All Chicago Tours &amp; Excursions in 2026

Photo Shoot in Chicago’s Urban Jungle Garden

40 minutesFree Cancellation

If you’ve got a flight to catch in Chicago, don’t leave getting to the airport to chance. Ride with a trusted chauffeur in your own air-conditioned luxury vehicle during this one-way private transfer to Midway Airport. Get picked up from anywhere within downtown Chicago and dropped off well in time for your departing flight. Fifteen minutes of free waiting time are included in case you have any last-minute packing to do.

Private SUV Transfer from Chicago Downtown to Midway airport

30 minutes to 1 hour 30 minutesFree Cancellation

This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by transformation from cemetery grounds to residential district. What traces of earlier history remain beneath modern streets? Architectural landmarks reflect 19th-century development and urban expansion. Historic venues such as theaters and pubs carry narratives passed through generations. These accounts reveal how memory and place intertwine within the city’s cultural fabric. The experience offers a thoughtful perspective on Chicago’s past through legend and documented history. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Private Historical Ghost Walking Tour in Chicago Lincoln Park

$869$826

Channel your inner detective on this immersive, self-guided scavenger hunt through Chicago’s Loop! Step back to 1923 as you gather clues, solve a murder mystery, and unlock secrets of Prohibition-era Chicago. Your group receives a mystery kit, then follows a story-driven trail at your own pace—no app required. Observe real landmarks and hidden clues as you work together, making this ideal for friends, families, and groups seeking a hands-on, flexible adventure. The perfect blend of history, teamwork, and local intrigue in the heart of Chicago.

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

1 hourFree Cancellation

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden details behind the buildings that shaped the modern city. What makes this experience unique: • Small-group tour for a more personal experience • Story-driven guiding that brings Chicago’s architecture to life • Focus on early skyscrapers and hidden architectural details • Visit iconic landmarks in the historic Loop • One complimentary copy of my book, Chicago Beyond the Bean, is included per booking.

Chicago Early Skyscraper Walking Tour in the Loop

Treat yourself to a VIP arrival in or departure from Chicago during this private pickup or drop-off at Chicago O'Hare Airport (ORD). Enjoy a personalized meet-and-greet from a professionally-trained chauffeur right outside your hotel lobby, private residence, or airport arrivals hall. Ride comfortably in a luxury vehicle with complimentary bottled water. Flight tracking and one hour of free waiting time is included in case of delays.

$39$37

Special Offer

Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car

Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Car

30 minutesFree Cancellation

$244

$232

Private Transfer Chicago Airport to Chicago by Luxury Car or SUV

45 minutesFree Cancellation

Fresh, vibrant and built on ingredients you can find anywhere – this Mediterranean cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, teaches three crowd-pleasing dishes that bring the coast straight to your kitchen. Your hands-on cooking experience features: - Hummus with chickpeas, lemon, cumin and olive oil - Greek Chicken With Lemon and Feta with chicken breast, Feta, thyme, lemon and white wine - Balsamic Berries With Greek Yogurt with Greek yogurt, honey, balsamic vinegar and mixed berries You will leave ready to recreate a full Mediterranean spread at home – from hummus to dessert. Guests are welcome to bring wine or beer to enjoy throughout the experience.

Mediterranean Cooking Class in Chicago (Includes 3-Course Meal)

Mediterranean Cooking Class in Chicago (Includes 3-Course Meal)

$110$105

Discover the fundamentals of sushi-making in Chicago during this immersive class hosted through Cozymeal. Limited to 8 guests, the workshop showcases the precision and artistry of Japanese cuisine. The menu you will prepare includes: - Sushi: Spicy ahi-tuna roll with avocado, cucumber and aioli - Sushi: Shrimp tempura roll with jalapeño, cucumber and miso aioli - Dessert: Tropical fruit with tōgarashi and honey With step-by-step guidance from your local sushi chef, you’ll gain confidence in rolling techniques and flavor pairing. Guests are welcome to bring wine or beer to complement the meal, making the evening both educational and enjoyable.

Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)

Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and untold stories that shaped the city’s cultural heart. Book your journey today! Tour is available in following language: English Spanish & French Highlights: • Explore Chicago’s Jewish heritage with a knowledgeable 5-Star Private Guide • Discover key Jewish landmarks and skip common tourist routes with ease • See historic monuments and hidden gems that shaped the city’s vibrant culture • Learn inspiring stories of Jewish contributions to Chicago’s art and history • Get custom tips for more cultural sites and experiences around the city Follow the footprints of Jewish history through Chicago’s vibrant streets!. On this private walking tour with Rosotravel, a Licensed Guide will tailor the experience to your interests, revealing hidden gems, fascinating stories, and historical treasures.

Chicago Jewish History Landmarks Private Guided Walking Tour

$227$216

Discover the streets of Lincoln Park, Chicago, and the Magnificent Lake Front on a high-quality electric bike rental from E-Z Rider Bike Shop. Our e-bikes provide effortless rides through the city, eliminating worries about traffic and parking. Experience the joy of biking while saving on gas and insurance costs. - Convenient location on Clark Street in Lincoln Park - Free demo test ride available - Ideal for leisurely exploration or thrilling rides - Expert advice to help you choose the right e-bike model

Electric Bike Tours in Lincoln Park

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

1 hourFree Cancellation

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk. Complete this solo or build a ScavSquad of up to 5 people and discover the city like never before! Use clues and hints within the app to complete the objectives (if you get stuck, you can skip and go back later). Some objectives have prizes so do your best to complete as many objectives correctly. Once complete, you can view the Leaderboard to see how you did against others.

Chicago Scav Hunt - An App-Guided Adventure

3 hoursFree Cancellation

For sightseers looking to put a spooky spin on their night and avoid the overpacked city tours that tell history most of us already know, this Chicago Family-Friendly Ghost Tour is just the thing. Stop at popular Chicago attractions, including the Flying Dragon sculpture, the Chicago Stock Exchange Arch, the Abraham Lincoln statue, and Buckingham Fountain, while a guide tells you ghost stories along the way.

Haunted Chicago: Lincoln Park Ghost & History Walking Tour

1 hour 30 minutesFree Cancellation

Join our exclusive cooking workshop series in collaboration with celebrity chef Tony Hu. In the first session, you'll learn to prepare two of his signature dishes—Chef’s Special Dry Chili Chicken and Crispy Lemon Shrimp. Featured on numerous TV shows and interviews, including NBC, ABC, FOX, and WGN, Chef Tony Hu is the founder of the iconic Lao Sze Chuan Restaurants with 14 locations across the country. This hands-on cooking workshop is more than just a culinary lesson—it’s a cultural experience. We invite you to connect with Chinese heritage in a warm, interactive setting where every dish tells a story, and every bite is a celebration of tradition. A minimum of 4 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

Cooking Class with Celebrity Chef Tony Hu

1 hour 30 minutesFree Cancellation

$135$128

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Pullman, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in Pullman - Led by knowledgeable Historian Dilla for an authentic experience

2 Hour Pullman/Roseland Chicago Tour

$45$43

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

THE LUXURY SEDAN OFFERS SEATING FOR 2 PASSENGERS, WITH LUGGAGE CAPACITY FOR 2 BAGS. Luxurious Fleet: Our fleet consists of top-of-the-line luxury vehicles, meticulously maintained to provide the utmost comfort and style during your journey. Whether you're traveling solo, with a group, or for a special occasion, we have the perfect vehicle to suit your needs. Professional Drivers: Our drivers are not only highly skilled behind the wheel but also epitomize professionalism and courtesy. They prioritize your safety and satisfaction, ensuring a smooth and enjoyable ride from pick-up to drop-off.

