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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5 experiences

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Bobby's Bike Hike - Chicago Bike, Walking & Food Tours
Chicago: Guided Bike Tour
01 Sep - 07 Nov
$55.00
Multiple locations
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
01 Sep - 15 Nov
$125.95
300 E Monroe St
Chicago Lakefront and Museum Campus Small-Group Segway Tour
02 Sep - 31 Oct
$70.00
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
01 Sep - 07 Nov
$59.00
550 E Grand Ave
Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach
4.8
(5)
02 Sep - 12 Oct
$40.00

Chicago Highlights: Experiences to Remember

Rosemont
Minecraft Experience: Villager Rescue
4.5
(2407)
02 Sep - 10 Oct
From $28.00
Stan Mansion
Murder on the Rocks: A Murder Mystery Cocktail Experience
25 Sep
$79.00
The Den Theatre
The Jazz Room: A Journey to the Heart of New Orleans
4.8
(224)
06 Sep - 16 Jan
Up to 20% Off
From $36.50 $29.20
Chop Shop
An Idiot’s Guide to Wine
4.1
(12)
20 Nov
$80.00
Athenaeum Center for Thought & Culture
Ballet of Lights: Sleeping Beauty in a Sparkling Show
4.1
(121)
17 Oct - 13 Feb
From $36.00
Laugh Factory Chicago
Chicago's Best Stand Up at Laugh Factory Chicago
4.3
(216)
01 Sep - 30 Dec
$30.00
Woodfield Mall
Wondra: Immerse yourself in the magic of nature
02 - 30 Sep
Athenaeum Center for Thought & Culture
Superminds Academy by Mindsee: The family challenge that trains focus through games kids love
24 Oct - 08 Nov
$30.00
Hammond Civic Center
AMMA: Armored Cage Fighting 2026 - Chicago-Land
26 Sep
From $40.00
Fever Hub Chicago | Immersive & Gaming Experience Center
Titanic: A Voyage Through Time
4.8
(130)
03 - 20 Sep
From $20.99

Chicago: Guided Bike Tour

Rosemont Indoor Skydiving: 2 Flights & Certificate

Chicago Lakefront and Museum Campus Small-Group Segway Tour

Bike Tour of Chicago's Lakefront Neighborhoods

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Chicago Highlights: Experiences to Remember

Minecraft Experience: Villager Rescue

Murder on the Rocks: A Murder Mystery Cocktail Experience

The Jazz Room: A Journey to the Heart of New Orleans

An Idiot’s Guide to Wine

Ballet of Lights: Sleeping Beauty in a Sparkling Show

Chicago's Best Stand Up at Laugh Factory Chicago

Wondra: Immerse yourself in the magic of nature

Superminds Academy by Mindsee: The family challenge that trains focus through games kids love

AMMA: Armored Cage Fighting 2026 - Chicago-Land

Titanic: A Voyage Through Time