Trips & Adventurous Activities in Chicago

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

🎄 The Elfed Up Christmas Crawl 🎅🏻

 Sat, 20 Dec at 02:00 pm 60610 USD 10 to 20

Chicago Auto Show

 Fri, 06 Feb at 06:00 pm South Building at McCormick Place

Chicago SantaCon 2025

 Sat, 20 Dec at 01:00 pm PB&J: Pizza Beer and Jukebox USD 0 to 31

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

 Sat, 06 Dec at 05:00 pm Old Crow Smokehouse - Wrigleyville

Saturday Night (Ages 25-39) | Chicago Speed Dating | Speed Chicago

 Sat, 15 Nov at 07:30 pm Tabu USD 39 to 44

Robert Plant's Saving Grace feat. Suzi Dian: Roar in the Fall

 Thu, 13 Nov at 07:30 pm 4544 N. Lincoln Ave., Chicago, IL, United States, Illinois 60625

GoldLink at House of Blues Chicago

 Sat, 29 Nov at 07:00 pm House of Blues Chicago

Saturday Night (Ages 25-39) | Chicago Speed Dating | Speed Chicago

 Sat, 22 Nov at 07:30 pm Time Out Market Chicago USD 39 to 44

Kevin Nealon at The Den Theatre

 Fri, 30 Jan at 07:15 pm 1331 N Milwaukee Ave, Chicago, IL, United States, Illinois 60622

Candlelight: Tribute to Adele

 Sat, 08 Nov at 06:00 pm Stan Mansion

Amazing Scavenger Hunt Adventure - Chicago, IL

 Sat, 21 Jun Dearborn Street Bridge USD 49

Chris D'Elia at Chicago Theatre

 Sat, 15 Nov Chicago Theatre

The Sunday Issue

 Sat, 15 Nov at 06:00 pm The Promontory

Pixel Grip at Metro Chicago

 Fri, 14 Nov Metro Chicago

Bryce Crawford

 Sat, 15 Nov at 06:00 pm Park West

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

 Sat, 14 Mar at 09:00 am 230 N Clark St USD 20 to 50

Mycelium New Music at Constellation Chicago

 Sun, 23 Nov at 08:30 pm Constellation Chicago

BYOB Sip & Paint Class “Northern Lights”

