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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540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
01 Mar
$59.00
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
20 Dec - 18 Feb
From $849.00
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
19 Dec - 24 Feb
$96.77
iFLY - Chicago Lincoln Park
Lincoln Park Indoor Skydiving: 2 Flights & Certificate
4.9
(15)
19 Dec - 01 Jan
$102.41

Chicago Highlights: Experiences to Remember

Waukegan
Edgar Allan Poe Speakeasy: Chapter Two - Waukegan
02 - 03 Jan
From $55.00
Athenaeum Center for Thought & Culture
Ballet of Lights: Sleeping Beauty in a Sparkling Show
23 Jan - 19 Apr
From $40.00
The Lounge At The Lion
Drunk Shakespeare Chicago!
4.8
(798)
19 Dec - 04 Jan
From $29.00
Santa's Secret Tent at Pioneer Court
Santa's Secret Immersive Holiday Experience
4.5
(78)
19 - 31 Dec
From $70.85
Philadelphia
Cirque du Soleil 2026: LUZIA in Oaks
08 May - 07 Jun
From $25.00
Pioneer Court
Passport to Santa
20 - 28 Dec
From $39.00
Chicago Botanic Garden
Lightscape at Chicago Botanic Garden
4.5
(46)
19 Dec - 04 Jan
From $16.00
Woodfield Mall
Wondra: Immerse yourself in the magic of nature
19 Dec - 28 Feb
The Art Institute of Chicago
The Art Institute of Chicago: Fast Pass
4.9
(36)
19 Dec - 28 Feb
$40.00
Dave & Buster's Vernon Hills
New Years Eve at Dave & Buster's - Vernon Hills
31 Dec
From $33.79

Bike Tour of Chicago's Lakefront Neighborhoods

Private 45-Minute Chicago Skyline Helicopter Tour

Rosemont Indoor Skydiving: 2 Flights & Certificate

Lincoln Park Indoor Skydiving: 2 Flights & Certificate

Chicago Highlights: Experiences to Remember

Edgar Allan Poe Speakeasy: Chapter Two - Waukegan

Ballet of Lights: Sleeping Beauty in a Sparkling Show

Drunk Shakespeare Chicago!

Santa's Secret Immersive Holiday Experience

Cirque du Soleil 2026: LUZIA in Oaks

Passport to Santa

Lightscape at Chicago Botanic Garden

Wondra: Immerse yourself in the magic of nature

The Art Institute of Chicago: Fast Pass

New Years Eve at Dave & Buster's - Vernon Hills