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Cultural tour activities in Illinois

Book unique activities hosted by local experts on Airbnb.

Top-rated cultural tours

View our most highly rated experiences, loved by guests.

4.87 out of 5 average rating, 362 reviews

Chicago's Famous Foods & Top Attractions Walk Tour

Taste your way through Chicago on this award-winning Chicago Food & Walking Tour! Enjoy five iconic tastings—deep dish pizza, hot dogs, Italian beef, Garrett's popcorn, brownie—plus top attractions.

4.95 out of 5 average rating, 358 reviews

Chinatown's Food & Culture Walking Tour in Chicago

Taste your way through Chicago’s Chinatown on this 1-mi award-winning Food & Culture Walking Tour! Enjoy 5 tastings—dim sum, chili chicken, lamb cumin, egg tarts, and more—plus tea & drink upgrades.

4.97 out of 5 average rating, 329 reviews

Award-winning Bikes, Bites & Views Tour - Adults

Ride through Chicago, tasting deep dish pizza, hot dogs, brownies & local beers (with VIP upgrade). This adults-only food/bike tour has day routes to Wrigley Field & night routes of top attractions.

4.93 out of 5 average rating, 973 reviews

Paint your own street art at Studio WIP

Unleash your creativity at this art hub in Chicago’s Uptown neighborhood. Local artists will show you how to spray-paint using insider tricks, and you’ll leave with finished art. Beginners welcome.

4.95 out of 5 average rating, 64 reviews

Ultimate City Bike Tour of Top Chicago Attractions

Ride Chicago’s top attractions—Millennium Park, Buckingham Fountain, Navy Pier, Museum Campus & Lakefront. Enjoy skyline views & fascinating stories on an easy bike tour through the heart of the city.

4.99 out of 5 average rating, 193 reviews

Walkin' With Colin Chicago Tour du Jour

A sensational journey through the history, mystery, comedy and tragedy of The Windy City.

4.94 out of 5 average rating, 286 reviews

Chicago in a Day: Food, History & Landmarks

Walk through Chicago’s vibrant heart, exploring iconic architecture and tasting classic local flavours like deep-dish, hot dogs, and Italian beef along the way.

4.91 out of 5 average rating, 477 reviews

Chicago Underground Pedway & Secret Interiors Tour

Explore Chicago's underground Pedway: hidden corridors of stained glass, quirky stories, and many secrets both underground and above, with stunning architecture and unexpected details.

4.94 out of 5 average rating, 17 reviews

Ride in a limo through Chicago

Experience a 3-hour Chicago limo tour with bar hopping, iconic sightseeing, and local history. Enjoy alcohol, soft drinks, and champagne included for a seamless VIP group experience this summer

4.98 out of 5 average rating, 184 reviews

Walk Oak Park's historic architecture district

Explore Oak Park's history, including Frank Lloyd Wright's designs and Hemingway district.

Latest Activities

Explore new local experiences, activities for everyone.

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A Woman's Place: The Chicago Women's History Tour

Meet the bold, brilliant women behind Chicago—from Ida B. Wells to Jeanne Gang—on a lively 2-hour downtown walk through striking spaces, secret interiors, and stories that changed the city.

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Chicago Haunted Interior Architecture Ghost Tour

Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them architecturally amazing!

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Chicago Suburbs Movie Sites Tour

Relive the mischief at Cameron’s iconic garage and dive into Chicago's cinematic history.

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Downtown Chicago TV & Movie Sites Tour

Explore The Dark Knight's film locations, including Bruce Wayne’s penthouse and Harvey Dent’s courtroom, with exclusive industry insight.

4.9 out of 5 average rating, 10 reviews

Golden Hour Architecture & Guided Photo Walk

Walk Chicago’s Loop exploring architectural canyons, the Riverwalk, and the Bean. Capture stunning photos with a photography-trained local guide. Day and golden hour/sunset tours available.

5 out of 5 average rating, 12 reviews

History and Architecture of Chicago Walking Tour

Join local expert guide Dave Lineal for a walking tour of enchanting downtown Chicago. You will learn the history, economics, & culture of the city while walking its streets & historic interiors.

5 out of 5 average rating, 7 reviews

Chicago Highlights & Attractions Walking Tour

Discover Chicago’s top sights on a fun, expert-led walking tour! Iconic landmarks, hidden gems, and local stories await—come explore the Windy City the best way possible: on foot.

4.75 out of 5 average rating, 24 reviews

Chicago Gangsters & Ghosts Official Guided Tour

Embark on a history-based guided walking tour and discover the stories of Chicago’s gangsters and ghosts. Learn about the city’s darker side and creepy past as you explore the Chicago Loop district.

5 out of 5 average rating, 20 reviews

Skip the line Tour at Art Institute of Chicago

Start with exclusive early access, before the museum opens, and explore iconic galleries.

5 out of 5 average rating, 16 reviews

Family Food Bike Tour - Explore Top Foods & Sites

Pedal to iconic downtown sites while sampling classic Chicago favorites. This family-friendly adventure blends skyline views, rich stories, & delicious bites into one unforgettable kid-friendly tour.

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