Best Water sports in Central Chicago

Local Recommendations from our My Guide Chicago team

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Chicago: Ghosts and Gangsters Night Kayak Tour

ExperiencesWater activitiesGuided toursOutdoor activitiesToursCulture & historyOutdoor sportsGhost & vampire toursWater sports

Paddle down the Chicago River on a night kayak tour. Hear stories of the city's notorious past, haunted spots, and infamous mobsters like Al Capone.

$70.85

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City Cruises Chicago: Seadog Lakefront Speedboat Ride

642 Reviews

ExperiencesOutdoor activitiesGuided toursWater activitiesNature & adventureToursWheelchair accessibleSightseeing on wheelsOutdoor sportsSightseeingWater sportsCruises & boat toursViewing pointsExtreme sports & adrenaline

Admire Chicago’s skyline and listen to city insights during an exciting speedboat ride on Lake Michigan. Choose the extreme thrills option to enjoy even faster speeds and a chance to be splashed.

$35.70

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Chicago: Sunset Kayak Tour on the Chicago River

5 Reviews

ExperiencesActivities for couplesOutdoor activitiesOutdoor sportsWater activitiesNature & adventureToursSunset toursWater sports

Paddle through downtown Chicago on a kayak tour during the golden hour. Admire the city's skyline, including the Willis Tower and Civic Opera Building, as the sun sets.

$57.50

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Chicago: Moonlight Paddle Tour on the Chicago River

11 Reviews

ExperiencesWater activitiesToursGuided toursOutdoor activitiesOutdoor sportsNature & adventureActivities for couplesPrivate toursWater sportsCruises & boat toursSightseeing

Paddle along the Chicago River at night and see the city’s skyline illuminated by the moonlight. Enjoy a serene and less-trafficked route through downtown Chicago.

$57.50

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Private Chicago Boat Rental - Explore Chicago's Skyline

ExperiencesWheelchair accessibleActivities for couplesLuxury experiencesToursWater activitiesFamily-friendly activitiesOutdoor activitiesPrivate toursWater sportsCruises & boat toursSightseeingArchitectureViewing points

We create unforgettable boating experiences, from river cruises to fireworks displays, showcasing Chicago’s skyline. Enjoy the lake and city with a charter designed for adventure and relaxation.

$2,750.00

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City Cruises Chicago: 75-min Speedboat Architecture Cruise

268 Reviews

ExperiencesOutdoor activitiesToursGuided toursWheelchair accessibleWater activitiesLandmarks & monumentsWater sportsArchitectureViewing pointsCruises & boat toursSightseeing

Enjoy Chicago's iconic skyline with an exciting speedboat tour departing from Navy Pier. View Chicago's unique architecture and famous landmarks from the water as you listen to the live narration.

$44.03

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Chicago Premium Driving Tour with River Boat Cruise

20 Reviews

ExperiencesCulture & historyLandmarks & monumentsToursDay Trips FromSightseeing on wheelsWater activitiesWheelchair accessibleOutdoor activitiesDay tripsGuided toursFamily-friendly activitiesWater sportsPrivate toursViewing pointsSightseeingCruises & boat toursDriving experiencesArchitecture

See the best of Chicago in just 1 day on this guided small group sightseeing tour. Visit iconic landmarks including Architecture River Cruise, Cloud Gate "the Bean", and Adler view point.

$254.00

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Chicago: Characters and Cons Guided Kayak Tour

ExperiencesOutdoor sportsToursOutdoor activitiesWater activitiesNature & adventureGuided toursCulture & historyLiterary activitiesWater sportsEducational activitiesCruises & boat tours

Embark on a kayak journey through Chicago, uncovering the story of Leo Koretz, a 1920s con man. Learn about the Leopold and Loeb murder case and enjoy a unique way to experience the city.

$62.68

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Chicago: 2-Hour Kayak Rental from North Rockwell

ExperiencesOutdoor sportsOutdoor activitiesWater activitiesNature & adventureWater sportsHidden gems

Paddle through Chicago's urban forest along the revitalized river. Enjoy a peaceful escape surrounded by nature's beauty.

$51.78

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Chicago: History and Architecture Guided Kayak Tour

3 Reviews

ExperiencesGuided toursDay tripsDay Trips FromLandmarks & monumentsOutdoor activitiesOutdoor sportsToursCulture & historyWater activitiesWater sportsArchitectureSightseeingEducational activities

Paddle through downtown Chicago on a guided kayak tour of the Chicago River. Learn about the city's history, pass under ironwork bridges, and enjoy views of the skyline.

$64.31

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Chicago: 2-Hour Downtown Kayak Rental

19 Reviews

ExperiencesWater activitiesOutdoor sportsNature & adventureOutdoor activitiesWater sports

Experience the thrill of kayaking on the Chicago River. Learn paddling techniques, choose between single or tandem kayaks, and explore the city's stunning architecture.

$62.68

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