Trips & Adventurous Activities in Chicago

Check out happening trips & adventurous activities events all around Chicago, IL

2026 Lollapalooza - 4 Day Pass at Hutchinson Field at Grant Park

 Thu, 30 Jul at 10:59 am Hutchinson Field at Grant Park

Morgan Wallen at Soldier Field

 Fri, 19 Jun at 05:30 pm Soldier Field

US Mens National Soccer vs Germany National Soccer at Soldier Field

 Sat, 06 Jun at 01:30 pm Soldier Field

Lionel Richie & Earth Wind and Fire

 Thu, 25 Jun United Center

Ed Sheeran

 Fri, 26 Jun Soldier Field

2026 Lollapalooza - Friday at Hutchinson Field at Grant Park

 Fri, 31 Jul at 12:00 pm Hutchinson Field at Grant Park

Ariana Grande

 Sun, 02 Aug at 06:00 pm United Center

John Mulaney at Wrigley Field

 Sat, 11 Jul at 08:00 pm Wrigley Field

Morgan Wallen Brooks & Dunn Gavin Adcock & Zach John King

 Thu, 18 Jun at 06:00 pm Soldier Field

Milwaukee Brewers at Chicago Cubs at Wrigley Field

 Mon, 18 May at 06:40 pm Wrigley Field

Foo Fighters with Queens of the Stone Age and Mannequin Pussy

 Sat, 08 Aug at 10:30 pm Soldier Field

BTS at Soldier Field

 Thu, 27 Aug at 08:00 pm Soldier Field

Olivia Rodrigo at United Center

 Sun, 11 Oct at 07:00 pm United Center

TBD at Chicago Bulls - Eastern Conference Finals (Home Game 3)

