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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6 experiences

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Navy Pier
Chicago Seadog: Extreme Thrill Ride
5.0
(1)
28 May - 18 Jul
From $37.45
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
29 May - 10 Aug
From $96.77
550 E Grand Ave
Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach
4.7
(3)
28 May - 10 Aug
From $50.00
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
28 May - 11 Aug
From $60.00
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
29 May - 09 Aug
From $849.00
iFLY - Chicago Lincoln Park
Lincoln Park Indoor Skydiving: 2 Flights & Certificate
4.9
(15)
29 May - 10 Aug
From $102.41

Chicago Highlights: Experiences to Remember

Aire Rooftop
Sinatra Under The Stars at AIRE
4.6
(438)
08 Jun - 27 Jul
From $40.00
About Last Knife
Dining in the Dark: A Unique Blindfolded Experience at About Last Knife
4.2
(343)
07 Jun - 06 Dec
From $67.00
The Lounge At The Lion
Drunk Shakespeare Chicago!
4.8
(788)
28 May - 31 Oct
From $29.00
Arts Center of Oak Park
We call it Flamenco: A Unique Spanish Dance Show
4.5
(123)
25 Jul - 27 Sep
From $39.00
The First Round: Meet New People Every Week
4.0
(43)
12 - 26 Jun
From $21.00
Morgan MFG
Bingo Loco: The Ultimate Bingo Party
4.3
(267)
06 Jun - 25 Jul
From $35.00
Wonderverse
Jumanji VR: Reverse the Curse
4.3
(142)
28 May - 31 Oct
From $29.00
Everything Bar
Wizards and Wands Experience: Magical Mixology - Chicago
14 Aug - 21 Sep
From $26.00
Wonderverse
Uncharted: Escape Room Trilogy
4.2
(60)
28 May - 01 Dec
From $25.00
Bolingbrook Golf Club
LIV Golf Chicago 2025 - Hospitality
08 - 10 Aug
From $198.55

Chicago Seadog: Extreme Thrill Ride

Rosemont Indoor Skydiving: 2 Flights & Certificate

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

Bike Tour of Chicago's Lakefront Neighborhoods

Private 45-Minute Chicago Skyline Helicopter Tour

Lincoln Park Indoor Skydiving: 2 Flights & Certificate

Chicago Highlights: Experiences to Remember

Sinatra Under The Stars at AIRE

Dining in the Dark: A Unique Blindfolded Experience at About Last Knife

Drunk Shakespeare Chicago!

We call it Flamenco: A Unique Spanish Dance Show

The First Round: Meet New People Every Week

Bingo Loco: The Ultimate Bingo Party

Jumanji VR: Reverse the Curse

Wizards and Wands Experience: Magical Mixology - Chicago

Uncharted: Escape Room Trilogy

LIV Golf Chicago 2025 - Hospitality