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THE 10 BEST Chicago Tours & Excursions

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1. Chicago Architecture River Cruise

2. Chicago River 90-Minute History and Architecture Tour

3. Chicago River 45-Minute Architecture Tour from Magnificent Mile

4. Chicago Architecture Center River Cruise aboard Chicago's First Lady

5. Chicago: Gangsters and Ghosts Walking Tour

6. Lake Michigan Sunset Cruise in Chicago

7. Chicago River Boat Architecture Tour

8. Skip-the-line: Art Institute of Chicago Guided Tour

9. Skydeck Chicago Admission Ticket

10. Chicago Favorites Ultimate Food and Walking Tour

11. Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-top Bus

12. Flyover in Chicago

13. Chicago Crime and Mob Bus Tour

14. 360 CHICAGO Observation Deck Admission

15. The Deep Pockets Of Graceland Cemetery Walking Tour

16. Chicago in a Day: Food, History and Architecture Walking Tour

17. Chicago CityPASS®

18. Chicago Lake and River Architecture Tour

19. Chicago's Secret Interiors Architectural Tour

20. Chicago River Cocktail Cruise

21. Chicago Craft Brewery Barrel Bus Tour

22. Chicago Gangster and Food Walking Tour

23. Chicago River Architecture Boat Tour

24. Chicago Buffet Lunch Cruise on Lake Michigan

25. Chicago Walking Food Tour With Secret Food Tours

26. Chicago City Minibus Tour

27. Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

28. Lake Michigan Skyline Cruise in Chicago

29. 2-Hour Guided Segway Tour of Chicago

30. Chicago's Chinatown Food and Walking Tour

What travelers are saying.

• Chicago Architecture River Cruise
• Chicago River 90-Minute Architecture Tour
• Chicago River 45-Minute Architecture Tour from Magnificent Mile
• Gangsters and Ghosts Tour in Chicago
• Chicago Architecture Center River Cruise aboard Chicago's First Lady
• Inside Chicago Walking Tours
• Chicago Greeter
• Bobby's Bike Hike Chicago
• Tours With Mike
• Babylon Tours Chicago
• Pizza City USA
• Chicago Private Tours
• Free Chicago Walking Tours
• Chicago's Finest Tours
• Walk Chicago Tours
• Absolutely Chicago Segway Tours
• Chicago Elevated
• 3rd Coast Charters
• Steve's Segway Tours
• Urban Kayaks
• City Cruises Chicago
• Windy City Sailing

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The 14 Best Chicago Tours

Foodies, architecture buffs and historians alike will appreciate these tours of the Windy City.

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There are a variety of ways to see Chicago's best sights.

Note: Some tour providers on this list may have limited or ceased operations due to COVID-19. Check with your tour operator about availability before you book.

One of the best ways to sightsee your way through a new city is with the help of a local. With this in mind, U.S. News rounded up 14 of Chicago 's best guided tours. Whether you're sailing past Willis Tower on a river cruise or sampling some of Chicago's best deep-dish pizza on a foodie excursion, you'll gain a cultural and historical understanding of the Windy City during these tours.

Chicago Food Planet – Gateway to the West Loop Food Tour

Chicago Food Planet's Gateway to the West Loop spotlights some of the tastiest dishes in the city – specifically pizza, doughnuts and burgers. The three-hour tour centers on the West Loop neighborhood's incredible food scene and provides insider insights to the history and culture of the area. Guides regularly win praise from travelers for their knowledge and enthusiasm. Ticket prices start at $65 for adults and $50 for children ages 12 and younger. Reviewers find the tour worth the price for the generous amounts of food provided. What's more, group sizes are restricted to 14 people and tours do not involve extensive walking. Tours are offered Thursday through Sunday at 1 p.m. Chicago Food Planet also offers tours of Chicago's Chinatown neighborhood.

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Absolutely Chicago Segway Tours – Chicago Lakefront/Museum Campus

The Chicago Lakefront/Museum Campus tour offered by Absolutely Chicago Segway Tours showcases many of the city's most popular attractions , including Millennium Park (the starting point), Grant Park, Monroe Harbor, the Field Museum, Shedd Aquarium , Soldier Field and the Adler Planetarium. The 8-mile journey on easy-to-ride, two-wheeled, battery-powered vehicles lasts approximately 2 1/2 hours. Participants praise tour guides for their insight and professionalism. Tickets cost approximately $65, depending on date and time. Note that riders must be at least 12 years old. Tours are available daily. The company offers several other tours, some centered around other parts of the city or with specific themes like architecture, crime and ghosts.

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Inside Chicago Walking Tours – Dazzling Interiors of the Loop

Inside Chicago Walking Tours' The World Within: Dazzling Interiors of the Loop tour reveals interior architectural details that visitors might otherwise miss. Highlights of the two-hour tour include a gilded 80-foot-high ceiling, art deco lobbies, early Frank Lloyd Wright designs and rooms with stained-glass mosaics. Reviewers describe this tour, which involves about 1 1/2 miles of walking, as an informative and entertaining way to learn about the history of Chicago and its diverse, distinctive buildings. Tickets start at $30 for participants 11 and older and $25 for children ages 5 to 10 and patrons 65 and older. Children ages 4 and younger tour for free. Outings run Saturdays at 11 a.m. Inside Chicago also offers other architecture-oriented tours as well as private tours.

Courtesy of Bobby's Bike Hike Chicago

Bobby's Bike Hike Chicago – Bikes, Bites & Brews Tour – Signature Dishes

This triple threat tour combines bicycling, food and beer. The four-hour, 13-mile ride traverses the Gold Coast, Lakeview, Wrigleyville and Lincoln Park neighborhoods with stops for pizza, beer, cupcakes and hot dogs. Reviewers find the tour provides a great introduction to the city and rate the guides highly. Tickets for adults, which include the bike rental as well as food and drinks, start at $76.99 for weekday rides (weekend rides are slightly more expensive). Participants must be at least 21 years old. If you're traveling with kids, try Bobby's Bike Hike Chicago's Family Food & Bike Tour.

Chicago Pizza Tours – Original Chicago Pizza Tour

Experience one of Chicago's unique culinary phenomena with the Original Chicago Pizza Tour. On this 3 1/2-hour tour, you'll visit four independently run neighborhood pizzerias and sample six or more slices. Many reviewers praise the informative and entertaining tour guides. Others insist that the tour is about more than just pizza and encompasses Chicago history, architecture and culture. Tickets start at $60 for adults and $36 for children. If you're interested in exploring the city's pizza from other angles, you can take one of the company's other food tours, which combine pizza and cocktails or focus on the city's biggest slices.

Courtesy of Big Bus Chicago

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago's Hop-On Hop-Off Tours permit guests to tailor excursions to their preferences by allowing them to spend as much time as they want at any of the 12 stops within the eight hours of the standard package. Tour-takers can "hop off" a bus and spend time at popular destinations like Skydeck Chicago , Navy Pier, Soldier Field or Millennium Park and then "hop on" a later bus. Buses run every 30 to 45 minutes and include guides that provide commentary. Travelers frequently describe guides as entertaining and informative. One pain point for riders is the signage: some found it difficult to locate the bus stops at certain attractions. Ticket prices start at $49 for adults and $30 for children (though you may be able to score a discount by purchasing online in advance). In addition to its classic ticket, Big Bus Chicago offers a premium ticket valid for two days.

Tastebud Tours – Taste of Chicago

Tastebud Tours' Taste of Chicago explores the city's downtown Loop area. The three-hour tour includes stops at multiple restaurants and shops for distinctive Chicago deep-dish pizza, popcorn, sandwiches and sweets. The tour also highlights non-food-related landmarks like the Chicago Cultural Center, the Art Institute of Chicago and the Marshall Field and Company Building, which visitors tend to appreciate. Guides consistently win praise for their knowledge of and enthusiasm for Chicago history. Tickets, which start at $59.50, include all food. (Adult beverages can be purchased separately where available.) Groups are limited to 18 people. Tastebud Tours also offers other food-centric excursions as well as private tours.

Chicago Architecture Foundation River Cruise

The Chicago Architecture Foundation's River Cruise ferries guests along the Chicago River as docents from the Chicago Architecture Center regale them with the stories behind more than 50 notable buildings. The volunteer docents repeatedly win high praise from reviewers for their in-depth knowledge of the city's history and its structures. The cruising vessels, part of the Chicago's First Lady Cruises fleet, can carry up to 250 people and boast full-service bars and open-air upper decks. Tickets for the 90-minute excursions cost around $45 for daytime cruises. Twilight outings are a few dollars more. For an additional $5, you can also gain admittance to the Chicago Architecture Center (which usually costs $12 on its own).

