Best Water Sports in Chicago

Local Recommendations from our My Guide Chicago team

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

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Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

2 Reviews

Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

Make the most of your day in Chicago by sampling Chicago's iconic style foods, seeing top attractions with a local, expert guide. Includes a FREE 2 hr bike or kayak rental to explore even more.

$99.99

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Chicago & North Shore Stand Up Paddle board lessons & tour

Learn how to safely paddle board on the beautiful Lake Michigan. You will gain paddling knowledge, ability, and confidence, resulting in both a great time and lasting skills for all future paddling adventures!

$150.00

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Chicago: Private Catamaran Sailing for up to 12 people

This exclusive sailing experience includes breathtaking views of the Chicago skyline, refreshing swims, and the luxury of private yachting including Chicago’s largest chartered Catamaran.

$1,500.00

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Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise

8 Reviews

Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise

Take an exciting educational adventure aboard Tall Ship Windy with this cruise from Navy Pier in Chicago. Watch as Great Lakes history and maritime traditions come to life.

$29.00

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Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

33 Reviews

Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

Climb aboard Windy, Chicago's official Tall Ship Ambassador, and experience breathtaking views from the water on this tall ship cruise. Sail along Lake Michigan and learn about Chicago's architecture.

$49.99

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