Top picks for Chicago Water activities

Discover 9 Water activities in Chicago on Trip.com, updated October 24, 2026, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From SEK 471.00 per person, with an average total of SEK 761.12. Choose the option that suits your plan.

With 16 verified reviews, Water activities Chicago boast an average rating of 4.7.

This week's most popular Water activities: "Chicago: 2-Hour Downtown Kayak Rental", with 9 reviews and a 5.0 rating.

Now on Trip.com: "Chicago: Food Tour + Bike or Kayak Rental", a 5-hour adventure in Chicago!

The next available day tour departs on October 25, 2026. Book now to secure your spot!

Chicago Water activities usually take about 5 hours — perfect for a relaxed, immersive experience!

October is the perfect time to visit Chicago! Choose from 9 available day tours, including seasonal favorites like Chicago: 2-Hour Downtown Kayak Rental.

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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9 results for Chicago Water activities

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Reviews/Trip Moments

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Reviews: Chicago: History and Architecture Guided Kayak Tour
Guest User2026-08-04
Very fun. Kind of long if you don’t know how to kayak. We were offered an easier route so take it if you aren’t strong.
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Guest User2025-07-24
This was a fun activity that puts you right in the middle of Chicago! All of the guides are great and take their time to make sure you are comfortable before the fun starts. Highly recommend!
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Reviews: Chicago: 2-Hour Downtown Kayak Rental
Guest User2026-08-03
We did not have a guide as we are pretty seasoned kayakers! Great place to start the adventure and it was a great day on the water! Highly recommend!