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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

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

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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.

Related Articles

• Last Updated On
• September 5, 2023

35 Best Weekend Getaways From Chicago — Quick Trips!

There’s no better way to discover the heart of America than through Chicago.

It’s the third largest city in the country, where its skyline meets the shoreline.

And your best weekend getaways from Chicago start the moment you arrive.

Its modern architecture, museums, vibrant music scenes, clubs, and outdoor activities are just some of the many things you can see and do here.

But in a city this vast, you may think and ask what to do and where to stay.

It is a question relatable to many.

As a traveler with years of experience, I visited Chicago and explored its beauty.

I stayed in some of the best properties and toured the city.

And to help you out, I compiled and ranked those places based on different and practical criteria.

Are you keen on knowing more?

Then check out my review with tips below.

Best Weekend Getaways From Chicago Compared

For your best weekend getaway in Windy City, review my guide below.

Editor’s Choice

Four Seasons Chicago

Four Seasons Chicago is the best place where you can marvel at the beauty of the city’s skyline.

• Room Variety: 5/5
• Comfort and Cleanliness: 5/5 
• Location: 5/5
• Affordability: 3/5
• Family-Friendliness: 4/5

#2nd Best Choice

Waldorf Astoria Chicago

If you want exclusivity in your stay in Chicago, choose Waldorf Astoria. It has 215 elegant guest rooms inclusive of oversize bathrooms with tubs.

• Room Variety: 4.5/5
• Comfort and Cleanliness: 5/5
• Family-Friendliness: 

#3rd Best Choice

The Peninsula Chicago

It is a five-star hotel that will surely level up your stay in the city.

• Affordability: 2.5/5
• Family-Friendliness: 5/5

Here are the top 35 weekend getaways in Chicago.

1. Four Seasons Chicago (Editor’s Choice)

120 E Delaware Chicago, IL 60611 (312) 280-8800 Visit Website Social Media Open in Google Maps

Ratings Criteria

• Beautiful city view
• Ideal for business or family trip
• Not so spacious lobby area

Chicago is the home to some of the world’s earliest skyscrapers.

And it is still renowned for its inspiring architectural design.

But it doesn’t stop there.

A luxurious stay here is guaranteed with exceptional service, facilities, and amenities.

Its lobby and lounge are designed ideally for entertainment and socializing.

And its restaurant and bar offer nothing but the perfect taste of Chicago. 

What’s more notable is its perfect location where you can revel in food, drinks, art, and music in the city center.

2. Waldorf Astoria Chicago

11 E Walton St Chicago, IL 60611 (312) 646-1300 Visit Website Social Media Open in Google Maps

• Complete amenities
• Spacious rooms
• Quite expensive

If you want exclusivity in your stay in Chicago, choose Waldorf Astoria.

It has 215 elegant guest rooms inclusive of oversize bathrooms with tubs.

Its suites are furnished with terraces where you’ll see the allure of the city’s skyscrapers right before your eyes.

Surrounded by the city’s highlights, you won’t miss a thing.

Go-to spots, shops, restaurants, and bars are just a breeze away.

And after a long day of being a tourist in Chicago, its spa and indoor lap pool is just waiting for you.

Or better yet, stay in your room or sit on the terrace and appreciate the glowing Chicago at night.

3. The Peninsula Chicago

108 E Superior St Chicago, IL 60611 (312) 337-2888 Visit Website Social Media Open in Google Maps

• Unsurpassed service
• Nice location
• Too expensive for what it offers

Whether it’s a weekday or weekend getaway you’re in, The Peninsula Chicago is just a step away.

Each part of it is designed for your perfect Chicago getaway.

Everything is incomparable, from its sophisticated rooms and suites to its fancy restaurant and rooftop spa.

Do you intend to stay longer?

Think about it as your third night is on them when you book at least three consecutive nights.

That’s a pretty reasonable offer, quite hard to resist.

Moreover, almost every must-visit spot is just a walk away from this property.

4. Grand Geneva Resort & Spa

7036 Grand Geneva Way Lake Geneva, WI 53147 (262) 248-8811 Visit Website Social Media Open in Google Maps

With its luxurious facilities, this 1,300 acres of AAA Four-Diamond resort is an excellent alternative to Waldorf Astoria Chicago and The Peninsula Chicago.

This resort encompasses 1,300 acres of countryside in Wisconsin.

It features two lodging options: The Grand Geneva and the Timber Ridge.

By car, Grand Geneva Resort & Spa is 1 hour and 27 minutes away from Chicago.

Enjoy an incredible getaway with the family in this popular resort.

The kids will enjoy the resort’s health and fitness facility, with its programs crafted especially for them.

They can participate in many kid-friendly activities in the adventure center, too.

If they prefer outdoor activities, they can go horseback riding or meet the animals in the zoo instead.

As for the adults, how does a spa treatment sound?

If you opt for physical activities, you can play water sports in Timber Ridge’s park or go wall climbing in the gym.

5. Milwaukee

Milwaukee, WI (414) 286-2489 Visit Website Social Media Open in Google Maps

This city in Wisconsin encompasses over 61,000 acres of land on Lake Michigan’s western shore.

It features breweries, museums, and event venues.

If you’re coming from Chicago, you can reach Milwaukee in 1 hour and 27 minutes.

Here’s one cool overnight trip you won’t forget.

Milwaukee has everything you need for the best weekend adventure.

Want some history?

Check out the Milwaukee Public Museum, with its beautiful recreation of the city at the turn of the 20th century.

If you’re more into nature, the Mitchell Park Horticultural Conservatory is the perfect destination.

It features three domes that each function as a greenhouse and botanical garden.

Enjoy the blushing peonies and firs for the complete nature experience.

Recommended Hotel: The Pfister Hotel

Related: Fun Day Trips From Milwaukee

Related: Hotels in Chicago

6. Indiana Dunes National Park

1215 North State Road 49 Porter, IN 46304 (219) 395-1882 Visit Website Social Media Open in Google Maps

This park stretches for 15,349 acres in northwestern Indiana.

It’s home to a visitor center, park trails, and historical structures.

The travel time from Chicago to Indiana Dunes National Park is 42 minutes.

Are you looking for short trips from Chicago for your weekend getaway with friends?

Head to the Indiana Dunes National Park.

Hike the Dunes Succession Trail, with its vast array of paths perfect for adventurers.

Wear comfortable shoes because you’ll have to walk sandy and wooden trails at the same time.

If you’re up for a challenge, climb 192 feet to the top of Mount Tom.

You’ll get rewarded with stunning views of the dunes and the lake.

Recommended Hotel: Spring House Inn

Madison, WI (608) 255-2537 Visit Website Social Media Open in Google Maps

Madison is the capital city of Wisconsin.

It’s on an isthmus surrounding Mendota, Monona, Waubesa, and Kegonsa lakes.

It’s also home to botanical gardens and architectural gems like the Wisconsin State Capitol.

You can reach Madison from Chicago in 2 hours and 18 minutes if you use a vehicle.

Madison is one of the best places near Chicago for vacation.

Visit any of the city’s nine national historical landmarks, including Jacobs I, a single-family home constructed in 1937.

Not much of a history buff?

Marvel at Jacobs I’s architecture instead.

The home built by architect Frank Lloyd Wright has been touted as the first Usonian home.

The Wisconsin State Capitol is a must-see, too, with its majestic dome and elegant gilded bronze statue on top.

Recommended Hotel: The Madison Concourse Hotel

Holland, MI (616) 355-1370 Visit Website Social Media Open in Google Maps

Spanning over 11,000 acres, Holland is the largest city in Ottawa and Allegan counties.

It’s a popular tourist destination for its rich Dutch heritage.

From Chicago, Holland is only 2 hours and 33 minutes away by car.

If you’re looking to have the perfect weekend getaway, Chicago and its nearby areas offer many options.

Chicago has beautiful parks and skyscrapers.

Meanwhile, Holland has deep Dutch roots evident in many of its landmarks.

In the Windmill Island Gardens, you’ll find the last working mill allowed to leave The Netherlands in 1964.

Check out Nelis’ Dutch Village, too.

The amusement park is home to a gorgeous reproduction of an 1800s Dutch village.

Recommended Hotel: CityFlatsHotel Holland, Tapestry Collection by Hilton

9. Wisconsin Dells

Wisconsin Dells, WI (608) 254-4636 Visit Website Social Media Open in Google Maps

Nestled on the Wisconsin River, this city stretches over 5,200 acres in Adams, Columbia, Juneau, and Sauk counties.

It features a wide array of water parks and nature spots.

You can reach Wisconsin Dells in 2 hours and 56 minutes if you’re driving a car from Chicago.

You and the kids will agree this is one of the best getaways in Chicago and nearby.

After all, who doesn’t like swimming in beautiful blue waters and going down long slides?

If you get tired of swimming in water parks, go on a duck boat tour instead.

Marvel at the beautiful creatures while floating on Lake Delton under the blue Wisconsin skies.

Recommended Hotel: Hilton Garden Inn Wisconsin Dells

Related: Restaurants in Wisconsin Dells, Wisconsin

Related: Weekend Vacations in Illinois

Geneva, IL (630) 232-7494 Visit Website Social Media Open in Google Maps

Geneva is in Kane County, located on the western side of Chicago.

It features an extensive bike trail system and historical sites, some dating back to the 1800s.

It’s a 49-minute drive from Chicago to Geneva.

Geneva is just the place to be if you want to bond with your significant other.

The city is one of the best romantic getaways from Chicago for its natural beauty.

Take a stroll in the beautiful Fabyan Forest Preserve.

Amid the lush greenery stands the majestic Fabyan Windmill, built between 1850 and 1860.

Check out the Fabyan Japanese Garden, too.

It’s a lovely oasis with a small pond and flora that stand out.

Recommended Hotel: Comfort Inn & Suites Geneva- West Chicago

11. Fox River Valley

Fox Valley Aurora, IL 60504 (630) 256-4636 Visit Website Social Media Open in Google Maps

Also known as the Fox Valley, this region extends from Antioch in northern Illinois to Ottawa in the south.

It’s home to the Fox River Trail, green spaces, and water bodies.

The travel time from Chicago to the Fox River Valley is 42 minutes.

This place will make any traveler’s list of inexpensive weekend getaways near Chicago.

The Fox River Valley, after all, is pure nature anyone can explore.

Bike a portion of the 32-mile Fox River trail for stunning views of Carpenters Dam and Tyler Creek.

You can rent a kayak if you prefer a water adventure.

Soak in the gorgeous nature views while gliding along the Fox River.

Recommended Hotel: Best Western Oswego Hotel

12. Harbor Country

Three Oaks, MI (269) 469-5409 Visit Website Social Media Open in Google Maps

This region consists of eight towns in southwest Michigan: New Buffalo, Three Oaks, Lakeside, Harbert, Michiana, Grand Beach, Sawyer, and Union Pier.

It features gorgeous beaches and wineries.

You can get to Harbor Country from Chicago in 1 hour and 12 minutes.

Harbor Country differs from many Chicago weekend getaways.

Unlike your cheap Chicago vacations, this one entails a bit of shelling out money.

After all, Harbor Country is an upscale weekend getaway destination.

Think of it as the Hamptons of New York or the Cape Cod of Boston.

But even if you’d need to shell out a bit, it’s worth it.

You can enjoy the region’s beaches with delicious wine.

Then spend the night in a luxurious bed and breakfast with amenities.

Recommended Hotel: Fairfield Inn and Suites New Buffalo

13. St. Joseph

St. Joseph, MI (269) 983-5541 Visit Website Open in Google Maps

This city stretches for over 3,000 acres on the shores of Lake Michigan.

It’s home to the sandy Silver Beach and parks.

You can get to St. Joseph in 1 hour and 35 minutes if you’re coming from Chicago.

If you prefer cheap vacations from Chicago, head to St. Joseph.

The city is a nature oasis you can enjoy anytime.

Have a picnic on the Silver Beach shore and enjoy the beautiful landscape.

If you prefer a more strenuous activity, go swimming in the gorgeous blue waters.

Are you a fitness enthusiast?

Go on a hike for your dose of exercise in Tiscornia Park.

Recommended Hotel: The Inn at Harbor Shores

14. South Haven

South Haven, MI (269) 637-0700 Visit Website Social Media Open in Google Maps

This city encompasses 2,240 acres of land in Van Buren and Allegan counties.

It features a gorgeous harbor and beaches.

If you’re driving from Chicago, you can reach South Haven in 2 hours and 2 minutes.

Commune with nature in this popular tourist destination.

The city’s seven public beaches aren’t just the perfect spots for swimming.

They make for beautiful pictures, too, with their gorgeous sea waters and shores.

If you get tired of the beach, check out the beautiful South Haven harbor.

Enjoy the stunning water views, then walk downtown for the perfect meal.

Recommended Hotel: Hampton Inn South Haven

Gurnee, IL (847) 599-7500 Visit Website Social Media Open in Google Maps

This village borders Waukegan in the Chicago metropolitan area.

Located 35 miles from Chicago, it’s home to the Six Flags Great America amusement park.

If you drive a vehicle from Chicago, you can get to Gurnee in 50 minutes.

Enjoy pure family fun in Gurnee, with its amusement park known for its adrenaline-pumping rides.

Try all 17 of Six Flags’ heart-stopping roller coasters for the complete adventure.

But if you’re not a thrill-seeker, don’t worry.

You can enjoy the park’s entertaining shows instead.

Or just explore Gurnee Mills, a mall that features over 170 stores.

Recommended Hotel: Country Inn & Suites by Radisson, Gurnee, IL

16. South Bend – Indiana

South Bend Indiana, United States (574) 233-0311 Visit Website Social Media Open in Google Maps

An hour and 44-minute drive from Chicago lies South Bend, Indiana.

It’s a great day trip destination to explore more of what’s outside Chicago.

This city is home to the University of Notre Dame, a prestigious university known for its gold-domed main building.

And if you proceed to the city center, you’ll witness its thriving art scene.

There lies the Studebaker National Museum which has numerous displays of classic cars.

Morris Performing Arts Theater, a 2,564-seat concert hall, is a shouldn’t-miss part, too.

Surely you’ll see all the must-sees in the city within a day; a perfect place for your weekend getaway from Chicago.

Recommended Hotel: Antioch Inn & Suites Near Gurnee

17. Lake Geneva

Lake Geneva, WI (262) 248-3911 Visit Website Social Media Open in Google Maps

Located on Geneva Lake, this resort city features gorgeous beaches, parks, and Gilded Age mansions.

It is 65 miles northwest of Chicago.

If you use a car, you can get to Lake Geneva in 1 hour and 24 minutes.

Head to Lake Geneva, and you’ll see why it’s one of the best long weekend trips from Chicago.

Although small in size, the city has a lot to offer the traveler.

Explore Shore Path for stunning views of spectacular mansions, some dating back to the 1800s.

Check out the Stone Manor built by real estate magnate Otto Young in 1899.

Blackpoint, constructed in 1888 by Chicago beer baron Conrad Seipp, has 74 species of evergreen trees in front of his mansion.

If you’re not into architecture, you can immerse in nature instead.

Ride a boat on the 5000-acre Geneva Lake and soak in the beautiful views.

Recommended Hotel: Mill Creek Hotel

18. Turkey Run State Park

8121 Park Road Marshall, IN 47859 (765) 597-2635 Visit Website Open in Google Maps

This park, created in 1916, is Indiana’s second state park.

It stretches for 2,382 acres of land in Parke County.

It’s also home to historical sites, a pool, and public sitting areas.

If you use a vehicle, the travel time from Chicago to Turkey Run State Park is 3 hours.

You won’t run out of things to do in this park.

Experience nature at its finest while hiking a portion of the 14 miles of trails with varying degrees of difficulty.

Are you a history enthusiast?

The park has individual sites listed on the National Register of Historic Places.

Check out the Lusk Home and Mill Site, which date back to 1822 and 1826, respectively.

The Richard Lieber Log Cabin, built in 1848, is a must-see, too.

Recommended Hotel: Turkey Run Inn & Cabins

19. The American Club Resort Hotel

419 Highland Drive Kohler, WI 53044 (800) 344-2838 Visit Website Social Media Open in Google Maps

Built in 1918 as a male dormitory for Kohler employees, this lodging institution is now a five-star hotel that offers wellness and recreational opportunities.

By car, The American Club Resort Hotel is 2 hours and 22 minutes away from Chicago.

Who says you can’t have some incredible me-time in one place?

At The American Club Resort Hotel, you can.

Have the ultimate relaxing experience at the Kohler Waters Spa.

After your spa, enjoy your favorite book in the hotel’s reading area.

You can also check out the Kohler Design Center instead, with its stunning bathroom designs.

Enjoy an upscale meal in The Immigrant for the perfect bonding moment with yourself.

20. Whistling Straits

N8501 Lakeshore Road Sheboygan, WI 53083 (800) 444-2838 Visit Website Social Media Open in Google Maps

This luxury golf resort, owned by Kohler Company, is along the Wisconsin coastline.

The resort consists of two golf courses: the Straits and the Irish.

You can reach Whistling Straits in 2 hours and 28 minutes if you travel by car from Chicago.

If you love golf, Whistling Straits should be your go-to place.

Enjoy state-of-the-art 36-hole links-style golf courses set against a beautiful nature landscape.

Whistling Straits offers incredible views of Lake Michigan and rolling hills.

The Irish, meanwhile, will transport you to the gorgeous European country with its rugged coastline and smooth grassy terrain.

You won’t just get to play your favorite sport here.

Recommended Hotel: Harbor Winds Hotel

21. Parke County

Parke County, IN (765) 569-3394 Social Media Open in Google Maps

This rural county stretches for over 284,000 acres of land along the Wabash River.

It lays claim to being the Covered Bridge Capital of the World.

If you’re coming from Chicago, Parke County is 3 hours and 26 minutes away by car.

Do you love architecture?

Go on a weekend getaway to Parke County, then.

You need more than enough time to visit the county’s 31 covered bridges, each with its unique architectural design.

The Portland Mills Covered Bridge is a must-see.

Built in 1856, it’s a single-span Burr Arch truss-covered bridge that’s also the second oldest in the county.

