Trips & Adventurous Activities in Chicago

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

2025 Chicago Winter Whiskey Tasting Festival (January 25) AE

 Sat, 25 Jan, 2025 at 02:30 pm Downtown Chicago USD 0 to 400

2025 Chicago St Patrick’s Day Bar Crawl (Saturday) All Access AE

 Sat, 15 Mar, 2025 at 12:00 pm Lincoln Park, River North, Wicker Park Bars All Access USD 8 to 14

Of The Trees at Salt Shed - Indoor Shed

 Sat, 25 Jan, 2025 at 08:00 pm Salt Shed - Indoor Shed

Pat McGann at Chicago Theatre

 Sat, 25 Jan, 2025 at 07:00 pm Chicago Theatre

Cre8tive Con 2025

 Fri, 21 Feb, 2025 at 05:00 pm InterContinental Chicago Magnificent Mile, an IHG Hotel USD 268

Disco Lines at Salt Shed - Indoor Shed

 Mon, 06 Jan, 2025 Salt Shed - Indoor Shed

Rubblebucket at Thalia Hall

 Fri, 24 Jan, 2025 at 08:00 pm Thalia Hall

Aespa at United Center

 Sat, 15 Feb, 2025 at 08:00 pm United Center

Psychic Fever at Riviera Theatre - IL

 Sat, 08 Feb, 2025 at 07:30 pm Riviera Theatre - IL

SoxFest at Ramova Theatre

 Sat, 25 Jan, 2025 at 05:00 pm Ramova Theatre

Rod Tuffcurls and The Bench Press at Joes on W**d Street

 Sat, 01 Feb, 2025 at 09:00 pm Joes on Weed Street

Yahzarah at City Winery - Chicago

 Sun, 26 Jan, 2025 at 07:00 pm City Winery - Chicago

Pancakes and Booze at Reggies Rock Club

 Sat, 15 Feb, 2025 at 08:00 pm Reggies Rock Club

Snapcase at Bottom Lounge

 Sat, 15 Feb, 2025 at 07:00 pm Bottom Lounge

Zack Fedor at Carols Pub

 Sat, 08 Feb, 2025 at 09:30 pm Carols Pub

Platinum Moon at Subterranean

 Sun, 02 Feb, 2025 at 07:00 pm Subterranean

The Dead Bolts at Thalia Hall

 Sat, 22 Feb, 2025 at 08:00 pm Thalia Hall

Christopher Dammann Sextet at Constellation Chicago

 Fri, 07 Feb, 2025 at 08:30 pm Constellation Chicago

Minnesota Wild at Chicago Blackhawks at United Center

 Sun, 26 Jan, 2025 at 06:00 pm United Center

The Terminator In Concert at Auditorium Theatre Chicago

 Sat, 22 Feb, 2025 at 07:30 pm Auditorium Theatre Chicago

Odd Mob at Concord Music Hall

 Fri, 31 Jan, 2025 at 10:00 pm Concord Music Hall

Tina Friml at Zanies Comedy Club Chicago

 Sat, 01 Mar, 2025 at 07:00 pm Zanies Comedy Club Chicago

Willis at Thalia Hall

 Sat, 08 Mar, 2025 at 08:00 pm Thalia Hall

Megan Stalter at Vic Theatre

 Sat, 08 Mar, 2025 at 07:30 pm Vic Theatre

Sam Grow at Carols Pub

 Thu, 23 Jan, 2025 at 08:00 pm Carols Pub

Post Sex Nachos at Bottom Lounge

 Fri, 28 Feb, 2025 at 08:00 pm Bottom Lounge

TAEMIN at Chicago Theatre

 Sun, 16 Feb, 2025 at 07:30 pm Chicago Theatre

Michael Marcagi at Thalia Hall

 Fri, 28 Feb, 2025 at 08:00 pm Thalia Hall

Porridge Radio at Thalia Hall

 Thu, 30 Jan, 2025 at 08:00 pm Thalia Hall

Cochise at Avondale Music Hall

 Fri, 28 Feb, 2025 at 08:00 pm Avondale Music Hall

SAVE THE DATE: Blues at the Bean 2025

 Fri, 06 Jun, 2025 at 11:00 am Forteza Fitness and Martial Arts

Sullivan King at Radius Chicago

 Fri, 14 Feb, 2025 at 10:00 pm Radius Chicago

Zainab Johnson at Zanies Comedy Club Chicago

 Sun, 23 Feb, 2025 at 07:00 pm Zanies Comedy Club Chicago

Naruto: The Symphonic Experience

