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

The Grateful String Band

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

An Evening with Eric Dregni

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

2026 Chicago Winter Whiskey Tasting Festival (January 24)

 Sat, 24 Jan at 02:30 pm Downtown Chicago USD 0 to 440

Orlando Magic at Chicago Bulls at United Center

 Fri, 02 Jan at 07:00 pm United Center

Dark 80s Nite at Beat Kitchen

 Sat, 06 Dec at 09:00 pm Beat Kitchen

Candlelight: Tribute to Queen

 Sat, 13 Dec at 06:00 pm Stan Mansion

Broadway In Chicago - Chicago

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

Home Alone - 7 Course Holiday Immersive Movie & Dinner Experience

 Fri, 12 Dec at 05:00 pm The Drake USD 23 to 194

Kevin Nealon at The Den Theatre

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

Amazing Scavenger Hunt Adventure - Chicago, IL

 Sat, 21 Jun Dearborn Street Bridge USD 49

Saturday in the City - A Food Wine and Spirits Adventure

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

Indiana Pacers at Chicago Bulls at United Center

 Fri, 05 Dec at 07:00 pm United Center

Joffrey Ballet: The Nutcracker

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

Lyric Opera of Chicago: Salome

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

Primitive Man at Reggies Chicago

 Sat, 20 Dec Reggies Chicago

Detroit Pistons at Chicago Bulls at United Center

 Sat, 21 Feb at 07:00 pm United Center

2026 Chicago Winter Tequila Tasting Festival (February 14)

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

State Champs at Salt Shed - Indoor Shed

 Fri, 09 Jan at 07:00 pm Salt Shed - Indoor Shed

Empire! Empire!

 Sat, 13 Dec at 06:00 pm Beat Kitchen

YCP Night at the Ballet - The Nutcracker

 Sat, 13 Dec at 07:00 pm Lyric Opera of Chicago

Chicago Santa Bar Crawl

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

Picnic & Purpose: A Vision Board Gathering

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

Charlotte Hornets at Chicago Bulls at United Center

 Sat, 03 Jan United Center

Shopping Extravaganza and Holiday Treat Stroll

 Sat, 06 Dec at 11:00 am Lakeview East Chamber of Commerce Free

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

Samantha Fish at House of Blues Chicago

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

Gospel Brunch at House of Blues Chicago

 Sun, 21 Dec at 10:00 am House of Blues Chicago

Cristela Alonzo at Vic Theatre

 Sat, 31 Jan at 07:30 pm Vic Theatre

Road Trip To Jungle Bells

 Fri, 12 Dec at 09:00 pm 2050 West Division Street, Chicago, Illinois 60622, United States

