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 - 17 Mar
$59.00
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
05 Jan - 16 May
From $849.00
iFLY - Chicago Lincoln Park
Lincoln Park Indoor Skydiving: 2 Flights & Certificate
4.9
(15)
04 - 17 Jan
$102.41
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
04 Jan - 17 Mar
$96.77

Chicago Highlights: Experiences to Remember

The Den Theatre
The Jazz Room: Tribute to Soul
4.6
(73)
10 Jan
$33.00
The Den Theatre
The Jazz Room: A Journey to the Heart of New Orleans
4.8
(101)
19 Feb - 07 Jun
From $33.00
Athenaeum Center for Thought & Culture
Ballet of Lights: Sleeping Beauty in a Sparkling Show
23 Jan - 19 Apr
From $40.00
Edlis Neeson Theater - MCA
The Jury Experience: Death on the Port Side
4.5
(20)
03 May
From $55.50
Morgan MFG
Bingo Loco: The Ultimate Bingo Party
4.3
(506)
16 Jan - 20 Mar
$35.00
Warwick Allerton - Chicago
Tea Time at the Tip Top Tap
18 Jan - 29 Mar
$75.00 $37.50
The Art Institute of Chicago
The Art Institute of Chicago: Fast Pass
4.9
(37)
04 Jan - 28 Feb
$40.00
Woodfield Mall
Wondra: Immerse yourself in the magic of nature
04 Jan - 28 Feb
Miami
Cirque du Soleil 2026: LUZIA in Miami
19 Feb - 25 Apr
From $48.00
Philadelphia
Cirque du Soleil 2026: LUZIA in Oaks
07 May - 07 Jun
From $25.00

Bike Tour of Chicago's Lakefront Neighborhoods

Private 45-Minute Chicago Skyline Helicopter Tour

Lincoln Park Indoor Skydiving: 2 Flights & Certificate

Rosemont Indoor Skydiving: 2 Flights & Certificate

Chicago Highlights: Experiences to Remember

The Jazz Room: Tribute to Soul

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

Ballet of Lights: Sleeping Beauty in a Sparkling Show

The Jury Experience: Death on the Port Side

Bingo Loco: The Ultimate Bingo Party

Tea Time at the Tip Top Tap

The Art Institute of Chicago: Fast Pass

Wondra: Immerse yourself in the magic of nature

Cirque du Soleil 2026: LUZIA in Miami

Cirque du Soleil 2026: LUZIA in Oaks