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Wateriders: Chicago Kayak Tours and Rentals

Benefiting Waterkeeper Alliance

"Shady Chicago" Ghosts and Gangsters Kayak Tour

Kayak through the breathtaking urban canyons of the Chicago River as the sun sets into twinkling darkness while learning about the lasting legacy of Chicago's infamous history of gangsters.

Chicago, IL

2.25 hours


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    The Experience

    On the "Shady Chicago" tour, you'll paddle kayaks past the illuminated architectural marvels of nighttime Chicago while stopping to learn about the city’s past.

    Discussed is our early "Wild West"reputation; how one man rose from poverty to become the most powerful man the city has ever seen; how one area of the river purportedly became haunted; why everyone in Chicago feared a man the size of a child; and all about the world-renowned Italian crime lineage including the likes of mobsters Jim Colosimo, Johnny Torrio, and, of course, Al Capone.

    Chicago did not go from a one-horse town to a global center of commerce without a significant push from the city's ruthless criminal underbelly. Much of Chicago's reputation is based on its corrupt legacy - and you'll delve right into the rich history that took place in our great city while taking in one of the most spectacular views of the city.


    • Kayaking tour of Chicago
    • Prior kayaking experience not necessary - we host a beginner's lesson before the tour
    • Bring water bottle and water-friendly clothing and footwear
    • We have plastic baggies for electronics, but suggest dry-bags if you have them
    • Includes life jacket, kayak, paddle, light
    • Located in River North, also very close to the Loop and West Loop
    • Validated discount parking - $4 for up to 4 hours
    • Weight limits: 275 lbs in a single, 435 pounds (combined) in a tandem

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