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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iFLY - Chicago Lincoln Park
Lincoln Park Indoor Skydiving: 2 Flights & Certificate
4.9
(15)
29 Jan - 12 Apr
From $102.41
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
01 Mar - 14 Apr
$59.00
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
29 Jan - 14 Apr
$96.77
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
30 Jan - 16 May
From $424.50

Chicago Highlights: Experiences to Remember

Edlis Neeson Theater - MCA
The Jury Experience – Death by AI: Will Chicago Make Justice?
4.7
(87)
08 Mar - 14 Jun
From $46.00
The Den Theatre
The Jazz Room: A Journey to the Heart of New Orleans
4.8
(111)
19 Feb - 07 Jun
From $33.00
Warwick Allerton - Chicago
Tea Time at the Tip Top Tap
4.5
(8)
01 Feb - 26 Apr
$75.00 $60.00
The Den Theatre
The Jazz Room: A Tribute to Frank Sinatra & Louis Armstrong
05 Apr - 03 May
From $43.50
Edlis Neeson Theater - MCA
The Jury Experience: Death on the Port Side
4.3
(40)
07 Mar - 10 Jul
From $46.00
455 N Cityfront Plaza Dr
Premier Dinner Cruise on the Chicago River
4.5
(18)
18 Feb - 29 Mar
$0.00
Morgan MFG
Bingo Loco: The Ultimate Bingo Party
4.3
(515)
13 Feb - 20 Mar
$35.00
Edlis Neeson Theater - MCA
The Jury Experience: Medical Disaster - Cut Open, Left Broken
29 Mar - 05 Apr
From $46.00
Miami
Cirque du Soleil 2026: LUZIA in Miami
20 Feb - 25 Apr
From $60.95
Philadelphia
Cirque du Soleil 2026: LUZIA in Oaks
07 May - 07 Jun
From $44.00

Experiences in Chicago

Lincoln Park Indoor Skydiving: 2 Flights & Certificate

Bike Tour of Chicago's Lakefront Neighborhoods

Rosemont Indoor Skydiving: 2 Flights & Certificate

Private 45-Minute Chicago Skyline Helicopter Tour

Chicago Highlights: Experiences to Remember

The Jury Experience – Death by AI: Will Chicago Make Justice?

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

Tea Time at the Tip Top Tap

The Jazz Room: A Tribute to Frank Sinatra & Louis Armstrong

The Jury Experience: Death on the Port Side

Premier Dinner Cruise on the Chicago River

Bingo Loco: The Ultimate Bingo Party

The Jury Experience: Medical Disaster - Cut Open, Left Broken

Cirque du Soleil 2026: LUZIA in Miami

Cirque du Soleil 2026: LUZIA in Oaks