's state stone. So see if you can tell the difference between different rocks and find one of these special stones with the little ones!

Things to note: Roads to Harbor Country are in good condition; just be aware of the chance of snow in the winter months.

There are lots of lovely, smaller country lanes in this region that you might want to explore slowly during your trip for views of the rolling hills, forests, and farms.

3. Lake Geneva

1 hour 40 minutes from Chicago (80 miles)

Why visit Lake Geneva with family? Go lake -hopping with your family! This road trip will not only take you to Lake Geneva but also to Lake Zurich and Fox Lake for the ultimate waterside adventure.

Lake Geneva is also a wonderful day trip or weekend destination for the family, including your little ones. With parks and playgrounds, walking trails, beaches, magic theaters and more, there is much to see and enjoy for everyone.

Driving to Lake Geneva from Chicago: Follow I-90 northwest and hop onto IL-53. You will soon reach Lake Zurich. After your visit, your next stop will be Fox Lake, and then US-12 will take you all the way to Lake Geneva.

Our highlights: Walking trails, slides, swings, and picnic tables can be found at Oak Ridge Marsh Park Playground by Lake Zurich on the way to Lake Geneva.

If you wish to head to the beach with your children, Riviera Beach on Lake Geneva is a good option. It is enjoyed by swimmers, sunbathers, hikers, and boaters alike.

At the small Tristan Crist Magic Theater, you can witness magic and illusion shows that are family-friendly and be amazed!

At Lake Geneva Ziplines & Adventures, your family can explore sky bridges and rope courses and take a zip line ride through the forest. The area also includes hiking and biking trails.

Did you know? Famous for its grand estates and as a former retreat for wealthy Chicago families, it's also known for being the birthplace of the tabletop role-playing game Dungeons & Dragons!

Things to note: Tristan Crist Magic Theater is the region's premier entertainment option, and it is a good idea to book tickets in advance if possible.

4. Peru and LaSalle

1 hour 30 minutes from Chicago (100 miles)

Why visit Peru and LaSalle with family? Peru-LaSalle twin cities provide much to enjoy for the entire family, from beautiful natural getaways to historic sites and a vibrant downtown area to explore with shops and restaurants. They are fabulous destinations from Chicago.

La Salle and its twin city, Peru, make up the core of the Illinois Valley. La Salle, or LaSalle, is known for its many historic sites, such as a replica canal boat and the Hegeler-Carus Mansion.

Driving to Peru and LaSalle from Chicago: Head northwest on I-55 and then switch to I-80 to reach LaSalle. Peru is a short drive from here on US-6.

Our highlights: Starved Rock State Park on the Illinois River is known for its sandstone canyons, some of which have waterfalls. The park has many in wooded trails and fascinating wildlife, and there are lovely viewpoints overlooking the river - perfect for a family outing.

Buffalo Rock State Park in LaSalle County contains a riverside bluff and almost 300 acres of nature, with walking trails, camping sites and fabulous picnic sites.

Visit the I&M Canal National Heritage Area to get a real feel of the life of the American frontier. Little ones traveling with you will especially love the 1880s replica Canal Boat and enjoy taking a boat tour of the canal, which starts with a crash course on “Mule Tending 101”!

Hegeler-Carus Mansion, built in 1874, is a grand Victorian-era home of 57 rooms and is a fascinating place to visit with the family. It features fine details all around; on its hand-painted walls and ceilings, beautiful woodwork, chandeliers, and large glass windows.

Things to note: Starved Rock and Buffalo Rock state parks are open all year round. In winter, it can be particularly special to visit Starved Rock State Park, to view the frozen waterfalls.

As with all roads in Illinois, winter months can see the roads covered in snow at times; be aware of this should you be doing the road trip in winter.

5. Milwaukee

Via kenosha.

2 hours from Chicago (110 miles)

Why visit Milwaukee with family? Milwaukee is a beautiful and fun city on the shore of Lake Michigan, home to splendid historical and cultural attractions for the younger members of the family as well as famous breweries for the parents!

Milwaukee is an easy 2-hour drive away and has lovely attractions for family members of all ages to explore, including museums, a zoo, a science center, shops, and great restaurants.

Driving to Milwaukee from Chicago: Follow I-94 heading directly north and then hop on WI-158 to visit Kenosha. Retrace your steps after your visit to get back on I-94 to arrive in Milwaukee.

Our highlights: In Kenosha, on the way to Milwaukee, you can visit the Dinosaur Discovery Museum to view dinosaur fossils - something exciting for all of the family members.

Milwaukee Public Museum is home to natural and human history exhibits. This museum is great to explore with children, and there is also a restaurant and a dining area.

If you want to visit other museums, Discovery World Science and Technology Museum is another must-see destination for families visiting Milwaukee.

Alternatively, you can visit Milwaukee County Zoo, home to over 3000 animals from 350 different species. This popular zoo receives 1,3 million visitors a year!

Did you know? Milwaukee is known for its major league baseball team, the Milwaukee Brewers, and its unique mascot, Bernie Brewer.

Things to note: Milwaukee winters are known to get cold, and driving conditions may be impacted by snow blizzards if you're doing this road trip in winter. Check ahead of time and prepare accordingly. Fortunately, the city has much to offer in warm and colder seasons!