Luxury Sedan O'Hare/Midway Airport (Curbside) Chicago One Way

Luxury Sedan O'Hare/Midway Airport (Curbside) Chicago One Way

30 minutes to 1 hourFree Cancellation

Tapas, paella and flan – this hands-on Spanish cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, takes you through three pillars of coastal Spanish cuisine in one vibrant, skill-building experience. Your hands-on cooking experience features: - Gambas al Ajillo with shrimp, garlic, lemon, chile flakes and sourdough - Seafood Paella with mussels, shrimp, saffron, bomba rice and chistorra - Mango Flan with eggs, milk, condensed milk, evaporated milk and mango purée You will leave with the skills to make authentic Spanish paella and tapas at home. Guests are welcome to bring wine or beer to enjoy throughout the experience.

Spanish Paella Cooking Class in Chicago (Includes 3-Course Meal)

Whether you're flying in for business or leisure, We ensures your journey is as smooth and stylish as your destination. Here's why travelers trust us: Luxury Fleet for Every Occasion Choose from executive sedans, SUVs, Sprinter vans, and minibuses Immaculately maintained, climate-controlled, and equipped with premium amenities Punctual & Reliable Real-time flight tracking ensures on-time pickups—even if your flight is early or delayed Chauffeurs arrive early and plan routes to avoid traffic delays Professional Chauffeurs Courteous, licensed, and experienced drivers Dressed professionally and trained in customer service and safety Easy Booking & Real-Time Updates Book online in minutes with instant confirmation Receive driver details and live tracking before your ride Perfect for Business & Leisure Ideal for corporate travel, family vacations, weddings, and group events Discreet, comfortable, and tailored to your needs

Private SUV Transfer from O'Hare Midway Airport to Chicago

1 hourFree Cancellation

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Along DE way, it connects iconic cities such as St. Louis, Tulsa, Amarillo, Albuquerque, Flagstaff and Los Angeles, offering a unique experience through varied landscapes, from the Midwest Plains to the Southwest Deserts, each with its own history and culture. Route Chicago : 50 points Route DE Chicago to St. Louis : 56 points Route San Luis : 13 points Route DE San Luis to Joplin : 56 points Route Joplin to Oklahoma city : 29 points Route DE Oklahoma City to Amarillo : 27 points Yellow Route to Santa Fe : 39 points Route DE Santa Fe to Las Vegas : 80 points Route DE Las Vegas to Los Angeles : 34 points Total DE DE DE DE l’Or points of interest: 384

Routes POR Route 66 with Audio Guide

6 daysFree Cancellation

Step into the vibrant, resilient heart of Chicago's South Side. On this immersive journey through Bronzeville, you will uncover the epic story of the Great Migration—a time when millions of African Americans fled the Jim Crow South to build a self-sustaining 'Black Metropolis'. From the birthplace of gospel music to the headquarters of a newspaper that changed the nation, discover the triumphs of entrepreneurship, the brilliance of cultural innovation, and the unyielding spirit of a community that shaped modern America. A 3.9 km self-guided tour with 7 stops over 121 min Ideal for travelers interested in Identity, Migration & Globalization and History & Memory Immersively told in a podcast style by experts and locals Matching audio content, AI guide and navigation through the app

Podcast Tour Chicago The Promised Land and the Black Metropolis

2 hours 1 minuteFree Cancellation

$7$6

This family friendly tour uncovers the powerful legacy behind Fort Dearborn, the devestation of the Great Chicago Fire, and the re-birth tied to the World's Columbian Exposition, while witnessing Chicago's world-famous skyline. Explore a variety of breathtaking iconic landmarks, legends, and resilence that shaped the city, while learning the meaning behind the symbols of the Chicago flag. Learn how each star, stripe and historic site tells the story of innovation, preserverence, and civic pride.