Courtesy of Chicago Prohibition Tours

Guides on Chicago Prohibition Tours can offer travelers suggestions on Prohibition-inspired drinks to order

Chicago Prohibition Tour – Original

Chicago Prohibition Tours explore a notoriously eventful moment in the city's history. Its flagship offering visits the sites of four former speakeasies via bus over the course of 3 1/2 hours. Guides provide historical information and share what kinds of drinks would be representative of those consumed illicitly during the Prohibition era. Additionally, you will be driven from location to location by the company. Reviewers rave about the fast-talking guide and say this is an experience both locals and visitors will enjoy. Others appreciate that each bar on the tour is unique. Tickets, which start at $55, do not include food or drinks, which can be ordered separately at tour-takers' discretion. There is also a walking version of this tour that lasts 2 1/2 hours.

Urban Kayak Chicago Riverwalk – Historic Chicago Tour

For a "duck's-eye," up-close view of the city, take Urban Kayak's Historic Chicago Tour. Starting at the Riverwalk , tour-takers paddle their kayaks on the main branch of the Chicago River with periodic stops at points of historical interest, where guides provide information regarding the city's famed architecture. Reviewers say this is a great experience, even for beginners. Meanwhile, others note that the experienced guides are skillful at navigating boat traffic. Tickets cost approximately $65 for a single kayak or $130 for a tandem (two-person) kayak for the approximately two-hour tour. Urban Kayak also offers kayak rentals and paddleboarding classes.

Shoreline Sightseeing – Skyline Lake Tours

Shoreline Sightseeing Skyline Lake Tours offer unrivaled views of Chicago's skyline, and many photo opportunities, via cruises along the Lake Michigan shoreline. The 6-mile trip provides views of notable landmarks, such as the John Hancock Center, the Willis Tower (aka the Sears Tower), Adler Planetarium and the Field Museum . According to reviewers, these iconic buildings are much more visible from the water than they are on the street. Many say this tour was the highlight of their Chicago trip. Tickets for the 40-minute, narrated boat rides start at $23 for adults and $8 for children ages 3 to 12. Kids 2 and younger ride free. Travelers can purchase drinks at the onboard cash bar. Shoreline Sightseeing also offers architecture-focused tours along the Chicago River.

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Ken Flisek | Courtesy of Tall Ship Windy

Tall Ship Windy – Chicago Skyline Sail

Tall Ship Windy's Chicago Skyline Sail features views of the city from the deck of a 148-foot, four-masted schooner. Reviewers tout the remarkable views of the city's impressive structures and, weather-permitting, the special experience of being able to actually sail and not rely on the boat's motor. What's more, tour participants commend the crew members for their professionalism. Tickets for the summer and fall excursions start at $37 for adults and $17 for children ages 12 and younger; infants 12 months and younger ride for $1. Tall Ship Windy has a full bar on board (drinks are not included in the ticket price.) In addition to the daily 75-minute excursions, Tall Ship Windy offers fireworks cruises on select dates as well as pirate-themed outings.

Chicago Crime Tours

Chicago Crime Tours explore famous crime scenes in a variety of Chicago neighborhoods, including the Gold Coast, Lincoln Park, the Loop, the Magnificent Mile , Old Town and River North. The bus tour, which lasts about two hours, includes stops at the spots where gangsters like Hymie Weiss were killed as well as the site of the St. Valentine's Day Massacre. It also visits locales associated with Al Capone, Frank "the Enforcer" Nitti and Leopold and Loeb, among others. Reviewers laud the tours for providing a unique angle on Chicago's colorful history. Tickets cost approximately $40 and can be purchased in advance (advised) or on the bus. A nighttime crime tour and a pizza and crime walking tour are also available.

City Cruises by Hornblower – Seadog Lakefront Speedboat Tour

Zip across Lake Michigan during this high-speed, musically enhanced 30-minute tour. During the ride, you'll see striking views of the Chicago skyline and hear some descriptions of the sights. Visitors praise the crew's knowledge and charisma. They also enjoy whipping along the waves. Tickets cost about $30 for adults and $20 for kids ages 3 to 12. Children ages 2 and younger ride free, but do require a ticket. The boat is open-air, which means travelers might get wet. City Cruises runs a myriad of other boating adventures, including an extreme thrill ride.

You may also be interested in:

• The Best Chicago Walking Tours
• The Best Chicago Segway Tours
• The Best Chicago Boat Tours
• The Best Things to Do in Chicago
• The Best Hotels in Chicago
• The Top Romantic Getaways in Illinois

Tags: Chicago , Travel , food and drink , Vacations , Tours , Illinois Vacations , Midwest Vacations , US Vacations

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Chicago Tours

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Chicago River by Private Boat Tour

Discover Chicago by private boat with a local Chicagoan to highlight its fascinating history and architectural marvels along the way!

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Chicago Loop by Train Experience: All Day CTA Pass with a Local Treat

Chicago is often defined by its wild architecture, satisfying staples such as its famous deep dish pizza, and iconic sculptures like “The Bean” of Millennium Park. But how do you get from one attraction to another with ease? The Chicago “L”!

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Private Chicago TV & Movie Locations Walking Tour

A tour designed to hit some of Chicago’s must-see TV & movie filming locations may include stops at locations from hit movies like The Dark Night, My Best Friend’s Wedding, and Ferris Bueller’s Day Off!

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Chicago City Private Driving Tour

Join us as we cover the absolutely iconic sites of Chicago! Take some photos at Millennium Park, view the soaring skyline of The Loop, see the city’s most iconic sites on The Chicago Riverwalk, and so much more in this custom experience!

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Best of Chicago: Architecture & Highlights City Private Tour

Get the best of Chicago with a local guide on this walking tour featuring the city’s best neighborhoods, top attractions, and the Chicago ‘L’!

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Private Chicago Neighborhood Food Walking Tour

Explore Chicago’s foodie scene! Visit legendary bakeries and sample incredible food with roots around the world, including Italian, Polish, German and many more.

WeVenture offers unique and authentic day tours around Chicago. They range from two-hour to one-day adventures and uncover back streets, hidden gems, and fascinating sights.

Step into the lives of locals, find out what makes the city tick, and get acquainted with the local food, culture, architecture, and traditions of Chicago.

A local expert guide provides knowledge and leads you through a fantastic urban experience.

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24 hours in downtown Chicago

With just one day to explore, you can make the most of your time with iconic, one-of-a-kind attractions and city experiences. Mix and match from the 10 itinerary stops below to create your perfect combination of restaurants, parks, museums, music, clubs, and rooftop views.

How to spend 24 hours in downtown Chicago: Stop 1: Visit Art Institute of Chicago Stop 2: See “The Bean” at Millennium Park Stop 3: Wander the Chicago Cultural Center Stop 4: See Buckingham Fountain at Grant Park Stop 5: Explore the lakefront Museum Campus Stop 6: Enjoy the view at SkyDeck Chicago Stop 7: Hear local legends at jazz & blues clubs Stop 8: Admire colorful street art Stop 9: Take an architecture river cruise Stop 10: Relax on the Chicago Riverwalk

Stop 1: A museum fit for Ferris Bueller

Anyone who loves the movie Ferris Bueller’s Day Off will know the Art Institute of Chicago . As you walk along Michigan Avenue, you’ll be greeted by two enormous bronze lions at the museum’s grand entrance. 

Once inside the Art Institute, you’ll experience one of the largest and oldest art museums in the United States, and one of the most expansive collections of Impressionist and Post-Impressionist artwork outside of the Louvre in Paris.

Make sure you visit the critically acclaimed Modern Wing, too, which houses an extraordinary collection of modern and contemporary masterpieces by Chagall, Dali, Matisse, Picasso, Pollack, Warhol, Magritte, and more. If you’d like to indulge in a little fine dining afterwards, head to Terzo Piano  on the Modern Wing’s upper level. In the summer, you can dine on the Bluhm Family Terrace amid rotating art installations and fabulous views of Millennium Park.

Stop 2: A giant bean and enormous rock climbing wall

Take the Nichols Bridgeway from the Modern Wing across to Millennium Park   and you’ll find an unprecedented combination of stunning architecture, sculpture, and landscape design all in one place. From the towering faces of Chicagoans at Crown Fountain to your own face reflected in the polished steel surface of Cloud Gate , aka “The Bean,” you’ll see exactly why Millennium Park is one of Chicago’s top bucket list contenders.

Exit Millennium Park via the BP Bridge, a 935-foot-long winding walkway that offers incomparable views of the Chicago skyline, Grant Park ,  and Lake Michigan. On the other side of the bridge sits Maggie Daley Park , a spectacular green space with massive rock-climbing walls, mini golf, picnic groves, tennis courts, and an amazing play garden. In the winter, the park’s in-line Skating Ribbon is transformed into a unique, meandering ice skating path. There’s another ice-skating rink at McCormick Tribune Plaza in front of “The Bean.” Over the summer months, ice makes way for a scenic outdoor patio right on the plaza.

Stop 3: A Tiffany jewel in the crown

On the corner of Michigan Avenue and Randolph Street, you’ll encounter the Chicago Cultural Center , a neoclassical landmark that houses the largest Tiffany stained-glass dome in the world. This stunning building is a humanities haven, with concerts, dance performances, theatre productions, films, lectures, art exhibitions, tours, and family events scheduled throughout the year — and all for free.

