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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iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
01 Nov - 13 Jan
From $96.77
iFLY - Chicago Lincoln Park
Lincoln Park Indoor Skydiving: 2 Flights & Certificate
4.9
(15)
01 Nov - 28 Dec
From $102.41
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
02 Nov
From $59.00
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
03 Nov - 03 Jan
From $849.00

Chicago Highlights: Experiences to Remember

Philadelphia
Cirque du Soleil 2026: LUZIA in Oaks - Waitlist
Edlis Neeson Theater - MCA
The Jury Experience: Death by AI: Who Pays the Price?
4.5
(20)
05 Dec - 14 Jun
From $46.00
About Last Knife
Dining in the Dark: A Unique Blindfolded Experience at About Last Knife
4.2
(363)
06 Dec
From $67.00
The Den Theatre
The Jazz Room: Tribute to Soul
4.5
(39)
16 Nov - 10 Jan
From $24.00
YMCA Camp Duncan
Harry Potter™: A Forbidden Forest Experience
4.6
(1624)
01 - 30 Nov
From $38.00
Headquarters Beercade
Trick or Drink Chicago Halloween Bar Crawl (3 Days)
01 Nov
From $30.00
Woodfield Mall
Wondra: Immerse yourself in the magic of nature
01 - 30 Nov
Recess
Bingo Loco: The Ultimate Bingo Party
07 Nov
From $35.00
Santa's Secret Tent at Pioneer Court
Santa's Secret Immersive Holiday Experience
28 Nov - 31 Dec
From $45.00
Pioneer Court
Passport to Santa
New!
29 Nov - 31 Dec
From $35.00

Rosemont Indoor Skydiving: 2 Flights & Certificate

Lincoln Park Indoor Skydiving: 2 Flights & Certificate

Bike Tour of Chicago's Lakefront Neighborhoods

Private 45-Minute Chicago Skyline Helicopter Tour

Chicago Highlights: Experiences to Remember

Cirque du Soleil 2026: LUZIA in Oaks - Waitlist

The Jury Experience: Death by AI: Who Pays the Price?

Dining in the Dark: A Unique Blindfolded Experience at About Last Knife

The Jazz Room: Tribute to Soul

Harry Potter™: A Forbidden Forest Experience

Trick or Drink Chicago Halloween Bar Crawl (3 Days)

Wondra: Immerse yourself in the magic of nature

Bingo Loco: The Ultimate Bingo Party

Santa's Secret Immersive Holiday Experience

Passport to Santa