 Fri, 14 Mar, 2025 at 06:00 pm Auditorium Theatre - IL

Spafford at Thalia Hall

 Sat, 22 Mar, 2025 at 07:00 pm Thalia Hall

Tobe Nwigwe at Riviera Theatre - IL

 Sat, 22 Mar, 2025 at 08:00 pm Riviera Theatre - IL

Windows95man at Thalia Hall

 Wed, 22 Jan, 2025 at 08:00 pm Thalia Hall

Phantom Siita at Vic Theatre

 Thu, 06 Feb, 2025 at 07:00 pm Vic Theatre

Nessa Barrett at Salt Shed - Indoor Shed

 Thu, 06 Feb, 2025 at 07:30 pm Salt Shed - Indoor Shed

Kino - Kang Hyung gu at Bottom Lounge

 Fri, 24 Jan, 2025 at 07:00 pm Bottom Lounge

Marten Hrger at PRYSM Nightclub

 Sat, 08 Mar, 2025 at 10:00 pm PRYSM Nightclub

Raanan Hershberg at Zanies Comedy Club Chicago

 Fri, 07 Mar, 2025 at 09:15 pm Zanies Comedy Club Chicago

The Verve Pipe at City Winery - Chicago

 Sat, 29 Mar, 2025 at 07:30 pm City Winery - Chicago

Jason Cheny at The Den Theatre

 Sat, 25 Jan, 2025 at 09:30 pm The Den Theatre

The 24th annual Midwest Awards Ball presents: Arcadia’s Paradise

 Sat, 19 Apr, 2025 at 05:00 pm Chicago Theater Works

Tyler Braden at Joes on W**d Street

 Thu, 13 Feb, 2025 at 08:00 pm Joes on Weed Street

Miami Heat at Chicago Bulls at United Center

 Wed, 09 Apr, 2025 at 07:00 pm United Center

Phoenix Suns at Chicago Bulls at United Center

 Sat, 22 Feb, 2025 at 04:00 pm United Center

The Fundamental Kink at Reggies Music Joint

 Wed, 05 Feb, 2025 at 07:30 pm Reggies Music Joint

Chasewest at Cermak Hall - Radius Chicago

 Sat, 15 Mar, 2025 at 10:01 pm Cermak Hall - Radius Chicago

NOTD at Concord Music Hall

 Sat, 15 Mar, 2025 at 10:00 pm Concord Music Hall

Papadosio at Park West

 Sat, 05 Apr, 2025 at 08:00 pm Park West

Teenage Bottlerocket at Reggies Rock Club

 Sat, 05 Apr, 2025 at 08:00 pm Reggies Rock Club

Flesh of Fruit at Constellation Chicago

 Fri, 21 Mar, 2025 at 08:30 pm Constellation Chicago

Marsupial Masterpiece: Opossum Paint and Sip! +21 BYOB

 Sat, 25 Jan, 2025 at 06:00 pm The Insect Asylum USD 71

St. Patrick's Day Lucky Charms River North Bar Crawl

 Sun, 16 Mar, 2025 at 12:00 pm River North USD 10 to 25

070 Shake at Salt Shed - Indoor Shed

 Sat, 08 Feb, 2025 Salt Shed - Indoor Shed

Seton Hall Pirates at DePaul Blue Demons Mens Basketball at Wintrust Arena

 Sun, 02 Feb, 2025 at 05:00 pm Wintrust Arena

DJ Seinfeld at Concord Music Hall

 Mon, 06 Jan, 2025 Concord Music Hall

Parsons Dance at Auditorium Theatre Chicago

 Sat, 12 Apr, 2025 at 07:30 pm Auditorium Theatre Chicago

The Super Wrestlers at Concord Music Hall

 Sun, 09 Mar, 2025 at 06:00 pm Concord Music Hall

Deathpact at Riviera Theatre - IL

 Fri, 31 Jan, 2025 Riviera Theatre - IL

Mekki Leeper at The Den Theatre

 Sat, 08 Feb, 2025 at 07:15 pm The Den Theatre

nano and Madkid at Park West

 Wed, 05 Feb, 2025 at 06:30 pm Park West

St. Patrick's Day Lucky Charms Wrigleyville Bar Crawl

 Sat, 15 Mar, 2025 at 10:00 am Wrigleyville USD 15 to 35

Seton Hall Pirates at DePaul Blue Demons Womens Basketball at Wintrust Arena

 Sat, 01 Feb, 2025 at 02:00 pm Wintrust Arena

Chicago Dream Team Kickoff: Meet, Inspire, Ride!