Stop 4: A waterfront landmark

Walking south and east through Grant Park , you’ll find yourself in the heart of a 319-acre green space, anchored by mesmerizing Buckingham Fountain . This Chicago landmark, one of the largest fountains in the world, was dedicated in 1927 and inspired by the Latona Fountain at the Palace of Versailles. Typically from early May through mid-October, the fountain produces a dazzling water display for 20 minutes every hour throughout the day. During these displays, a center jet shoots water to a height of 150 feet, with lights and music beginning at dusk.

Stop 5: Explore museum campus

Walking south from the fountain, head to Chicago’s legendary Museum Campus. This gorgeous green space directly on Lake Michigan and is home to three of the city’s most popular museums. The Field Museum will be the first museum you encounter and well worth a trip inside. It’s home to thousands of natural history artifacts spanning thousands of years, including the largest dinosaur ever discovered.

Shedd Aquarium  sits right next door. Here, in one of the largest aquariums in the world, you’ll meet 32,000+ aquatic creatures, including beluga whales, dolphins, sea otters, sea lions, penguins, stingrays, and sharks.

Just beyond the Shedd is Adler Planetarium , which, upon opening in 1930, became the first planetarium in the Western Hemisphere. The building is more than a museum; it’s a laboratory, a classroom, and a community exploring the universe together. Visitors flock to the Adler to experience interactive exhibits, live planetarium shows, hands-on educational programs, and world-class collections.

Stop 6: Views from towering heights

Sky deck at Willis Tower invites you to step on The Ledge, a glass box that extends approximately four feet from the building’s facade — over 1,300 feet above ground level. Willis Tower is one of the tallest buildings in the world, and, as you might expect, the views from Skydeck are amazing.

Stop 7: A music mecca or two

Two neighboring music clubs, one blues and one jazz, are must stops for the full Chicago experience. Buddy Guy’s Legends   was made famous around the world by its namesake, Grammy-award-winning blues guitarist Buddy Guy. There’s live music every night of the week, with free acoustic shows during lunch and dinner hours. Established in 1947, Jazz Showcase has hosted some of the greatest names in the business. The 170-seat club features local, national, and international acts nightly.

Stop 8: Picasso and Chagall on the street

Public art lives large in Chicago. And nowhere is this better seen than at Daley Plaza   and nearby Chase Tower Plaza. Picasso’s 50-foot-tall untitled sculpture takes center stage at Daley Plaza. When it made its debut in 1967, The Picasso , as it’s known, caused some controversy, with people comparing it to a large insect or baboon. Today, it’s an enduring symbol of Chicago itself.

At Chase Tower Plaza, Chagall’s monumental The Four Seasons   mosaic mural represents the arrival of spring, summer, winter, and fall. It’s composed of thousands of inlaid fragments in over 250 colors, and was created in Chagall’s studio in France before being dedicated to the city in 1974.

Stop 9: Architectural history on the waterfront

Head toward the river and you’ll find One Illinois Center, the Mies van der Rohe-designed home of the Chicago Architecture Center . Check out the to-scale skyscraper models in the Skyscraper Gallery and the approximately 4,200-piece immersive City of Chicago model on the main level, before picking the perfect architectural walking, bus, or boat tour at the center’s box office.

The Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady  is a crowd pleaser, and was voted Chicago’s #1 tour by TripAdvisor users. It’s led by knowledgeable Chicago Architecture Center docents who’ll tell you the fascinating history behind approximately 50 of the city’s iconic downtown buildings.

Stop 10: Relax along the river

The award-winning Chicago Riverwalk  is a 1.25-mile pedestrian stretch filled with coves, restaurants, bars, museums, public art, kayaking, boat excursions, bird-watching, fishing — and Art on theMART, the largest video projection art installation in the world. Illuminating over 2.5 acres of theMART’s river-facing façade, you can view the work of notable video artists from 7:15 – 9:15 p.m. Wednesday through Sunday, from March through April, and daily from May through December

Inside tip: Take a free Chicago Greeter tours

See Chicago like a local, with a local, with a free, customizable Chicago Greeter tour . Pick your neighborhood, theme, and language, then team up with a friendly guide who’ll show you both classic Chicago and its off-the-beaten-track gems. Book today .

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Chicago Day Trip (Spending One Day in Chicago)

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Welcome to the Windy City, where every street whispers tales of history, art, and vibrant culture, inviting you to embark on an unforgettable day trip . Chicago's streets are a canvas blending iconic architecture with Lake Michigan's soothing waves, and the scent of deep-dish pizza fills the air. Experience the essence of this city in a day—where each moment reveals excitement and Midwestern warmth.

From the towering skyscrapers of the Loop to the artistic charm of Millennium Park, this city is a playground for urban explorers on captivating day trips. Prepare for an exhilarating adventure packed into a single day, as even a glimpse of Chicago promises to leave you in awe. Fasten your seatbelts, for we are about to conquer the heart of the Midwest in an enchanting 24-hour journey!

Explore Chicago's gems with an Exclusive and Private 4-hour Small-Group Tour!

Is one day enough for Chicago?

Absolutely! In just one day, you can absorb the essence of Chicago with a well-organized itinerary. Begin with Parks, venture into museums, relish diverse culinary experiences, and engage in outdoor and indoor activities. Explore the dynamic neighborhoods boasting art galleries, shops, and a variety of dining options. 

This strategic approach allows you to experience the cultural richness and vibrant spirit of Chicago efficiently. Each attraction offers a unique perspective on the city, ensuring you make the most of your time in this bustling metropolis. Capture the essence of Chicago's diverse offerings, from contemporary art to breathtaking views and historic landmarks, all within a short timeframe.

Credit: Bhargava Marripati/Pexels

What to Do in Chicago in a Day?

Delectable breakfast: a feast to jumpstart your day.

Begin your day on a delightful note with the renowned pancake stack at Lou Mitchell's, savoring a taste of culinary excellence that sets the perfect tone for the morning. Elevate your experience with a visit to Intelligentsia Coffee, where a carefully crafted caffeine boost awaits, providing a satisfying and flavorful kick to energize your day.

Artistic Expedition: Dive into a World of Creativity!

After treating your taste buds to breakfast bliss, continue your morning with an artful exploration at the Art Institute of Chicago. Explore art at the Art Institute of Chicago, featuring Van Gogh's "Starry Night" and a diverse collection spanning centuries and cultures. Dive into Shedd Aquarium's mesmerizing underwater world, embark on a cosmic journey at Adler Planetarium, or discover the Field Museum's captivating natural history exhibits. The choice is yours for a diverse and enriching experience.

Explore Millennium Park: A World of Magic Awaits!

Next, visit Millennium Park and capture the perfect selfies with the iconic Bean sculpture, officially known as Cloud Gate. Watch as it reflects the city's skyline on its polished surface. Stroll through Lurie Garden, where seasonal blooms create a picturesque landscape, providing a tranquil oasis. Experience the captivating blend of water displays and digital art at the interactive Crown Fountain for a refreshing and engaging moment.

Uncover the Wonders of Chicago on Foot with Our Premier Walking Tour Experience!

Satisfy Your Cravings: Afternoon Delights!

Embark on an afternoon lunch adventure in Chicago, home to some of the best pizzas in the world. Whether you're a devotee of the city's famous deep-dish pizza or simply seeking something uniquely delightful, you've come to the right place. Your lunch is more than just a meal; it's an experience, an exploration of local delicacies guaranteed to leave your taste buds dancing. Don't miss the chance to try the iconic Chicago-style Hot Dog for a flavorful twist.

Indiana Dunes Bliss: Nature Awaits Your Exploration!

After lunch visit Indiana Dunes National Park, a nature lover's haven along Lake Michigan's southern shore. The park unveils diverse landscapes, from pristine beaches to lush forests. Begin your journey by traversing scenic trails, taking a refreshing dip in Lake Michigan's crystal waters, and exploring the rich biodiversity. Discover rare species and a wide variety of flora, creating a unique and captivating Midwest experience for each visit.

Road Trip Marvels: Explore, Discover, Enjoy!

Embark on an exhilarating road trip from the vibrant city of Chicago! Begin your adventure by driving along the scenic Purple Line, a mere 20-minute journey from Michigan Avenue. Head towards the Discovery Center Museum, a fascinating destination featuring interactive exhibits that promise to engage and inspire. Delve into the museum's immersive displays, offering a blend of education and entertainment.

Skyline Splendor: Chicago's Architectural Wonders!

As the day tour draws to a close, indulge in an Architectural Boat Tour down the Chicago River. Gain insights into iconic structures like the Wrigley Building and Tribune Tower while basking in the scenic beauty that surrounds you. Let the tranquil cruise be the perfect finale for your Chicago exploration, offering a unique perspective on the  city's architectural marvels .

Credit: Radhika Chopra/Pexels

One Night in Chicago:

Sunset bliss: chase the day's final glow.