Check out the Jackson Covered Bridge, built on a base of hewn stone in Rockport.

Constructed in 1861, it’s the oldest standing bridge built by the acclaimed J.J. Daniels.

Galena, IL (815) 776-9200 Visit Website Social Media Open in Google Maps

This city in Illinois is the largest in Jo Daviess County.

Located in an unglaciated area in the northwest portion of the state, it’s famous for its rolling hills and 19th-century architecture.

Galena is a 3-hour drive from Chicago.

Although a city by classification, Galena exudes a small-town vibe, making it a popular destination.

Picture gorgeous red-brick structures lining the main road where traditional carriages occasionally ply.

Go kayaking along the river to experience stunning views of nature wherever you look.

You can walk through native prairies and interact with goats here, too.

Cap off your weekend with a challenging game of golf on any of the city’s 11 picturesque courses.

Recommended Hotel: Country Inn & Suites by Radisson, Galena, IL

23. Dubuque

Dubuque, IA (563) 589-4100 Visit Website Social Media Open in Google Maps

Nestled along the Mississippi River, Dubuque encompasses over 19,000 acres of land at the junction of Iowa and Wisconsin.

It’s a go-to place for its unique architecture and historical sites.

You can get to Dubuque from Chicago in 3 hours and 16 minutes by car.

Dubuque is heaven for architecture and history buffs.

Head downtown, and you’ll find the Dubuque County Courthouse.

It’s in the Beaux Arts architectural style, built from 1891 to 1893.

The Holy Ghost Catholic Church in the North End is a must-see, too.

Formed in 1896, the beautiful church’s Romanesque Revival style stands out.

In the South End, check out St. Raphael’s Cathedral.

The church traces its roots way back in 1833.

Enjoy its Gothic Revival Style amid Dubuque’s nature landscape.

Recommended Hotel: Hotel Julien Dubuque

24. Field of Dreams

28995 Lansing Road Dyersville, IA 52040 (563) 875-8404 Visit Website Social Media Open in Google Maps

Built in 1988 for the movie Field of Dreams, this baseball field now functions as a sports venue and pop culture destination.

It’s also home to a souvenir shop and a 2,600-square-foot barn that serves as an event center.

By car, Field of Dreams is 209 miles away from Chicago. So you can get to the iconic baseball field in approximately 4 hours.

This isn’t your ordinary baseball field.

It has pop culture significance as the filming site of the Academy Award-nominated movie Field of Dreams.

So when you get to the place, you can also tour the Kinsella family house as shown in the movie.

You can also purchase official Field of Dreams apparel from Baseballism, the movie’s on-site official retail store.

Spend a night in the newly remodeled three bed-room farmhouse for the complete movie experience.

Recommended Hotel: Super 8 by Wyndham Dyersville

25. Ann Arbor

Ann Harbor, MI (734) 794-6000 Visit Website Social Media Open in Google Maps

This city stretches for over 18,600 acres in the Midwestern state of Michigan.

It is home to the University of Michigan, museums, and parks.

The travel time from Chicago to Ann Arbor is 4 hours and 33 minutes by car.

Ann Arbor has everything you need for the perfect weekend getaway.

The University of Michigan Museum of Art will give you a one-of-a-kind artistic experience, with its collection spanning over 150 years.

If you’re more of a history buff, the Kelsey Museum of Archaeology is just the place for you.

It’s home to over 100,000 artifacts, including mummies.

Don’t worry if you’re not much of a museum-goer.

Ann Arbor has gorgeous parks you can explore, too.

Go paddle-boarding on the Huron River for fantastic views of the Michigan skies, flora, and fauna.

You can also hike the trails of Gallup Park and explore its 69 acres of open green spaces and water bodies.

Recommended Hotel: Graduate Ann Arbor

26. Traverse City

Traverse City, MI (231) 947-1120 Visit Website Social Media Open in Google Maps

This city stretches for over 5,500 acres in Grand Traverse and Leelanau counties.

It’s the largest city in the Northern Michigan region.

It’s home to beaches, at least 30 public parks, and historical sites.

By car, you can get to Traverse City in 5 hours and 8 minutes if you’re coming from Chicago.

The trip from Chicago to this city may take longer than your usual day trips outside.

However, it’s worth it.

Immerse in history with a tour of landmark sites, such as the City Opera House and Novotny’s Saloon.

Take the kids to Indian Woods Park, where they can also use playground equipment in a beautiful nature landscape.

If you want some physical activity, try hiking.

Just take your pick from the over 30 trails that meander through gorgeous woodlands and open green spaces in the city.

Recommended Hotel: Country Inn & Suites by Radisson, Traverse City, MI

27. Louisville

Louisville KY (502) 379-6109 Visit Website Social Media Open in Google Maps

Nestled on the Ohio River, Louisville is Kentucky’s largest city.

It features boxer Muhammad Ali’s home, some Fortune 500 companies, and a wide array of dining options.

If you’re driving from Chicago, you can reach Louisville in 4 hours and 47 minutes.

Experience the big city life in Louisville.

Marvel at the gorgeous skyscrapers that jut into the Kentucky skies.

The 400 West Market stretches 549 feet above the ground.

A close second is the National City Tower, with a height of 512 feet.

Then head to Mall St. Matthews for your shopping needs.

The mall features over 140 specialty retailers, which means you’re bound to find something to take home.

Recommended Hotel: The Brown Hotel

28. St. Louis

St. Louis, MO (314) 421-1023 Visit Website Social Media Open in Google Maps

This city is along the Mississippi River.

Commonly known as the Gateway to the West, the city has independent frontier-town roots and a vibrant blues music scene.

From Chicago, St. Louis is 4 hours and 35 minutes away by car.

If you love history, don’t miss out on St. Louis.

The city is home to majestic structures, some of them dating way before the Civil War.

Drop by the Basilica of St. Louis, built between 1831 and 1834.

The Christ Church Cathedral is a must-visit, too, with its Gothic Revival style completed in 1867.

Don’t forget to check out the arch that gave St. Louis its Gateway to the West moniker.

Completed in 1965, the long arch is also an architectural beauty, standing 630 feet tall.

Recommended Hotel: Angad Arts Hotel

Related: Fun Day Trips From St Louis

Zion, IL (847) 746-4000 Visit Website Social Media Open in Google Maps

This city encompasses over 6,300 acres of land in Lake County at an elevation of 187 meters.

It boasts beautiful parks and historical structures.

You can get to Zion in 58 minutes if you’re coming from Chicago.

Have the ultimate nature experience in Zion, with its 24 parks offering incredible views of flora.

Go biking through Edina Park, with its serene pond and open spaces

Hermon Park is perfect for picnics, with its tall trees surrounding green grass.

If you still have energy for more workout activities, hike a portion of the trail that cuts through Carmel Park.

You’ll get stunning views of the clear Illinois skies and lush greenery.

Recommended Hotel: The Inn On Sheridan

30. Elkhart Lake

Elkhart Lake, WI (920) 876-2231 Visit Website Social Media Open in Google Maps

This village in Sheboygan County runs along Elkhart Lake.

It’s famous for its natural beauty, museums, and road race events.

If you drive from Chicago, you can reach Elkhart Lake in 2 hours and 30 minutes.

You’ll enjoy your weekend getaway in Elkhart Lake with the tons of activities you can do here.

Hike the 3.35-mile segment of the Ice Age National Trail for beautiful views of rolling hills.

If you get tired of hiking, visit Road America, which stretches over 4 miles around the lake.

The track that has been around since the 1950s continues to host racing events.

Time your visit to the city based on the racing schedule so you can attend one.

Recommended Hotel: Baymont by Wyndham Plymouth

31. Richland County

Richland County, WI (608) 647-8821 Visit Website Social Media Open in Google Maps

This county stretches for 376,960 acres in southwestern Wisconsin.

Richland County is home to Frank Lloyd Wright architecture, parks, and museums.

Richland County is 3 hours and 37 minutes away from Chicago by car.

Richland County has something to offer, whether you’re a history buff or a nature enthusiast.

Check out the Albert D. German Warehouse, designed by acclaimed architect Frank Lloyd Wright in 1915.

You can unwind at Alana Springs Campground, where you can set up your tent amid gorgeous nature.

The Pier County Park is a must-see, too, with its layered and blocked sandstone rising for about 60 feet.

Recommended Hotel: Ramada by Wyndham Richland Center

Related: Best Weekend Getaways From Minneapolis

32. Door County

Door County, WI (920) 743-5511 Visit Website Open in Google Maps

Situated on a peninsula between Green Bay and Lake Michigan, Door County is home to many beaches and parks.

Chicago is 244 miles away from Door County.

If you travel from Windy City by car, you can get to Door County in 3 hours and 48 minutes.

Door County has a little bit of everything for everyone.

For the nature buff, Cave Point County Park is a must-visit.

The park is home to gorgeous underwater caves and limestone cliffs you can explore.

For the history enthusiast, check out the Eagle Bluff Lighthouse, built in 1868.

The Door County Maritime Museum is a great destination, too, with its comprehensive exhibits on Great Lakes history.

Door County even has something for the wine lover.

Enjoy delightful wines made from California grapes in Stone’s Throw Winery.

Recommended Hotel: Gordon Lodge

33. Vilas County

Vilas County, WI (715) 479-3600 Visit Website Open in Google Maps

This county stretches for 548,480 acres in northern Wisconsin.

It’s home to nearly 90 scenic forest trails and over 1,300 lakes.

From Chicago, the drive to Vilas County will take you 5 hours and 44 minutes.

It’s quite a long journey from Chicago to Vilas County.

But when you get to the place, you’ll conclude the trip is worth all your time and effort.

After all, the place is a nature oasis.

Go boating on Eagle Lake and soak in the gorgeous lush greenery around you.

You can hike the 1.5-mile loop near Eagle River afterward.

Whatever you do, you’re in for a beautiful nature immersion.

Recommended Hotel: Hiawatha Lodge Inn

34. Shawnee National Forest

Herod, IL 629646 (618) 253-7114 Visit Website Social Media Open in Google Maps

Nestled in southern Illinois between the Ohio and Mississippi Rivers, this national forest stretches for 289,000 acres.

It’s home to forests, lush canyons, and ridges.

The travel time from Chicago to Shawnee National Forest is 5 hours and 25 minutes.

Travel to one of nature’s wonders for the perfect weekend trip.

Experience Cedar Lake a different way, on board a beautiful horse and under the gorgeous Illinois skies.

You can hike in the park if you prefer to walk.

How about exploring a portion of the 160-mile River Trail that will take you to gorgeous forest streams and greenery?

Recommended Hotel: Baymont by Wyndham Marion

35. Pictured Rock National Lakeshore

N8391 Sand Point Road Munising, MI 49862 (906) 387-3700 Visit Website Social Media Open in Google Maps

This tourist destination encompasses the south shore of Lake Superior in Michigan.

It’s home to unusual sandstone formations and shipwrecks.

You can reach Pictured Rock National Lakeshore in 6 hours and 12 minutes by car.

This is one of the best weekend getaways from Chicago for a reason.

The place is a visual treat, with its magnificent cliffs.

The cliffs can go as high as 200 feet above sea level, with formations ranging from human profiles to castle turrets.

Bring your camera because you’ll want to take pictures of everything here.

Recommended Hotel: Comfort Inn & Suites Munising – Lakefront

Getaway Guide 

Comparing destinations: which one is right for you.

Knowing the pros and cons of each destination will help you decide which one is ideal for you.

And remember that your preference also plays a vital role in picking what’s best.

The Four Seasons Chicago lives up to what it promises guests: a luxurious and relaxing stay.

But for years in business, some parts need an update already.

Meanwhile, Waldorf Astoria Chicago is indeed a luxury hotel with unsurpassed facilities and amenities, but it also comes with a high cost.

On the other hand, The Peninsula Chicago has everything you need and expect from a five-star hotel.

But just like other luxury hotels, it’s also quite expensive.

Finally, Grand Geneva Resort & Spa has an array of activities for fun and relaxation for everyone.

But its customer service could be better. 

How I Picked The Destinations 

With years of experience as a blogger and traveler, I have learned much about picking the best destination and property to stay.

I thoroughly researched where to stay and what to do in Chicago.

My fellow travelers also gave reliable suggestions, and when I got there, I tried them myself.

My research and experience in the city strengthen my conclusion of what’s best.

Our Property Rating Method 

I rate these properties based on the following criteria:

• Room Variety: I use this to rate the room options offered by every property. What room types are available? Can it accommodate different budgets, group sizes, and preferences? I ask myself these questions when evaluating the property’s room variety. 
• Comfort and Cleanliness: This measures the overall cleanliness and comfort of the accommodations. Does it have comfortable beds? Are the rooms spotless and dust-free? These are important factors I consider when rating comfort and cleanliness. 
• Location: This is used to evaluate how convenient and accessible the property is. How close is it to the attractions? Are there good public transportation options near the location? Is it easily accessible for families? These questions are important when I rate the location of every accommodation. 
• Affordability: I use this to evaluate the property’s affordability. Are the room rates reasonable? Does the property have any additional fees? Does the property offer discounts or packages? I ask myself this in order to rate affordability. 
• Family-Friendliness: This evaluates the family-friendliness of each property. Does it offer babysitting services and children’s activities? Does it have connecting rooms for families? I use these questions to rate the family-friendliness of the property. 

Frequently Asked Questions 

What are cities 3 hours from chicago.

Milwaukee, Rockford, and Michigan City are within a two-hour drive from Chicago.

How Far Is Lake Geneva From Chicago, And What Can I Do There?

Lake Geneva is about a 90-minute drive from Chicago. It offers a range of activities including boating, fishing, golfing, hiking, and skiing in the winter. The area is also home to several spas and wellness centers.

A stay in a property with a perfect location will give you nothing but only the best weekend getaways from Chicago. 

My Waldorf Astoria Chicago experience was beyond impressive.

I had a relaxing and with-a-view room.

The excellent location for shopping and restaurants was what I love most about The Peninsula Chicago.

And the variety of activities I did at Grand Geneva Resort & Spa was immense.

My favorite was the view of the calm lake

But the top pick of the bunch is the Four Seasons Chicago.

The welcoming staff, fancy and modern facilities, and countless amenities made me enjoy my stay. 

During my stay at the Four Seasons Chicago, I particularly enjoyed their renowned spa, indulging in a rejuvenating massage and a soothing swim in the indoor pool.

My family and I savored the diverse breakfast options, with my children relishing the fluffy pancakes. 

When exploring the surrounding areas, we appreciated the hotel’s proximity to the iconic Magnificent Mile, making it easy to shop and dine.

My kids had a blast at the nearby Navy Pier, where we enjoyed a fun-filled afternoon. 

Four Seasons Chicago offered the ideal blend of relaxation and adventure for our family getaway.

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Best Weekend Getaways From Chicago

By Nina Kokotas Hahn

All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

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 Olivia Morelli

By Matt Ortile

By Jessica Puckett

By Juliet Kinsman

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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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.

9 weekend getaways from Chicago

Whether you want waterparks, historic districts, or nature hikes.

Chicago is a timeless vacation destination for countless reasons: fascinating culture, history, shopping, entertainment, and maybe a slice of deep-dish pizza (or three). A trip to the Windy City can only be made better with a quick detour outside of its city limits. Whether you’re a local looking for an escape to recharge or a visitor who wants to see what else the Midwest has to offer, we've curated a list of the top nine weekend getaways within driving distance of Chicago.

The outdoorsy paradise: Starved Rock State Park, IL

1.5 hours from chicago by car or 2 hours by train.

If you want to ditch the city lights for a more natural scene, Starved Rock State Park on the Illinois River has wildlife, waterfalls, wooded hiking trails, and scenic rock formations. Spend the day on a scenic hike full of cascading waterfalls and bald eagles sightings. If you have more time to explore the area, take a guided fishing excursion or go kayaking before heading to a nearby winery. While you can camp at the Starved Rock State Park Campground , the Grand Bear Resort at Starved Rock is another option that offers standalone cabins and access to the resort’s family-friendly indoor waterpark.

The cultural immersion: Holland, MI

2 hours and 40 minutes from chicago by car or 3 hours by train.

Immerse yourself in Dutch culture without flying all the way to Europe with a visit to Holland, MI. Roam the Windmill Island Gardens before a bit of shopping at the De Klomp Wooden Shoe & Delft Factory . More highlights include the Nelis' Dutch Village , Holland Harbor Lighthouse (locally known as Big Red), and the DeGraaf Nature Center . If you love flowers, don't miss the annual Tulip Time Festival in May. Book a stay at the modern Haworth Hotel & Conference Center or the Centennial Inn , if you’re looking for cozier vibes.

The museum lover’s dream: Milwaukee, WI

2 hours from chicago by car or 1.5 hours by train.

Well known for its breweries and basketball team, Milwaukee understandably attracts beer-loving sports fans. But there is much more to Wisconsin's largest city: a diverse cultural scene, rich history, shopping, and entertainment. Many art galleries and museums—including the impressive Harley Davidson Museum , Betty Brinn Children's Museum , and the North Point Lighthouse—are worthwhile stops. Don’t forget to check out Holler House , an authentic tavern with the oldest bowling alley in America. Then try your luck at the Potawatomi Hotel and Casino , or go bar hopping to sample some more local brews. There are plenty of hotels in the area, but you can’t go wrong with a stay at Aloft Milwaukee Downtown , thanks to its proximity to the city’s best restaurants and nightlife.

The beach trip: Michigan City, IN

1 hour from chicago by car.

Michigan City is only an hour from Chicago and presents the perfect blend of city life and natural surroundings. Visit the shores of Lake Michigan and the Indiana Dunes National Park , both of which contrast beautifully with the vibrant urban side of the city. Washington Park's lovely lighthouse and pier are a hot spot come sunset. And when it comes to entertainment, there are restaurants, art galleries, breweries, and a massive outlet mall to check out. Shady Creek Winery is a great locale for a long, leisurely lunch after pedaling the picturesque Calumet Bike Trail through the lakefront national park. Book a stay at a local vacation rental, like this family-friendly, eight-bedroom retreat just steps from the shore, or at the Hampton Inn & Suites Michigan City , which sits right outside of the downtown area.

