Top picks for Chicago Outdoor & sports

Discover 10,213 Outdoor & sports in Chicago on Trip.com, updated November 2, 2026, with experiences lasting from 1 to 2 hours. Find the perfect adventure for your day!

From QAR 0.30 per person, with an average total of QAR 214.40. Choose the option that suits your plan.

With 13.993k 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 3, 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 10,213 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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10213 results for Chicago Outdoor & sports

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Outdoor & sports

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RecommendedAttractions (47337)Shows & events (2)Day tours (146)Boat tours (41)Culture & history (59)Food & drink (27)Outdoor & sports (2)City sightseeing (60)Nature & wildlife (1)Water activities (7)Travel photography (3)Aerial tours (2)SIM card (35)Visas (7)

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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: United States 5G eSIM | Tri-network · Supports ChatGPT & Google Maps | 500MB/day - Total 100GB | 1–90 days | 24 hr billing | QR code
Guest User2026-09-23
eSIM was easy to installed. I tap on the phone from the order and done in about 3 minutes, activate data roaming and off you go, can access everything from WhatsApp to YouTube. Google in China. Speed outs good and upload is fast. Chew through data a bit.
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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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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 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 User2024-09-13
Every seat on the boat brought exceptional views! The recorded tour guide gave wonderful information and facts about the scenery

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