Top picks for Chicago Outdoor & sports

Discover 47,529 Outdoor & sports in Chicago on Trip.com, updated November 1, 2026, with experiences lasting from 1 to 2 hours. Find the perfect adventure for your day!

From QAR 102.07 per person, with an average total of QAR 232.53. Choose the option that suits your plan.

With 10.745k verified reviews, Outdoor & sports Chicago boast an average rating of 4.8.

This week's most popular Outdoor & sports: "Chicago Architecture River Cruise", with 4.695k reviews and a 4.9 rating.

The next available day tour departs on November 2, 2026. Book now to secure your spot!

Chicago Outdoor & sports usually take about 1 hours — perfect for a relaxed, immersive experience!

37% of Chicago Outdoor & sports now offer English-speaking guides

November is the perfect time to visit Chicago! Choose from 47,529 available day tours, including seasonal favorites like Chicago Architecture River Cruise.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

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47529 results for Chicago Outdoor & sports

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RecommendedAttractions (47312)Shows & events (2)Day tours (149)Boat tours (43)Culture & history (60)Food & drink (27)Outdoor & sports (2)City sightseeing (60)Nature & wildlife (2)Water activities (7)Travel photography (3)Aerial tours (2)SIM card (35)Visas (7)Boat tickets (1)

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Reviews/Trip Moments

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Reviews: Chicago CityPASS
Guest User2026-01-03
This citypass is good idea for tourist easy to manage. We can visit Chicago in a short time with good memories. I will recommend to my relatives and friends if they visit Chicago.
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Reviews: BIG BUS Chicago hop-on hop-off bus tour
Guest User2026-05-21
Easy to book the big tour bus tickets in Chicago via trip.com.
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Guest User2026-04-23
A must do in Chicago! The buildings here are rich in history and architectural meaning.
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Guest User2025-12-17
It was seriously so, so good ㅠ It was the highlight of my Chicago trip... This makes up almost 80 percent of my Chicago memories, and I have no regrets. The buildings are really huge and super beautiful. Make some memories there!
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Guest User2024-06-10
Best museum in North America imho. Bunch of valuable pieces from Picasso and Monet as well as historical artifacts from all around the world. You go there more for the paintings than the other things though.
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Reviews: Chicago CityPASS: 5 attraction admission tickets
Guest User2026-08-11
It works great, but remember to use a virtual email address or call customer service when logging in, otherwise you won't be able to log in.

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