The city adventure: Indianapolis, IN

3 hours from chicago by car or 1 hour by plane.

Indianapolis is a city full of attractions like the Indianapolis Motor Speedway , the Children's Museum of Indianapolis , and the Indianapolis Zoo . For something a little bit different, try duckpin bowling at the Fountain Square Theater Building or take a self-guided scavenger hunt around town for an unexpected way to take in the sights. Expect a buzzy nightlife with lots of late-night options, including live music at bars. Start the night off at a jazz club, a beer garden, or a trendy restaurant, then dance the night away at a trendy nightclub. Set the scene for a weekend getaway by booking a stay at the Bottleworks Hotel —the building was originally a Coca Cola bottling company and the hotel bar is a local favorite.

The small-town feel: Geneva, IL

1 hour and 20 minutes from chicago by car or 1 hour by train.

Welcome to Geneva , a lovely city with major European vibes. Indulge in some locally-made chocolate and ice cream, admire the street murals and sculptures and do some shopping before taking a leisurely stroll along the Fox River Trail. Make sure you stop by the Fabyan Windmill for some photos before checking out the Fabyan Villa Museum with its beautiful gardens, private zoo, and charming farmhouse. Set your home base at The Herrington Inn & Spa , which is located right on the waterfront.

The family-friendly getaway: Wisconsin Dells, WI

3.5 hours from chicago by car or train.

Known for its indoor and outdoor waterparks, Wisconsin Dells is a great year-round getaway for those with kids in tow. This city has a seemingly never-ending rotation of theme shows, amusement parks, wildlife parks, zoos, and luxury shopping. All aboard the small gauge train at the Riverside and Great Northern Railway , which starts at a quaint station before weaving through the scenic countryside. And you don't need kids to join in the fun at mini golf, go-karts, and the MACS-Macaroni and Cheese Shop . Kids will love a hotel stay on-site at one of the many waterparks. Check out Kalahari Resort if you want to keep water slides just a few steps away.

The urban nature retreat: Rockford, IL

1.5 hours from chicago by car.

Even though Rockford is the third largest city in Illinois, the pace of life is peaceful, especially at the Anderson Japanese Gardens and Rock Cut State Park . There's an impressive collection of museums and the Nicholas Conservatory and Gardens is spectacular day and night. If you’re traveling with a group, take your picks of things to do, from the Prairie Street Brewhouse and the Coronado Theatre to the Discovery Center Museum . For water views from your room, book a stay at the Embassy Suites by Hilton Rockford Riverfront .

The history lesson: Galena, IL

2.5 hours from chicago by car.

Take a step back in time and surround yourself in the charm of Galena and its storied past. Once home to President Ulysses S. Grant, this town along the Mississippi River has beautiful architecture and an immersive museum dedicated to the president and town history, complete with a working blacksmith shop where an onsite historian will walk you through the details. See the city from a hot air balloon during the day and catch Amelia's Under the Lamplight Dinner Theater , which puts on outstanding musical and comedy performances, at night. Haunted tours , magic shows, and goat yoga are all on the agenda when you head to Galena for a mini break from Chicago. If you want to stay in the heart of the historic district, check into the Brierwreath Manor Bed and Breakfast .

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The Best Weekend Escapes from Chicago

Whether your idea of unwinding involves wine tasting, hopping onto a boat, wandering antique stores or strolling art galleries, we’ve got you covered.

While there’s plenty to do in Chicago , sometimes you need a weekend away from the hustle and bustle. Whether your idea of unwinding involves wine tasting, hopping onto a boat, wandering antique stores or strolling art galleries, there are plenty of getaways surrounding Chicago where you can do just that—and they’re all within a five-hour drive. Blessed with the Great Lakes and many smaller, inland lakes, as well as rivers, chances are you will wake up by the water.

Getting away from the city, however, doesn’t mean losing access to culture. In fact, many of these small towns near Chicago thrive on fine dining, art and natural parks that will make you want to whip out your phone to capture the striking images. Be sure to pack hiking boots, too, to explore gorgeous trails, and sandals to walk on the beach or stroll around town. That this part of the Midwest isn’t super spread out also means you don’t need to drive very far for a weekend escape, which translates to spending less time in the car and more time enjoying your vacation.

Here are five destinations to check out, ensuring you come back to the city relaxed and reinvigorated. If a road trip is calling and you’re not sure where to go, this cheat sheet will help.

Lake Geneva, Wisconsin

1.5-Hour Drive

Architecture geeks and The Gilded Age fans will love the grand, historic estates dating back to the late 1800s and early 1900s that surround Geneva Lake, accessible via a stroll around a section of the 26-mile Lake Shore Path or aboard a narrated Geneva Cruise Line boat tour . Dine with a lake view on the patio at Barrique Bistro & Wine Bar or linger over Italian-American food like wild-boar Bolognese pasta at Sopra Bistro on Main Street. Shop downtown for cheese curds and cheddars flavored with whiskey, dill and more at Hill Valley Dairy’s storefront , and poke into the Lake Geneva Public Library , designed by Frank Lloyd Wright protégé James Dresser and featuring stained-glass windows from Wright’s now-demolished Lake Geneva Hotel. For whimsical décor finds and entertaining frills, head to the other side of the lake to Fontana Home . The best design-oriented spot for a beer is at Topsy Turvy Brewery , within a 1910 former church.

Where to Stay

Featuring an outdoor pool with striped umbrellas and a speakeasy-style bar, Maxwell Mansion ’s 28 rooms are divided between the main house and former horse stables. For a full-service experience that includes a spa, steakhouse, Italian restaurant and outdoor pool, try the  Grand Geneva Resort & Spa , whose interconnected buildings were once home to the Playboy Club. Today, you can sip cocktails in the lobby’s sunken lounge.

Saugatuck, Michigan

2.5-Hour Drive

Hugging Lake Michigan’s western shoreline, Saugatuck, fittingly known as “The Art Coast,” is home to dozens of galleries. Most are sprinkled downtown near shops and restaurants, although the two-story, 12,000-square-foot J. Petter Galleries just outside of town is worth a trip, and hosts a wine bar within. In nearby Douglas, one of the nation’s oldest artist residencies— Ox-Bow , affiliated with the School of the Art Institute of Chicago, also a destination for art and writing classes—hosts an art gallery and boutique (Ox-Bow House) in an adorable white church dating back 152 years. Modales Wines in Fennville pours wines crafted by its Napa Valley-born winemaker, formerly of Duckhorn. Explore further on a vertical hike down sand dunes at Opal Beach, or rent a 1950s electric boat from Retro Boat Rentals to cruise along the Kalamazoo River to live our your IRL Emily Henry novel dreams.

Owned by Chicago design firm Soucie Horner , the 11-room Wickwood Inn  is a new, modern revamp of The Silver Palate Cookbook author Julee Rosso ’s inn. Rosso also owned a gourmet-foods shop of the same name in New York City. Antiques and artwork tie into a clear coastal vibe that includes outdoor s’mores and French bistro chairs on the patio.

Kohler, Wisconsin

This company village town—nearly everyone works for the luxury plumbing manufacturer—also excels at hospitality. The Immigrant Restaurant has long been considered one of Wisconsin’s best fine-dining restaurants; it embraces early-American art and décor while serving a five-course tasting menu, plus delicacies like caviar and 16 artisan Wisconsin cheeses. At the three-level, 36,000-square-foot Kohler Design Center , rooms by celebrity designers can be toured and the design staff is available to chat. Then, at Kohler Waters Spa, hydrotherapy treatments incorporate Kohler’s Vichy shower. On your way into town, swing by Art Preserve , a museum dedicated to artist-built environments by folk artists. Tours of the Kohler factory across the street from the hotel are led by retired employees.

The American Club is the most luxurious of the three Kohler properties, with 241 rooms. Built in 1918 for single male immigrant employees, it’s now one of Wisconsin’s most coveted properties, with a spa, yoga studio, multiple restaurants, golf courses and shops all within a short walk and managed by the resort.

Galena, Illinois

3-Hour Drive

Situated along the Mississippi River, Galena boasts an adorable downtown dotted with antiques stores (like the 200-some vendors at Elizabeth’s Grand Antique Co. in a former school) and unique boutiques along Main Street. That includes Galena Apothecary (formerly of Chicago, the owner opened the shop in her favorite weekend-getaway town), Galena Book & Paper (books and stationery) and Galena River Goods (candles, skincare products, barware and clothing). Sip bubbles in Champagne on Main ’s outdoor courtyard and choose your dinner spot after a walking tour with Galena Foodie Adventures , visiting five different eateries.

Tuck in at night at Goldmoor Inn , a castle-like structure just outside of town with 13 suites and breakfast included. Massages are also available on-site, in the inn’s dedicated spa room, including a hot-stone massage to work out the kinks.

Traverse City, Michigan

5-Hour Drive

This emerging wine region is also a great spot to hike; make sure to take in the soaring bluffs at Sleeping Bear Dunes National Lakeshore and to sail. The Wind Dancer , offers sunset sails nearly daily as well as Champagne Sails on Sunday afternoons. Short on time but still want to experience a local winery? Head to the 155-acre Brys Estate Vineyard & Winery , where the vineyard views from an elevated deck are nothing short of picturesque, with vistas of a lavender field and gardens blooming with flowers and herbs. The winery also serves frosé, plus cheese and charcuterie boards. Perusing downtown Traverse City’s shops, including two bookstores, can easily fill an afternoon. History buffs will love Trattoria Stella ’s cave-like environment, located at The Village at Grand Traverse Commons , a former state-run mental hospital with a philosophy that a beautiful environment is healing.

 Delamar Traverse City ’s perch above the West Arm of Grand Traverse Bay means water views for days and the on-site yoga studio puts wellness within easy reach, plus a restaurant wildly popular with locals. Or, wake up next to the grapes at the 10-room Inn at Black Star Farms , which also hosts private yoga classes in its vineyard.

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9 easy must-do weekend trips from Chicago

Chicago is blessed with world-class museums, an amazing food scene, some of the best breweries in the country, and everything else you’d ever want to do. But even the most passionate Chicagoans need to escape the city every now and then. Luckily, there are dozens of superb weekend getaway destinations, all within a few hours’ drive of the Windy City. 

There are miles upon miles of Lake Michigan coastline to explore, there are national and state parks with gorgeous nature, and there are charming cities and towns all over the Great Lakes region where you can find a little bit of quaint comfort. Planning will go a long way to ensure a successful weekend trip. So research where to go, find luggage storage in Chicago if you need to drop the bags off, book lodging, plan where to eat and what to do, and hit the road. 

Here are the best weekend getaways from Chicago: 

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Dubuque, Iowa 

Located on the banks of the Mississippi River, Dubuque is the ideal weekend getaway for history buffs and older tourists. Baseball fans will want to visit the famous “ Field of Dreams ” ballpark, which is now the home of special events hosted by Major League Baseball. 

The town itself has been revitalized somewhat in recent years, with art galleries, breweries, murals, and restaurants opening in downtown Dubuque. Dubuque is heavy on the small-town charm and well worth a visit. 

Distance from Chicago 

It takes just under three hours to reach Dubuque from Chicago. Driving is the only option for transit. 

Our activity recommendations

This historic town is a delightful change from downtown Chicago, with a picturesque old-school Main street with many pre-Civil War buildings, like the Black Horse Inn. There’s also the Febekon Place Elevator, which is a scenic railway that overlooks the city and provides a spectacular aerial view. 

Best season to visit

Summer, fall, and spring are the best times of year to visit Dubuque. 

Holland, Michigan 

Western Michigan has a ton of delightful towns for weekend getaways, and Holland is one of the best family-friendly options. Located less than a mile from the stunning Lake Michigan coastline, Holland is famous for its large Dutch immigrant population and its furniture-making industry. 

Distance from Chicago

You’ll have to drive south and east for about two and a half hours to get to Holland. Driving really is the best way to get there, although Amtrak runs a train as well. 

Explore Holland’s (aptly-named) Dutch heritage by exploring delightfully kitschy attractions like Nelis’ Dutch Village, De Klomp Wooden Shoe, and the Windmill Island Gardens . 

In proper Dutch fashion, Holland (Michigan) celebrates the annual blooming of tulips every springtime. With millions of tulips planted across the area, it’s a gorgeous time of year to visit. Summer is also ideal, with the Lake Michigan shore and beaches only a mile away from town and gorgeous Lake Macatawa providing plenty of outdoor recreation. 

Grand Rapids, Michigan 

While far from the largest city in the country, Grand Rapids has a massive beer scene. Since the industry’s boom in the past two decades, Grand Rapids has quickly become one of the craft beer meccas, drawing thousands of beer nerds to its taprooms and breweries. 

It’s a three-hour drive from Chicago to Grand Rapids, probably less if you miss Friday traffic. Amtrak also runs a service from Union Station directly into downtown Grand Rapids, the train ride is about four hours. 

Beer truly is the main draw for visitors, with companies like Founders, Brewery Vivant, Saugatuck Brewing, and Grand Rapids Brewing all operating popular taprooms. The food isn’t bad at all either, with local favorites Forty Acres Soul Kitchen and Terra GR being high-end dining options.

When you’re not drinking, renting kayaks or bikes to enjoy the riverfront are great ways to stay active. Lake Michigan is less than 30 minutes away by car too.

Summer and fall are perfect for enjoying some time outdoors, especially if you’re looking at kayaking and swimming along the river or Lake Michigan. Winter is also a great time to do a long weekend because you can hit the slopes at the nearby Cannonsburg Ski Resort. Also, the many Grand Rapids breweries are great for a cozy pint to warm up.

Indiana Dunes National Park, Indiana

The sandy dunes overlooking Lake Michigan have finally gotten their due and were made into a national park. Indiana Dunes National Park is the closest conservation and recreation area of its kind to Chicago and the perfect weekend getaway (or day trip) for outdoor enthusiasts.  

It’s only about 90 minutes by car (which is the most convenient way to get there) from downtown Chicago. Unless you want to explore the whole area and stay in a cabin, Indiana Dunes National Park is one of the best day trips from Chicago. The South Shore Line will also take you to the Indiana Dunes, but driving is easier and more flexible. 

There are over 15 miles of beautiful Lake Michigan shoreline to explore and enjoy. You can enjoy the beach, go for a swim, hike the trails along the dunes, and even go horseback riding. 

Summer and fall are the best times to go. Visiting during winter is absolutely inadvisable because of lake effect weather. Spring is better, but the weather brings frequent rain that impacts the hiking trails and terrain.

Kohler, Wisconsin 

Located north of Milwaukee along Lake Michigan, Kohler is famous for its resorts and golf courses. The American Club is a bucket-list course for golfers, and there are a number of spas and restaurants that make Kohler a relaxing destination. 

Kohler is a two-and-a-half-hour drive from Chicago. A great way to break up the trip is to stop in Milwaukee for lunch.

Our activity recommendations 

The upscale resorts and golf courses are the main draw at Kohler, which makes them frequent weekend getaway destinations for older travelers. The Kohler Waters Spa is the perfect place to unwind, and the American Club boasts one of the best golf courses in the country. 

For weekend getaways based around golf, summer and fall are the best times of year to head up to Kohler. Kohler is also a wonderful destination for spas and resorts during the winter. 

Lake Geneva, Wisconsin 

Of all the weekend getaways from Chicago, this one has to be the most popular. Lake Geneva is Chicago’s equivalent of The Hamptons. Basically, everyone knows someone with a house up there. This makes sense, given it’s only a 90-minute drive from Chicago, just over the Wisconsin border. There are plenty of hotels, like The Abbey and Grand Geneva Resort . Multiple golf courses surround the lake as well. But the main reason to head to Lake Geneva is to appreciate the natural beauty with friends and family. 

Lake Geneva is about as close to Illinois as you get, and it only takes about 90 minutes to get there from Chicago by car, which is the only real way to get there. 

All the best activities in Lake Geneva are based around the water. Renting a boat from one of the marinas is a great way to get the family out on the water. There are multiple public beaches as well. 

During the winter, there is a village of ice castles made by expert sculptors that’s worth checking out. Alpine Valley Ski resort is nearby, which also hosts concerts during the summer. 

Summer is the best time to take a weekend trip to Lake Geneva, but it does get busy during this time of year. During the fall, Lake Geneva gets a boost when the leaves change color, despite it being too cold for boating and swimming. 

Madison, Wisconsin 

Wisconsin’s capital city is one of the most popular weekend getaways from Chicago. All the best Wisconsin culture is represented in Madison, which mostly consists of beer, brats, and Badger Football. The University of Wisconsin’s gorgeous campus is located right in Madison, which gives the city energy when students are on campus. But there’s a nice variety of outdoor activities and culture in the city as well. 

Madison is a three-hour drive from Chicago. There are also bus routes between downtown and Madison that take about three hours and 30 minutes. 

For such a small city, there’s plenty to do in Madison. Snowshoeing in the winter, hiking in the summer, appreciating the leaves in the fall, and drinking all year long. 

Just outside of Madison is the Wisconsin Dells area, which has indoor and outdoor water parks and other outdoor activities. It’s a great excursion from Madison and less than an hour’s drive from the capital. 

Summer and fall are the best times to visit, especially when the leaves change and the University is in full swing.

Milwaukee, Wisconsin

Chicago’s neighbor to the north is an obvious choice for weekend getaways. There is culture, there’s beer (and plenty of it), there are several pro sports teams, and there’s a lot of character. Milwaukee has all the amenities of a larger city, just without all the inconvenience of getting around a place like Chicago. 

If you’re driving up to Door County or Kohler, it’s well worth it to stop in Milwaukee for lunch. 

There is a train from Union Station that lands you right in downtown Milwaukee. This takes less than two hours and can save you some traffic headaches. The drive up to Beer City only takes about 90 minutes. 

There are a number of amazing museums to visit, including the Milwaukee Art Museum, which is a gorgeous modern building along the lakefront. There’s also the Harley Davidson museum which details the story of how Milwaukee became the largest builder of motorcycles in the world. 

Outside of that, there are world-class breweries, restaurants, and bars. Definitely make sure to try a famous Bloody Mary dressed up Wisconsin-style. 