 Fri, 21 Nov at 07:00 pm Sip & Paint USD 43

Madama Butterfly at Lyric Opera House

 Sat, 14 Mar at 07:30 pm Lyric Opera House

Singles Events (Ages 32-44) | Chicago Speed Dating | Speed Chicago

 Sun, 23 Nov at 06:00 pm Recess USD 36 to 39

Sensory Friendly Gathering

 Sat, 15 Nov at 02:00 pm Third Space Chicago Free

Mariachi Herencia de México: Herederos at Thalia Hall

 Sun, 07 Dec at 07:00 pm Thalia Hall

DJ Diesel at Salt Shed - Indoor Shed

 Sat, 20 Dec at 09:00 pm Salt Shed - Indoor Shed

Broadway In Chicago - Chicago

 Fri, 12 Dec at 08:00 pm Broadway Playhouse at Water Tower Place USD 826

Bikes & Bonfires

 Sat, 22 Nov at 04:00 pm Burnham Park Promontory Point Free

Cranksgiving Chicago

 Sat, 22 Nov at 12:00 pm Cosmic Bikes Inc. Free

Civic Orchestra of Chicago: The Planets

 Sun, 16 Nov at 06:00 pm Orchestra Hall At Chicago Symphony Center

Indiana Pacers at Chicago Bulls at United Center

 Fri, 05 Dec at 07:00 pm United Center

Boyce Avenue at Park West

 Sat, 15 Nov at 07:30 pm Park West

Rebirth Brass Band at Thalia Hall

 Sat, 17 Jan at 08:00 pm Thalia Hall

2026 Chicago Winter Tequila Tasting Festival (February 14)

 Sat, 14 Feb at 02:30 pm Downtown Chicago USD 0 to 440

Speed Dating in Chicago (Ages 24-36) | Speed Chicago | Singles Events

 Thu, 20 Nov at 07:00 pm Untitled Supper Club USD 36 to 39

Damien Escobar at City Winery - Chicago

 Sun, 07 Dec at 05:00 pm City Winery - Chicago

God of Chaos Christmas at Byline Bank Aragon Ballroom

 Sat, 20 Dec at 07:00 pm Byline Bank Aragon Ballroom

Tape B at Salt Shed - Indoor Shed

 Fri, 21 Nov at 08:00 pm Salt Shed - Indoor Shed

Yelawolf at House of Blues Chicago

 Sun, 23 Nov at 07:00 pm House of Blues Chicago

Raheem Devaughn - 20 Lessons of Love at City Winery - Chicago

 Fri, 26 Dec at 06:00 pm City Winery - Chicago

Singles Event In Chicago

 Sun, 30 Nov at 07:00 pm Taco Maya USD 25 to 29

Direct Hit!

 Fri, 28 Nov at 06:00 pm Beat Kitchen

Songs 'n Swings: Music with Mr. Ray

 Sun, 16 Nov at 11:00 am 3409 W Cortland St Free

An Evening with Eric Dregni

 Sat, 06 Dec at 05:00 pm Eataly Chicago USD 108

Picnic & Purpose: A Vision Board Gathering

 Sat, 20 Dec at 06:00 pm 5412 N Clark St #201 USD 48

A Taste of Mexico! A Tour of Little Village

 Sat, 15 Nov at 01:00 pm Little Village Arch USD 61

King 810 at Bottom Lounge

 Sun, 16 Nov at 07:00 pm Bottom Lounge

Waterparks at Salt Shed - Indoor Shed

 Fri, 28 Nov at 07:00 pm Salt Shed - Indoor Shed

Salsa For Singles

 Sun, 30 Nov at 07:30 pm Taco Maya USD 28

The Phantom Of The Opera at Cadillac Palace

 Sat, 13 Dec Cadillac Palace

85 South at Wintrust Arena

 Fri, 28 Nov at 08:00 pm Wintrust Arena

Chicago New Years Eve Bar Crawl

 Wed, 31 Dec at 06:00 pm Chicago USD 0 to 46

Moon Taxi at Garcias Chicago

 Fri, 26 Dec Garcias Chicago

The Beths at Salt Shed - Indoor Shed

 Sun, 23 Nov at 08:00 pm Salt Shed - Indoor Shed

The Grateful String Band

 Sat, 06 Dec at 08:00 pm Garcia's Chicago

Wait Wait...Don't Tell Me

 Wed, 17 Sep at 06:00 pm Studebaker Theater

Strong Towns Board Game Night!

 Tue, 11 Nov at 06:30 pm Snakes & Lattes Chicago Free

Eric Reprid at Reggies Chicago

 Sat, 10 Jan at 08:30 pm Reggies Chicago

Samantha Fish at House of Blues Chicago

 Sun, 07 Dec at 07:00 pm House of Blues Chicago

Fragrance Making Class - Create Your Own Signature Scent

 Sat, 20 Jul at 01:00 pm Reggie Hathorn Candles and Home Fragrances | Candle Making Classes USD 93