6. South Bend and Mishawaka

2 hours 10 minutes from Chicago (100 miles)

Why visit South Bend and Mishawaka with family? Visiting South Bend and Mishawaka makes for a lovely trip for the family. South Bend is a university town home to affordable restaurants and fantastic playgrounds.

Both South Bend and Mishawaka areas are famous for the wonderful parks and trail systems present here, as well as for museums, galleries, shopping, and historic spots. These include historic parks, sky-high playgrounds, and green areas with beautiful nature trails.

Driving to South Bend and Mishawaka from Chicago: Heading out of the city in the southeast direction, follow I-90 and then IL-2 to drive into La Porte. From here, the same highway will take you to South Bend and then Mishawaka to the east.

Our highlights: Sky Zone Trampoline Park in Mishawaka offers tons of fun indoors. You can buy single-day passes to access the various activities offered at this park. You can expect lots of bouncing, playing, jumping and flipping here!

The entire family can enjoy a day of entertainment at the Strikes and Spares Entertainment Center. Activities available include go-karts, bowling, mini-golf, and bumper cars. Food and drinks are also available and a toddler area for the youngest members of the family.

Potawatomi Zoo is a zoological park in South Bend. There are animal exhibits and educational programs at the zoo, and even train rides available for the family to enjoy.

At South Bend Chocolate Co. Factory you can get behind the scenes and take a tour to explore the factory floor and observe how the best chocolates are made. The perfect way to spend the afternoon, especially if you or your family have a sweet tooth!

Meanwhile, at The History Museum's Kidsfirst Children's Museum, children have a chance to get a close look at the area's local history and the way of life of the pioneers in South Bend.

Central Park is a popular park in Mishawaka, with a splash pad, playground, and the river running through the park with lovely walking trails alongside it.

Did you know? There are a few explanations as to the origin of the name Mishawaka. It may have derived from the local Potawatomi language in which it would have meant "firewood-tree land".

Alternatively, it might come from the name of a local chief's daughter who, long ago, fell in love with a white trader. She was a princess, also giving the city its nickname, the "Princess City".

Things to note: South Bend and Mishawaka area is especially a good choice for a family trip during the winter time, because of the many indoor attractions present here, as well as the opportunity to enjoy ice skating and other outdoorsy winter activities.

Via Indiana Dunes National Park and Michigan City

2 hours 50 minutes from Chicago (150 miles)

Why visit Holland with family? Circling the southern and eastern shores of Lake Michigan, this road trip will allow you to explore the beaches, dunes and scenic sights along the way, and it eventually takes you to unique Holland, with lovely cycling routes, and tulip fields.

Holland is best known for its Dutch heritage, which is visible in the city's identity. For families, there are plenty of fun activities: explore the area's parks for hiking, picnicking, and playing, or go swimming, paddle boarding, or boating on the lake Macatawa that the city surrounds.

Driving to Holland from Chicago: Follow I-90 out of Chicago and follow the coast towards Indiana Dunes National Park and then Michigan City. From here, I-94 and then I-196 will take you to Holland.

Our highlights: Indiana Dunes National Park is an exciting family-friendly destination. It runs for 20 miles along the shore of Lake Michigan, offering plenty of opportunities to explore the coastline and the dunes. This is also a highly biodiverse area, with a mix of forests and vegetation types to admire and hike through.

Washington Park Zoo in Michigan City is full of magic. This historic zoo, spread out over natural hillside terrain, is home to numerous animals that come from conflicting backgrounds and would not be able to live out their lives in the wild anymore.

Instead, the tigers, tamarins, alligators, and many other animals housed here are now great educators about the natural world for children and adults alike.

Holland State Park in Holland is also a great destination if you're visiting with your children. You can observe deer and migratory birds here, and there are also snack shops and a lovely big playground at the park.

Windmill Island Gardens is home to a 250-year-old windmill called De Zwaan. You can also admire tulip fields and gardens in this beautiful destination.

Outdoor Discovery Center is another fascinating attraction. This nature preserve has an educational facility with exhibitions on native animals, and it also has play areas for children.

Did you know? In Holland, Michigan, you really feel at times like you could be in the Netherlands! Each year, a Tulip Time Festival takes place, during which tulips are seen, planted and exhibited around the city.

Things to note: Should you wish to truly admire the wonderful tulips, visit Holland in May when the Tulip Time Festival takes place.

Indiana Dunes State Park is open all year round, though some hiking trails are closed during the winter months.

Via Rockford

2 hours 50 minutes from Chicago (160 miles)

Why visit Madison with family? Madison is an all-around interesting, big city to explore, and it makes a great day or longer vacation destination from Chicago. If you're visiting with your family, there are plenty of indoor and outdoor attractions to enjoy and explore.

With a free zoo, a large farmer's market, plenty of exciting museums and over 250 parks, you will find plenty to do and explore with your family in Madison.

Driving to Madison from Chicago: Out of Chicago, I-90 will take you northwest to Rockford. From here, the interstate will head directly north to Madison.

Our highlights: Discovery Center Museum at Rockford, Illinois, hosts over 250 interactive exhibits and offers fun and educational activities for both children and their parents.

Henry Vilas Zoo in Madison is another great family destination in this beautiful city. The zoo offers free entry and is home to animals from all over the world.