The Milwaukee lakefront is incredible, and there are frequent festivals and events going on, so summer is an amazing time for a weekend trip. But there is enough culture that visiting Milwaukee is fun year-round. If you’re free during the first few weeks of July, hit up Milwaukee Summerfest , which is the largest music festival in the world. 

Starved Rock State Park, Illinois

As far as outdoor activities go, Chicago is hardly the best city in the world. But the area’s best hiking area is absolutely worth visiting. Starved Rock State Park, with waterfalls and topography (rare in a painfully flat state like Illinois), makes for a perfect weekend getaway for outdoorsy types.  

It’s only a two-hour drive from Chicago, but you’ll want to leave early to beat traffic and have a head start on the other hikers. Leaving yourself a full day to explore the nooks and crannies of this park is the best way to go. 

Essentially, there’s really only one thing to do at Starved Rock, and that’s hiking. With 13 miles of trails winding through glacier-carved canyons and terrain, it’s the best hiking Illinois has to offer. There are gorgeous waterfalls and winding streams to take a dip in if you’re hiking during the sweltering Illinois summer. 

Late spring, summer, and early fall are the best times of year to explore Starved Rock. Winter is basically out of the question. Early spring and late fall are entirely weather-dependent.

It’s hard for locals and transplants to find a place they love more than Chicago because there is a lot to love. But getting out of the city for a weekend getaway is a necessary way to recharge and reset. You’ll be more in tune with nature, you’ll feel a little more relaxed after taking a break from traffic, and you’ll have a new appreciation for the gorgeous region surrounding Chicago. If you’re short on time, you can always opt for a fun day trip from Chicago as well, and if you only have a limited time in the city itself, check out our guide on how to spend 3 days in Chicago to maximize your itinerary.

Planning one of the many fun weekend getaways from Chicago is a great way to find a new appreciation for not only the Midwest but also Chicago. Because you can only stay away from that deep dish for so long… 

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5 Best Weekend Getaways Near Chicago For Every Traveler

Few destinations can stand up to Chicago, but sometimes we all need a break from the concrete, crowds, and traffic. Some prefer the relaxing vibe of small-town charm, others an escape into the great outdoors, or perhaps a little of both.

With this in mind, we consulted with current and former Chicago residents, pulled out our maps, and mixed it all up in our super scientific trivago lab and came up with the best weekend getaways near Chicago.

Chesterton, Indiana — 47 Miles

If you’re planning a road trip to Chesterton, Indiana, you’ll want to make sure you’re there by Saturday morning when the town hosts a weekly (from May through the end of October) family/artisanal European Market .

For the afternoon, head over to the Indiana Dunes State Park where you have access to hiking trails (including the nine-mile Calumet Trail), camping, and a number of events, like Beach Yoga, critter feeding, and an “edibles walk” where you learn what you can eat along the trails—meaning no more hangry fights with your significant other who forgot to bring a snack.

Hotels & Vacation Rentals - Chesterton

Where to stay in chesterton.

You get bang for your buck at the Best Western Indian Oak in Chesterton, but there are opportunities to splurge a bit if you like. Rooms can come with a fireplace, a balcony, a spa, and even adjoining rooms if you’re traveling with a large group or family.

Indian Oak also offers massage service, a steam room, an indoor pool, hot tub, and exercise facilities. Hungry? You’ll find Gelsomo’s, an Italian restaurant, right across the street with other nearby restaurants covering everything from Mexican to Thai.

Best Western Indian Oak

Lake geneva, wisconsin — 80 miles.

Locals say it’s easy to fall in love with Lake Geneva, pointing to the diversity of opportunities packed into the town of about 8,000. One of the more popular adventures for weekend getaways and road trip travelers from Chicago is the canopy tours. Lake Geneva Canopy Tours will get you out on the ropes year-round for a canopy course with eight different zip-lines covering 100 acres. Prefer staying closer to the ground? They’ve also got nine miles of hiking and mountain biking trails.

Hotels & Vacation Rentals - Lake Geneva

Where to stay in lake geneva.

You’ll want to call the Grand Geneva Resort & Spa home by the time you’re done with your stay. The AAA Four Diamond resort has everything you could possibly want in a pampered weekend getaway from Chicago. Rooms come equipped with flat-screen televisions, a minifridge, coffee maker, and a writing desk should you be so compelled to jot down some memories.

If you’re one to earn your relaxation, there are tennis courts, two golf courses, and skiing facilities (if it’s the season) where you can work up a sweat. Then, switch right back into relaxation mode by heading to the spa and melting away at one of the property’s pools before dinner and partying it up at the nightclub.

Grand Geneva Resort & Spa

Starved rock state park — 94 miles.

Look through a gallery of images from Illinois’ Starved Rock State Park and you’d never guess it’s just 90-minutes outside of Chicago. Although you can walk for miles on end across the Wind City, there’s no substitute for the crunch of the trail, and at Starved Rock, you’ve got 13 miles-worth waiting for you around the Illinois River and the seasonal waterfall at St. Louis Canyon. You can also sign up for a canyon tour for $25/person that will take you for a scenic stroll to Council Overhang and Ottawa Canyon.

Hotels & Vacation Rentals - Oglesby

Hotel near starved rock.

Brightwood Inn is situated conveniently just four minutes (by car) south of Starved Rock State Park and within the confines of Matthiessen State Park. This B&B is perfect for a romantic getaway or even for travelers simply looking for a bit of peace and tranquility surrounded by the serenity of the wilderness. Brightwood makes it easy to relax with your in-room hot tub, fireplace, and a homemade breakfast every morning. They’ll also help you get your heart pumping with state park trails, canoeing on the Fox River, horseback riding, skydiving, cycling on the I&M Canal towpath, and white water rafting on the Vermillion River.

Brightwood Inn

Saugatuck, michigan — 142 miles.

Freshwater beaches, natural serenity, and a creative art community encapsulate Saugatuck, Michigan. You might not know much about it, but travel media have long taken note of this region with Condé Nast Traveler crediting Saugatuck with one of the “Top 25 Beaches in the World” where travelers can find a secluded stretch of sand and take in an awe-inspiring sunset.

More active travelers can work their way through rolling dunes or, come winter time, go cross-country skiing along the frozen shore or in the snow-covered woods. Once you’ve inevitably worked up an appetite, the plethora of locally-sourced restaurants and neighborhood coffee shops are there to energize you before you head back into the wild.

Hotels & Vacation Rentals - Saugatuck

Where to stay in saugatuck.

At Hidden Garden Cottages & Suites , you get privacy and convenience. Located right in the heart of downtown Saugatuck, everything you could possibly need is within walking distance — and we’re not just talking about restaurants. Oval Beach is under a mile away as well as Mt. Baldhead Park and the Saugatuck Harbor Natural Area. When you’re at the Inn, you’ll be treated to 27 years-worth of hospitality with a number of package specials available for a little icing on the cake on your weekend getaway.

Hidden Garden Cottages & Suites

Sheboygan, wisconsin — 148 miles.

More Lake Michigan fun awaits in the Wisconsin town known as “The Spirit on the Lake.” Bonus points for holding claim as the bratwurst capital of the world. Need proof? Head to the Old Wisconsin Sausage Outlet Store , a local favorite for over 50 years. Needless to say, you’ll need to make the most of the outdoors to burn up those bratwurst calories and Sheboygan does not disappoint.

The lake itself offers surfing, kite surfing, windsurfing, sailing, kayaking, jet skiing, boating, and fishing. By land, you can bike, hike, climb, and golf before celebrating your healthy excursions with more food and drink. Then again, Sheboygan also keeps more zen-like travelers in mind with spas to relax the body.

Hotels & Vacation Rentals - Sheboygan

Where to stay in sheboygan.

Right downtown and steps away from Lake Michigan, you’ll find one of the town’s highest guest-rated hotels in GrandStay Sheboygan . No matter what you book, you’ll get a full kitchen and a number of modern amenities in this pet-friendly hotel. If you’re staying for a few nights, you’ll have to take advantage of the indoor pool & whirlpool and exercise room.

Need help finding your way around? GrandStay Sheboygan can point you in the right direction of restaurants, shopping, nearby attractions, and upcoming events, like the annual Dairyland Surf Classic—the globe’s largest lake surfing competition.

Grandstay Hotel & Suites Downtown Sheboygan

Featured image courtesy of  Aaron Burden  on  Unsplash

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20 Best Weekend Getaways from Chicago

Last Updated By VI on May 17, 2024 in Things to Do in Illinois & Places to Visit , Map

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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10 Weekend Getaways Near Chicago Families Will Love

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Perhaps Chicago is home and you’re looking for a change of scenery for a few weekend getaways near Chicago for families . Or maybe you’re planning to visit the Windy City and want to know about other nearby options. Either way, there are plenty of amazing road trip options within a five-hour drive from Chicago . From Chicago’s convenient location in Illinois, you’ll find nearby nature escapes or new cities to explore with these family getaways from Chicago for families in several nearby states. Head north to Wisconsin to Madison or Milwaukee. Or, visit western Michigan to see adorable towns like Saugatuck and Holland along Lake Michigan. Even if you stay in Illinois, you’ll find history and quaint towns in Springfield and Galena. No matter what type of adventure you’re looking for, you can’t go wrong with one of these weekend getaways from Chicago for families . 

Michigan Weekend Getaways Near Chicago for Families

If you need a quick weekend getaway near Chicago with kids, you’ll love these options in Michigan ! From stunning views of Lake Michigan to days outdoors, your road trip from Chicago with kids is sure to leave you with a lifetime of memories.

Saugatuck, Michigan

One of the cutest lake michigan towns.

Along Lake Michigan’s shores are towns perfect for weekend getaways near Chicago for families . While we love Saugatuck , but you can’t go wrong if you stop in St. Joseph or South Haven on the way. Or, keep driving to Holland . Because Saugatuck is just about two hours away from Chicago , it’s the perfect driving distance for a weekend road trip. Of course in the summer, you’ll want to spend time at the beach. Luckily, Oval Beach is ranked as one of the best in the world . Another way to enjoy the sand is by taking a dune buggy ride with Saugatuck Dune Rides . Then for a less bumpy ride, try the Saugatuck Chain Ferry which is pulled across the Kalamazoo River. Certainly, this is a faster way to reach Oval Beach and you’ll find it conveniently located in the adorable downtown area at Water Street .  

Please note : The Chain Ferry and Dune Rides are seasonal, please check the respective websites to ensure availability before departing.

Where to Stay in Saugatuck with Kids

If you’re looking for a place to stay in Saugatuck with kids, you’ll find a variety of Vrbo options, and many that are along Lake Michigan. However, if you’d rather enjoy the amenities of a resort, families love the Beachway Resort and Hotel , which has a variety of room choices. As an alternative option to Saugatuck, The Beach House in nearby Holland, is a boutique resort with townhome-style accommodations and optional golf packages.

VRBO has great options for lodging in Saugatuck. Check out the accommodations here!

Wisconsin Weekend Getaways Near Chicago for Families

Next, head to Wisconsin for amazing weekend getaways near Chicago for families ! Whether you are interested in living the lake life or visiting a nearby state capitol, this list of Wisconsin getaways has you covered.

Lake Geneva, Wisconsin

Midwest lake living at its best.

Lake Geneva , located in southern Wisconsin, is an ideal family getaway near Chicago . Depending on where you begin, you can drive to Lake Geneva in between one to two hours from Chicago . From Lake Geneva’s adorable downtown with shops and award-winning restaurants to outdoor adventures , everyone will be satisfied here. Since there are four beaches and options for boating (check out Lake Geneva Cruise Line ), your time at Lake Geneva will likely center around time on the water. Another way to explore this weekend getaway from Chicago is by walking the Geneva Lake Shore Path . For any animal lovers in your family, don’t forget to check out Safari Lake Geneva , a conservation park, then reserve your spot to see the beautiful horses at the Dancing Horses Theater . Finally, know that Lake Geneva is also a perfect winter family getaway from Chicago due to its popular Winterfest.  

Where to Stay in Lake Geneva with Kids

When you take a weekend road trip from Chicago with kids to Lake Geneva , consider staying at the Grand Geneva Resort and Spa and you’ll never run out of things to do. That’s because the resort offers two golf courses and ski hills for the winter. Alternatively, consider staying at The Abbey Resort which is a destination within itself with its kids camp, live entertainment, boat rentals, and much more. 

Madison, Wisconsin

Small city, big fun.

Just two and a half hours from Chicago , Madison , Wisconsin, is a perfect family getaway near Chicago . Certainly, a highlight in Madison is the Henry Vilas Zoo , one of the few free zoos in North America. Located in downtown Madison , you’ll see the big cats, reptiles, and rainforest exhibits. While in the area, check out Vilas Park with the swimming lake next to the zoo. Also in downtown Madison , be sure to include time to walk down State Street , which is a half-mile-long pedestrian mall anchored by the Wisconsin State Capitol at one end and the University of Wisconsin-Madison at the other. Then, check out the performances at the Overture Center for the Arts and add a show or musical performance to your weekend away. Finally, families with young children will definitely want to plan a visit to the Madison Children’s Museum . 

Where to Stay in Madison with Kids

A favorite urban resort in downtown Madison is The Edgewater , which is located both on the edge of Lake Mendota and steps away from downtown. Another convenient hotel in the downtown area is The Madison Concourse Hotel . If you’re up for taking a long road trip from Chicago with kids , the Wisconsin Dells is just another hour away and boasts many waterpark resorts like the Wilderness Resort and the Kalahari , which are guaranteed to be a blast for your family. 

RELATED: Best Zoos in the Midwest For Families

Port Washington, Wisconsin

A milwaukee twist.

If you’d like a twist on a familiar place, take a weekend road trip to Port Washington , Wisconsin . Just north of Milwaukee, you’ll find new places to explore in this family getaway near Chicago . Because it’s directly on Lake Michigan, you can charter a salmon or trout fishing adventure with Nicky Boy Charters . Alternatively, take the kids and fish at Harrington Beach State Park . For other outdoor adventures, hike along the bluffs of Lion’s Den Gorge Nature Preserve . Parents know that sometimes kids simply love playing at a new playground and Possibility Playground . This universally accessible playground in Port Washington is a fantastic choice. It even overlooks Lake Michigan! Because Milwaukee is nearby, it’s easy to add on favorite things to do in Milwaukee like Betty Brinn Children’s Museum , Discovery World , The Domes living museum. Or, even to catch a show at First Stage Children’s Theater . 

Where to Stay Near Port Washington with Kids

Use Hotels.com to book your stay at The Harborview or the TownePlace Suites Milwaukee Grafton !

When you get away to Port Washington , The Harborview is an ideal location to stay. That’s because it’s located along Lake Michigan and next to the Port Washington Marina, an ideal spot for watching the boats. Another favorite option with room to spread out is the TownePla c e Suites Milwaukee Grafton . If you’d rather stay in nearby Milwaukee, there are many lodging options there too. 

Illinois Weekend Getaways Near Chicago for Families

You don’t have to leave the state for amazing weekend getaways near Chicago with kids ! Don’t miss these charming locations for a quick trip with kids.

Galena, Illinois

Historic and quaint family fun.

One of the cutest towns in the Midwes t is Galena , Illinois, and it’s just a three-hour road trip from Chicago . When you wander down Main Street, you’ll discover more than 100 charming shops and your kids will love the candy and ice cream parlors. If you have history-enthusiasts in your group, visit the Apple River Fort , which tells the tale of the 1832 Black Hawk War fought between settlers and the indigenous Sauk tribe. Also, when you take a weekend getaway from Chicago to Galena , plan to spend time outdoors. Chestnut Mountain Resort offers adventures like an alpine slide, Segway tour, and more. Alternatively, head to Fever River Outfitters and rent kayaks, paddleboards, or e-bikes. If you prefer more thrills, try a canopy zipline tour with Long Hollow Canopy Tours . Finally, for a truly unique experience, check out Hoof It and sign-up for a goat trekking experience.

Where to Stay in Galena with Kids

Reserve your stay at the Chestnut Mountain Resort on Expedia here!

Need somewhere to stay in Galena with kids ? We’ve already mentioned Chestnut Mountain Resort , which is a favorite place to play as well as a lodging option with so many things to do. Still, there are many other options in the area including historic places like the Hellman Guest House . With standard rooms and a suite, you’ll find stunning views and quick access to outdoor activities. Or consider the Irish Cottage Inn & Suites , nestled among the rolling hills and a quick drive from downtown Galena. 

Springfield, Illinois

Abraham lincoln history in the heart of central illinois.

Springfield, Illinois, plays an important part in U.S. history, specifically related to Abraham Lincoln. Accordingly, no road trip to Springfield is complete without visiting the Lincoln Home and the Abraham Lincoln Presidential Library and Museum . In addition to these Lincoln sites, plan to walk the trails and soak in nature’s beauty at Lincoln Memorial Gardens . Then, for another Lincoln experience drive twenty miles down the road to New Salem , a reconstructed village representing where Lincoln lived. If you’re lucky, you’ll catch a live performance while there. Certainly, history is just one reason why Springfield makes a great family getaway near Chicago . Nearby you’ll find Knight’s Action Park , an exciting water park and entertainment center just the right size for families. Be sure to round out your weekend away by visiting the Kidzeum of Health and Science to learn and discover while playing in the healthy exhibits.

Where to Stay in Springfield with Kids

To complete your Abraham Lincoln weekend in Springfield , stay in the Presi d ent Abraham Lincoln Doubletree in downtown Springfield . When you stay here, you’ll be downtown and a short walk from many attractions.

Springfield, US Vacation Rentals: house rentals & more | Vrbo

Indiana Weekend Getaways Near Chicago for Families

Did you know there is a national park near Chicago ? There is, and it’s one of our favorite Indiana weekend getaways with kids ! Keep reading to find two great options for your next weekend trip from Chicago for families .

Indiana Dunes, Indiana

Sand dunes and lake michigan.

