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)
23 May - 04 Jul
From $37.45
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
11 May - 25 Jul
From $96.77
550 E Grand Ave
Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach
4.5
(2)
11 May - 24 Jul
From $50.00
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
11 May - 25 Jul
From $60.00
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
19 May - 19 Jul
From $849.00
iFLY - Chicago Lincoln Park
Lincoln Park Indoor Skydiving: 2 Flights & Certificate
4.9
(15)
11 May - 25 Jul
From $102.41

Chicago Highlights: Experiences to Remember

Bolingbrook Golf Club
LIV Golf Chicago 2025 - General Admission
08 - 10 Aug
From $33.15
Chopin Theatre
The Jury Experience: An Immersive Courtroom Case
4.2
(55)
17 May - 08 Jun
From $41.00
The Lounge At The Lion
Drunk Shakespeare Chicago!
4.8
(785)
11 May - 31 Oct
From $29.00
The First Round: Meet New People Every Week
15 May - 26 Jun
From $21.00
Metropolitan Club of Chicago
Sensory Feast: A Magical Dining Experience
16 May - 28 Jun
From $125.00
Aire Rooftop
ABBA Under The Stars at AIRE
4.5
(73)
15 Jun - 24 Aug
From $40.00
A Nightmare on Strip Street: A Burlesque Parody - Chicago
Morgan MFG
Dayshift Party
24 May
From $22.00
The Newport Theater
The Newport Peekeasy: Burlesque and Variety Show
4.6
(12)
17 May - 27 Jun
From $20.00
Wonderverse
Sunday Funday Family Brunch
4.2
(72)
11 - 25 May
From $0.00

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

LIV Golf Chicago 2025 - General Admission

The Jury Experience: An Immersive Courtroom Case

Drunk Shakespeare Chicago!

The First Round: Meet New People Every Week

Sensory Feast: A Magical Dining Experience

ABBA Under The Stars at AIRE

A Nightmare on Strip Street: A Burlesque Parody - Chicago

Dayshift Party

The Newport Peekeasy: Burlesque and Variety Show

Sunday Funday Family Brunch