Dane County Farmer's Market runs on Saturday mornings between April and November. This large farmer's market has a superb selection of produce and snacks for the little ones!

Madison Children's Museum is a must-visit attraction if you visit Madison with your children. This museum for children contains exhibits on arts, sciences, history, culture, and much more.

Things to note: The roads between Chicago and Madison are generally kept in great condition. Of course, if doing this road trip during winter months, you'll need to be prepared for snowy conditions on the roads.

Click here to skip back to the top.

Family-friendly weekend trips from Chicago (3-5 hours each way)

Have a holiday that conveniently coincides with a Monday? Then, these weekend and long weekend trips from Chicago will be amazing drives to enjoy with your family. From charming coastal towns to buzzing cityscapes, you will have plenty of options to choose from.

9. Galena and Chestnut Mountain Resort

3 hours from Chicago (170 miles)

Why visit Galena and Chestnut Mountain Resort with family? This road trip takes you to the fascinating city of Galena, with great attractions for the entire family to explore. You will also get to enjoy great skiing and snowboarding at the nearby Chestnut Mountain Resort.

Galena attracts around a million visitors each year to admire its old-town charm, cobbled streets, and historic buildings, stroll through the city's many antique shops and wineries, or explore the hilly country surrounding the Mississippi River.

Driving to Galena and Chestnut Mountain Resort from Chicago: You will follow I-90 from Chicago until you reach Rockford and then hop onto US-20 to head into Galena. From here, W Blackjack Road will take you to Chestnut Mountain Resort.

Our highlights: When taking this road trip from Chicago, we recommend stopping at the Discovery Center Museum in Rockford on the way to explore their 250 interactive exhibits and workshops.

Once you arrive in Galena, you can take in the views and listen to the stories of the historic Galena on a city tour provided by Galena Trolley Tours.

P.T. Murphy Magic Theater offers an intimate, magical performance experience at a small 24-seat private theater in the historic heart of Galena.

Chestnut Mountain Resort, on a ridge overlooking the Mississippi River, offers skiing and snowboarding slopes for all levels. The resort also offers river cruises, an indoor pool, restaurants, and wonderful lodging options.

Things to note: The drive to Galena from Chicago along US-20 is generally a smooth one, just be prepared for snowy conditions in the wintertime.

Galena itself offers much to see and do in all seasons, and in winter, the historic city is adorned in colorful Christmas decorations, which only make the atmosphere more cheerful and festive!

It is good to book tickets in advance for the P.T. Murphy Magic Theater show because the theater only has 24 seats.

10. Sheboygan and Manitowoc

Via milwaukee.

3 hours from Chicago (175 miles)

Why visit Sheboygan and Manitowoc with family? If you're traveling to Sheboygan and Manitowoc with your family, you're in for a treat on the western shores of Lake Michigan. You'll find a great array of attractions and activities to enjoy here, from scenic parks and beaches to engaging museums and water parks.

Sheboygan is especially known as the outdoor enthusiasts' heaven because of its location and geography: it is dubbed the world's Freshwater Surf Capital, and Lake Michigan also offers much else to a visitor in the form of fishing, sailing, and long sandy beaches. Manitowoc is also known for water-based activities and attractions.

Driving to Sheboygan and Manitowoc from Chicago: Follow I-94 until you reach Milwaukee and then switch to I-43 to visit Sheboygan and then Manitowoc.

Our highlights: On the way to Manitowoc, you might want to stop at Milwaukee to visit the large Milwaukee County Zoo. The accredited zoo is home to over 2,000 animals from more than 300 species and is a great learning experience for families.

Bookworm Garden in Sheboygan is a beautiful, playful botanical garden inspired by popular children's books.

Show Family Playground is a large, well-equipped playground in Sheboygan. This all-inclusive playground has various unique features - great fun for the children of the family.

At the Wisconsin Maritime Museum, you can learn about the maritime history of the Great Lakes region. There are ship models, boats, a WWII submarine, and more to explore at this fascinating museum.

Cedar Crest Ice Cream Factory & Parlor is one landmark destination in Manitowoc. Meet the giant cow standing in front of this popular ice cream parlor, and have a seat outside to enjoy your favorite flavors of ice cream.

Did you know? Sheboygan is dubbed the "Bratwurst Capital of the World," so get ready to enjoy this delicious sausage in all shapes and forms during your visit here.

Things to note: As with other family road trips from Chicago, be aware of possible snowy driving conditions, traffic, and adverse weather if making this road trip in the winter months.

11. Indianapolis

3 hours from Chicago (185 miles)

Why visit Indianapolis with family? Indianapolis is home to well-known sporting events and locations, a range of historic sites and districts, various museums and monuments, and fun attractions.

Indianapolis has a not-too-large, walkable downtown area, and various attractions suitable for the entire family. This makes it a great weekend destination away from Chicago at any time of the year.

Driving to Indianapolis from Chicago: Follow I-94 south out of Chicago and hop onto I-65 to reach Indianapolis.

Our highlights: The Children's Museum of Indianapolis fosters a sense of discovery through its learning experiences and exhibits in that focus on science, arts, and humanities.

