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)
28 Jan - 12 Apr
From $102.41
540 N Lakeshore Dr Condo
Bike Tour of Chicago's Lakefront Neighborhoods
5.0
(1)
01 Mar - 09 Apr
$59.00
iFLY Indoor Skydiving
Rosemont Indoor Skydiving: 2 Flights & Certificate
4.8
(9)
28 Jan - 12 Apr
$96.77
Schaumburg Regional Airport
Private 45-Minute Chicago Skyline Helicopter Tour
30 Jan - 16 May
From $424.50

Chicago Highlights: Experiences to Remember

Athenaeum Center for Thought & Culture
Ballet of Lights: Sleeping Beauty in a Sparkling Show
19 Apr
From $43.50
Experience 868
AirOtic Soirée Presents: LoveStruck (Chicago)
05 - 28 Feb
From $47.50
Warwick Allerton - Chicago
Tea Time at the Tip Top Tap
4.5
(8)
01 Feb - 26 Apr
$75.00 $60.00
455 N Cityfront Plaza Dr
Premier Dinner Cruise on the Chicago River
4.5
(18)
18 Feb - 22 Mar
$0.00
Above Average Candle Studio
90's R&B Sing-A-Long + Mini Candle Making
5.0
(2)
01 Feb - 20 Sep
From $45.00
Clara Cocktail Bar
Luminous Party Run: Meet New People in a Neon Night Run
10 - 11 Apr
$37.00
Morgan MFG
Bingo Loco: The Ultimate Bingo Party
4.3
(515)
13 Feb - 20 Mar
$35.00
The Art Institute of Chicago
The Art Institute of Chicago: Fast Pass
4.9
(37)
28 Jan - 27 Apr
$40.00
Woodfield Mall
Wondra: Immerse yourself in the magic of nature
28 Jan - 28 Feb
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

Ballet of Lights: Sleeping Beauty in a Sparkling Show

AirOtic Soirée Presents: LoveStruck (Chicago)

Tea Time at the Tip Top Tap

Premier Dinner Cruise on the Chicago River

90's R&B Sing-A-Long + Mini Candle Making

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

Bingo Loco: The Ultimate Bingo Party

The Art Institute of Chicago: Fast Pass

Wondra: Immerse yourself in the magic of nature

Cirque du Soleil 2026: LUZIA in Oaks