Did you know there’s a national park near Chicago ? In fact, Indiana Dunes National Park is less than an hour from many parts of the city. Of course, this makes it a perfect family getaway near Chicago . Here, you’ll find sand and water along the 15 miles of Lake Michigan. Plan to spend time at the beach and also climb and run down the rugged sand dunes. Perhaps your family will want to conquer the 3 Dune Challenge ! Along with the dunes, there are over 50 miles of hiking trails . Add a stop at the Dorothy Buell Visitor Center for educational displays and perhaps to sign up for a guided tour . What’s more, there are many other things to do nearby including one of America’s Top Ten Drive-in Theaters, 49’er . Plus, the animal farm, Broken Wagon Bison , and the Hoosier Bat Company , perfect for baseball fans of all ages.

Where to Stay Near Indiana Dunes with Kids

While Indiana Dunes is near enough to Chicago to experience as a day trip, why not stay the night? Families will adore a stay at Riley’s Railhouse which is a former rail station! This is the place to stay for train-loving kids! Alternatively, Indiana Dunes National Park is a beautiful place to camp .

Indianapolis, Indiana

Children’s museum and the arts.

Indianapolis is just three hours away ! Here, your family will discover many things to do on your road trip from Chicago . Surely, The Children’s Museum can’t be missed. With five floors of fun and learning, this museum is the largest children’s museum in the world ! Kids of all ages will love the museum and sporty kids may never want to leave the Sports Legends Experience . Stay multiple days in Indianapolis and you’ll have time to visit orangutans and dolphins at the Indianapolis Zoo , which is located conveniently in White River State Park . While in Indianapolis , enrich your arts experiences by taking the family to the Newfields art museum. Here, kids can actually climb on the art! Then, head to the Rhythm Discovery Center (aka percussion museum). Before heading home, step back in time at Conner Prairie , where you’ll find pioneer life being acted out all around you. 

Where to Stay in Indianapolis with Kids

Book your stay at the Courtyard Indianapolis Downtown or, book the Residence Inn Indianapolis Downtown on the Canal with Travelocity today!

When location matters, stay at Indianapolis ’ Courtyard Indianapolis Downtown and you will be within walking distance of restaurants, have access to the sky bridge to the Indiana Convention Center. Plus, it’s less than two miles from the Indianapolis Zoo. Another hotel with a pretty location along the downtown canal is the Residence Inn Indianapolis Downtown on the Canal .

Ohio Weekend Getaways Near Chicago for Families

Do you desire weekend getaways filled with thrills? Look no further than this weekend trip near Chicago for kids !

Kings Island, Ohio

Get ready for wild rides and splashes.

At just under five hours away , Kings Island , near Cincinnati, Ohio, is one of the most thrilling getaways near Chicago for families . In fact, this notable amusement park and water park offers thrilling roller coasters like Orion, Diamondback, and The Beast, as well as family-friendly rides everyone will enjoy. Families with young kids will especially want to spend the day at Planet Snoopy , which has rides and experiences that are fun yet not too scary. Not only is Kings Island a fun amusement park, but access to the waterpark is also included with the ticket. This means your family can also experience the many water slides, two wave pools, and a relaxing lagoon. While you may only have time to explore Kings Island , extend your road trip to Ohio and explore nearby Cincinnati . There you’ll find many family-friendly things to do including the Cincinnati Zoo and Newport Aquarium . 

Where To Stay Near Kings Island With Kids

If you want to keep the fun going throughout your stay, bring along your RV or book a cottage at C a mp Cedar . This luxury outdoor resort is located just a mile away from Kings Island. Another family-friendly lodging option nearby is the Great Wolf Lodge in Cincinnati. Of course, you’ll find many other local hotels with more laid-back atmospheres. 

Iowa Weekend Getaways Near Chicago for Families

Families will adore visiting nearby Iowa on weekend getaways near Chicago . Here is a fantastic option for your next weekend trip with kids!

Quad Cities, Iowa

Four cities located along the mississippi river.

Next, head west to the Quad Cities of Moline, Rock Island, Davenport, and Bettendorf. Certainly, your family will enjoy exploring along the Mississippi River. One place to learn about the mighty river is the Mississippi River Visitor Center Locks & Dam 15 where you can watch boats navigate the locks. Or, take a ride on the Channel Cat Water Taxi . Perhaps you’ll even spot bald eagles nearby. Then, head to the Putnam Museum Science Center where you’ll discover hands-on exhibits like digging for dinosaur bones and interacting with robots. Also, pick out which of the 3D movies you want to watch on the GIANT screen. Don’t miss the Family Museum , where your kids will enjoy a day of learning through play. Before you head home from your family getaway near Chicago , stop at the John Deere Pavilion where your kids will love getting to sit in John Deere’s biggest machines.

Where to Stay in the Quad Cities with Kids

Reserve your room at the Stoney Creek Inn or The Blackhawk at Hotels.com now!

For unique and family-friendly lodging in the Quad Cities , look no further than the Stoney Creek Inn in Moline . Here, you’ll find suites, bunk beds in family rooms, and of course, a swim-through pool that kids will love. There are plenty of other options in the area, but how about a hotel with a bowling alley in the lower level? That’s what you’ll find at Hotel Blackhawk , a hotel combining historic and hip. 

Thank You To Our Community! 

A special thank you to the Families Who Love To Travel Facebook community who shared their travel recommendations for this list of Family Getaways Near Chicago . We could not have compiled such a thoughtful and helpful list without their dedication to our community. Families Who Love To Travel is a group of amazing families who also love adventure and exploring through travel. For more family vacation recommendations and inspiration, be sure to join us on Facebook at Families Who Love To Travel . We’re a community of experienced traveling families who love adventure and exploring the world. Plus, follow us on Instagram ( @families.love.travel ) to connect with other families who love the unique experiences travel has to offer. 

*Due to the COVID-19 pandemic, some of the attractions, accommodations, or things to do on this list may be closed. Please ensure availability before making your decision.

*This post may contain affiliate links that may earn us a small commission, at no additional cost to you. Affiliate links in no way inform the hotels, sights, products, or other recommendations included in our articles. All opinions and recommendations expressed here are compiled from submissions submitted by the generous members of our Families Who Love To Travel community.

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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 Road Trips From Chicago

Top road trip destinations from chicago.

Wisconsin Dells

🚗 200 miles ⏱️ 3 hours

The best place for family fun and outdoor adventures is Wisconsin Dells, known as the "Waterpark Capital of the World." Here, you will enjoy thrilling water rides, scenic boat tours, and picturesque hiking trails amidst natural beauty.

On this drive to Wisconsin Dells, we recommend putting aside some time to visit Rockford and Madison .

Mackinac Island

🚗 470 miles ⏱️ 6 hours, 20 minutes

Imagine an idyllic getaway where horse-drawn carriages and bicycles replace cars. On Mackinac Island, you will also enjoy breathtaking views of Lake Huron and treat yourself to the island's famous fudge.

On this scenic drive, you can also visit Benton Harbor and Grand Rapids en route.

Niagara Falls

🚗 555 miles ⏱️ 8 hours, 30 minutes

Niagara Falls is one of the most famous natural wonders on the planet and rightfully so. The awe-inspiring beauty and sheer power of its waterfalls, along with its dramatic scenery make it one of the most beautiful panoramas in the world.

En route, you can add visiting beautiful Lake Erie cities such as Cleveland and Erie to your road trip plans.

Indiana Dunes

🚗 50 miles ⏱️ 1 hour

Perfect for a day trip, this drive to Indiana Dunes will take you to a magical landscape where beautiful beaches and stunning dunes await. While enjoying the scenery, you will also have opportunities for outdoor activities by Lake Michigan.

On your way, you can take a stroll on Wolf Lake Boardwalk and visit Gary Aquatorium , a great destination for the entire family.

New York City

🚗 805 miles ⏱️ 12 hours

Whether you are looking for sightseeing, amazing shopping experiences or some of the best museums in the country, Big Apple has it all! Here, you can visit iconic landmarks like the Statue of Liberty, watch Broadway shows and stroll through Central Park.

Don't miss out on visiting Cleveland and Pittsburgh en route, and make a detour to Philadelphia if you have time.

🚗 470 miles ⏱️ 7 hours, 10 minutes

This is the ultimate road trip for any music lover. "Music City" is famously home to amazing live performances, important historic sites and some of the best BBQ restaurants in the area.

If you are an urban adventurer, don't forget to add Indianapolis and Louisville to your itinerary en route.

Badlands National Park

🚗 940 miles ⏱️ 14 hours

A drive through Badlands National Park's rugged beauty will stay with you forever. Here, you can admire dramatic landscapes and unique geological formations, hike through otherworldly terrain, and enjoy the stunning vistas.

If you have more time, why not stop at Minneapolis and Sioux Falls on the way to Badlands?

Washington DC

🚗 670 miles ⏱️ 11 hours

If you want to tick some iconic landmarks off of your bucket list, then Washington DC is one of the best destinations from Chicago. Some of the amazing places you can visit include the White House, National Mall, and the Smithsonian Museums.

Some of the big cities you can visit en route are Indianapolis and Columbus , Ohio.

Philadelphia

🚗 760 miles ⏱️ 11 hours, 30 minutes

Step back in time in Philadelphia, where the founding of the United States comes to life. Explore historic sites like Independence Hall and the Liberty Bell, and don't forget to try Philly's famous cheesesteaks.

We recommend putting aside some time to visit Cleveland and Pittsburgh on the way to Philly.

Great Smoky Mountains National Park

🚗 600 miles ⏱️ 9 hours, 30 minutes

There is no place as scenic and brooding as the Great Smoky Mountains with its majestic and hazy landscape. This national park is also home to fascinating wildlife, green forests, scenic hikes and cascading waterfalls.

Before you lose yourself in the stunning scenery of the Great Smoky Mountains, you can visit Indianapolis and Louisville en route.

New Orleans

🚗 940 miles ⏱️ 14 hours, 10 minutes

A road trip that will satisfy any kind of road tripper from foodies to music lovers, New Orleans is an amazing destination to visit from Chicago. Check out the live jazz gigs, enjoy delicious Creole cuisine and explore the famous French Quarter.

On this drive towards the Gulf of Mexico, you will also get to visit St Louis and Memphis for a taste of the charming South.

🚗 560 miles ⏱️ 8 hours, 30 minutes

Discover the soulful music and rich history of Memphis, the birthplace of blues, soul, and rock 'n' roll. Visit iconic attractions like Graceland, Beale Street, and Sun Studio, and don't forget to sample city's famous barbecue cuisine.

On your way to Memphis, we recommend stopping at St Louis to visit the famous Gateway Arch .

🚗 650 miles ⏱️ 10 hours

For a stark contrast in scenery, travel from Lake Michigan's shores towards the Blue Ridge Mountains and visit Asheville. This beautiful city is surrounded by gorgeous scenery, and is a great gateway to the beloved Blue Ridge Parkway.

Before you reach Asheville, you can stop at Knoxville and even make a detour to the Great Smoky Mountains National Park .

Minneapolis

🚗 415 miles ⏱️ 6 hours, 15 minutes

From one big city to another, this drive to Minneapolis will take you to the banks of the Mississippi River. Take some time to explore art galleries, bike trails, and world-class dining in this dynamic Midwestern city.

Madison , Wisconsin Dells and Eau Claire are only a few of the amazing places you can discover en route.

🚗 650 miles ⏱️ 10 hours, 10 minutes

Getting to Canada from Chicago is easier than you might think and Toronto is one of the closest big cities you can visit across the border. Here, make sure to add the famous CN Tower to your list of must-see places.

Before you cross the border, you can explore Lansing and Port Huron if you'd like to extend your road trip.

🚗 460 miles ⏱️ 7 hours

Cleveland sits by the shores of Lake Erie, and is known for its world-class museums and scenic waterfront. Take some time to explore the Rock and Roll Hall of Fame while here; the perfect stop for any music lover.

This route will allow you to make detours to charming small towns such as South Bend and Findley on your way to the big city.

🚗 300 miles ⏱️ 4 hours, 30 minutes

Unleash your inner urban adventurer and visit Louisville, famous for its Southern charm and historic landmarks. This riverside city is also well known for its great restaurants serving delicious Southern cuisine.

Indianapolis is located directly on this route, and we recommend spending some time here to visit Indianapolis Zoo .

🚗 95 miles ⏱️ 1 hour, 30 minutes

This short road trip to Milwaukee is a great idea for a day's adventure. Here, you can enjoy a meal by the waterfront, and take a brewery tour or two. There are plenty of different neighborhoods to explore in this historic city on Lake Michigan's shores.

On the way, you can spend some time at Six Flags Great America Amusement Park in Gurnee , a great stop for families!

🚗 250 miles ⏱️ 4 hours

Toledo sits on the banks of the scenic Maumee River and is a destination where you can enjoy both city vibes and laid-back small-town charm in a single place. Spend some time in the downtown area and visit the city's amazing museums.

This drive is dotted with lovely towns such as South Bend and Elkhart , just short detours from the route.

🚗 147 miles ⏱️ 2 hours, 30 minutes

For a relatively short drive, Madison is a great destination to visit from Chicago with a perfect combination of colorful neighborhoods and outdoor adventures. You will also find some great dining options in the capital city of Wisconsin.

If you have time, we recommend also visiting the cute towns of Rockton and Janesville en route.

🚗 130 miles ⏱️ 2 hours, 20 minutes

Visit Switzerland right in the heart of Wisconsin. Monroe in Wisconsin boasts a proud Swiss heritage, and is home to cheese factories and a charming downtown. Take a walk along its quaint streets and taste the award-winning cheeses of this pretty town.

This is a relatively short drive so you can easily make a detour to Rockford to visit Anderson Japanese Gardens .

Great River Road

🚗 300 miles ⏱️ 6 hours

The scenery you will get to enjoy on this drive along the Great River Road will take your breath away. Think of the beautiful river views, charming river towns, and historic landmarks you will see following the banks of the Mississippi River!

For the best scenery and to enjoy a meal, we recommend stopping at Galena and continuing your journey until La Crosse .

Grand Rapids

🚗 186 miles ⏱️ 2 hours, 45 minutes

This road trip to Grand Rapids is a beautiful drive on the shores of Lake Michigan before you head inland to Grand Rapids, where you can visit craft breweries and explore the city's museums and dine at local eateries.

Why not spend some time on the lakeshore if you have some time and visit Benton Harbor and Saugatuck ?

Harbor Country

🚗 80 miles ⏱️ 1 hour, 20 minutes

A short road trip from Chicago will take you to Harbor Country where you can visit beautiful beach towns, gawk at scenic vistas and have fun outdoors. This destination sits right on the scenic shores of Lake Michigan.

To enjoy the coastal scenery, you can make stops at Indiana Dunes National Park and Warren Dunes State Park en route.

Branson, Missouri

🚗 550 miles ⏱️ 8 hours, 10 minutes

Branson is nicknamed the entertainment capital of the Midwest, where live shows, family attractions, and outdoor adventures abound. From music theaters to theme parks, Branson offers fun for all ages.

On the way, you can also visit Springfield , Illinois, and the Lake of the Ozarks for a fabulous getaway.

🚗 145 miles ⏱️ 2 hours, 20 minutes

Fennville, Michigan is known for its picturesque orchards, fabulous vineyards, and beautiful countryside. Explore the scenic beauty of Southwest Michigan and sample the local flavors of this idyllic destination.

As you drive hugging the coast of Lake Michigan, we recommend checking out Benton Harbor and South Haven .

New Glarus, Wisconsin

🚗 145 miles ⏱️ 2 hours, 40 minutes

You don't need to travel to Europe for the perfect Swiss experience, you can find it nearby at New Glarus in Wisconsin. Treat yourself to a genuine Swiss meal, hop on a scenic drive in the New Glarus Woods State Park and enjoy a laid-back getaway in this picturesque town.

If you'd like to expand this relatively short drive, you can make detours to Rockford and Monroe .

🚗 112 miles ⏱️ 2 hours

Cedarburg, Wisconsin is a lovely small town where you will find the perfect balance of historic charm, local artisans, and scenic beauty. Make sure to explore the quaint streets lined with shops and galleries and experience the welcoming atmosphere firsthand.

On your way to Cedarburg, you can stop at Milwaukee for a taste of the big city before your small-town experience.

🚗 100 miles ⏱️ 1 hour, 30 minutes

For the perfect small-town experience, enjoy a short and scenic drive from Chicago to Utica, Illinois. This laid-back town is just a short distance from the beautiful Starved Rock State Park.

You can make detours to Joliet and LaSalle on this short drive, and enjoy the scenery of Illinois River if you have time.

Longer road trips from Chicago

Yellowstone National Park

🚗 1,450 miles ⏱️ 21 hours, 30 minutes

Yellowstone National Park is home to impressive geysers, beautiful hot springs, majestic waterfalls, fascinating wildlife, and stunning landscapes.

🚗 1,750 miles ⏱️ 26 hours

Experience the dazzling lights and non-stop entertainment of Las Vegas, and enjoy world-class casinos, extravagant shows, and vibrant nightlife.

Yosemite National Park

🚗 2,140 miles ⏱️ 33 hours

The stunning Yosemite National Park is famous for its towering granite cliffs, cascading waterfalls, and ancient sequoia trees.

Myrtle Beach

🚗 1,060 miles ⏱️ 16 hours, 20 minutes

Escape to the sunny shores of Myrtle Beach, where miles of sandy beaches, thrilling attractions, and world-class golf courses await.

🚗 1,000 miles ⏱️ 14 hours, 30 minutes

Explore the Mile High City of Denver, surrounded by the stunning Rocky Mountains and discover outdoor adventures and craft breweries.

Zion National Park

🚗 1,740 miles ⏱️ 25 hours

The breathtaking landscapes of Zion National Park are home to red rock cliffs and narrow slot canyons where you can hike iconic trails.

Los Angeles

🚗 2,020 miles ⏱️ 29 hours

Los Angeles is famously home to Hollywood, as well as beautiful beaches, amazing theme parks and world-class museums waiting for you to explore.

Grand Canyon

🚗 1,700 miles ⏱️ 25 hours

Grand Canyon is one of the world's most breathtaking natural wonders and the vast expanse of the canyon is dotted with scenic viewpoints and hiking trails.