Indianapolis Zoo is actually a zoo, an aquarium, and a botanical garden all in one. It is home to over 1,400 animals and nearly 50,000 plants! It is a wondrous place for all the family members to explore.

Visit Rhythm! Discovery Center in downtown Indianapolis; here, you and your children can explore the world's only drum and percussion museum. You may admire historical artifacts or experience and try various hands-on percussion instruments.

If you and your family prefer to spend time outdoors, you can view beautiful nature and interactive art installations at Virginia B. Fairbanks Art & Nature Park.

Did you know? Indianapolis hosts the annual automobile race Indianapolis 500 - the world's largest single-day sporting event. Other well-attended, popular sporting events also take place in the city, one example being another racing event, Brickyard 400.

Things to note: Do check the opening times of Rhythm! Discovery Center, for the attraction, has usually been closed on specific days of the week.

Though Indianapolis doesn't get as much snow as many other long-winter cities, it is still good to be prepared for snowy driving conditions or snowfall during your outings if visiting the city in the winter months.

12. Saugatuck and Grand Rapids

Via benton harbor and south haven.

3 hours 20 minutes from Chicago (185 miles)

Why visit Saugatuck and Grand Rapids with family? This road trip takes you northeast along the shores of Lake Michigan, past lovely small towns and scenic landscapes, to the unique, fascinating cities of Saugatuck and Grand Rapids.

The cities offer much to see and do for children and adults. Saugatuck is known for its award-winning beaches, thriving art scene, and scenic waterways, while Grand Rapids is home to fabulous museums and galleries and also a number of wonderful craft breweries.

Driving to Saugatuck and Grand Rapids from Chicago: You will basically follow the shore of Lake Michigan, heading northeast on this road trip. Take I-90 from Chicago and then switch to I-94 and I-196, which will take you all the way to Saugatuck and Grand Rapids.

Our highlights: Visit Sarett Nature Center in Benton Harbor, where you can walk along meandering nature trails, enjoy observation platforms, participate in nature classes, or admire live animals and a butterfly house.

South Haven Lighthouse, in South Haven on the way, is a beautiful, historic place to take a walk with your family.

You'll find many beaches on your drive up towards Grand Rapids. In Saugatuck, Oval Beach is perhaps the most popular - and historic - beach. White sands and blue waters, nestled in sand dunes and bordered by the Kalamazoo River, present a wonderful opportunity to spend a day out swimming, picnicking, or exploring nature.

Grand Rapids Public Museum offers adventure and fun on three floors. You'll find history and science exhibits here, as well as a historic carousel, a theater, and a planetarium.

Frederik Meijer Gardens & Sculpture Park in Grand Rapids is visited by hundreds of thousands yearly. This botanical garden also has an art museum and an outdoor sculpture park.

Things to note: Winters in these areas of Michigan are known to get very cold, and you might also do well to prepare for possible icy conditions on the roads if making this road trip during the colder season.

13. Wisconsin Dells

3 hours 10 minutes from Chicago (200 miles)

Why visit Wisconsin Dells with family? Wisconsin Dells is a great destination to visit with family. It is especially well known for its many fun and adventurous water parks and for the stunning scenery of forests and gorges to be admired on the Wisconsin River.

Driving to Wisconsin Dells from Chicago: Follow I-90 northwest to Rockford and then to the outskirts of Madison in the north. The interstate will then take you directly to Wisconsin Dells.

Our highlights: About 10 minutes from downtown Wisconsin Dells, Noah's Ark Water Park is one of the largest water parks in the US. Your children (and yourself!) will love the exciting water slides and endless fun to be had at this famous park.

Take a boat tour to view the Dells of the Wisconsin River. These tours leave from the heart of Wisconsin Dells and take you to view mesmerizing glacier-carved gorges and sandstone formations.

Mt. Olympus Water and Theme Park is another fabulous family destination. Inspired by ancient Greece, this theme park has a water park section and a classic theme park section with rides and rollercoasters.

Mirror Lake State Park has wetlands, swimming beaches, trails, and camping facilities. In the summer, you can go boating and canoeing on the lake, and in the winter, skiing and snowshoeing are possible activities.

Did you know? Known as the "Waterpark Capital of the World," Wisconsin Dells a paradise for visitors of all ages. You will find over 20 indoor and outdoor waterparks here during your visit!

Things to note: At Mirror Lake State Park, some of the campsites and facilities are only open during the summer months.

READ MORE - Road Trip from Chicago to Wisconsin Dells

14. Door County

4 hours 30 minutes from Chicago (270 miles)

Why visit Door County with family? For a very scenic road trip, head up north from Chicago to Door County. It is a fabulous weekend or longer vacation destination for the family, with beautiful views, beaches, family-friendly attractions and farmer's markets.

Door County on the Door Peninsula offers spectacular views over Green Bay on one side and Lake Michigan on the other. The area is known for picturesque coastal towns, fruit orchards, lighthouses, and scenic views.

Driving to Door County from Chicago: Head directly north out of Chicago, following the coast of Lake Michigan on I-94 and I-43 until you reach the outskirts of Manitowoc. From here, drive to Green Bay on the interstate and then hop onto WI-54 to reach Door County.

Our highlights: On the shore of Lake Michigan stands Door County's most iconic lighthouse, Cana Island Lighthouse. Explore the island, including the light tower and lighthouse keeper's home.

