Sport & Adventure in Chicago

Get your adrenaline pumping with thrilling sports and adventure activities in Chicago. Whether you're into hiking, rock climbing, or extreme sports, we've got you covered.

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Bobby's Bike Hike - Chicago Bike, Walking & Food Tours
Chicago: Guided Bike Tour
26 Oct - 07 Nov
$55.00
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
26 Oct - 22 Apr
$59.00
300 E Monroe St
Chicago Lakefront and Museum Campus Small-Group Segway Tour
26 - 31 Oct
$70.00
Multiple locations
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
25 Oct - 22 Apr
From $125.95

Chicago Highlights: Experiences to Remember