Marvel at the mesmerizing sunset from Skydeck Chicago Observatory, especially from The Ledge. Watch as the sun gracefully sets, casting a warm glow over  the city's skyline . The horizon transforms into a breathtaking display of vibrant colors, painting the Chicago sky with hues of orange, pink, and purple. It's a serene and awe-inspiring moment to unwind and appreciate the city's natural beauty.

Cinematic Charm: Immerse in Dazzling Live Shows

After the mesmerizing sunset viewing, experience the thrill of live theater at one of the world's most prestigious venues. Whether it's a gripping drama or a captivating musical, immerse yourself in the lives of the actors and the artistry of a production that transports you into a world of creative and emotional expression. This cultural experience is guaranteed to captivate and entertain, creating a truly memorable evening.

Culinary Delights Awaits: A Delightful Dinner Feast!

Savor an exquisite dining experience in Chicago, where culinary delights await. Choose from a diverse range of restaurants, each offering its unique flair. Whether you're in the mood for classic Chicago deep-dish pizza, upscale fine dining, or international cuisine, the city's vibrant culinary scene has something to satisfy every palate. Immerse yourself in the local flavors, ambiance, and culinary creativity for an unforgettable dining adventure.

Rooftop Bliss: Night's Last Embrace!

Wrap up your evening with a touch of glamor at either Cindy's Rooftop or The Aviary. Indulge in handcrafted cocktails, each a masterpiece, while absorbing the panoramic cityscape below. As the city sparkles in the night, immerse yourself in the enchanting starlit sky. Bid farewell to your whirlwind Chicago adventure with style and sophistication, creating a memorable and refined conclusion to your night on the town.

Immerse in the Charm of Chicago at Night with Our Scenic Night Tour!

Chicago One-Day Tour Package:

Best of chicago tour:.

Embark on an exclusive journey through the heart of Chicago with our small-group tour, thoughtfully limited to just six people. Immerse yourself in the city's iconic skyline as you gain admission to the Skydeck Chicago Observatory, featuring The Ledge—an exhilarating glass-floored platform suspended high above the city streets. Brace yourself for breathtaking views that capture the essence of Chicago's architectural marvels.

Cruise along the Chicago River with the Shoreline Architecture Cruise, enjoying unique views of the city's grandeur. Visit iconic spots such as the Chicago Bean, Adler Viewpoint, and Buckingham Fountain for a curated experience. Our tour offers hotel pick-up and drop-off in downtown Chicago, ensuring a seamless adventure through the Windy City's cultural and architectural highlights.

Scenic Chicago Night Tour:

Embark on our Scenic Chicago Night Tour for an unforgettable experience. Witness the city come alive as you explore iconic sites, enjoy a delightful boat tour along the shoreline, and experience the mesmerizing light show at Buckingham Fountain. Capture the essence of Chicago's nighttime charm with a scenic shoreline cruise, offering stunning views.

Experience a fully narrated small group tour of Chicago with complimentary hotel pick-up. Enjoy seamless transportation and skip-the-line access to all attractions. Our knowledgeable local guide ensures an engaging exploration. Conclude your night tour with a stop at Cloud Gate, affectionately known as the Chicago Bean , for an iconic photo opportunity. Immerse yourself in the beauty and energy of Chicago after dark, creating lasting memories.

Credit: Brian Miller/Unsplash

Private Tour of Chicago:

Discover Chicago's best with our 4-hour private small-group tour. Enjoy the luxury of private transportation, ensuring a seamless and personalized journey through the city's iconic landmarks. Your knowledgeable guide will lead you to explore the unique architecture of the Chicago Bean and the majestic Buckingham Fountain, offering insights into their historical and artistic significance.

Indulge in VIP treatment with all-inclusive admissions, covering key attractions such as the Adler viewpoint, Skydeck Chicago with The Ledge, and an architectural cruise along the Chicago River. This curated experience guarantees an unforgettable adventure, allowing you to delve into the heart of Chicago's vibrant architectural heritage. Immerse yourself in the stories behind each landmark and witness the city's beauty unfold in grandeur.

Best of Chicago Walking Tour:

Discover Chicago's best on our engaging Best of Chicago Walking Tour! Step into a day of exploration as your guide greets you at the iconic Willis Tower. The adventure starts with an exhilarating ascent to the 103rd floor of Skydeck Chicago, where a breathtaking 360-degree view of the city awaits. Experience an adrenaline rush on The Ledge's glass balconies, extending 4.3 feet outside the building for a thrilling, once-in-a-lifetime experience.

In a small and intimate group setting, immerse yourself in the artistic wonders of Millennium Park. Explore highlights like the iconic Cloud Gate sculpture, affectionately known as "The Bean," and the interactive Crown Fountain, creating a perfect blend of art and technology. To conclude your day, embark on a Shoreline Architecture Cruise, where you'll witness the city's magnificent skyline from the serene waters of the Chicago River, gaining insights into the architectural marvels that define the Windy City.

Discover Chicago's Best with Our Ultra Small Group Tour: Where Every Landmark Tells a Story!

Final Thoughts:

In just a day, Chicago promises to create lasting memories in your travel journey. Whether you’re entranced by the city’s iconic skyline, captivated by its rich culture, enriched by its rich sounds and sights, or delighted by its varied cuisine, the city will provide an unforgettable experience.

Immerse yourself in the enchantment of Chicago with  Tripshepherd . Secure your tour today to explore cultural gems, iconic landmarks, and hidden gems. Experience the enchanting magic as you explore the intricate tapestry of Chicago's history, culture, and culinary wonders.

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One Day in Chicago Itinerary

Chicago, the third largest city in the USA, is a fantastic city to visit.

If you only have 24 hours in Chicago to spend, we want you to make the most of it.

Therefore we compiled a Chicago itinerary of things to do and things to bring on your next trip to the windy city.

The people here are friendly, the food is delicious, and Chicago's architecture along with its skyline is exquisite.  

Of course, we recommend you spend as much time as you can to enjoy the wonderful things that Chicago has to offer.

However, if you only have one day and really just want to experience the most famous “highlights”- here is your guide.

Check out our Chicago Visitors Guide , with budget advice, travel guides, and information about local Chicago attractions.

Tip: Save more money in Chicago with a tourist discount pass , which offers one-day attraction discounts.  Read our post to see if one is worth it for you.  

We also offer several pay-what-you-like walking tours .  

Wh at should you bring with you for a day in the city?

• Cash, an I.D., your phone (and/or a map)
• A refillable water bottle
• SmartPhone/Camera
• Comfortable walking shoes
• Umbrella/Layered clothing if the weather is forecasted to be rainy and/or cold

Click the map to enlarge or click here for a movable map.

Breakfast in Chicago

We recommend you start the day with some food, so you can easily accomplish this full day of Chicago fun!

There are so many delicious breakfast food places in the city.  

For breakfast downtown, one suggestion is Pittsfield Café at Washington and Wabash ( map ) for a hearty diner-style meal. 

They open at 7:00 a.m. every day, so you can start your day early.

Enjoy the stunningly beautiful architecture inside the Pittsfield Building while you dine.

If you have a sweet tooth and just want a quick bite, try one of Chicago’s boutique donut shops. 

Our suggestion is Stan's Donuts at Randolph and Dearborn ( map ) open daily from 7 am - 2 pm.

They are known for their original glazed, and we recommend the Nutella pocket, birthday cake donut, or a Stanwich! Don't forget your coffee.

Another great place for coffee is Dollop Coffee Co ., which has several options in the downtown neighborhood.

Visit the Cultural Center Chicago

If you just ate at the Pittsfield, the Cultural Center is across the street at Washington and Michigan.

The Cultural Center offers free admission with traveling exhibits on different floors. 

Check out the second floor to see a 38-foot-wide stained-glass Tiffany dome - the largest in the world!

Hours: Open 10 am to 5 pm daily.

At the bottom level, there is a visitor’s center with maps galore.

If you don’t have a map or a smartphone - we recommend you pick one up here.

Tour Downtown Chicago (the Loop) & Millennium Park

Taking a walking tour is always a great idea to better get to know a city, to meet a local guide and possibly some other nice travelers, and to gain some general orientation of Chicago.  

Free Tours by Foot offers many different tours and frankly, they all show different wonderful sections of Chicago but if you only spend 24 hours in Chicago we recommend the Loop & Millennium Park tour .

The Loop Tour runs several times per week, but please check the calendar to choose your date and to reserve a spot click here .

We also offer it as a GPS-led audio tour , which you can take any time of day.

Your Chicago-loving guide will take you on a journey through the downtown Loop district of the city which begins near State and Lake.

You will see the Chicago Theatre , Marshall Fields, the Picasso, and the Sears Tower (aka Willis Tower).  

While learning the history of Chicago you will gaze up at the magnificent skyscrapers and appreciate the architectural genius that is in Chicago’s concrete landscape.

The tour ends at Millennium Park the famous sculpture “Cloud Gate” (aka “The Bean”). You can also see the Crown Fountain nearby.

Alternatively, Maggie Daley Park is also a great option, especially with kids, which offers activities like ice skating, mini golf, a climbing wall, playgrounds, and scenic strolls in its beautiful gardens.