Peninsula State Park on the shores of Green Bay is a popular camping destination, which is also great for swimming, hiking, biking, or just slowly driving through the park to view the high bluffs and sandy beaches.

The Farm Historic Living Museum in Sturgeon Bay is a great place for children or adults to visit. Here, you can view exhibits on rural farming and heritage and visit farm animals and bottle-feed baby animals in natural farm surroundings.

Don't forget to get on the ferry to cross Death's Door to get onto Washington Island. Children will enjoy the 30-minute ferry ride and explore the island with nature to view, as well as shops and restaurants.

Did you know? Door County is famous for its cherries and is a popular place to go cherry picking. These cherries usually reach their peak ripeness from mid-July to mid-August, when you and your family can experience the joy of picking your own fresh produce.

Things to note: Though Door County is obviously a beautiful, activity-filled summer holiday destination, it is also wonderful in winter. You can do skiing, snowshoeing or ice fishing, and even, if you're lucky, view the northern lights that are often seen here due to less light pollution than elsewhere in Wisconsin.

Just be aware that, although there will always be attempts to keep roads clear during the snowy periods of the winter months, plowing may take some time; it is good to be prepared with proper winter tires and gear if making this road trip in the cold season.

The Farm Historic Living Museum is not open during the months of November until May.

15. Ann Arbor and Detroit

4 hours 30 minutes from Chicago (285 miles)

Why visit Ann Arbor and Detroit with family? This road trip takes you from Chicago by the shores of Lake Michigan to Detroit, on the shores of Lake St. Clair. Museums, amusement parks, outdoor adventures, parks and Detroit Zoo are but some of the examples of child-friendly things to do in this vibrant city.

On the way to Detroit, Ann Arbor is another fabulous place for a stopover; it is especially known for its many interactive, science-focused activities and attractions.

Driving to Ann Arbor and Detroit from Chicago: A road trip from Lake Michigan to Lake St Clair, follow I-94 heading east to reach Ann Arbor. The switch to M-14 and I-96 to arrive at Detroit.

Our highlights: Ann Arbor Hands-On Museum and Leslie Science & Nature Center is a must-see destinations in Ann Arbor for families with children. This museum has engaging, interactive exhibits and activities on various scientific fields and topics.

Detroit Zoo has over 2,000 animals living on its 125 acres of various habitats. The zoo features many award-winning exhibits such as the Wildlife Interpretive Gallery, the Great Apes of Harambee, and the Arctic Ring of Life.

Detroit is known as the automobile capital of the world; Henry Ford built his first car here in 1896, and the city led the manufacturing of cars in this part of the US in the early 20th century. Nowadays, various automobile museums in Detroit are a testimony to this history.

Henry Ford Museum of American Innovation commemorates the life and accomplishments of this famous entrepreneur. The museum features various exhibits on the history of automobiles, and children can take part in interactive games and activities.

Visit Greenfield Village to experience 90 acres of preserved historical buildings, interactive activities, and costumed characters related to Detroit's living history. You can even ride on a horse-drawn carriage or a steam-powered train.

At C.J. Barrymore's play park, you'll find lots of family-friendly fun, from golfing, go-karts, and bowling to thrill rides, video games, and laser tag.

Did you know? Detroit is well known as the birthplace of the distinctive Motown Sound.

Things to note: Be aware of traffic while traveling to Detroit with your family; the large city's streets may experience heavy traffic at times, and conditions can be especially difficult during the snowy winter months. Even Interstate 94, leading to Detroit, can be affected due to snowy or icy conditions during winter.

16. Cincinnati

Via indianapolis.

4 hours 40 minutes from Chicago (300 miles)

Why visit Cincinnati with family? This beautiful riverside city is called "Paris of America" due to its stunning architecture and fantastic museums and theaters.

If you're visiting Cincinnati with your family, some of the fun things to do together include riverfront parks, a zoo, a botanical garden, and museums.

Driving to Cincinnati from Chicago: Head southeast following I-94 and I-65 to reach Indianapolis. From here, switch to I-74 to arrive in Cincinnati.

Our highlights: On the way to Cincinnati, visit the Children's Museum of Indianapolis, the world's largest children's museum. There are over five floors of exhibitions on dinosaurs, space stations and more.

Located on the banks of the Ohio River, Cincinnati is a city known for its arts, world-class breweries, a lovely riverfront, and beautiful 19th-century buildings.

Cincinnati Zoo & Botanical Garden has a large variety of animals, habitats, and gardens to explore. It is dedicated to adventure, education and conservation.

Highfield Discovery Garden at Glenwood Gardens has a variety of activities and adventures for families. There is a fantasy playground where you can explore fairy gardens, a butterfly garden, and trains.

Kings Island is a famous amusement park near Cincinnati. It contains various rides, rollercoasters, water parks, and play areas.

Did you know? Cincinnati is the city where the first concrete skyscraper of the whole world was built; Ingall's Building, finished in 1903. Another first for the city is that the first professional baseball team ever came from here, the Red Stockings of Cincinnati.

Things to note: Take some basic measures to stay safe on the roads if you're making this road trip in winter; have proper winter tires and take it easy in the traffic.