Journey of the Chicago Flag Bus Tour

Special Offer

Step into the grit and glory of Michael Jordan’s 1990s Chicago Bulls dynasty. We trace the physical collision between global basketball myth and the reality of the Near West Side. From high school talent pipelines and pickup courts to working-class fan taverns, the vanished Chicago Stadium, and the redeveloped housing projects across Lake Street, this walk explores how an industrial city rebranded itself into an international sports capital—and what that transformation meant for the neighborhood living in the arena's shadow. - A 3.9 km self-guided tour with 8 stops over 139 min - Ideal for travelers interested in Pop Culture & Media Landscapes and History & Memory - Immersively told in a podcast style by experts and locals - Matching audio content, AI guide and navigation through the app

Self Guided Podcast Tour Chicago Michael Jordan's West Side

2 hours 19 minutesFree Cancellation

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Must-Dos in Chicago

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What are people saying about Chicago

Flyover in Chicago

Willie_P, Nov 2026

Great Experience

Flyover is an indoor simulated flying experience at Navy Pier. You're suspended in moving seats in front of a massive curved screen, with wind, mist, sound, and other effects making you feel like you're soaring over Chicago Incredible views of Chicago's skyline and landmarks. Feels similar to Disney's Soarin' ride. Great indoor activity when Chicago weather is cold. Exciting visuals and realistic motion effects.

Chicago River 90 Minute Architecture Tour

Tiffany_P, Oct 2026

Chicago experience everyone should try!

Such a beautiful way to experience Chicago! Watching the sunset over the skyline and then seeing the city light up at night made this boat ride so memorable. You really get the best of both views! Our tour guide made the experience even better with his hilarious puns and playful commentary. I really appreciated the effort he put into getting the crowd excited and keeping everyone entertained. His energy added so much to an already stunning evening. Definitely a highlight of my Chicago trip!

Chicago Favorites Ultimate Food and Walking Tour

Jessica_S, Oct 2026

Biggest Bang for Your Buck

A great way to pack a day’s worth of food and history into a few hours. Food? Delicious! Tour? Awesome! Guide? Epic! Cassandra (Caddie) brought the history of Chicago’s food, architecture, and art to life with her energetic and entertaining delivery. She was friendly and funny, making the hours fly by. As a solo traveler I was made to feel part of the group which was so comforting. I also can’t wait to take a bike ride around the river and lake with the included bike rental! This tour really packs in so much bang for your buck! 20/10 Highly Recommend!

Chicago By Night River and Lake Cruise

Melissa_F, Oct 2026

Great tour of the river and Lake

This cruise was fantastic. I have done just a river cruise before but this was better. I loved hearing about the architecture in the river areas but also going out onto the lake was fabulous. You get to transverse through the lock that takes you out into Lake Michigan and learn about the the skyline from the East and West sections of the lake. Our tour guide was fabulous, informative and funny.

Chicago Architecture Center River Cruise aboard First Lady

Mary_M, Oct 2026

Absolutely lived up to the hype!

An exceptional tour from start to finish. We took the 11:00 AM slot and had perfect weather, which made for stunning photos of the skyline. The CAC docent was fantastic, delivering a masterclass in Chicago history and architecture without it ever feeling dry. The boat was spacious, clean, and very well-run. Booking through Viator was seamless. Don't look at any other boat tours—this is the official one you want to choose.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Jeanine_O, Oct 2026

Fabulous way to spend an evening!

The night cruise along Chicago River was awesome. Kay, our tour guide was knowledgeable and funny and made the 45 minutes fly by! What was a happy surprise was that ALL passengers had a seat up top. Looked like so many, but they did it right. I would do it again during the day as well to see the contrast. Great value for your your dollar!

Chicago Architecture River Cruise

Dwella_G, Oct 2026

A must do experience in Chicago.

When planning your Chicago itinerary, put this tour at the top of your list. The Chicago Architecture River Cruise was a must-see experience. The weather was great. Our tour guide was very knowledgeable about the city and its buildings, which made the experience enjoyable. It’s nice for all ages. Make sure you dress warmly.

Chicago River 90-Minute Architecture Boat Tour

Chris_S, Oct 2026

David is the best in the city!

This was an excellent tour. The the ride was comfortable, though. I would’ve liked something a little bit better than folding chairs, but everybody had space it was a very stable comfortable ride. David was absolutely fantastic. I cannot say enough good things about him as the tour guide. His knowledge was excellent. His timing was fantastic. He was personable. He was funny. If I come back, I’ll probably go see him again even though it will be a repeat experience because he was just that enjoyable highly recommend 10/10