Acadia National Park

🚗 1,260 miles ⏱️ 19 hours, 20 minutes

Acadia National Park is where rocky shorelines, forested trails, and scenic vistas come together for the perfect outdoor adventure.

🚗 1,180 miles ⏱️ 14 hours, 30 minutes

Savannah is a charming and historic city with cobblestone streets, historic squares, museums and antebellum architecture.

🚗 1,330 miles ⏱️ 20 minutes

As you drive to Austin from Chicago, you can explore the heartland of America and the vibrant culture of Texas along the way.

🚗 1,080 miles ⏱️ 17 minutes

Boston is a beautiful New England city with historic streets, and is home to some of the most prestigious universities in the country.

🚗 1,385 miles ⏱️ 21 minutes

For the ultimate beach road trip, head to Miami, where you can enjoy the sunshine, swimming in the Atlantic Ocean and amazing nightlife.

🚗 1,320 miles ⏱️ 22 minutes

Welcome to "The Themepark Capital of the World!" In Orlando you can visit some of the best amusement parks like the Walt Disney World Resort.

🚗 2,200 miles ⏱️ 36 hours

The sunshine and beaches you will get to enjoy in San Diego will be worth the long mileage of this epic road trip from Chicago.

San Francisco

🚗 2,470 miles ⏱️ 38 hours

Visit the City by the Bay and soak in the beauty of the California sunshine. You will admire stunning coastal vistas and iconic landmarks here.

🚗 2,100 miles ⏱️ 30 hours

Admire the iconic skyline of Seattle, explore its great museums, and enjoy a cup of coffee at one of its many Third-Wave Coffee shops.

🚗 1,230 miles ⏱️ 19 minutes

Enjoy the famous Florida sunshine in Tampa and relax by the beach with Gulf Coast's beautiful scenery right in front of you in this tropical paradise.

🚗 1,750 miles ⏱️ 25 hours

Explore the beauty of the American Southwest and discover Tucson and its famous desert landscapes, especially in Saguaro National Park.

3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary

Chicago is a vibrant city that feels very alive, and with the perfect 3 days in Chicago itinerary, it’s possible to sample the best of the city over a long weekend!

The city is always on the move, and there isn’t an hour in the day that you won’t find at least 10 unique and adventurous things going on around town.

Music and food festivals pull out all the stops in Chicago, on top of the arts and cultural events that dot the city throughout the year.

Are you into food and drinks, lake views, and most of all, fun? Then Chicago is the place to be. There is enough here to explore for months, and we are going to pack all of the best events and activities into a 3 day long weekend itinerary to experience the essence of Chicago. 

Note: this Chicago blog post was written for Our Escape Clause by former Chicago locals Zach & Julie Ruhl, the travel couple behind Ruhls of the Road . Thanks for joining us, guys!

Table of Contents

Day 1 in Chicago Itinerary: The Bean, Skydeck & Great Chicago Food

Day 2 in chicago itinerary: lincoln park, wrigley field & beyond, day 3 in chicago itinerary: magnificent mile, navy pier & an afternoon adventure, where to stay for 3 days in chicago, where to eat during your chicago weekend getaway, getting around during 3 days in chicago, when to spend a long weekend in chicago.

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

Chicago is an enormous place. The city covers miles in each direction, with awesome things to do located all over the map. Therefore, this Chicago itinerary is going to thoughtfully take you from place to place, minimizing travel time and maximizing adventure.

Your first day in any new city should no doubt include some of the most signature sightseeing highlights there–and this Chicago itinerary is no exception, starting with a popular activity that is relatively new in Chicago: the Riverwalk. The current version of the Riverwalk was completed in 2017 and is an excellent place to start your Chicago weekend getaway.

Start your weekend in Chicago with a walk on the Chicago Riverwalk.

The Chicago Riverwalk starts at Wolf Point, near where the Chicago River turns from East/West to North/South. From there, the Riverwalk continues for over a mile, to the point where the Chicago River meets Lake Michigan.

Along this beautiful walk, you’ll pass a few awesome cafes and restaurants. This is a great place for a morning coffee, watching the morning hustle and bustle of America’s third-largest city. On top of that, the morning walk counts as your exercise for the day!

If you fall in love with the Riverwalk, then come back for a happy hour one evening. Riverside wineries and bars open up during the evening, complete with sets of outdoor games, live music, and some great entertainment! 

Check out Millennium Park.

At the end of the Chicago Riverwalk, you’ll reach Lake Michigan. Turn right here and head South to Millenium Park, where you’ll find an excellent location for soaking in the Chicago skyline from a beautiful park in the huge city center.

Millennium Park is an awesome Chicago sightseeing destination for two reasons. First off, it is just a great park full of fun things to do in Chicago !

There is an awesome playground for kids to play on, a great dog park for your four-legged friends, a huge green space to sprawl out for a picnic, a live music amphitheater, the Crown Fountain with a reflecting pool, endless gardens, and so much more!

You could spend a whole day at Millenium Park and not grow bored.

The second reason Millenium Park is so great is its proximity to everything. The park is great, but what makes it so impressive is that you are literally in a natural oasis amidst the concrete jungle of downtown Chicago.

Look around you while in the park, and you’ll see the towering structures of the Willis Tower, the Aon Center, and the rest of the enormous Chicago skyline.

Snap photos at The Bean.

At the edge of Millenium Park is The Bean, AKA Cloud Gate, Chicago’s most photographed (unofficial) monument.

The Bean is a huge monument, standing over 30 feet tall and 60 feet long, that is made of polished chrome and has no visible seams. This structure is truly unique and is an awesome downtown Chicago sight. 

The Bean is perfectly reflective, and due to its shape, the reflections can make for very fun images. It is essentially a gigantic magic mirror, placed in the middle of a bustling downtown environment.

Spend some time enjoying the fun reflections you can see as you walk in a circle around and under The Bean, then head for some food.

Downtown Chicago should have plenty of options on your way to your next stop: the Willis Tower. 

Admire views of Chicago from the Willis Tower Skydeck.

The Willis Tower is Chicago’s tallest building and the second tallest in the United States. At one point, this skyscraper was even the tallest building in the whole world, and held that title for 25 years! There’s no doubt that this is a must-see spot on any 3 day Chicago itinerary.

When you visit the Willis Tower, there are really two things you need to do. First off, admire the size of this monstrosity from below. The building literally reaches into the sky, and from the bottom seems impossibly huge. Walk around it marveling upwards, just make sure to lose your attention and wander into the city streets!

The other way to see the Willis Tower is, of course, from the top. The Skydeck is at the very top of the building, where you can see Chicago stretch beneath you for miles and miles in each direction into the horizon.

If you have the stomach for it, there is even a glass-bottomed section where you can literally step out into the sky, or at least it looks that way. From the glass floor, you can see down over 1,000 feet to the streets beneath you. This is quite an incredible experience and one that you won’t get anywhere else in the United States!

Book your Skydeck tickets for the Willis Tower today!

Finish your first day in Chicago in West Loop on Randolph.

The West Loop is an up-and-coming neighborhood in Chicago. This area seemingly has a great new restaurant pop up each week and has some of the most delicious food and one of the most fun atmospheres in the city.

Randolph Street in the West Loop is the culinary center of the neighborhood and is where you should head for dinner and drinks on your first day in Chicago. If you have the time and energy, the very best activity is to have a drink at a few different places, hopping from place to place and soaking up as much of this wonderful neighborhood as you can.

Each restaurant will have a unique vibe and atmosphere, so keep hopping around until you find the one you love best.

Want to make sure you experience the best food in the neighborhood? Add this popular West Loop Food Tour to your Chicago itinerary!

Close out your first night in Chicago at an Irish pub.

Chicago has a huge Irish population, and therefore quite a few Irish pubs located around the city. Our best recommendation is to find one close to your hotel and pop in for a Guinness as a night-cap. Enjoy the Chicago atmosphere, and then head to your hotel to get some sleep before heading off on your second day’s worth of fun things to do in Chicago!

Day 2 in Chicago is going to be a day full of exploring Chicago’s famous North Side. The North Side is awash with classic Chicago food options (Chicago loves its food…) as well as awesome sites to see and things to do. First up is the famous Lincoln Park.

Start the day with a stroll through Lincoln Park.

Lincoln Park is a huge and sprawling greenspace alongside Lake Michigan for 7 long miles. This is, in fact, the largest park in all of Chicago! And it also may very well be the most beautiful.

Alongside Lake Michigan, Lincoln Park has a few different beaches, as well as seemingly endless biking and walking trails. If you would rather bike than walk, then there are many bike rental options scattered all around the park, and around Chicago as a whole.

While strolling or biking through Lincoln Park, make sure to stop and see the Belmont Rocks, North Pond, and the Signal of Peace Monument. Along the way, admire the natural beauty and enjoy the sounds of birds singing as you bring on your second day in Chicago.

Soak up the sun at North Avenue Beach.

North Avenue Beach is one of Chicago’s largest and most popular beaches. Located right alongside Lake Michigan, this vast expanse of white sand makes for a great place to enjoy the beautiful Chicago summer sun.

If you are traveling with a group, then there are opportunities for some beach volleyball at North Avenue Beach! At the beach, you can rent a net and a ball (rentals are by the hour) and play some volleyball on the sand in view of the Chicago skyline!

While at North Avenue Beach, you must make a stop at the famous beach house that is shaped like a boat. This is also the location of Castaways, a bar and grill on the roof of the beach house serving yummy drinks with an incredible view. 

Head to Wrigley Field & Wrigleyville.

You can’t visit the North Side of Chicago and not see Wrigley Field. As one of the most famous baseball stadiums in existence, and the home of the Chicago Cubs, this is a must-see stadium, especially for sports fans.

Wrigley Field is located right in the heart of Wrigleyville on the North Side. Surrounded by residential areas and a huge bar and restaurant scene, this area is a magnet for good times, especially when the hometown Cubs are lacing up their cleats for a game.

If you are fortunate enough to be in Chicago while the Cubs are playing, head to Wrigley just for the experience of people watching and cheering on the hometown team. If you’d like, you could even try and buy some tickets, and usually, you can get a good deal on seats if you are okay purchasing them after the game is already in the 2nd or 3rd inning.

Wrigleyville, the neighborhood surrounding Wrigley Field, is an excellent place to hang out, have a drink, and hop around a few of the local establishments. Each of them has a great atmosphere, delicious, food, and of course a wide array of beers on tap.

Sample some Malort.

Malort is a Chicago specialty liquor and is something anyone over 21 should try when they visit the Windy City.

The liquor itself is not good because of taste, in fact, it tastes pretty bitter, and most people find it awful. However, it is all about the experience of trying something the locals love! If you’d like to experience the local culture of Chicago, then you have to try Malort at least once.

Finish the Day at the John Hancock Center Signature Lounge.

The John Hancock Center is the best building in Chicago. That may be a controversial opinion, but it is so true. The enormous slanted walls of the Hancock reach over 1,000 feet into the Chicago sky, with huge beams in a crisscrossing X pattern the entire way up. The building is an architectural masterpiece and is a wonder to see from the base.

The best place to experience the Hancock Center, however, is not from the base. It is from the Signature Room.

What is the Signature Room? It is an incredible 95th-floor bar and restaurant with an absolutely stunning view of Chicago. The Signature Room offers a 360-degree view of Chicago from above and is especially breathtaking as the sun sets and the sea of lights emerges beneath you.

Experiencing an evening at the Signature Room is a wonderful experience, and will be a highlight of your visit to Chicago. If you are visiting on a budget, just order a drink here, as dinner can be expensive!

Day 3 is going to be spent exploring more awesome sites and destinations in downtown Chicago. It is going to be a day where you can see as much as you want, and take it all in at your own pace. Choose your own adventure and make today special as you finish up your long weekend in Chicago!

Walk down the Magnificent Mile.

Start the day with a trip down the Magnificent Mile. This is a section of Michigan Avenue that is the retail center of Chicago. The street is lined on both sides with tons and tons of flagship stores, boutiques, and shopping malls.

Along the Magnificent Mile, in addition to all of the premier shopping, there are a few awesome sights you’ll see during this part of your Chicago weekend getaway.

The Wrigley Building is an awesome structure located right where Michigan Avenue meets the Chicago River. The Tribune Tower and the Chicago Water Tower are also wonderful landmarks along this stretch.

Explore Navy Pier.

Just a few blocks from the Magnificent Mile is Navy Pier, an absolute must-visit destination on any Chicago visit. The Navy Pier is, as the name suggests, a large pier, formerly used by the Navy, that extends straight out into Lake Michigan. 

These days, Navy Pier is an awesome destination that is used for a wide variety of attractions. First off, there is almost always some form of live entertainment or shows that are happening over a weekend at Navy Pier. On top of that, the pier is lined with awesome bars and restaurants, as well as shops and boutiques.

The view from the end of Navy Pier is excellent. First off, you’ll get to see the vast expanse of Lake Michigan on 3 sides of the pier. However, when you look back at the city, you’ll get a view of the full skyline including the Willis Tower and the Hancock Center. Do you want an even better view? Because there is one way to get it… There is a HUGE Ferris wheel that you can ride to get a stupendous view of the entire Chicago skyline and Lake Michigan!

Visit Buckingham Fountain in Grant Park.

After exploring Navy Pier, head to Grant Park, another of Chicago’s excellent downtown parks. Here you’ll have the chance to explore a huge area of green space, complete with monuments, statues, and a great lakeside walkway. At the heart of Grant Park, you’ll see Chicago’s most famous and beautiful fountain: Buckingham Fountain

Buckingham Fountain is at the center of Grant Park and is a great place to sit and enjoy a coffee or picnic. The fountain itself is beautiful, but it is made even better by the great Chicago skyline in front of you, and Lake Michigan behind.

Further South in Grant Park you’ll find three other excellent Chicago sightseeing spots to consider adding to your 3 day Chicago itinerary:

Field Museum, Shedd Aquarium + Adler Planetarium

On the south side of Grant Park are 3 beautiful buildings, each of which houses an awesome adventure. The Field Museum is one of the largest natural history museums in the world and is home to some of the best exhibits you can possibly imagine. When we visited in the past, the dinosaur exhibit left us astounded, as they had a full-size Tyrannosaurus Rex named Sue!

The Shedd Aquarium is a world-class aquarium located just east of the Field Museum on Lake Michigan. This aquarium is stunning both from the outside and inside and offers hours of exploration as you make your way through the grounds.

Finally, the Adler Planetarium, America’s FIRST planetarium, is a wonderful place. This place offers the chance to explore things that are out of this world, literally. If you are at all interested in space, astronomy, or astrophysics, then you will have the time of your life at the Adler Planetarium.

Finish your long weekend in Chicago at River North.

River North is the area just north of the Chicago River. Whoever named it wasn’t very creative, but they were very accurate.

River North is absolutely FULL of awesome bar and restaurant destinations. As with many neighborhoods in Chicago, the best way to experience it is by hopping from place to place. When you find a place you love, stay as long as you’d like, then move along to the next place! That is the Chicago way of experiencing the nightlife.

Chicago is an enormous place, sprawling for miles and miles. The downtown area has many neighborhoods, each of which has pros and cons for visitors to the Windy City.

The best places to stay for 3 days in Chicago are near the Chicago River, specifically River North, Gold Coast, Streeterville, and The Loop.

In addition to those, a few more great neighborhoods are Lakeview, Lincoln Park, West Loop (which is home to great Chicago street art ), Near North, and Old Town.

Here are a few great hotel recommendations for budget, mid-range, and luxury travelers.

Godfrey Hotel — The Godfrey Hotel is in the River North neighborhood, and is right in the middle of many of the best activities on your 3 day Chicago itinerary. On top of the great location, the hotel is beautiful on the inside and gets excellent reviews. The Godfrey Hotel is a wonderful place to hang your hat while exploring Chicago.

Check rates & book your stay at The Godfrey Hotel today!

Hyatt Regency Chicago — The Hyatt Regency Chicago is located in The Loop neighborhood, right on the Chicago River.

Many of the rooms in the Hyatt Regency have beautiful views of the Chicago River, the skyline, and the city streets.

The rooms are wonderful, the price is good, and the location is excellent. Additionally, the fitness center, meeting rooms, an on-site bar and restaurant, and access to Chicago activities make the Hyatt Regency one of the best places to stay in Chicago.

Check rates & book your stay at the Hyatt Regency Chicago today!

The Langham — Now, to the creme de la creme. If you’re a luxury traveler looking for the best hotel in Chicago, look no further than The Langham.

First off, the location could not be better. Located right on the Chicago River in River North, you’ll be within walking distance of nearly everything on your itinerary.

Additionally, The Langham pulls out all the stops when it comes to amenities. The on-site spa, fitness center, pool, and deluxe bar and restaurant are all five stars. Of course, the rooms are wonderful as well, and nearly all have stunning views of the cityscape.

Check rates & book your stay at The Langham today!

Chicago and food go hand in hand. You could explore a new food destination in Chicago every night for the rest of your life, and not eat at the same place twice. Not going to fact check that, but it is probably true. There are awesome restaurants on every corner, all across the city!

Here are four must-visit restaurants in Chicago that we love. 

Chicago-Style Pizza – Giordano’s

You can’t come to Chicago and not try some Chicago-style pizza. You literally can’t, it is impossible. The best Chicago-style pizza is at Giordano’s. The pizza here is absolutely LOADED with cheese and toppings, more than you have ever had, guaranteed. One slice and you’ll be satisfied, two slices and you’ll be stuffed. Be prepared to have leftovers!

Portillo’s is a Chicago institution. This started as The Dog House, a hot dog stand, and grew into Portillo’s, a delicious restaurant serving beef, burgers, and Chicago-style hot dogs all across the city. Portillo’s is yummy, quick, and is a Chicago must. Try the chocolate cake shake, you’ll be glad you did.

Happy Camper

Happy Camper is an excellent classic pizza place located in the Near North neighborhood, which offers an excellent atmosphere. This is a great place to watch sports, meet friends, enjoy a happy hour, and of course, try some pizza!

The toppings are creative at Happy Camper, and the pizza is DELICIOUS. There is also a huge selection of local and imported beers to try.