Longer family-friendly trips from Chicago (Over 5 hours each way)

Mid-semester breaks or any other holidays mean having more time to spend with your family! From visiting incredible zoos to admiring world-famous waterfalls, longer road trips from Chicago can be the ultimate family road trip adventure.

17. Sandusky and Cedar Point Amusement Park

Via fort wayne.

5 hours 40 minutes from Chicago (315 miles)

Why visit Sandusky and Cedar Point Amusement Park with family? This road trip first takes you to one of the biggest cities in Indiana, Fort Wayne, where you can visit amazing family attractions such as a children's zoo and a botanical conservatory.

You'll then continue on to the shores of Lake Erie, to beautiful Sandusky, a place with miles of sunny beaches, lovely nature trails, world-class amusement parks, and interesting arts and architecture.

Driving to Sandusky and Cedar Point Amusement Park from Chicago: Head to Fort Wayne from Chicago on US-30 driving southeast. Then hop onto US-24 towards Toledo and switch to I-90 past Waterville. From here, you will drive on OH-4 to reach Sandusky and Cedar Point.

Our highlights: Fort Wayne Children's Zoo is arguably one of the best zoos in the country. Here, you can have close-up experiences with over a thousand animals housed at the zoo.

Cedar Point Amusement Park is located on Lake Erie Peninsula in Sandusky. It is the second-oldest amusement park in the country, operating since 1870.

Less expensive than its counterparts in the larger cities of the US, Cedar Point contains 70 amazing rides, as well as restaurants, hotels, and a waterpark. Please keep in mind that the waterpark has a separate entry.

The Merry-Go-Round Museum in Sandusky contains a historic 1939 Allan Herschell carousel, beautiful historic artifacts and a gift shop, all related to this world-famous, beloved amusement park ride.

Hungry for know knowledge? The Maritime Museum of Sandusky contains exciting exhibits on boats, pirates, and shipwrecks. This is the perfect for any pirate-loving young members of the family to visit.

Pipe Creek Wildlife Area, consisting largely of wetlands, is a beautiful place to do birdwatching and walks in nature. You can enjoy a nice walk here with your family once you have had your fill of all the amazing rides and museums this road trip has to offer.

Did you know? Cedar Point is known as "The Roller Coaster Capital of the World," thrilling for adventure-seekers of all ages!

Things to know: Visiting Cedar Point Amusement Park may turn out cheaper if you book tickets in advance online, rather than buying at the entrance.

18. St Louis

Via peoria and springfield.

5 hours from Chicago (335 miles)

Why visit St Louis with family? St Louis is a fabulous vacation destination for the family, over a long weekend or a longer stay; the city area contains amazing public parks, as well as several free attractions suitable for families with children.

On the way to St Louis, you can stop at Peoria to enjoy the many family-friendly activities here or explore historic sites and attractions in Springfield.

Driving to St Louis from Chicago: Following I-55 southeast of Chicago, use Exit 163 and then 101 to reach Peoria. After your visit, head south on I-155 to Springfield and switch to I-55 to reach St Louis.

Our highlights: On the way to St Louis, Peoria PlayHouse, a children's museum, is worth visiting. It features interactive exhibits on arts, sciences, and music.

Also on the way, you can explore the historic sites of Springfield, including the Abraham Lincoln Presidential Library and Museum. You and your family can learn about history through interactive displays and films.

A must-stop and exciting activity once in St Louis is visiting Gateway Arch. You can ride the tram up to take in views of the Mississippi River and the surrounding city from the top of this 630-foot tall steel structure, or you can visit an interactive museum on site with history exhibitions covering 200 years.

Citygarden Sculpture Park is another lovely destination for a family with children in St Louis. During your visit, you can enjoy beautiful trees and nature, view art displays, and splash in shallow pools and waterfalls. There are food trucks serving food and drinks as well.

Saint Louis Science Center has over 700 interactive exhibits covering various topics. Both children and adults will enjoy a day of exploration and fun at this center. General admission is free; you only pay for certain special exhibits and the IMAX Theater.

Did you know? St Louis is home to many firsts: the first commercial peanut butter was sold here, the first kindergarten in the US was operated in St Louis, and the city was also the birthplace of products such as ice cream cones, 7up, and ice tea.

Things to note: Should you wish to take the tram to the top of Gateway Arch when visiting here, booking tickets in advance is a good idea, as they're often sold out on the busier days.

READ MORE - Road Trip from Chicago to St Louis

19. Cleveland and Cuyahoga Valley National Park

5 hours 50 minutes from Chicago (365 miles)

Why visit Cleveland and Cuyahoga Valley National Park with family? Visit Cleveland with your family to wander through the many city parks and nature areas of this "Forest City", as Cleveland is lovingly nicknamed.

The surroundings of Cleveland, along the shores of Lake Erie, also include beautiful scenic spots and beaches to enjoy.

Driving to Cleveland and Cuyahoga Valley National Park from Chicago: Heading east from Chicago, follow I-90 all the way to Cleveland and then dip south to visit Cuyahoga Valley National Park.

Our highlights: On the way to Cleveland, you can stop at beautiful Toledo by Lake Erie. At the riverfront, you'll find Imagination Station, a hands-on science museum that has over 300 exhibits for children and curious minds to explore.

