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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The Staley
Luminous Party Run: Meet New People in a Neon Night Run
15 - 16 May
$37.00
Chicago's Signature Dishes
Chicago Bike Rental
02 Apr - 02 Jun
From $75.94
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
02 Apr - 14 Jun
$59.00
550 E Grand Ave
Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach
4.8
(5)
02 May - 11 Jul
From $50.00
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
02 Apr - 14 Jun
$131.20
iFLY - Chicago Lincoln Park
Lincoln Park Indoor Skydiving: 2 Flights & Certificate
4.9
(15)
02 Apr - 14 Jun
From $102.41

Chicago Highlights: Experiences to Remember

The Den Theatre
The Jazz Room: A Tribute to Frank Sinatra & Louis Armstrong
05 Apr - 31 Jul
From $44.00
Athenaeum Center for Thought & Culture
Ballet of Lights: Sleeping Beauty in a Sparkling Show
17 Oct - 19 Dec
From $40.00
Palmer House a Hilton Hotel
Chicago's Theatre of Magic
New!
09 May
From $59.00
The Lounge At The Lion
Drunk Shakespeare Chicago!
4.8
(804)
02 Apr - 12 Sep
From $29.00
Lincoln Park Grove 2
Lakeshore Music Festival - Waitlist
The Den Theatre
SAW The Musical: The Unauthorized Parody of Saw - Direct from New York (Off-Broadway National Tour) - Live in Chicago
26 Jun - 06 Sep
From $50.49
Germania Place
Titanic: A Voyage Through Time
16 Apr - 31 May
From $20.99
Dave & Buster's Lombard
All Access Madness at Dave & Buster's - Lombard
06 Apr
$29.99
Fever Hub Chicago | Immersive & Gaming Experience Center
Virtual Zone: VR Gaming Point
16 Apr - 28 Jun
From $35.00 $29.75
Philadelphia
Cirque du Soleil 2026: LUZIA in Oaks
07 May - 07 Jun
From $44.00

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

Chicago Bike Rental

Bike Tour of Chicago's Lakefront Neighborhoods

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Rosemont Indoor Skydiving: 2 Flights & Certificate

Lincoln Park Indoor Skydiving: 2 Flights & Certificate

Chicago Highlights: Experiences to Remember

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

Ballet of Lights: Sleeping Beauty in a Sparkling Show

Chicago's Theatre of Magic

Drunk Shakespeare Chicago!

Lakeshore Music Festival - Waitlist

SAW The Musical: The Unauthorized Parody of Saw - Direct from New York (Off-Broadway National Tour) - Live in Chicago

Titanic: A Voyage Through Time

All Access Madness at Dave & Buster's - Lombard

Virtual Zone: VR Gaming Point

Cirque du Soleil 2026: LUZIA in Oaks