 Thu, 28 May United Center

Martin Garrix

 Wed, 24 Jun at 06:00 pm Huntington Bank Pavilion at Northerly Island

J Cole at United Center

 Tue, 11 Aug at 08:00 pm United Center

Ed Sheeran Myles Smith & Ellie Banke

 Fri, 26 Jun at 06:00 pm Soldier Field

International Friendly: United States vs. Germany

 Fri, 05 Jun at 06:00 pm Soldier Field

Karol G at Soldier Field

 Fri, 24 Jul at 07:00 pm Soldier Field

Doja Cat

 Fri, 02 Oct at 06:00 pm United Center

Noah Kahan with Gigi Perez

 Tue, 14 Jul at 11:30 pm Wrigley Field

ASAP Rocky

 Tue, 26 May United Center

Lollapalooza - 4 Day Pass - with Charli XCX, Tate McRae, Lorde and more

 Thu, 30 Jul Grant Park - Chicago

Chicago White Sox at Chicago Cubs at Wrigley Field

 Mon, 17 Aug at 07:05 pm Wrigley Field

Foo Fighters at Soldier Field

 Sat, 08 Aug at 05:30 pm Soldier Field

Chicago Symphony Orchestra - Hilary Hahn at Chicago Symphony Center

 Sun, 24 May Chicago Symphony Center

2026 Lollapalooza - Thursday at Hutchinson Field at Grant Park

 Thu, 30 Jul Hutchinson Field at Grant Park

Chicago Cubs vs. Los Angeles Dodgers

 Sun, 02 Aug at 06:00 pm Wrigley Field USD 27 to 7,560

Usher and Chris Brown

 Sat, 22 Aug at 12:00 am Soldier Field

ASAP Rocky at United Center

 Wed, 27 May at 07:30 pm United Center

Parking New York Yankees at Chicago Cubs

 Sat, 01 Aug Wrigley Field

Parking Germany at U.S. Mens National Soccer Team

 Sat, 06 Jun at 06:30 pm Soldier Field

Martin Garrix at Huntington Bank Pavilion at Northerly Island

 Thu, 25 Jun Huntington Bank Pavilion at Northerly Island

Noah Kahan at Wrigley Field

 Tue, 14 Jul at 06:30 pm Wrigley Field

Lil Wayne at Huntington Bank Pavilion at Northerly Island

 Fri, 17 Jul at 07:00 pm Huntington Bank Pavilion at Northerly Island

Chicago Cubs vs. San Francisco Giants

 Thu, 04 Jun at 06:00 pm Wrigley Field USD 40 to 5,250

John Mulaney

 Fri, 10 Jul at 06:00 pm Wrigley Field

2026 Chicago Bears Season Tickets at Soldier Field

 Sat, 01 Aug Soldier Field

Gorillaz at United Center

 Thu, 08 Oct at 07:30 pm United Center

Mumford and Sons Caamp & Dylan Gossett

 Wed, 10 Jun at 06:00 pm Wrigley Field

A$AP Rocky

 Thu, 28 May at 12:30 am United Center

Martin Garrix

 Thu, 25 Jun at 11:30 pm Huntington Bank Pavilion at Northerly Island

Mumford and Sons at Wrigley Field

 Thu, 11 Jun at 06:30 pm Wrigley Field

2026 Lollapalooza - Sunday at Hutchinson Field at Grant Park

 Sun, 02 Aug at 12:00 pm Hutchinson Field at Grant Park

Liverpool FC vs. Leeds United

 Sat, 01 Aug at 06:00 pm Soldier Field

Chicago Bears vs. Philadelphia Eagles (Date: TBD)

 Sun, 26 Jul at 06:00 pm Soldier Field

Matt Rife

 Sat, 24 Oct at 06:00 pm United Center

The R&B Lovers Tour: Keith Sweat Joe Dru Hill & Ginuwine

 Thu, 18 Jun at 06:00 pm Credit Union 1 Arena

2026 Beyond Wonderland Chicago - 2 Day Pass at Huntington Bank Pavilion at Northerly Island

 Sat, 06 Jun at 11:59 pm Huntington Bank Pavilion at Northerly Island

2026 Riot Fest - 3 Day Pass at Douglass Park

 Fri, 18 Sep at 10:59 am Douglass Park

Bob Dylan

 Tue, 07 Jul at 06:00 pm Huntington Bank Pavilion at Northerly Island

Windy City Smokeout Festival: Blake Shelton Warren Zeiders & George Birge - Sunday

 Sat, 11 Jul at 06:00 pm Windy City Smokeout

TBD at Chicago Bulls - Eastern Conference Finals (Home Game 2)

 Sun, 24 May United Center

Chicago Cubs vs. Minnesota Twins

 Thu, 16 Jul at 06:00 pm Wrigley Field USD 36 to 5,250

Chicago Cubs vs. Detroit Tigers

 Sun, 19 Jul at 06:00 pm Wrigley Field USD 26 to 123

Claypool Gold: Primus Les Claypool's Frog Brigade & The Claypool Lennon Delirium

 Tue, 02 Jun at 06:00 pm The Salt Shed Outdoors - Chicago

Joji with Nate Sib and Corbin

 Tue, 23 Jun at 11:30 pm United Center

Karol G Chicago Tickets

 Fri, 24 Jul at 07:00 pm Soldier Field EUR 120

J. Cole Chicago Tickets

 Tue, 11 Aug at 08:00 pm United Center EUR 76

Joji at United Center

 Tue, 23 Jun at 06:30 pm United Center

Chicago Cubs vs. San Diego Padres

 Sun, 28 Jun at 06:00 pm Wrigley Field USD 13 to 5,250

Chicago Cubs vs. Colorado Rockies

 Sun, 14 Jun at 06:00 pm Wrigley Field USD 10 to 7,560

Lionel Richie with Earth, Wind & Fire

 Sat, 27 Jun at 12:30 am United Center

TBD at Chicago Bulls - NBA Finals (Home Game 1)

