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 - 21 Apr
$59.00
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
07 Feb - 23 Apr
$131.20
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
09 Feb - 16 May
From $424.50

Chicago Highlights: Experiences to Remember

Miami
Cirque du Soleil 2026: LUZIA in Miami
20 Feb - 25 Apr
From $60.95
Athenaeum Center for Thought & Culture
Ballet of Lights: Sleeping Beauty in a Sparkling Show
19 Apr
From $53.00
The Lounge At The Lion
Drunk Shakespeare Chicago!
4.8
(801)
08 Feb - 12 Sep
From $29.00
The Den Theatre
The Jazz Room: A Journey to the Heart of New Orleans
4.8
(112)
19 Feb - 07 Jun
From $33.00
Germania Place
Titanic: A Voyage Through Time - Waitlist
New!
Edlis Neeson Theater - MCA
The Jury Experience – Death by AI: Will Chicago Make Justice?
4.7
(88)
08 Mar - 14 Jun
From $46.00
455 N Cityfront Plaza Dr
Premier Dinner Cruise on the Chicago River
4.5
(18)
18 Feb - 04 Apr
$0.00
Clara Cocktail Bar
Luminous Party Run: Meet New People in a Neon Night Run
10 - 11 Apr
$37.00
Edlis Neeson Theater - MCA
The Jury Experience – Death on the Port Side: Will Chicago Deliver Justice?
4.4
(47)
07 Mar - 10 Jul
From $46.00
Morgan MFG
Bingo Loco: The Ultimate Bingo Party
4.3
(517)
13 Feb - 03 Apr
$35.00

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

Cirque du Soleil 2026: LUZIA in Miami

Ballet of Lights: Sleeping Beauty in a Sparkling Show

Drunk Shakespeare Chicago!

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

Titanic: A Voyage Through Time - Waitlist

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

Premier Dinner Cruise on the Chicago River

Luminous Party Run: Meet New People in a Neon Night Run

The Jury Experience – Death on the Port Side: Will Chicago Deliver Justice?

Bingo Loco: The Ultimate Bingo Party