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)
12 Feb - 26 Apr
From $102.41
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
01 Mar - 26 Apr
$59.00
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
12 Feb - 28 Apr
$131.20
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
16 May
From $849.00

Chicago Highlights: Experiences to Remember

Germania Place
Titanic: A Voyage Through Time
New!
09 Apr - 31 May
From $20.99 $17.84
Edlis Neeson Theater - MCA
The Jury Experience – Death by AI: Will Chicago Make Justice?
4.7
(88)
13 Feb - 14 Jun
From $45.50
The Den Theatre
The Jazz Room: A Tribute to Frank Sinatra & Louis Armstrong
05 Apr - 31 Jul
From $43.50
Experience 868
AirOtic Soirée Presents: LoveStruck (Chicago)
4.8
(17)
12 - 28 Feb
From $62.00
Clara Cocktail Bar
Luminous Party Run: Meet New People in a Neon Night Run
10 - 11 Apr
From $37.00
Kings Dining & Entertainment
2026 Chicago Winter Tequila Tasting Festival (February 14) FU
14 Feb
$20.00
Edlis Neeson Theater - MCA
The Jury Experience: Medical Disaster - Cut Open, Left Broken: Will Chicago Deliver Justice?
29 Mar - 05 Apr
From $46.00
Woodfield Mall
Wondra: Immerse yourself in the magic of nature
12 - 28 Feb
Miami
Cirque du Soleil 2026: LUZIA in Miami
20 Feb - 25 Apr
From $60.95
The Art Institute of Chicago
The Art Institute of Chicago: Fast Pass
4.9
(37)
12 Feb - 11 May
$40.00

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

Titanic: A Voyage Through Time

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

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

AirOtic Soirée Presents: LoveStruck (Chicago)

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

2026 Chicago Winter Tequila Tasting Festival (February 14) FU

The Jury Experience: Medical Disaster - Cut Open, Left Broken: Will Chicago Deliver Justice?

Wondra: Immerse yourself in the magic of nature

Cirque du Soleil 2026: LUZIA in Miami

The Art Institute of Chicago: Fast Pass