 Thu, 23 Jan, 2025 at 06:00 pm Harris (Harriet) Park Free

Magic City Hippies at Metro Chicago

 Fri, 31 Jan, 2025 at 09:30 pm Metro Chicago

We Them Ones Comedy Tour at Wintrust Arena

 Sat, 19 Apr, 2025 at 08:00 pm Wintrust Arena

Whitechapel at House of Blues Chicago

 Fri, 28 Mar, 2025 at 06:30 pm House of Blues Chicago

Speed Dating | Ages 36-48 | Chicago Singles Night | SpeedChicago

 Sun, 09 Feb, 2025 at 06:00 pm Tabu USD 39

Jersey at The Outset

 Wed, 22 Jan, 2025 The Outset

Sip, Mingle, Repeat. – a Singles Mingle Mixer

 Sat, 15 Feb, 2025 at 08:00 pm Picnic Wine & Provisions USD 20

Stereophonics at Vic Theatre

 Sun, 30 Mar, 2025 at 07:30 pm Vic Theatre

Wallice at Subterranean

 Mon, 10 Feb, 2025 at 08:00 pm Subterranean

Portland Trail Blazers at Chicago Bulls at United Center

 Fri, 04 Apr, 2025 at 07:00 pm United Center

Winnipeg Jets at Chicago Blackhawks at United Center

 Sat, 12 Apr, 2025 at 06:00 pm United Center

Portal: The Chicago Winter Escape

 Fri, 07 Feb, 2025 at 08:00 pm Bucktown USD 14 to 61

Washington Wizards at Chicago Bulls at United Center

 Fri, 11 Apr, 2025 at 07:00 pm United Center

Love is LoveFest IV presented by Ritual Rhythms Chicago

 Sat, 22 Feb, 2025 at 09:30 pm The Newport Theater USD 29 to 45

Gustavo Cortinas at Constellation Chicago

 Fri, 11 Apr, 2025 at 08:30 pm Constellation Chicago

Adventurous Single Parents Meetup @ 2025 Chicago Polar Bear Plunge!

 Sat, 25 Jan, 2025 at 12:00 pm Oak Street Beach Free

Eric Bellinger at Vic Theatre

 Fri, 07 Feb, 2025 at 08:00 pm Vic Theatre

Grad Show - Student Comedy at The Lincoln Lodge

 Mon, 20 Jan, 2025 The Lincoln Lodge

Ollie Wride at Subterranean

 Wed, 26 Feb, 2025 at 07:00 pm Subterranean

Nanocluster (Immersion | SUSS)

 Sat, 22 Mar, 2025 at 08:30 pm 3111 N Western Ave Chicago IL 60618

PAW Patrol Live! "A Mighty Adventure"

 Sat, 05 Apr, 2025 at 05:30 pm The Chicago Theatre

Villanova Wildcats at DePaul Blue Demons Mens Basketball at Wintrust Arena

 Wed, 05 Feb, 2025 at 08:00 pm Wintrust Arena

San Diego FC at Chicago Fire at Soldier Field

 Sat, 12 Jul, 2025 at 07:30 pm Soldier Field

LO Great Lakes | LO x Bikes N Roses: Winter Cycling Workshop

 Fri, 07 Feb, 2025 at 05:30 pm Bikes N' Roses Free

David Nihill at Vic Theatre

 Mon, 06 Jan, 2025 Vic Theatre

Jody Wisternoff at PRYSM Nightclub

 Fri, 24 Jan, 2025 at 10:00 pm PRYSM Nightclub

Fly Sh*t Only: The Pisces Bash

 Sat, 22 Feb, 2025 at 09:00 pm Chalet USD 0 to 55

Plant Workshop: Planting New Goals for 2025

 Thu, 30 Jan, 2025 at 07:00 pm Time Out Market Chicago USD 54

Connor Price at Riviera Theatre - IL

 Sat, 22 Feb, 2025 Riviera Theatre - IL

Luke Null at Zanies Comedy Club Chicago

 Mon, 20 Jan, 2025 Zanies Comedy Club Chicago

Flore Laurentienne at Constellation Chicago

 Sun, 06 Apr, 2025 at 08:30 pm Constellation Chicago

Varietopia with Paul F. Tompkins at Riviera Theatre - IL

 Sat, 26 Apr, 2025 at 07:30 pm Riviera Theatre - IL

Asim Azhar x AUR at Park West

 Mon, 23 Dec, 2024 Park West

Jeffrey Osborne at Auditorium Theatre Chicago

 Fri, 14 Feb, 2025 at 08:00 pm Auditorium Theatre Chicago