Girl and the Goat

Girl and the Goat is an absolutely EXCELLENT restaurant located in the West Loop neighborhood on Randolph Street. T he food here is delicious and is very creatively and expertly prepared.

Call ahead for a reservation at Girl and the Goat, as there may be a long wait if you just show up asking for a table. If you do just show up, however, this is worth the wait.

And you can walk across the street to one of the many bars on Randolph while you wait for a table at Girl and the Goat!

Bonus: take a Chicago food tour!

In a city as centered around food as Chicago, taking a food tour is one of the best ways to explore the city’s cuisine. 

Not only will you be able to sample a wide variety of classic dishes without committing to a whole portion, you’ll also learn plenty about Chicago’s history and culture along the way!

This popular food tour gets rave reviews and is an excellent addition to your long weekend in Chicago.

Book your food tour in Chicago today!

Getting around for 3 days in Chicago is in most ways easy, but can sometimes be challenging.

The public transport system is the easiest and most inexpensive way to get around, followed by cabs/Uber/Lyft, and finally driving yourself.

Much of the 3 days in Chicago itinerary laid out above, however, can all be completed by exploring on foot, especially from the recommended hotels. The awesome destinations and great parks are relatively close together and can be reached with a nice walk in the Chicago air.

Chicago has one of the best public transport systems in the US. The elevated train, AKA the ‘L’, brings people across Chicago east, west, north, and south. The ‘L’ stops at all of the amazing sites in the city, as well as O’Hare Airport, Midway Airport, and all the major thoroughfares.

If you would rather avoid public transportation, then the best way to travel around during this 3 day Chicago itinerary is with a cab/Uber/Lyft. Traveling this way is likely the fastest if you can avoid rush hour, and the most convenient. However, it will be more expensive than using the ‘L’ trains.

Finally, you, of course, have the option of driving yourself around town. In our opinion, this is the most stressful way to get around, as you’ll have to worry about parking in the busy downtown streets. This is a challenge and is made worse considering that many hotels offer parking fees.

The best time to plan a long weekend in Chicago is during the summer. The weather during the summer is absolutely perfect, and it’s definitely the easiest time to pack light for a Chicago vacation (if you visit during the blustery winter, be sure to carefully consider what to wear in Chicago !). This is also the best time to explore the awesome parks, beaches, and outdoor destinations in the Windy City.

Each year in the summer, Lollapalooza brings huge crowds looking for an awesome time and great music. Lollapalooza draws many of the best music acts in the world, so traveling to Chicago during the music festival is a great opportunity. On top of this festival, many great music artists perform regularly at Wrigley Field, Soldier Field, the United Center, and the other great venues across Chicago.

Coming in a close second to the Chicago summer is the spring when the city defrosts after its long Chicago winter and comes alive. There is nothing quite like spending 3 days in Chicago when the atmosphere is on the rise, as it is in spring.

Also during this time is St. Patrick’s Day, one of the largest holidays in Chicago. On St. Patrick’s Day the river is dyed bright green, and the partygoers are out in force.

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4 thoughts on “3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary”

I’d like to follow for future information

Thanks for this comprehensive guide! It made planning a trip to Chicago so much easier!

As a frequent traveler to Chicago, who lives just a few hours away, I want to mention a few places that truly make Chicago iconic. The Palmer House Hotel is the best in the City. Right outside the doors of the Palmer House is a Chicago favorite, with a long history, called Miller’s Pub. Grab an Allagash White beer on tap – a local favorite. Don’t miss a food tour of Chinatown. There is so much history there, and the food is really amazing! Other amazing foodie spots in Chicago are Bongo Room for brunch and Cafe Babareba for Spanish style tapas (do not miss the baked goat cheese in tomato sauce). An architectural tour on the Chicago River is a lovely way to spend the day and if that isn’t your thing, the water taxis are a fun way to get around.

Agrred with the other poster–This itinerary is hugely missing the architecture tours! Best thing to do in the city. River north is fine, but kind bro-y for lack of a better descriptor. Bongo room is in Wicker Park which I describe as our Williamsburg. Not quite as artsy and cool as it was 5 years ago but still very fun!

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Things to do in Chicago this Memorial Day weekend: Beach openings, festivals and more

M emorial Day weekend is nearly here and there will no shortage of things to do and ways to enjoy the long holiday weekend - no matter the weather -- in Chicago.

As you look to plan your Memorial Day weekend in and around Chicago, here's a roundup of events taking place, what to know if you plan to head to the beach and more.

Chicago Beaches Open

According to the Chicago Park District, beaches will open for the first time on Friday, and will remain open daily through the Labor Day holiday.

Additional security measures will be put into place once the summer swimming season begins, according to the park district.

Starting Friday, a beach mobile unit with six prominently marked vehicles and security officers in bright yellow will be visible along the lakefront.

According to the the park district, swim conditions are updated each day around 11 a.m. "based on weather and surf conditions, and around 1:30 pm based on water quality conditions."

"Flags may be updated throughout the day as needed," the park district said.

Several beaches are currently closed due to erosion, including Fargo Beach, Howard Beach, Juneway Beach, and Rogers Beach. More information  can be found on the park district website.

Beachgoers are reminded that there is no smoking or alcohol consumption allowed on beaches. No dogs are allowed except at designated dog-friendly beaches, and residents are not to feed birds or wildlife.

Here's how to check the water temperature at Lake Michigan .

Memorial Day Things to Do

Festivals, flea markets, farmers markets, food and more will be on display this Memorial Day weekend in Chicago. Here's a glimpse into some of the events planned across the city and suburbs.

Sueños Music Festival

The Latin music festival brings reggaeton and Latin artists from across the globe to Chicago. This year's lineup includes Rauw Alejandro, Young Miko, Bizarrap and more, the fest takes place Saturday and Sunday in Grant Park. The event also features a number afterparties and other events . The full lineup  can be found here .

Passes are currently on sale  and begin at $310.

Randolph Street Market

The fan-favorite Randolph Street Market, a curated, vintage and antique market takes place Saturday and Sunday and includes more than 200 vendors.

Tickets  are required and begin at $12. The market takes place from 10 a.m. to 5 p.m. Saturday and Sunday, at 1341 W. Randolph St.

Farmers markets

Chicago Farmers Market season kicked into high gear Thursday as the Daley Plaza Farmers Market opened to the public -- and that's not the only market opening this week.

Already the Division Street Farmers Market was underway on Saturdays and coming up next is the return of the Maxwell Street Market in its original home.

According to officials, the market will be back on Maxwell Street for the first time since 1994 , taking place on the final Sunday of each month during the summer.

According to officials, the first market will take place on May 26, and will take place on the last Sunday of each month, with the exception of the Sept. 1 event.

The market takes place from 9 a.m. to 2 p.m. Maxwell Street between South Halsted Street and South Union Avenue and on South Union Avenue between West Rochford Street and West Liberty Street.

Belmont-Sheffield Music Festival

The 39 th annual Belmont-Sheffield Music Fest is know for highlighting national tribute bands and local entertainers. The festival runs from 11 a.m. to 10 p.m. Saturday and Sunday.

Navy Pier Fireworks

The iconic fireworks  displays at Navy Pier will make their return this Memorial Day weekend, with the biweekly shows set to last throughout the summer.

The fireworks take place at 10 p.m. on Saturdays, and 9 p.m. on Wednesdays.

Here's a full list of other events taking place.

Giant Bounce House in Orland Park

The "ultimate bounce hour experience" is coming to Orland Square this weekend. Beginning Saturday and continuing through June 9, the Bounce the City Tour will bring an immersive bouncing obstacle course and several other supersized bounce houses for "all kinds of inflatable fun for every age."

See below for tickets:

May 25-26– Tickets

June 1-2 – Tickets

June 8-9 – Tickets

Bluey X Camp

Everyone’s favorite Australian cattle dog will be coming to Chicago, as the immersive “Bluey x Camp” experience will make its debut.

The experience, which will be located at 647 W. North Ave. in the Old Town neighborhood, will give fans of “Bluey” a chance to experience a real-life version of the Heeler’s home, as well as a meet-and-greet with Bluey and her sister Bingo.

According to the website , all tickets will allow visitors a one-hour experience in a 5,000-square foot recreation of Bluey’s house. Attendees will be able to play all of Bluey’s favorite games, including “Keepy Uppy” and many more.

More information, including on “low-sensory experience” times and other special events,  can be found on the attraction website .

Mayfestiversary 

Dovetail Brewery and Begyle Brewing joining forces for Mayfestiversary , an annual street fest to benefit a neighborhood food pantry, The Friendship Center. The event takes place both Saturday and Sunday between Begyle and Dovetail, at the corner of Ravenswood and Belle Plaine Avenue in the Ravenswood Corridor.

Details here.

WingOut Chicago

For wing aficionado’s or first timers, WingOut Chicago is the ultimate chicken wing block party. Pre-sold tickets are sold out, but the fest is accepting walkups at 5 p.m. Saturday and Sunday. The event is located at Wrigleyville’s Gallagher Way, 3635 N. Clark Street.

Mole De Mayo Festival

Mole de Mayo is the only outdoor mole cook-off event celebrating Latino culture and Mexican cuisine. The event takes place Friday through Sunday and is located on 18th Street, between Morgan and Halsted in the city's Pilsen neighborhood.

Gaming Festival: Combo Breaker

Combo Breaker, an annual gaming festival dedicated to competitive fighting games, will take over the Schaumburg Convention Center this weekend. The event takes pale from Friday to Sunday at 1551 Thoreau Dr N. in Schaumburg.

Balkan Music Night

Balkan Music Night on Friday celebrates Balkan and Klezmer music, with Fugu Dugu, Cloud Farmers and Vox Maris. Head to Reggies Comedy Shack at 2105 S. State St. in Chicago to enjoy the festivities.

Concert: Gregory Porter with special guest Terisa Griffin

Jazz vocalist, songwriter and musician Gregory Porter brings his smooth sounds to the Chicago area, along with Chicago singer Terisa Griffin . Listen in on Friday at the Venue at Horseshoe Hammond, located at 777 Casino Center Dr. in Hammond, Indiana.

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26 Things To Do In Chicago This Weekend: A Margarita Fest, Garden Fair, Mayfest And More

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CHICAGO — Spring markets, art exhibitions, street festivals and cooking events are all on deck this weekend. From Mayfest and the Lincoln Roscoe Art Fair to the Hyde Park Garden Fair and a pop-up Bosnian Sijelo, there is no shortage of events happening around Chicago this weekend.

Here’s a roundup of 26 things to do in Chicago this weekend:

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Art Gives Us Hope

Saturday art exhibit and 5:30 p.m. Saturday party

ERIS Brewery and Cider House, 4240 W. Irving Park Road

In honor of May being Mental Health Awareness Month, ERIS is hosting a “festival of self-expression” to support suicide prevention. There will be art on display through Saturday by artists Mosher, Myron Laban, Allison Poplett, Steven Agpawa and Julia Jacquez.

Alongside an art raffle and auction, there will be a Saturday night celebration with a food buffet, live murals, games and music with local band Model Stranger.

Learn more and buy tickets here .

Helmchen Plays Beethoven

7:30 p.m. Saturday

Chicago Symphony Orchestra, 220 S. Michigan Ave.

German pianist Martin Helmchen takes on Beethoven’s “Piano Concerto No. 1” at the Chicago Symhony Orchestra this weekend. Conductor Kazuki Yamada will open the program with Toru Takemitsu’s “How Slow the Wind” and César Franck’s “Symphony in D Minor.”

Buy tickets for Saturday here starting at $35.

‘The Prodigal Daughter’

7:30 p.m. Saturday and 3 p.m. Sunday

Raven Theatre, 6157 N. Clark St.

Chicago playwright Joshua Allen’s “The Prodigal Daughter” opens Thursday at the Raven Theatre in a commissioned world premiere. The show unfolds in Chicago’s Black Belt during the Red Summer of 1919, which is “boiling over” from ruthless hot temperatures and “the intensifying racial conflict gripping America.” There, saleswoman Virginia Bass pays her hometown and family a visit and is faced with “unresolved tensions, deep-seated tension, and a deadly urban clash.”

Through June 22, the theater will offer mask-only nights, industry nights, a student night, a Black Out night, closed captions, a touch tour and a talkback.

Learn more and buy tickets for $15-35 online .

Hyde Park Garden Fair

9 a.m.-4 p.m. Saturday

Hyde Park Shopping Center, 5450 S. Lake Park Ave.

Neighbors can shop herbs, vegetables, native plants, shrubs, annuals, perennials and more at the 63rd annual Hyde Park Garden Fair .

Chicago Mayfest

noon-10 p.m. Saturday and noon-9 p.m. Sunday

On Armitage Avenue from Sheffield to Racine

Kick off Chicago’s summer festival season at Mayfest with music, food, libations and more. There will be two performance stages with Too Hype Crew, 16 Candles, Monty Kiddo, Nicky B, Mr. Simpson and more than a dozen other acts. Festgoers can also try their hand at glass blowing classes on the hour and enjoy a Pet Parade noon Saturday.

There is a $10 suggested donation to support the Ranch Triangle Community Conservation Association. Learn more about this free festival here .

Chicago Margarita Festival

Through Sunday

1800 S. Peoria St.

This first-of-its-kind Pilsen festival features more than 15 margarita flavors, Latin bites, local vendors, live DJs and musicians and more. Headliners include Fuze, a Santana cover band and Revolución de Amor, a Maná cover band.

The festival is free, and there is a $5 suggested donation upon entry. Learn more here .

Garden Boys Set

7 p.m. and 9 p.m. Saturday

The Den Theatre, 1331 N. Milwaukee Ave.

After 10 years together, Chicago music comedy group Garden Boys is taking to the stage for their first-ever full-length special.

Tickets are available online .

Summer50 Fest

10 a.m.-2 p.m. Saturday

United Center, 1901 W. Madison St.

This inaugural fair provides parents and teens opportunities to connect with youth programs, educational initiatives, athletics, jobs and internships across Chicago’s 50 wards. Local agencies, educational groups and community organizations will have booths, where families can learn more and enroll on the spot. There will also be fun clinics, pop-ups, raffles, a DJ and more.

Learn more here .

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Spring Lincoln Roscoe Art Fair

10 a.m.-7 p.m. Saturday and 10 a.m.-5 p.m. Sunday

Lincoln Avenue from Roscoe to School

This free North Side event is back with more than 75 local artisans, painting classes, festival food, family-friendly art activities, face painting and more. Fairgoers can shop home decor, paintings, sculptures, fiber pieces, jewelry and more handmade goods.

Admission is free. Learn more here .

Neighborhood Cookout With Chef Jernard

11 a.m.-1 p.m. Saturday

Mariano’s Bronzeville, 3857 S. Martin Luther King Drive

Chef Jernard Wells, host of “New Soul Kitchen” on Cleo TV, is coming to town for a neighborhood cookout, where he’ll be making recipes from his latest cookbook. There will be music, book signings, samples and a chance to buy the cookbook.

Seeds Of Fire Family Program

11 a.m.-2 p.m. Saturday

Winthrop Family Historical Garden, 4628 N. Winthrop Ave.

Families and neighbors can watch fire dancers, make torches, bake bread in a fire oven and more in Uptown this weekend. There will also be food, refreshments and activities without fire, like making bubbles by pedaling a stationary bike and planting seeds.

May Indoor Farmers Market

11 a.m.-3 p.m. Saturday

Plant Chicago, 4459 S. Marshfield Ave.

Shop local businesses and enjoy family-friendly activities, food and more at this indoor farmers market. The vendor list is subject to change but currently includes Aztec Vegan Kitchen, Bee-utiful Honey & Candles, Cedillo’s Fresh Produce, Viva la Horchata, Chicago Training Center, Stef’s Plants & Art and more. There will also be free bike repairs and tuneups.

Learn more here.

Bike Out Negativity 2024

Noon Saturday

3147 W. Douglas Blvd.

Bike Out Negativity is a community bike ride that aims to give kids a safe and fun way to ride through the neighborhood. There will be a pre-ride community resource fair to connect residents with social services, youth programs and health resources.

The six-mile ride kicks off at 3 p.m. The event is a symbol of unity and peace, organizer Derek Brown previously told Block Club .

Sign up for free online .

Humboldt Park Boathouse Ribbon-Cutting

Noon-4 p.m. Saturday

Humboldt Park Boathouse Gallery, 1301 N. Sacramento Blvd.

The Humboldt Park Boathouse is hosting a ribbon-cutting to celebrate its new shower facilities. There will be special guests, food, desserts, haircuts for the unhoused, live music, an ice cream truck and more. Learn more here .

Trolley Tour Of Chicago’s Labor History

12:45-4 p.m. Saturday

4704 N. Broadway

On this trolley tour by Chicago Fair Trade, Chicagoans will visit locations significant to Chicago’s labor movement, like Haymarket Square, where a confrontation between activists and police in 1886 had a worldwide impact.

Learn more and buy tickets for $55 here .

Chicago Bacon & Bourbon Fest

2-6 p.m. Saturday

Headquarters Beercade, 213 W. Institute Place

Enjoy bourbon tastings, bacon bites, free arcade games and discounted cocktails at River North’s Headquarters Beercade.

Tickets start at $29 online .

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4:30 p.m. Saturday

Sister City Library, 2842 W. Chicago Ave.

In observation of the Day of Remembrance of the Victims of the Crimean Tatar Genocide of 1944, the Ukrainian Daughters Foundation is hosting a community event with music, food, art, a film screening and more to honor the indigenous people of Crimea.Learn more and buy tickets for $45 online . Proceeds will benefit the Crimean Battalion of the Armed Forces of Ukraine.

What’s Rum Got To Do With It? A Mixology Masterclass

5-7 p.m. Saturday

After a trolley tour for Chicago’s labor history, Chicago Fair Trade is hosting a mixology masterclass where attendees will learn not only how to concoct their own cocktails, but also about the exploitative history of conventional rum production and how Chicago Cane Cooperative is turning things around.

Learn more and buy tickets for $10 online .

Chicago Jazz String Summit

Logan Center for the Arts, 915 E. 60th St. and other locations

For ten years, the Chicago Jazz String Summit has showcased the contributions of string players to jazz, improvised and experimental music. Alongside performances, there will be an improv session with past and present summit artists.