Chicago Museums

Chicago's museums are world-renowned, and certainly a highlight for many visitors. There are several options to choose from.

For adults and teenagers, the Field Museum and Art Institute of Chicago are two of the most popular, and largest museums.

You won't be able to see everything inside in one day, but you can spend a few hours at one of them.

If you're traveling with children, the Adler Planetarium and Shedd Aquarium are wonderfully educational - and fun! - places to visit.

Also, check out the Chicago Children's Museum.

Be sure to read our post on free museums in Chicago

Lunch          

By now you’ve probably worked up an appetite. We recommend heading over to Al’s Beef at 548 N Wells St. ( map ) for a quick bite to eat. 

They have Chicago-style hotdogs, which are all beef, with mustard, tomatoes, onions, relish, pickle, hot peppers, celery salt, a poppy seed bun, and NO KETCHUP and Italian Beef Sandwiches. 

Although we call them Italian, this sandwich is certainly not from Italy. Most Chicagoans ask for Italian Beef with mozzarella cheese, and sweet or hot peppers (which we call giardiniera).

We ask for it to be “dipped”, which means the cook will take your entire sandwich and dunk it into seasoned meat juice. 

It is messy, but so delicious.

Water Tower

Let’s leave the Chicago Loop and head north to see one of Chicago’s oldest buildings to survive the Great Fire of 1871.

It's the Water Tower and Pumping Station – a real Chicago gem at Michigan and Chicago Streets.

The Water Tower now hosts a series of rotating free exhibits and the Pumping Station is now the Looking Glass Theatre.

It’s free to visit and open daily from 10 am - 6:30 pm (except Holidays).

Magnificent Mile

If you are a shopper, the Mag Mile is like the American Champ-Elysees on Michigan Ave. (For real: that was Daniel Burnham’s intention as the city planner in the late 1800s).

It is an entire mile of shopping and historic hotels.

You’ll find Coach, Gucci, Burberry, Apple, H&M, and even a Nordstrom’s Rack, among others.

Along the road are some architectural highlights, including the Tribune Tower, the Wrigley Building, NBC Studios, and Trump Tower.

Eat the Chicago Deep Dish Pizza Dinner?

You can’t come to Chicago without trying the famous Chicago-style deep-dish pizza .  

Our favorites are Pizzeria Uno’s at Wabash and Ohio ( map ) and Gino’s East at Michigan and Superior ( map ). 

According to the Chicago Tribune newspaper, Uno’s is the original deep-dish pizza.

Their pizzas are great, and the restaurant feels like a friendly underground lounge.

Gino’s East also has a lot of character. Their crust deviates from the Chicago original by using cornmeal as the base. Very tasty.

(Bring a permanent marker since you are encouraged to “leave your mark” on the walls.)  

Visit the Hancock Building, 360 Chicago, and the Signature Lounge

Now is the time to see one of the best views of the city.

If you want to get a bird’s eye perspective of Chicago, head to the Hancock Building, 4 th tallest building in Chicago at Michigan Avenue and Chestnut.

We do recommend you visit the Chicago Observation Deck , 360 Chicago.

It's worth the ticket price and you can take great photos and enjoy the view from the 94th floor.

From 360 Chicago Skydeck, you can see Lake Michigan with its cruises and lakefront trails, Navy Pier with the Centennial Wheel, Chicago River with its river cruises, The Museum Campus, Wrigley Field stadium (home of the Chicago Cubs), Lincoln Park Zoo and other architectural marvels of Chicago.

You can also experience TILT which is a glass enclosure that tilts outward, offering stunning views of the city from a unique angle.

If you want to save yourself the admission fee though and instead spend the money on a cocktail or two instead, ride the elevator up to the 95 th floor to the Signature Lounge (you’ll have to show your I.D. here for age proof). 

The Signature Lounge is a great place for cocktails and/or dessert.

The food is wonderful and the view is unbeatable. Sip your cocktail while looking at the Sears Tower (aka the Willis Tower). 

Even though the line to get into the bar can be long (especially on weekends) the wait is worth it.

Also, attention ladies: use the ladies’ bathroom to enjoy the splendid views from the top. Sorry pals, no view for you in the bathrooms!

By now, it is either nighttime or the lights are lining the streets or perhaps the sun is about to set, so enjoy your drinks.

Enjoy Chicago Improv OR Blues

For the last event of the night, head to a blues club , or venture down to a comedy club to see some improv. There are options for both that are only a few train stops away. A taxi or rideshare service can also take you directly there for a fee.

For improv, we recommend Second City at Wells and North Ave ( map ) to see a late-night show.

Second City is famous for training some of the best comedians like Tina Fey, Mike Myers, and the Belushi Brothers.

The closest Blues club would be Buddy Guys Legends at Wabash and Balbo, which is a great local spot.  

Either choice is a perfect end to a Chicago visit, especially because Chicago is known for the blues and improv.

Safe travels!

FREQUENTLY ASKED QUESTIONS

Is Chicago walkable?

Yes, Chicago is generally walkable, especially in its downtown area.

The city has a well-maintained grid system, sidewalks, and pedestrian-friendly areas.

However, the size of Chicago means that some attractions may require public transportation or other means of getting around for convenience.

What is the cheapest/fastest way to get around Chicago?

The cheapest way to get around Chicago is typically by using the public transit system, including buses and the 'L' train.

The fastest way for short distances is often walking, while ridesharing services like Uber and Lyft can be convenient for longer or less accessible routes.

Biking is also an economical and efficient option for getting around certain areas of the city.

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One-Day Itinerary

One Day in Chicago: The Perfect Itinerary

TripSavvy / Cory Giguere 

Don’t let the winds blowing off Lake Michigan scare you— Chicago , the Windy City, is a metropolis full of culture and history. Sightseers flock to the birthplace of the skyscraper, for its: Michelin-starred restaurants ; major league sports teams; world-class theater, dance, music, and film; festivals; 26 miles of lakefront; well-curated museums ; and stellar shopping. Chicago is also full of green spaces that are worth exploring like Chicago Botanic Garden and The Morton Arboretum . No matter what you do, or where you go, you’ll appreciate the city’s midwestern allure, with a bit of urban edginess. 

This walking-city, with 2.7 million residents, utilizes speedy public transportation to get from point A to point B. As you get on and off the elevated rail, or L, you’ll notice a mashup of sleek and modern buildings with loads of history and nods to the past throughout Chicago’s 46 historic districts and 77 vibrant neighborhoods. Chicago River architecture tours or walking excursions will highlight the City of the Big Shoulders’ storied past—the rise of a transportation hub, the Great Chicago Fire, the World’s Columbian Exposition of 1893, prohibition era, and Chicago’s public enemy number one, Al Capone .

Whether you’re a first-time visitor to the Second City, or a seasoned local, peruse this 24-hour itinerary for an across-the-board exploration of what Chicago has to offer, highlighting must-see tourist spots as well as local neighborhood gems.

The Night Before

Night: Arrive in Chicago and check-in to your accommodations—there are 119 hotels to choose from in the central business district. Luxurious options in the city include: Waldorf Astoria Chicago , Four Seasons Hotel Chicago (the spa here is fantastic), The Langham Chicago , Park Hyatt Hotel Chicago , and The Peninsula Chicago (the lobby is exquisite). Other well-located alternatives are Hotel Zachary , near Wrigley Field (the second oldest ballpark in Major League Baseball); Hotel EMC2 , with a robot concierge; and InterContinental Chicago Magnificent Mile , with a hidden hole in the wall for a prohibition-era alcohol stash.

Intrepid families that would love to spend a night at one of the museums can bring a sleeping bag and a sense of adventure to Adler Planetarium’s Astro Overnights, the Field Museum’s Dozin’ with the Dinos, Overnights at the Shedd Aquarium , or the Museum of Science and Industry’s Science Snoozeum.

7:30 a.m.: Take advantage of waking up in one of the best cities in the world and go for a leisurely jog or a fast-paced walk along the Chicago Riverwalk, a 1.25-mile stretch that has Adirondack chairs toward the east end for catching your breath. You’ll pass by stunning architecture, art installations, and boats cruising up and down the Chicago River. Continue on to the paved Chicago Lakefront Trail, along Lake Michigan, which runs from Ardmore Street on the north side to 71st Street on the south side, traversing many historic neighborhoods like Lincoln Park, South Loop, Bronzeville, and Hyde Park. The skyline views, when you’re facing south, are incredible, especially at this time of day. You can see Navy Pier , Chicago’s most-visited attraction, from the trail, with its Centennial Wheel rising high in the sky. For great people watching, linger at Oak Street Beach for a beat. (The 606, in Logan Square, is another great place to run that is popular with locals. This neighborhood park was created on the old elevated Bloomingdale train line—similar to New York’s High Line .)