Cleveland Museum of Art is a truly fascinating and awe-inspiring place, with over 30,000 works of art spanning 5,000 years of history from around the world.

The Rock and Roll Hall of Fame is fun to explore with the whole family. There are interesting artifacts of famous musicians, such as Jimi Hendrix's guitar and John Lennon's bed. Exhibitions with mature themes are marked, which helps if you visit with children.

At the Cleveland Museum of Natural History, you and the family can enjoy fascinating sections such as a dinosaur exhibit, an earthquake simulator, and a live animal wildlife center.

Cuyahoga Valley National Park, close to Cleveland, is home to beautiful landscapes of forests, rolling hills, farmlands and the winding Cuyahoga River. You can explore and learn about the history of the Ohio & Erie Canal or admire the native plants and wildlife.

Did you know? Superman was born in Cleveland! At least in the sense that the creators of the beloved character created the early Superman prototype while still in high school here, in 1933.

Things to note: I-90 from Chicago to Cleveland is generally in great condition. Of course, be aware of traffic during busy periods, and be prepared for snowy conditions if you're doing the road trip in winter.

Though not required, it is best to book tickets in advance online for attractions such as the Rock and Roll Hall of Fame and the Cleveland Museum of Natural History.

READ MORE - Road Trip from Chicago to Cleveland

20. Minneapolis and the Mall of America

6 hours 20 minutes from Chicago (420 miles)

Why visit Minneapolis and the Mall of America with family? This relatively longer road trip from Chicago offers opportunities to visit Madison and Eau Claire on the way. Minneapolis, known for its parks and lakes, is the perfect mix of urban sophistication and natural beauty.

Just walking around the city is an experience in itself; the city is located on the scenic banks of the Mississippi River, and Minneapolis offers both architectural and natural gems to admire.

Driving to Minneapolis and the Mall of America from Chicago: You will be heading northwest on this road trip from Chicago on I-90, which will take you past Madison and Wisconsin Dells before you merge onto I-94. Follow this interstate to reach Minneapolis and the Mall of America.

Our highlights: On the way, you can make a stop at Eau Claire to visit the Children's Museum. It includes imagination-spurring activities and exhibits, such as a construction zone, a miniature city, Water Works, and a Body Parts area.

Walker Art Center in Minneapolis, connected with the Sculpture Garden, contains exhibits of contemporary art. It can be a great way to introduce children to contemporary art, for the center offers activities especially geared towards children.

Minnehaha Park is an old and popular park in Minneapolis. It contains lovely nature trails, and the stunning Minnehaha Falls waterfall is a well-known attraction.

You could easily spend a whole day exploring the Science Museum of Minnesota, located in St Paul, Minneapolis's twin city across the river. It offers four stories of science-related fun, and the interactive exhibits include a news center, "quackery museum," and IMAX theater.

Mall of America is an amazing shopping mall. As one of the biggest shopping malls in the country, it might not be surprising to see more than 500 stores during your visit to the mall!

There are also 50 restaurants and plenty of great activities for the family - the most famous is the Nickelodeon Universe, an indoor amusement park that fits entirely within this enormous mall.

Things to note: If you wish to visit Minneapolis in winter, there is plenty to do, as well as in the summer months; the city's many indoor attractions take care of that.

Just remember to be cautious if traveling on snowy roads during the winter months, and be prepared with proper equipment.

READ MORE - Road Trip from Chicago to Minneapolis

21. Niagara Falls

Via cleveland.

8 hours 30 minutes from Chicago (560 miles)

Why visit Niagara Falls with family? Niagara Falls is a bucket-list destination and is a great place to visit with family. The drive to Niagara Falls from Chicago is lovely as well, with options to stop at diverse cities and nature areas on the shores of Lake Erie.

At Niagara Falls, not only can you visit the world-famous waterfall and view it on a boat tour, but you can also explore beautiful walks, great museums, a waterpark, and a butterfly conservatory in the city.

Driving to Niagara Falls from Chicago: Although this is a longer road trip on our list, it is quite a straightforward drive. Simply follow I-90 from Lake Michigan shores to Lake Erie coastline and head northeast until you reach Cleveland, and then follow this interstate to Buffalo.

From here, head north on I-190 to reach Niagara Falls.

Our highlights: Cleveland is a great stop on the way from Chicago to Niagara Falls. Cleveland Museum of Natural History has exciting exhibits for people of all ages to enjoy, from a dinosaur exhibit to an earthquake simulation and a wildlife center.

A must-see when visiting Niagara Falls is, of course, the famous waterfall. It is said to be best viewed from the Canadian side or from Skylon Tower, so if you have your passports with you, you can see for yourself and decide!

On the USA side, the Maid of the Mist Boat Tour will take you as close as possible to the thundering waterfalls. You'll don a poncho and sail into the heart of the falls, experiencing the mist, roar, and sheer power of Niagara Falls. Please note that these tours can be seasonal and check before visiting.

Cave of the Winds Tour will take you to the base of the Bridal Veil Falls, where you can explore the wooden walkways just a few feet away from the cascading water. The highlight is the "Hurricane Deck," where you can experience tropical storm-like conditions.