 Fri, 05 Jun United Center

Houston Astros at Chicago Cubs

 Fri, 22 May Wrigley Field

Eric Clapton at United Center

 Fri, 11 Sep at 07:30 pm United Center

Solomun at Union Park

 Fri, 22 May at 04:00 pm Union Park

Hot Wheels Monster Trucks Live Glow-N-Fire at United Center

 Sat, 01 Aug at 11:30 am United Center

Jack White

 Fri, 24 Jul The Salt Shed - Outdoors

2026 Riot Fest - Friday at Douglass Park

 Fri, 18 Sep at 11:59 pm Douglass Park

Parking San Francisco Giants at Chicago Cubs

 Fri, 05 Jun at 08:30 am Wrigley Field

Windy City Smokeout Festival: Lainey Wilson Hudson Westbrook & Vincent Mason - Friday

 Thu, 09 Jul at 06:00 pm Windy City Smokeout

2026 Windy City Smokeout - 4 Day Pass at United Center

 Thu, 09 Jul at 10:59 am United Center

Chris Lake at East End Plaza at Navy Pier

 Fri, 10 Jul at 04:00 pm East End Plaza at Navy Pier

Jill Scott at Chicago Theatre

 Thu, 20 Aug at 07:30 pm Chicago Theatre

Bob Dylan with Lucinda Williams

 Thu, 09 Jul at 12:00 am Huntington Bank Pavilion at Northerly Island

Parking Morgan Wallen with Brooks & Dunn, Gavin Adcock, Zach John King

 Fri, 19 Jun at 10:30 pm Soldier Field

Zayn

 Sun, 26 Jul at 06:00 pm United Center

BTS

 Wed, 26 Aug Soldier Field

Robyn at United Center

 Sat, 12 Sep at 07:30 pm United Center

Gorillaz

 Wed, 07 Oct at 06:00 pm United Center

Les Miserables

 Tue, 12 May at 06:00 pm Cadillac Palace

World Naked Bike Ride Chicago 2026 20th Anniversary

 Sat, 11 Jul at 05:00 pm TBD Free

Chicago Sky vs. Las Vegas Aces

 Sat, 27 Jun at 06:00 pm United Center

Parking Pittsburgh Pirates at Chicago Cubs

 Fri, 10 Apr at 08:30 am Wrigley Field

Toronto Blue Jays at Chicago Cubs

 Fri, 19 Jun at 08:30 am Wrigley Field

New Orleans Saints at Chicago Bears

 Mon, 25 May at 08:30 am Soldier Field

Ludovico Einaudi

 Mon, 05 Oct at 01:00 am Chicago Symphony Center

Khalid at Huntington Bank Pavilion at Northerly Island

 Wed, 20 May at 07:30 pm Huntington Bank Pavilion at Northerly Island

The Black Keys at Salt Shed - Outdoor Fairgrounds

 Thu, 16 Jul at 07:30 pm Salt Shed - Outdoor Fairgrounds

Green Bay Packers at Chicago Bears (Date TBD) Tickets

 Tue, 21 Jul at 03:30 am Soldier Field EUR 286

Chicago Cubs vs. Houston Astros

 Thu, 21 May at 06:00 pm Wrigley Field USD 8 to 61

Chicago Cubs vs. Milwaukee Brewers

 Sun, 17 May at 06:00 pm Wrigley Field USD 27 to 5,250

Chicago Symphony Orchestra - Brahms, Strauss & Ravel

 Fri, 29 May at 12:30 am Chicago Symphony Center

Windy City Smokeout Festival: Hootie and The Blowfish Jordan Davis & Lainey Wilson - 4 Day Pass

 Wed, 08 Jul at 06:00 pm Windy City Smokeout

Metric with Broken Social Scene and Stars

 Fri, 24 Jul at 11:30 pm Byline Bank Aragon Ballroom

Ludovico Einaudi at Chicago Symphony Center

 Sun, 04 Oct Chicago Symphony Center

WNBA All-Star Game 2026 Tickets

 Sat, 25 Jul at 03:00 pm United Center EUR 299

Chicago Cubs vs. Atlanta Braves

 Sun, 13 Sep at 06:00 pm Wrigley Field USD 22 to 103

Miami Marlins at Chicago Cubs at Wrigley Field

 Tue, 22 Sep at 06:40 pm Wrigley Field