AIRBNB EXPERIENCES

Sightseeing activities in Illinois

Book unique activities hosted by local experts on Airbnb.

Top-rated sightseeing activities

View our most highly rated experiences, loved by guests.

4.88 out of 5 average rating, 329 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, 56 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.

4.97 out of 5 average rating, 319 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.

4.99 out of 5 average rating, 182 reviews

Walkin' With Colin Chicago Tour du Jour

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

4.99 out of 5 average rating, 67 reviews

Walk and photograph the city with a local

Uncover Chicago’s best photo spots and fun facts while I capture your memories. *message me for personal photoshoot requests!

4.94 out of 5 average rating, 16 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

4.86 out of 5 average rating, 58 reviews

Explore Chicago's skyline from the air

Take a flight over Chicago, including Lake Michigan, Navy Pier, Wrigley Field, and Willis Tower.

5 out of 5 average rating, 61 reviews

Learn to fly a plane - Discovery Flight

With no experience required, we offer a rare chance to experience the thrill of flight, guided by an FAA-certified instructor. Weight limit of 190lbs. Subject to weather. No passengers

5 out of 5 average rating, 12 reviews

Skip the line Tour at Art Institute of Chicago

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

4.92 out of 5 average rating, 36 reviews

Chicago's Lakefront Neighborhoods Bike Tour

Ride through Chicago's North Side, finding quiet streets, city parks, and sunny beaches.

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