Jon McLaughlin at Park West

 Sat, 06 Dec at 07:30 pm Park West

South Loop Culinary Crawl

 Thu, 13 Nov at 06:00 pm 2600 Michigan Ave USD 62 to 110

Joffrey Ballet: The Nutcracker

 Thu, 04 Dec at 06:00 pm Lyric Opera House - IL USD 132 to 159

Tom Morello & Friends

 Thu, 13 Nov at 07:30 pm The Vic Theatre

Tape B at Ramova Theatre

 Fri, 21 Nov at 11:55 am Ramova Theatre

The New Mastersounds at Ramova Theatre

 Fri, 14 Nov at 08:00 pm Ramova Theatre

Lyric Opera of Chicago: Salome

 Sat, 24 Jan at 06:00 pm Lyric Opera House - IL

PARKING: Chicago Bears vs. Pittsburgh Steelers

 Sat, 22 Nov at 06:00 pm Soldier Field Parking Lot

The Armed at Thalia Hall

 Fri, 12 Dec at 08:00 pm Thalia Hall

Being Human in an Artificial Age - A World Philosophy Day Event

 Sun, 23 Nov at 03:00 pm New Acropolis Chicago Free

Yung Kai at Bottom Lounge

 Sat, 11 Apr at 07:30 pm Bottom Lounge

The Nasty Show: Tiny Thickemz

 Fri, 14 Nov at 06:00 pm The Laugh Factory - Chicago

Northwestern Wildcats vs. Michigan Wolverines

 Fri, 14 Nov at 06:00 pm Wrigley Field

Celebrating Motown Soulful Music Holiday Lights Trolley BYOB

 Sat, 06 Dec at 06:30 pm 230 W North Ave USD 78

Mersiv & Ravenscoon

 Fri, 14 Nov at 06:00 pm Radius - IL

Sam Harris at Chicago Theatre

 Wed, 19 Nov Chicago Theatre

Moonchild at Thalia Hall

 Fri, 13 Mar at 08:00 pm Thalia Hall

The Lone Bellow at Thalia Hall

 Fri, 20 Feb at 07:30 pm Thalia Hall

The Record Company at Thalia Hall

 Fri, 06 Mar at 08:00 pm Thalia Hall

Atreyu at Concord Music Hall

 Fri, 28 Nov at 06:00 pm Concord Music Hall

Orquesta Sinfonica De Mineria

 Sat, 17 Jan at 06:00 pm Orchestra Hall At Chicago Symphony Center

Minus the Bear at Metro Chicago

 Sun, 16 Nov at 08:00 pm Metro Chicago

Chromeo at Thalia Hall

 Thu, 20 Nov Thalia Hall

Saturday in the City - A Food Wine and Spirits Adventure

 Sat, 06 Dec at 02:00 pm Hotel Chicago USD 155

Avery Sunshine at City Winery - Chicago

 Sat, 31 Jan City Winery - Chicago

Calgary Flames at Chicago Blackhawks at United Center

 Tue, 18 Nov United Center

Sarah Kang: Before & After at Bottom Lounge

 Tue, 16 Dec at 07:00 pm Bottom Lounge

WWE: NXT Live

 Fri, 14 Nov at 06:00 pm Byline Bank Aragon Ballroom

PREMIER ONE DANCE CONSERVATORY-JINGLE JANGLE MADNESS

 Sat, 13 Dec at 05:30 pm Morgan Park Academy USD 32

Mark William Lewis

 Fri, 14 Nov at 06:00 pm The Empty Bottle

Ax and the Hatchetmen at Metro Chicago

 Fri, 21 Nov at 09:00 pm Metro Chicago

Chicago Blackhawks vs. Anaheim Ducks

 Sat, 29 Nov at 06:00 pm United Center USD 23 to 663

Real American Freestyle - RAF03

 Sun, 30 Nov at 02:00 am Wintrust Arena

Tiffany Yu in Conversation with Jessica Jordan Ping

 Wed, 19 Nov at 06:30 pm Three Avenues Bookshop USD 0 to 36

Celebrating Motown Soulful Music Holiday Lights Trolley BYOB

 Fri, 05 Dec at 06:30 pm 230 W North Ave USD 78

Jason Isbell and The 400 Unit at Salt Shed - Indoor Shed

 Fri, 06 Mar Salt Shed - Indoor Shed

Marcus Rezak's Gumbo at Garcias Chicago

 Thu, 18 Dec at 08:00 pm Garcias Chicago

Queensryche with Accept

 Fri, 14 Nov at 12:00 am House of Blues Chicago

Polar Party

 Sat, 06 Dec at 10:00 am 1200 West 35th Street, Suite 0E-5010, Chicago, IL

Minnesota Wild at Chicago Blackhawks at United Center

 Wed, 26 Nov at 07:30 pm United Center

Anaheim Ducks at Chicago Blackhawks at United Center

 Sun, 19 Oct at 06:00 pm United Center

Demetri Martin

 Fri, 21 Nov at 06:00 pm Vic Theatre

The Barr Brothers at Thalia Hall

 Tue, 11 Nov at 08:00 pm Thalia Hall