10 a.m.: Make your way to Cindy’s for brunch, located on the rooftop of the famed Chicago Athletic Association Hotel , formerly a men-only social club. You won’t believe the terrace view of Millennium Park, The Art Institute of Chicago (the “Historic Route 66” begins in front of the Art Institute), Lake Michigan, and the shops and restaurants below at street level. Make reservations well in advance—this place is always packed—and order the avocado toast and the roasted vegetable strata. Save room for the house-made vanilla mascarpone Danish, with roasted cherries.

Noon: Across from Cindy’s is the 24.5-acre Millennium Park , a well-loved public space that is home to the Jay Pritzker Pavilion, Cloud Gate—the Instagram-worthy shiny bean-shaped sculpture, Crown Fountain, and Lurie Garden. Millennium Park Campus is also where you’ll find Maggie Daley Park, the best place to go if you have kids in tow.

1:00 p.m.: Meet up with Chicago Architecture Foundation ’s guide to learn about Chicago architecture and history on a two-hour walking tour through the city. You’ll get the lay of the land and learn more than you dreamed possible to enrich your time spent in the city. On the way, caffeinate with a cold brew or bulletproof coffee at Goddess and the Baker , located at Wacker Drive and Lasalle Street.

3:00 p.m.: You can’t leave Chicago without weighing in on which pizzeria serves up the best slice of deep dish . Is it Giordano’s, Lou Malnati’s, Pizzeria Due, Gino’s East, Piece, or Home Run Inn? You decide.

5:00 p.m.: Walk off that heavy pizza and stroll along the Magnificent Mile , a 14-block stretch of Michigan Avenue—from the Chicago River to Oak Street—that is mecca for shopping. Here, you’ll find malls and boutiques full of designer threads as well as affordable clothing brands. Keep in mind, this area is usually congested with shoppers, especially around the holidays and on weekends, so it’s best to plan out which shops you’d like to see in advance. Take a few snaps in front of the famous Chicago Water Tower , built in 1869, on the north end of Michigan Avenue. If shopping isn’t your thing, why not take an Intro to Climbing class at Chicago’s Brooklyn Boulders , located in Greek Town, west of the river, near Ogilvie Transportation Center?

6:00 p.m.: Take the high-speed elevator up to the observatory at 360 Chicago (formerly The Hancock Observatory) where, on a clear day, you can see Michigan, Indiana, and Wisconsin. Test your fear of heights on the Skydeck open-air viewing deck and see Michigan Avenue, 1,000-feet below, in the TILT attraction.

7:00 p.m.: You’ll want to experience Chicago’s diverse theater, music, or dance scene—the city has more than 250 theaters, 225 music venues, and 200 dance companies. Long-standing theaters include: The Second City in Old Town, Goodman Theatre and Chicago Theatre in the Loop, Music Box Theatre in Lakeview, Blue Man Group at Briar Street Theatre in Boystown, Steppenwolf Theatre Company , Chicago Shakespeare Theater , Lookingglass Theatre Company , just to name a few. And, of course, Chicago has no shortage of great live music, especially blues and jazz music (the term “jazz” was coined in Chicago). Music festivals like Chicago Blues Festival, Chicago Jazz Festival , Lollapalooza , Pitchfork Music Festival and Riot Fest are well-attended and loved in this city. Not to be missed is Chicago Symphony Orchestra , Lyric Opera and the Joffrey Ballet . The Harris Theater for Music and Dance is home to major Chicago dance troupes. You can’t do it all of course, so pick wisely and plan on returning to Chicago for another go-round in the future.

10:00 p.m.: For late-night noshes, local beers, and inventive cocktails, pop over to Lincoln Park’s Broken Barrel Bar , with Chef Bryant Anderson at the helm. This place is great for that non-touristy neighborhood feel that Chicago is really known for and you’ll get a sense of what one Chicago community is like by playing a game of bags or hanging around in the beer garden. Other great options, with completely different environments are: The Berkshire Room in River North, Milk Room in the Loop, The Aviary in the West Loop , The Violet Hour in Wicker Park, River Roast on the Chicago River, and The Optima in Old Town.

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(312) 659-8687

Chicago Minibus Tour

With the option to add the, chicago river architecture boat tour, our comfortable, climate controlled, award-winning chicago mini-bus tour takes you on an entertaining, narrated journey through the downtown area, and to several distinct neighborhoods., you’ll learn about the windy city's colorful past, cosmopolitan present and exciting future., photo stops include: the buckingham fountain * the loop/rookery building the riverfront/wrigley building amazing skyline view/lakefront lincoln park ** * may-october ** november-april, below are some of the many famous sights you will see:.

The Loop Millennium Park

Museum Campus & Skyline View

Buckingham Fountain

Chicago River

Lincoln Park

Loop/Millennium Park

Millennium park.

Museum Campus

Adults: $47.95 * Children: $37.95 (ages 4-12) *

(children 3 and under ride free when not occupying a separate seat), 10:00 am, 1:00 pm tuesday-sunday 2 hour tour, with 4 photo stops., (stops and route subject to change) complimentary pickups available from most downtown hotels., for reservations call: (312) 659-8687, or click the 'book now" button below * enter promo code 'mini' to receive $5.00 off per person, parking if you are not staying downtown, we can pick you up from the front of: the doubletree hotel magnificent mile- 300 e. ohio st. parking is available in several structures surrounding the hotel. go to www.spothero.com for reduced parking prices. there is nobody to check in with. please be waiting on the ohio st. side of the hotel. pickup time at the doubletree is 9:30 for the 10:00 tour and 12:30 for the 1:00.

Chicago Minibus Tour plus the Chicago River Architecture Boat Tour

At the conclusion of your chicago mini bus tour, we’ll take you to the magnificent mile. there, you will board a shoreline sightseeing chicago river architecture tour boat, architecture, you’ll enjoy a 75-minute cruise along the scenic chicago river in a large open air tour boat, while learning a thing or twenty about architecture, chicago history and even how to reverse the direction of a river, not to bury the lead, but there is a bar on the boat, for those in need of a refreshing or relaxing libation., this tour ends at michigan ave and wacker drive. most downtown hotels are within a mile of this location. , chicago minibus tour plus the popular chicago river architecture boat tour , adults: $99.95 * children: $65.95 (ages 4-12) *, 10:00 am, 1:00 pm tuesday-sunday, mini bus + boat tours together last approximately 4 hours. the mini bus and boat tours do not have to be taken consecutively. complimentary pickups available from most downtown hotels., or click the 'book now" button below * enter promo code 'boat' to receive $8.00 off per person, parking if you are not staying downtown, we can pick you up from the front of: the doubletree hotel magnificent mile- 300 e. ohio st. parking is available in several structures surrounding the hotel. go to www.spothero.com for reduced parking prices. there is nobody to check in with. please be waiting on the ohio st. side of the hotel. pickup time at the doubletree is 9:30 for the 10:00 tour and 12:30 for the 1:00 the chicago river architecture boat tour begins and ends less than 3 short blocks from the doubletree magnificent mile., private chicago tours, just you and your family and friends is the most convenient way to tour, our chicago bus tour picks you up and drops you off at your hotel or anywhere else in  downtown chicago. at the end of the tour, we can drop you off pretty much anywhere, too. want to finish at millennium park fine. the willis tower sure. the art institute of chicago, no problem. our other tours pick you up, but even then, you generally have to ride around to several more hotels while we pick up the others on your tour. with our private tour, we pick you up and away you go, when you are touring with others, you’re usually expected to be quiet and respectful of them. on a private tour, you can let loose, tell inside jokes, laugh and just be silly. bottom line, you can have more fun as for the tour itinerary, you can either leave that up to us, or we can focus on the things that you want to see. private tours are, of course, fully customizable., private chicago sightseeing tour prices, 1-11 people 2-hours: $479 3-hours: $599 4-hours: $699 12 or more: call for pricing, (prices include 9% city and 3% county amusement taxes), for this tour, you must call us at (312) 659-8687 to book.

How long are the tours? Our Chicago mini bus tour is two hours. The combination with the bus and Chicago River Architecture boat tour about 3.5-4 hours.

Where do we start the tour? Our tour picks up at most of the downtown Chicago hotels. If you are not staying at one of them, give us a call and we’ll tell you where to go (in the nicest possible sense).

Will there definitely be seats for us? Yes. Several of our competitors over-sell their tours, so that sometimes there are seats, sometimes not. Once you reserve with us, your seats will be yours for the entire tour. Also, our seats are nice and plush. Not plastic seats or wooden benches.

Can we take lots of photos? Absolutely. While you can take pics throughout the tour, we have 3 (sometimes 4) photo stops. They are located in the best places to get the most amazing pictures of Chicago.

Can we easily ask questions of our guide? Our mini buses hold just 14 guests. That way, you’ll be close to the guide and able to ask questions (and get correct answers)

Are Your Tour Guides Experienced? Our guides are all very experienced and knowledgeable about Chicago. They have all lived here for at least 20 years. You can ask them anything.

Will we see anything designed by Frank Lloyd Wright? Only a couple of walking tours and ours take you inside one of the first skyscrapers ever built, The Rookery. The awe inspiring lobby was designed by Mr. Wright. You may recognize it from the movies “The Untouchables” and “Home Alone Part 2”.