On the Canadian side, the Skylon Tower is a 764-foot-tall observation tower with an arcade and a revolving restaurant. It offers magnificent views of the waterfall and the surrounding city.

While in Canada, you can also visit the Niagara Butterfly Conservatory. Wander through this tropical paradise and view its plants, flowers, and over 2,000 butterflies. You can watch an introductory video and take your time to meander through the garden.

Did you know? Beyond its breathtaking natural beauty, it's also known for daredevil stunts, like tightrope walks across the falls.

Things to note: Niagara Falls waterfall can be magical to view in winter as well! Then, parts of the falls freeze over, and special light displays further increase the enchantment of the falls.

Though not absolutely necessary, booking tickets to Skylon Tower in advance is recommended.

READ MORE - Road Trip from Chicago to Niagara Falls

22. Dollywood, Gatlinburg and Great Smoky Mountains National Park

Via louisville.

9 hours 20 minutes from Chicago (590 miles)

Why visit Dollywood, Gatlinburg and Great Smoky Mountains National Park with family? This scenic road trip will take you south from Chicago, through the states of Indiana and Kentucky, into Tennessee and the Great Smoky Mountains National Park.

he national park is full of stunning trails, viewpoints, and picnic spots. Gatlinburg is an attraction-filled mountain town and a gateway to the nearby national park. You can also visit the Dollywood theme park for fun and thrilling experiences on the way.

Driving to Dollywood, Gatlinburg and Great Smoky Mountains National Park from Chicago: Heading out of Chicago on this longer drive, use I-94 and then I-65 to drive through Indianapolis and then Louisville. Switch to I-75 past Lexington to arrive at your destination in Knoxville.

After your visit, follow I-40 to Dollywood and then Gatlinburg, your gateway to the beautiful Great Smoky Mountains National Park.

Our highlights: In Louisville, there are many unique attractions to visit. These include the Kentucky Derby Museum and Louisville Mega Cavern, where you can enjoy fully underground aerial rope challenges, ziplines, and adventure tours.

Dollywood, owned by Dolly Parton, is full of enchanting attractions, from rollercoaster rides and waterparks to children's playgrounds and country restaurants. What better way to start your family road trip?

Be ready to be astonished at Ripley's Aquarium of the Smokies in Gatlinburg, where you can admire over 10,000 exotic sea creatures spread over ten themed galleries.

Ober Mountain is another fantastic place to visit in Gatlinburg. This mountainside amusement park offers minigolf, wildlife encounters, and hiking in summer, and skiing and snowboarding in winter, and you can enjoy stunning views over the Great Smoky Mountains National Park any season of the year.

Great Smoky Mountains National Park is a vast, beautiful area to explore. Take a picnic in the forest, view wildlife, and explore the rivers and waterfalls. It will be an experience to remember for the entire family.

Did you know? While exploring the Great Smoky Mountains, you may encounter a diverse range of wildlife: there are over 4,000 plants, 65 species of mammals, 200 species of birds, nearly 70 species of fish, and over 80 species of reptiles and amphibians that call this region home.

The national park is also called the "Salamander capital of the world," for the park is home to 30 different species of salamander!

Things to note: Great Smoky Mountains National Park is open year-round, although certain visitor facilities will be closed in winter.

Be extra careful and prepared with the correct equipment on the mountainous roads of this region if making this road trip in winter.

23. Orlando

Via atlanta.

18 hours from Chicago (1,160 miles)

Why visit Orlando with family? This epic, longer road trip from Chicago is the perfect one to do with older children and will take you south through various states, past several buzzing metropolises into sunny Florida and Orlando, a theme park capital of the world.

Take your time with the family to stop at the various cities and nature areas along the way. Enjoy the landscapes of rolling hills around Louisville and the forests of Tennessee and Georgia, and visit the various attractions in cities such as Nashville and Atlanta.

In Orlando, you can spend days and days exploring the various theme parks around the city, the most famous of which are perhaps Walt Disney World Resort, Universal Orlando, and Legoland.

Driving to Orlando from Chicago: The road trip from Chicago to Orlando is the longest on our list, but it is fairly easy to follow as most of the driving will take place on the interstates.

From Chicago, head south through Indianapolis and Louisville on I-65 until you reach Nashville. From here, hop onto I-24 and then I-75 past Chattanooga. This interstate will take you all the way into Florida, Florida's Turnpike will then take you to Orlando.

Our highlights: Atlanta is one of the many amazing places to stop on this road trip. In Atlanta, we recommend visiting the stunning Atlanta Botanical Garden. It is a world of magic and beauty, with unique plant centers, features, and gardens.

Walt Disney World Resort is one of the most popular attractions in Orlando. This entertainment resort complex is a world of magic and fun, home to four theme parks and two water parks.

Universal Orlando also has famous attractions, rides, and live shows. Our favorite places to visit here with family are the Wizarding World of Harry Potter and the Minions section, but maybe you will discover a new favorite!

Did you know? Did you know that Walt Disney World Resort is about the same size as San Francisco? This vast theme park is Florida's most popular tourist destination, attracting almost 60 million people every year. The park offers something to everyone, whatever your age or background!

Things to note: It is a good idea to book tickets to Orlando theme parks in advance to avoid any disappointments or waiting times.

READ MORE - Road Trip from Chicago to Orlando

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