MJFF Chicago Run/Walk

8:30 a.m. Sunday

Guaranteed Rate Field, 333 W. 35th St.

Chicagoans can lace up their sneakers and run, jog or walk through Guaranteed Rate Field this weekend to help raise funds for Parkinson’s disease research and patients. The annual event is hosted by the Michael J. Fox Foundation and open to all ages. Donate, learn more and register for $20-40 online .

View this post on Instagram A post shared by Michelle Hartney (@michellehartneyart)

Mending Workshop With Michelle Hartney

11 a.m.-12:30 p.m. Sunday

21c Museum, 55 E. Ontario St.

Led by artist Michelle Hartney, this crafting workshop for trans families allows attendees to alter clothes to reflect their gender identities. Attendees should bring baby clothes, whether its their own or to affirm a loved one. This beginner-friendly workshop is open to families and free to attend.

Ommi Foods: A Bosnian Sijelo

11 a.m.-2 p.m. Sunday

Guild Row, 3130 N. Rockwell St .

After two sold-out Palestinian food events, Ommi Foods is back with a Bosnian-themed pop-up sijelo. Attendees can share Bosnian dishes, desserts, coffee and drinks while learning about the ingredients and stories behind each one.

Tickets are $75 online .

Hyde Park Handmade

11 a.m.-3 p.m. Sunday

The Promontory, 5311 S. Lake Park Ave.

Back on at The Promontory this weekend, Hyde Park Handmade brings together a lineup of artisan vendors and foodmakers. Shoppers can also enjoy tunes by DJ Sean Alvarez and an open bar.

American Writers Festival

11 a.m.-5 p.m. Sunday

Harold Washington Library Center, 400 S. State St.

The American Writers Festival returns for its second edition this weekend. The free literary festival will have conversation with a diverse lineup of writers, from sci-fi authors and game designers to journalists and opens. There will also be children’s storytimes, photobooths, literary-themed crafts, book signings and mini writing workshops for all ages.

The Patio Theater’s Princess Movie Party

Noon-6 p.m. Sunday

Patio Theater, 6008 Irving Park Road

Kids and families can pretend they’re in a fairytale this weekend with a princess-themed party at Patio Theater. Attendees can meet more than 10 princesses, including Belle Ariel, Mirabel, Cinderella, Elsa and Anna, get their autographs, play games, browse an “enchanted market” and more. There will also be storytimes, princess short films and feature films, including “Beauty and the Beast” (1991) and Encanto (2021).

Buy tickets here .

Reggies Crawfish Boil

1 p.m. Sunday

Reggies Music Joint, 2105 S. State St.

Feast on all-you-can-eat crawfish while jamming to live music at Reggies Crawfish Boil. Featured music acts are Chicago Soul Explosion, singer-songwriters Aage Birch and funk-jazz group Vince Willis All-Stars.

Learn more and buy tickets for $50 here .

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Memorial Day weekend travel gets underway

Entertainment | What to do in Chicago for Memorial Day weekend

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• Music and Concerts
• The Theater Loop
• TV and Streaming

Things To Do

Entertainment.

“English”: Sanaz Toossi’s Pulitzer Prize-winning drama “English” ostensibly follows four Iranian adults as they prepare for a language test, but its real work is in examining the expression of identity.   Through June 16 at the Goodman Theatre, 170 N. Dearborn St.; tickets $20-$55 at goodmantheatre.org

Ana Belaval: You may know her from WGN-TV’s morning news, but Ana Belaval has been performing bilingual standup for more than a decade. Her comedy explores the gaps between Puerto Rican and American culture. 7:15 p.m. May 24-25 at Zanies Comedy Club, 5437 Park Place, Rosemont; tickets $30 at rosemont.zanies.com

Sueños Chicago: Rauw Alejandro, Peso Pluma, Maluma and Young Miko headline a lineup featuring more than 25 Reggaeton and Latin artists. Noon to 10 p.m. May 25-26 in Grant Park; suenosmusicfestival  

LCD Soundsystem: Go see if James Murphy is losing his edge as LCD Soundsystem brings its Kinda Tour to the Aragon Ballroom for a four-night stand. 8 p.m. May 24-27 at the Byline Bank Aragon Ballroom, 1106 W. Lawrence Ave.; tickets $90.50 and up (ages 18+) at lcdsoundsystem.com

“Back Home: Polish Chicago” : Consider how Polish immigrants shaped Chicago since the mid-1800s in an exhibition featuring more than 100 photographs and 90 artifacts and documents. Artwork by Voytek Glinkowski, Andrea Jablonski, Andrzej Krukowski, Monika Lozinska and Irena Siwek punctuates the exhibit, exploring themes of duality and industry. 9:30 a.m. to 4:30 p.m. Monday-Saturday, noon to 5 p.m. Sunday through June 8 at the Chicago History Museum, 1601 N. Clark St.; tickets $15-$29 at chicagohistory.org

“Level Up: Gamers & Writers”: A new exhibit explores the evolution of role-playing and video games and their place in American culture. From Dungeons & Dragons ( invented in Lake Geneva ) to Baldur’s Gate 3, soak up 50 years of this unique narrative form and then try it for yourself: The exhibit features a room where visitors can play storytelling games. Opens May 24 at the American Writers Museum, 180 N. Michigan Ave.; tickets $10-$26 at americanwritersmuseum.org  

Sundays are For Lovers: R&B Day Party and Fever II: The Ultimate Afrobeats Rave: It’s a long weekend, so treat Sunday like it’s Saturday. Consider an afternoon of R&B or stay out late with Mo Gwala, DJ K.O. and DJ Certified. R&B at 3 p.m., Fever II at 10 p.m. to 2 a.m. May 26 at The Promontory, 5311 S. Lake Park Ave.; tickets (ages 21+) $13.86-$168.86 at promontorychicago.com

Game Changer Wrestling: Feeling aggressive? Hardcore professional wrestling takes over Thalia Hall. 8 p.m. May 25 at Thalia Hall, 1807 S. Allport St.; tickets $34.99-$52.99 at ticketweb.com

Garden Movies: Outdoor movies have returned to the Music Box Theatre’s patio. Wrap up Memorial Day Weekend with the launch of Christopher Guest Week: “For Your Consideration” screens Monday and Tuesday, with “A Mighty Wind” following on Wednesday and Thursday. Additional films will play in the garden throughout the summer, featuring such themes as John Waters, Grey Gardens and School’s Out. 8:30 p.m. most Mondays-Thursdays at the Music Box Theatre, 3733 N. Southport Ave.; tickets $8 at musicboxtheatre.com

Have something to do around Chicago? Email events to [email protected] .

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The most romantic getaways from Chicago for couples

Skip town for an intimate weekend full of scenic hikes, relaxing spa treatments and hotel rooms strewn with rose petals.

A romantic escape doesn’t need to require plane tickets or a lot of advance planning. If you want to get out of Chicago for a weekend  getaway , there are plenty of destinations you can drive to in just a few hours for a change of scenery that will let you and your significant other enjoy some quality time without the distractions of home. The adventurous can spend the day hiking , skiing or boating while those looking for relaxation can visit a museum or winery . Either way, you should plan on booking a hotel so you can relax after a full day by soaking in a hot tub or curling up by the fireplace. Feel the love when you head out on one of these romantic getaways from Chicago.

RECOMMENDED: Discover the  best day trips from Chicago

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The most romantic getaways from Chicago

Driving time from Chicago: Two-and-a-half hours

Just west of Sheboygan, Wisconsin sits the small village of Kohler. It’s home to Destination Kohler , a five-diamond resort operated by the Kohler Company (yes, the brand best known for its plumbing products), and a perfect romantic escape for couples. You’ll want to book a stay at the American Club , a century-old luxury hotel that’s brimming with both historic charm and modern amenities. Start your morning with Yoga on the Lake before embarking on an adventure around a 500-acre wilderness preserve. Food and beverage options are aplenty, from the aptly-named Lodge Restaurant set inside a cabin and the casual Horse & Plow pub to a quaint greenhouse-turned-cafe. Of course, no getaway would be complete without a visit to Kohler Waters Spa , where you can pamper yourself with rejuvenating massages, hydrotherapy treatments and dips in relaxation pools.

Mackinac Island, MI

Driving time from Chicago: Six-and-a-half hours

The abundance of natural beauty and car-free streets make Mackinac Island a popular destination for weddings. See why by booking a romance package at Cloghaun Bed and Breakfast , which includes half a dozen roses and a private carriage ride. Bring your sweetheart to Original Murdick’s Fudge , which uses a recipe dating back to 1887. Walk the eight miles around the island to take in the views, heading to the west side in time to see the sunset. You can get an even better view from the water during a sunset cruise from Great Turtle Kayak Tours .

Door County, WI

Driving time from Chicago: Four hours Spanning 300 miles of shoreline, the peninsula between Green Bay and Lake Michigan boasts numerous hiking trails and perfect spots to watch both the sunrise and sunset, plus spectacular stargazing at Newport State Park . Visit Door Peninsula Winery , where you can try some of their 60 varieties of wines and ciders, and pick up a bottle of your favorite to enjoy at one of the area’s many cozy bed and breakfasts like Eagle Harbor Inn , where the suites are outfitted with a fireplace and giant whirlpool tub.

Driving time from Chicago: Three hours

Book a romantic getaway package at Goldmoor Inn and they’ll have a dozen roses on display in your room. Rent a tandem kayak from Nuts Outdoors and spend two hours paddling on the Galena River, starting against the current so you can relax and float on your way back to the dock. Head back to the hotel for a bath in your two-person whirlpool tub then grab dinner on Galena’s historic Main Street at Fritz and Frites , which combines German and French fare. You can also relax with a couples massage at the Galena Day Spa , which ends with chocolates and Champagne in your private relaxation room.

Lake Geneva, WI

Driving time from Chicago: One-and-a-half hours

Chicagoans have been escaping to Lake Geneva since the late 19th century and the city is home to numerous resorts and vacation rentals. Get a sense of that history at Maxwell Mansion , which was built as a summer home in 1855 and hosts a cocktails bar with outdoor bocce ball courts and fireplaces. For a luxurious retreat, book a room at the Grand Geneva Resort & Spa , a popular wedding venue that features skiing, golf, indoor and outdoor pools, and a spa. Stop by Geneva Lake Distilling + Studio Winery for a tasting during the afternoon or live music on the weekends.

Milwaukee, WI

Driving time from Chicago: One and a half hours

Milwaukee is best known for beer, and hop lovers can share their passion with brewery tours or pints paired with cheese curds and sausages. There are plenty more conventionally romantic attractions like pedaling a swan boat through the Veterans Park lagoon or taking in the views of the Milwaukee River while slurping oysters at Vault . Head to At Random Cocktail Lounge to share their Love Bowl and see why the place has been a date night staple since 1964. Stay downtown at Kimpton Journeyman Hotel for a package including a bottle of bubbly, chocolates and late checkout.

Madison, WI

Driving time from Chicago: Two-and-a-half hours Madison has a fantastic food scene, including plenty of romantic destinations like French farm-to-table spot L’Etoile and the lakeside bistro Sardine . You can also enjoy the city’s five lakes by visiting one of Madison Boats ’ three locations and renting a tandem kayak or canoe. After sharing some time on the water, retire to your suite at Mansion Hill Inn , where you can warm up in front of the fireplace. Sweeten your time together with a visit to Gail Ambrosius Chocolatier , which offers pairing suggestions for beers to accompany truffles with varieties including lemongrass with ginger and shiitake mushroom.

Traverse City, MI

Driving time from Chicago: Five hours

Spend the day walking along the beach and taking in spectacular views of Lake Michigan from the bluffs at Sleeping Bear Dunes . Then visit the Traverse Wine Coast , a group of 26 wineries providing an opportunity to chat with the winemakers and taste their works. Pick up a bottle and head back to the Glen Arbor Bed & Breakfast , where you can book a romantic package and have a bouquet of flowers and a box of organic truffles from Grocer’s Daughter Chocolate waiting for you.

Indianapolis, IN

Created in 1970, Robert Indiana’s steel “LOVE” sculpture is one of the most iconic pieces at the Indianapolis Museum of Art at Newfields , which also hosts works by Rembrandt and ancient sculptures from around the world. While you’re there, stroll through The Garden which features 52 acres of winding paths, fountains and plants. Imagine you’ve been transported to Venice when you book a gondola ride on the city’s Central Canal, a popular option for proposals and anniversaries. Toast to a great trip with a glass of bubbly and dessert at Gallery Bistro & Bar .

Indiana Dunes, IN

Driving time from Chicago: One hour Share your love of the outdoors by taking a dip at West Beach and then strolling along the lakefront at Indiana Dunes National Park . Equally impressive is the Indiana Dunes State Park, where you can take the 3 Dune Challenge and trek 1.5 miles up a series of hills to see some spectacular views. You can grab dinner right on the beach at The Pavilion , a popular wedding destination, then head back to your room at the Songbird Prairie Inn and Spa to soak your tired muscles together in a whirlpool bath.

St. Louis, MO

Reserve one of the five rooms at the Fleur-De-Lys Mansion , a 19th-century manor popular with honeymooners, and they’ll throw in free tickets to the nearby Missouri Botanical Garden . The 79-acre space features one of the largest Japanese gardens in North America plus an impressive sculpture collection. Take in the city’s skyline at sunset with a ride on The St. Louis Wheel , where you’ll go 200 feet up in a fully enclosed gondola. Then share a romantic meal at Annie Gunn’s , where you can order steak and seafood a la carte or let the chef pick a four-course dinner with wine pairings.

Woodstock, IL

Best known as the filming location for Groundhog Day , the historic town is filled with nostalgic charm. Take a walking tour of spots featured in the movie including the Woodstock Opera House , which hosts concerts, dance performances and art exhibits. Enjoy some natural beauty with a stroll through the Pleasant Valley or Dufield Pond conservation areas. The area is full of farms, so depending on the season you can pick your own strawberries and raspberries from Heider’s Berry Farm or take a hayride to apple picking at All Seasons Orchard . Stay the night at the Cherry Tree Inn B&B , which can have flowers, chocolates, wine and cheese ready for you and arrange a private dinner for two. 

Long Grove, IL

Driving time from Chicago: One hour

Travel back in time to this picturesque town known for the numerous festivals hosted in its historic downtown area, which you can explore by walking down cobblestone pathways lined with flowers. Highlights include the Chocolate Fest in May and Strawberry Fest in June, but it’s worth a visit any time to check out its quaint shops and enjoy some wine, cheese and charcuterie at Broken Earth Winery . For a real taste of history, share dinner at The Village Tavern : established in 1847, it’s the oldest restaurant in continuous operation in Illinois.

Sheboygan, WI

Stay right on the shore of Lake Michigan at Blue Harbor Resort & Conference Center , a popular wedding destination which offers large suites with a whirlpool tub, fireplace, balcony and patio plus a spa where you can get an hour-long couples massage. Walk along the beach or hike along the sand dunes at Kohler-Andrae State Park , then share a romantic dinner at Lino Ristorante Italiano , which uses local organic products in decadent dishes like pappardelle with slow-roasted lamb ragu and lasagna made with Italian sausage. 

Syracuse, IN

Driving time from Chicago: Two-and-a-half hours Located between Syracuse Lake and Lake Wawasee, Syracuse offers plenty of opportunities for waterfront fun. Walk or bike through trails that will take you through area wetlands and into the downtown area while providing some stunning views, and then grab a hand-breaded cod sandwich and a hurricane on the water at Channel Marker . Book the romantic getaway package at Brook Pointe Resort and your room will be decorated with candles and rose petals and there will be a chilled bottle of bubbly waiting for you. If you prefer to be closer to the water, stay at the Oakwood Resort and explore the lake in a pontoon boat.

Kenosha, WI

The city on Lake Michigan is a haven for outdoor enthusiasts year-round thanks to its many beaches, parks and hiking trails. Get a private sailing lesson from Sail Away Charters , whose two-hour outings are regularly used for anniversaries or marriage proposals. Couples who like to share thrills can navigate the bridges and ziplines at Boundless Adventures during the summer or hit the slopes at Wilmot Mountain during the winter. Get dressed up for a day of jousting, music and wild costumes at the Bristol Renaissance Faire ,  then share an intimate meal at old school Wisconsin supper club Hobnob .

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• our chicago

Our Chicago: Memorial Day weekend and summer travel

CHICAGO (WLS) -- Memorial Day weekend is the unofficial kick-off to summer. AAA expects 43.8 million Americans will travel 50 miles or more over the holiday.

ABC7 Chicago is now streaming 24/7. Click here to watch

But what about the rest of the summer? Airlines for America, an industry trade organization, forecasts that U.S. airlines will transport 271 million passengers between June 1 and Aug. 31.

That's up more than 6% from 2023, which was a record breaking year. But what will travelers find when they go to buy plane tickets?

"If they plan early, they will help themselves because flights are full this summer. nd the ones that are nearest in are going to cost you the most," said AAA Vice President of Travel Debbie Haas said. "The other thing they can do is work with a travel advisor because travel advisors have access to inventory that an individual might not find on their own and travel advisors know ways to bundle hotels and flights to get extra value."

Ja'Vonne Harley is the owner of Advantage International and hosts the radio program Traveling Culturati. She said domestically, Chicago is a popular travel destination, along with Las Vegas and New York.

Our Chicago: Part 2

International flights aren't too behind on demand.

"You're talking about London, you're talking about Paris, of course, Rome and Japan." Harley said. "Japan was very slow reopening after the pandemic. They actually opened in October of 2022, so many people are still traveling there. It's only been about a year-and-a-half since they reopened."

Another destination that some might have considered is Scandinavia.

"Folks are increasingly gravitating towards Scandinavia, particularly in summer because of the cooler weather up there," Haas said.

Harley added that it's not too late to plan an international trip.

"You can still get some good prices now, but don't delay. Because not only are we looking at record travel numbers for the summer, but also understand that air traffic controllers are still short about 3,000 and that has caused airlines to limit some of the flights that they would have otherwise had. So, there may be a shortage of some flights and that's why so many are full already," Harley said.

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