How does the architecture boat tour portion work? At the end of your mini bus tour, we will take you to the Shoreline Sightseeing dock on Michigan Ave. The boat tours leave about every 30-45 minutes and you can use your tickets at any time, even on a different day. Let’s say that it is raining or too hot (or both), you have the option to wait until a better time to ride the boat.

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Laurie Simmons: Big Camera/Little Camera Members’ Preview. Photo: Braxton Black for Jeremy Lawson Photography, © MCA Chicago.

Want to know more about what’s on view? Docents give tours of the museum’s exhibitions that take a deeper dive into the work on view. Tours meet at the second-floor admissions desk and last about 45 minutes.

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The 23 most unique day trips from Chicago

Break the mold with these under-the-radar, kitschy or otherwise unique trips within a few hours' drive of Chicago.

When it comes to a much needed escape from the city, there are countless day trips from Chicago if time doesn’t allow for a full weekend getaway . And luckily for the adventurous and curious, there are plenty of opportunities to swap typical activities like kicking back with brews for hiking  among bison or spelunking in an ancient cave. Many sites and experiences within driving distance of Chicago take you far beyond the norm, from year-round Christmas at an amusement park to (not so similar) replicas of some of the world’s most celebrated cultural sites. Midwesterners may love their weekend lake house tradition, but they also love the wacky, meaningful and unexpected. Here are the most unique day trips from Chicago.

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The most unique day trips from Chicago

1.  Explore the country’s largest magic museum

Driving time from Chicago: About three hours

You'll find everything from obscure conjuring tomes to equipment used in Harry Houdini's most famous escape acts at the American Museum of Magic in Marshall, Michigan, home to the biggest collection of magic ephemera in the United States. With more than 350,000 artifacts onsite, there's more than enough magical entertainment to fill an afternoon: Take a self-guided tour through magic history, try to squeeze into a replica of Houdini's Milk Can Escape or book an appointment at the museum's Lund Memorial Library to pore over archival materials.

2.  Spot bison at Midewin National Tallgrass Prairie

Driving time from Chicago: About one hour

Want to get a firsthand look at why Illinois is nicknamed the Prairie State? Take a trip southwest of the city to Will County, where a herd of bison roam the 9,000-acre expanses of the Midewin National Tallgrass Prairie as part of an ongoing habitat restoration project (the area once housed the Joliet Army Ammunition Plant and bunkers still remain). Spotting the herd isn't a sure thing—it's a massive park, after all—so you're best off bringing a pair of binoculars and starting at the Iron Bridge Trailhead, which puts you closest to the bison pasture area. From there, a three-mile round trip hike will lead you to an overlook point outfitted with viewing scopes and benches to rest on.

3.  Go spelunking inside Cave of the Mounds

Wander among soda straws, flowstones, helictites and other stunning geological formations inside of Cave of the Mounds, a natural limestone cave near Blue Mounds, Wisconsin. Once home to a limestone quarry, the cave is now open for guided (or self-guided) tours through mineral deposits in shades of white, reddish brown, black, purple and gray. Fun fact: Whether you're visiting on a hot summer day or during the frigid depths of winter, the subterranean expanse is always a cool 50 degrees, so be sure to dress accordingly.

4.  See the Batmobile (and tons of other famous cars) at the Volo Auto Museum

Driving time from Chicago:  About an hour and a half

Don't think that you're a car person? A visit to the Volo Auto Museum just might change your mind. Throughout this suburban attraction's 33 exhibits, you can ogle everything from '50s-era Thunderbirds and Oldsmobiles (Vintage Cars), to Britney Spears' 2006 Mercedes-Benz and Elvis Presley's 1974 Cadillac (Cars of the Rich and Famous), to Scooby Doo's Mystery Machine and the Subaru driven by Paul Walker in Fast & Furious 7 (TV and Movie Cars). There's even an entire exhibition dedicated to different iterations of the Batmobile. Plus, if you're really hoping to find some artifacts that aren't car-related, check out the museum's collection of planes, antique card games, animatronics and music machines, or shop for new home decor at the nearby Volo Antique Malls.

5.  Tour modernist architecture in Columbus, IN

Driving time from Chicago: About four hours

Thanks to a highly successful funding program in the mid-20th century, the small-ish town of Columbus, Indiana is home to some of the Midwest's most stunning examples of Modern buildings, structures and public art, with works by Eero Saarinen, I.M. Pei, Richard Meier and other architectural luminaries dotting its downtown thoroughfares. You can pay for a guide to lead you through the highlights, but the town also offers a free audio tour app that leads listeners through 18 of the most prominent buildings in the area.

6.  Paddle along the African American Heritage Water Trail

Driving time from Chicago: About 40 minutes 

Chicagoans who love active, experiential learning can take an impactful day trip of paddling through history along the Little Calumet River, a waterway which, along with others, connects Lake Michigan with the Mississippi River. In a span of just seven miles, experience nearly two centuries of African American history, from the underground railroad and civil rights to the birth of environmental justice. Beginners can join an organized group paddle during the summer season while experienced water recreationists can follow a self-guided paddle outlined on the Openlands website .

7.  Hike around the iconic Farnsworth House

Driving time from Chicago: About an hour and a half

Located in Plano, Illinois at the banks of the Fox River, the glass-walled Farnsworth House—designed by Bauhaus architect Ludwig Mies van der Rohe as a weekend retreat for Dr. Edith Farnsworth—is both a National Historic Landmark and one of the area's foremost examples of Modernist architecture. Though the house has been besieged by floods throughout its 70-year history, ongoing preservation efforts have kept it in tip-top condition. Book a docent-led tour through the building (the summertime moonlight tours, which commence at dusk and loop around a lighted exterior path, are an especially beautiful option) and take some time to soak in the natural beauty of the home's 60-acre wooded grounds.

8.  Check out Amish Country in Shipshewana, IN

Driving time from Chicago: About two and a half hours

Escape the bustle of city life among the placid streets of Shipshewana, a teeny town nestled in the center of northern Indiana's Amish Country. Kick off your day with a tour of Menno-Hof—a museum dedicated to Amish and Mennonite history—or book a sight-seeing expedition aboard a horse and buggy, then fuel up with traditional Amish eats at family-style restaurants like A Taste of of Shipshewana (where you'll also find live cooking and quilting demonstrations). In the market for antiques and tchotchkes? Plan a visit on Tuesdays or Wednesdays from May through September, when the town hosts the Midwest's largest flea market.

9.  Explore the Bahá'í Temple

Driving time from Chicago: Around 30 minutes

No doubt you’ve seen pictures or driven by the striking Baha’i House of Worship in Wilmette, but make a day of it and actually witness the interior details. The temple of the Baha’i faith was built in 1953 after 50 years of planning and construction. It is currently open to the public daily with free admission to the temple’s domed auditorium and surrounding gardens. 

10.  Wander through a Tudor-style castle in Oregon, IL

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Driving time from Chicago:  About two hours

Back in the late 1920s, Chicago Daily News publisher and owner Walter A. Strong began construction on a Tudor-style manor to serve as his family's summer home. The end result—a 10-bedroom, 8-bathroom behemoth with a couple of secret passages to boot—can be explored in the present day through an hour-long tour, which covers the history of the Strong family, the castle's architecture and a brief history of medieval life. If you're got time after the tour, head to the nearby Castle Rock State Park (unaffiliated with the aforementioned castle, in case you were wondering) to hike among gorgeous sandstone bluffs.

11.  See the Great Pyramids without leaving Illinois

Driving time from Chicago: About one hour and five minutes 

One of the most unexpected I-94 sights is the Gold Pyramid House, a 1970s-era family compound featuring replicas of the Great Pyramid of Giza, a 55-foot statue of Ramses II and King Tutankhamun’s tomb. Full of objects and decor leaning from kitschy to cult-like, visitors can meander the grounds and attend events, and even take home Gold Pyramid Water and Gold Pyramid Vodka as souvenirs, though it’s unclear whether either were on sale in ancient Egypt. House tours on select Saturdays and by appointment only. 

12.  Meander through an English-style village next to the largest inland oil refinery

Driving time from Chicago: About 35 minutes 

Marktown Historic District may not be one of the seven wonders of the world, but it's certainly a marvel of Northwest Indiana. Built in 1917 as a planned worker community by renowned architect Howard Van Doren Shaw—10 years after the last home was sold in nearby planned community Pullman—Marktown became famous after its appearance in Ripley's Believe It or Not! for being  the only town in North America where cars park on the sidewalk and neighbors walk on the streets. Today, the quaint Tudor revival-style homes with bright colors and cheerful window boxes are in eerie contrast to the surrounding heavy industry. Learn about architecture and the area’s history in steel on a self-guided tour.  Then, refuel at Hegewisch favorite Pudgy’s Pizza before heading home.

