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)
11 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)
11 Feb - 26 Apr
$131.20
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
12 Feb - 16 May
$849.00

Chicago Highlights: Experiences to Remember

Germania Place
Titanic: A Voyage Through Time
New!
09 Apr - 31 May
From $20.99 $17.84
Athenaeum Center for Thought & Culture
Ballet of Lights: Sleeping Beauty in a Sparkling Show
19 Apr
From $53.00
455 N Cityfront Plaza Dr
Premier Dinner Cruise on the Chicago River
4.5
(18)
18 Feb - 04 Apr
$0.00
The Lounge At The Lion
Drunk Shakespeare Chicago!
4.8
(801)
12 Feb - 12 Sep
From $29.00
Edlis Neeson Theater - MCA
The Jury Experience – Death by AI: Will Chicago Make Justice?
4.7
(88)
08 Mar - 14 Jun
From $45.50
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
From $20.00
Woodfield Mall
Wondra: Immerse yourself in the magic of nature
11 - 28 Feb
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

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

Ballet of Lights: Sleeping Beauty in a Sparkling Show

Premier Dinner Cruise on the Chicago River

Drunk Shakespeare Chicago!

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

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

2026 Chicago Winter Tequila Tasting Festival (February 14) FU

Wondra: Immerse yourself in the magic of nature

Cirque du Soleil 2026: LUZIA in Miami

Cirque du Soleil 2026: LUZIA in Oaks