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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4 experiences

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540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
01 Mar - 26 Apr
$59.00
iFLY - Chicago Lincoln Park
Lincoln Park Indoor Skydiving: 2 Flights & Certificate
4.9
(15)
19 Feb - 03 May
From $102.41
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
19 Feb - 03 May
$131.20
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
21 Feb - 16 May
$849.00

Chicago Highlights: Experiences to Remember

Athenaeum Center for Thought & Culture
Ballet of Lights: Sleeping Beauty in a Sparkling Show
19 Apr - 19 Dec
From $40.00
455 N Cityfront Plaza Dr
Premier Dinner Cruise on the Chicago River
4.5
(18)
21 Feb - 19 Apr
$0.00
The Lounge At The Lion
Drunk Shakespeare Chicago!
4.8
(803)
23 Feb - 12 Sep
From $29.00
Warwick Allerton - Chicago
Tea Time at the Tip Top Tap
4.6
(10)
01 Mar - 26 Apr
$75.00 $60.00
Edlis Neeson Theater - MCA
The Jury Experience – Death by AI: Will Chicago Make Justice?
4.6
(116)
08 Mar - 14 Jun
From $45.50
Experience 868
AirOtic Soirée Presents: LoveStruck (Chicago)
4.8
(55)
19 - 28 Feb
From $65.00
The Den Theatre
The Jazz Room: A Journey to the Heart of New Orleans
4.8
(112)
19 Feb - 07 Jun
From $32.50
Woodfield Mall
Wondra: Immerse yourself in the magic of nature
19 Feb - 30 Apr
Germania Place
Titanic: A Voyage Through Time
09 Apr - 31 May
From $20.99 $17.84
Philadelphia
Cirque du Soleil 2026: LUZIA in Oaks
07 May - 07 Jun
From $44.00

Experiences in Chicago

Bike Tour of Chicago's Lakefront Neighborhoods

Lincoln Park Indoor Skydiving: 2 Flights & Certificate

Rosemont Indoor Skydiving: 2 Flights & Certificate

Private 45-Minute Chicago Skyline Helicopter Tour

Chicago Highlights: Experiences to Remember

Ballet of Lights: Sleeping Beauty in a Sparkling Show

Premier Dinner Cruise on the Chicago River

Drunk Shakespeare Chicago!

Tea Time at the Tip Top Tap

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

AirOtic Soirée Presents: LoveStruck (Chicago)

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

Wondra: Immerse yourself in the magic of nature

Titanic: A Voyage Through Time

Cirque du Soleil 2026: LUZIA in Oaks