13.  Ride a vintage train at the Illinois Railway Museum

The country's largest railway museum sits just outside the Chicago metropolitan area in Union, Illinois, where you can check out a massive collection of antique train cars and hop aboard working streetcars, steam and diesel trains that loop around the 100-acre campus. Plan for an entire day of exploration: The museum's buildings house all kinds public transportation artifacts, including an 1859 horse-drawn streetcar, every kind of CTA 'L' car and a display of working railroad signs and signals.

14.  Take a nature walk through Cantigny Park

Driving time from Chicago: About 45 minutes

This verdant Wheaton park—formerly the estate of the publishers of the Chicago Tribune— offers 29 acres of gardens and 160,000 plants, complete with two and a half miles of nature paths perfect for a leisurely afternoon stroll among the flowers. Military history buffs will also want to check out the First Division Museum on the park's grounds, which chronicles U.S. military history from World War I to the present.

15.  Find your zen in the Anderson Japanese Gardens

Driving time from Chicago: About two hours

Once you've thoroughly explored the lovely Garden of the Phoenix in Jackson Park, set your sights on a visit to the Anderson Japanese Gardens in Rockford. Designed by landscape architect Hoichi Kurisu, the 12-acre gardens feature trails, waterfalls, tranquil ponds, gravel gardens and an abundance of Japanese maples, among other plant life. Plan ahead and book the "Frank Lloyd Wright Meets 16th Century Japan Tour" that guides visitors through the garden's 16th century Sukiya-style tea house and the Laurent House, which has the distinction of being the only home Wright designed for a client with a physical disability.

16.  Learn about America’s RVs at a niche museum

Driving time from Chicago: About two hours 

Get inspired to embark on your version of the great American road trip as you browse permanent collections of trailers, motorhomes, housecars and more ranging from the 1910s to present at Elkhart’s RV/MH Hall of Fame (RV/MH stands for recreational vehicle and manufactured housing). Step back in time with Instagram-worthy vintage airstreams, Model T campers and motorhomes that look like they stepped off the set of Stranger Things . After your visit, explore the thousands of archives at the RV/MH Library, where you can glimpse into the recreational lives of North Americans in the 1960s issues of Trailer Life or 1980s issues of Camping Today .

17.  Visit Frank Lloyd Wright's home and studio

Just outside the city limits is the birthplace of Frank Lloyd Wright’s iconic architectural style. Early design concepts are filled in Wright’s Oak Park home and studio, with the surrounding residential district containing the most Wright-designed homes in the world. Visitors can enjoy a guided interior tour of the residence as well as a walking tour of the neighborhood for just $30 per person. Afterwards, pick up your favorite breads and pastries at Publican Quality Bread's Oak Park outpost.

18.  Take a picture with a (smaller) Leaning Tower of… Niles

Driving time from Chicago: About 25 minutes 

Sitting at a half the size its original at 94 feet tall and leaning 7.4 feet, the replica of the Leaning Tower of Pisa in suburban Illinois is an unlikely site and guaranteed out-of-the-box day trip. In the 1930s, a local businessman wanted to disguise a water tower and the answer was—obviously!—to craft a leaning tower. Taking an illusion photo holding up the tower is a must, and if you’re not too tired, head to nearby North Branch Trail and surrounding forest preserves for nature spotting or cozy up with your next great read at New Book Joy .

19.  Watch an outdoor play at American Players Theatre

Driving time from Chicago: About three and a half hours

Spring Green, Wisconsin is perhaps best known as the home of Taliesin, Frank Lloyd Wright's Prairie style summer estate set amid the limestone outcroppings of Wisconsin's Driftless Area. You should make a stop at the house if you have time—Wright's estate offers a huge variety of guided tours—but the 1,089-seat outdoor ampitheater at American Players Theatre is an equally unbeatable summertime attraction. The company's repetoire is mostly classical , though you'll find more contemporary works on the lineup as well.

20.  Celebrate Christmas in July at Santa’s Village

Driving time from Chicago: About an hour

Sure, Six Flags is fun, but there's only one suburban amusement park where you'll run into Santa Claus year-round, and that's Santa's Village Azoosment & Water Park in East Dundee. Despite its wintry theme, the family-friendly park is best visited in summer: Splash around in the Caribbean Christmas-themed Santa Springs water park—featuring two 300-foot, candy cane-colored slides—or take a spin on thrill rides like the Blizzard, which swings riders 40 feet in the air on a spinning pendulum.

21.  Eat fried chicken on Historic Route 66

Driving time from Chicago:  About 35 minutes

Fried chicken with a side of history? We’ll take it. At Dell Rhea’s Chicken Basket, you’ll be eating food that has been satisfying hangry travelers and folks simply looking for a good meal since 1946. This gas station lunch counter-turned-dining room is conveniently located off Route 66, its gleaming lights a beacon for those traveling to or from Chicago. Listed on the National Register of Historic Places, step into the nearly unchanged brick building and devour a Famous Fried Chicken Dinner, hand breaded and deep fried half chicken served with mashed potatoes and biscuits.

22.  Say “prost” in Germantown, WI

Despite its name, the Milwaukee suburb of Germantown, Wisconsin doesn't quite have the transportative qualities of other places in the Midwest that look like Europe . Still, there's a lot to love about this historically German settlement—sip a stein full of Krombacher Pils at the Von Rothenburg Bier Stube , check out more than 5,000 antique bells at the Sila Lydia Bast Bell Museum & Fire Hall or don your best lederhosen/dirndls for Maifest, the annual three-day festival held in honor of the beginning of spring.

23.  See some giant things in Casey, Illinois

Just under four hours south of Chicago, the intriguing town of Casey prides itself on being filled to the brim with giant things—literally. The town is home to 12 of  world’s largest items . From a 28-foot Chevy truck key to a 42-foot long wind chime to a 46,000-pound rocking chair behemoth, these public sculptures are really one-of-a-kind.

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Billie Eilish announces ‘Hit Me Hard and Soft’ world tour coming to Chicago’s United Center

NEW YORK — Billie Eilish is hitting the road.

The pop performer will embark on a worldwide arena tour this fall, kicking off in Quebec City in Canada on Sept. 29 and concluding in Dublin on July 27, 2025. She'll hit many major cities in North America, including Chicago’s United Center Nov. 13-14, in 2024 before heading to Australia and then Europe.

Presale begins Tuesday, and any remaining tickets will become available Friday at billieeilish.com . A percentage of proceeds will benefit the environmental nonprofit REVERB.

Earlier this month, Eilish announced her highly anticipated third studio album, “Hit Me Hard and Soft,” will be released May 17.

The news arrived via Instagram, where Eilish shared the album artwork showing the pop singer floating in a body of water after being ejected from a door. In the caption, she wrote that she will not drop singles in advance of the release.

“I wanna give it to you all at once,” she captioned the image. “I truly could not be more proud of this album.”

Eilish worked with her brother and longtime collaborator Finneas on “Hit Me Hard and Soft.” The pair recently took home their second Oscar for their big “Barbie” ballad “What Was I Made For?” In doing so, Eilish, 22, became the youngest person to have won two career Oscars.

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'The Daily Show' coming to Chicago for Democratic convention

It’s the second late-night series to announce local convention plans, after cbs’ “the late show with stephen colbert.”.

“The Daily Show” host Jon Stewart meets with writers at a commercial break while broadcasting from St. Paul, Minnesota, during the 2008 Republican National Convention.

Ethan Miller/Getty Images

Keeping up its tradition of onsite political nomination coverage, “The Daily Show” plans to be in Chicago for Democratic National Convention in August, Comedy Central announced Monday.

The comedy news show also will be in Milwaukee in July for the Republican convention.

It’s the second late-night series to announce Chicago convention plans, after CBS’ “The Late Show,” starring “Daily Show” alum Stephen Colbert. While Colbert will be setting up shop at the Auditorium Theatre during DNC week, his show will be staying put in New York for the GOP meetup.

“The Daily Show” did not reveal the venue where its episodes will originate or who will anchor them. In recent months, returning host Jon Stewart has been handling Monday night episodes, with Tuesday-Thursday shows fronted by the team’s various senior correspondents.

The series was last in Chicago in 2017 for a week of episodes at the Athenaeum Theatre starring former host Trevor Noah.

• John Mulaney returns to St. Ignatius for playful, sometimes poignant David Letterman chat

Music and Concerts | Billie Eilish announces concert tour with…

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Music and concerts | billie eilish announces concert tour with chicago dates this fall.

Billie Eilish’s newly announced concert tour will bring her to Chicago for two shows at the United Center in November.

The world tour will be in support of her soon-to-be-released third studio album, “Hit Me Hard and Soft,” set for May 17.

The tour is slated to arrive in Chicago for concerts at 7 p.m. Nov. 13-14. Tickets go on sale in American Express and fan club presales at noon April 30, then to the public at noon May 3. Tickets for the Live Nation tour will be sold via Ticketmaster .

The tour, announced Monday , is slated to begin with North American concerts in Quebec on Sept. 29, then a first U.S. show in Baltimore in early October. It wraps up U.S. dates in December, then heads to Australia in February before moving on to Europe and the U.K.

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