Unwind & Create: Exotic BYOB Paint & Sip for Young CHICAGO Professionals

 Fri, 14 Mar at 09:00 pm 5425 W Lawrence Ave USD 33

Celebrating Motown Soulful Music Holiday Lights Trolley

 Sun, 07 Dec at 04:00 pm 230 W North Ave (inside Lobby) USD 80

The Armed at Thalia Hall

 Fri, 12 Dec at 08:00 pm Thalia Hall

Madama Butterfly at Lyric Opera House

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

Its Murph at Radius Chicago

 Sat, 06 Dec at 10:00 pm Radius Chicago

Celebrating Motown Soulful Music Holiday Lights Trolley BYOB

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

S.Rose Chicago Hat Painting Experience

 Sat, 06 Dec at 04:00 pm Strugglebeardbakery USD 55

David Spade at Riviera Theatre - IL

 Sat, 31 Jan at 08:00 pm Riviera Theatre - IL

The NAUGHTY Little Madrigal at The Newport Theater

 Thu, 11 Dec The Newport Theater

Brett Eldredge at Chicago Theatre

 Thu, 04 Dec at 08:00 pm Chicago Theatre

Home Alone in Concert

 Sat, 13 Dec at 07:30 pm Chicago Symphony Center

Xaviersobased at Bottom Lounge

 Sun, 07 Dec at 08:00 pm Bottom Lounge

Daniel Villarreal - Artist

 Sat, 06 Dec at 06:00 pm The Promontory

PREMIER ONE DANCE CONSERVATORY-JINGLE JANGLE MADNESS

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

Terrapin Flyer at Garcias Chicago

 Fri, 23 Jan Garcias Chicago

Josh Meloy at Joes on W**d Street

 Fri, 05 Dec at 08:00 pm Joes on Weed Street

SML and SML at Thalia Hall

 Sun, 14 Dec Thalia Hall

Winter Wonderland Christmas River North Bar Crawl

 Sat, 20 Dec at 04:00 pm Joy District USD 13 to 18

Home Alone - Chicago

 Sat, 13 Dec at 07:30 pm Chicago Symphony Center

Young Culture at Beat Kitchen

 Fri, 12 Dec at 08:00 pm Beat Kitchen

WGCI Big Jam at United Center

 Sat, 06 Dec at 07:00 pm United Center

Battle of the Bands

 Thu, 11 Dec Reggie's Rock Club

Celebrating Motown Soulful Music Holiday Lights Trolley BYOB

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

Chicago New Years Eve Bar Crawl

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

Samantha Fish Cedric Burnside & Jon Spencer

 Sat, 06 Dec at 06:00 pm House Of Blues - Chicago

Rebirth Brass Band at Thalia Hall

 Sat, 17 Jan at 08:00 pm Thalia Hall

Parlor Greens at Garcias Chicago

 Sat, 13 Dec Garcias Chicago

Ghostface Killah at Ramova Theatre

 Sat, 07 Feb at 08:00 pm Ramova Theatre

Doors open for Delaney Bailey concert at Beat Kitchen at Beat Kitchen

 Fri, 05 Dec at 08:00 pm Beat Kitchen

Arlene MC

 Thu, 04 Dec at 06:00 pm V Live- Chicago

Rob Anderson at Park West

 Fri, 05 Dec Park West

Loyola Chicago Ramblers vs. Chicago State Cougars

 Sat, 13 Dec at 06:00 pm Gentile Center

Christkindlmarket Family Outing

 Sat, 06 Dec at 11:00 am Gallagher Way

Jay Illa at The Promontory

 Sun, 14 Dec at 04:00 pm The Promontory

Yoga with Cats!

 Sun, 14 Dec at 05:00 pm 2914 N Elston Ave, Chicago, IL, United States, Illinois 60618

Santa Cycle Rampage 2025

 Sat, 13 Dec at 12:00 pm DIEGOChicago

Cleveland Cavaliers at Chicago Bulls at United Center

 Wed, 17 Dec United Center

Zarna Garg at Riviera Theatre - IL

 Sat, 25 Apr at 07:30 pm Riviera Theatre - IL

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

 Fri, 19 Dec at 05:00 pm Old Crow Smokehouse - Wrigleyville USD 78 to 101

DJ Diesel at Salt Shed - Indoor Shed

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

Santa Story Time with Miss Beth!

 Sat, 13 Dec at 09:00 am Loews Chicago Hotel USD 29

Rascal Flatts at United Center

 Fri, 06 Feb at 07:00 pm United Center

Foxing at Thalia Hall

 Wed, 03 Dec at 08:00 pm Thalia Hall

Taste the Movies - Elf 7 Course Immersive Dinner & Movie Experience

 Fri, 12 Dec at 08:30 pm The Drake Hotel (140 E Walton Pl, Chicago)

Jagged Edge at Arie Crown Theater

 Sun, 14 Dec at 07:30 pm Arie Crown Theater

Celebrating Motown Soulful Music Holiday Lights Trolley BYOB

 Fri, 19 Dec at 06:30 pm 230 W North Ave USD 78

Celebrating Motown Soulful Music Holiday Lights Trolley BYOB

 Fri, 12 Dec at 06:30 pm 230 W North Ave USD 78

Drinking & Dragons

 Sun, 14 Dec at 04:00 pm 2833 N. Sheffield, Chicago, IL, United States, Illinois 60657

Queen of Hearts Art Exhibit

 Sat, 21 Feb at 03:00 pm Little Black Pearl Workshop USD 29

NFC Wild Card Home Game: Chicago Bears vs. TBD (Date: TBD - If Necessary)

 Sat, 10 Jan Soldier Field

SML & SML XL

 Sat, 13 Dec at 06:00 pm Thalia Hall

Columbus Blue Jackets at Chicago Blackhawks at United Center

 Fri, 30 Jan at 07:30 pm United Center

Rod Wave at United Center

 Mon, 15 Dec at 08:00 pm United Center

Cherish the Ladies: Celtic Christmas

 Sat, 20 Dec at 07:00 pm Mayfair Theatre USD 38

Pier Pressure: Alison Wonderland & San Holo Wholseom Riddim Set - Night 2

 Fri, 26 Dec Aon Grand Ballroom Navy Pier

Brandenburg Concertos at Harris Theater

 Thu, 04 Dec at 07:30 pm Harris Theater

Chicago Cinco De Mayo Bar Crawl

 Tue, 05 May at 05:00 pm PB&J: Pizza Beer and Jukebox USD 7 to 31

City Wide Symphony Holiday Concert

 Fri, 12 Dec at 06:00 pm Copernicus Center

Origami Fold and Sip (Wrigleyville)

 Wed, 10 Dec at 06:00 pm 3443 N Sheffield Ave USD 18

Chicago Bulls vs. Detroit Pistons

 Fri, 20 Feb at 06:00 pm United Center USD 39 to 499

Space Squirrel

 Tue, 02 Dec at 06:00 pm Reggie's Music Joint

Mischief and Mistletoe at City Winery - Chicago

 Sun, 21 Dec at 07:00 pm City Winery - Chicago

Handmade Botanical Ornaments in Clay, Dec 8

 Mon, 08 Dec at 06:30 pm 1919 N Springfield Ave USD 116

Merry Merry Chicago at Chicago Symphony Center

 Fri, 19 Dec at 07:30 pm Chicago Symphony Center

WPB Winter Wonderland & Tree Lighting

 Sat, 06 Dec at 01:00 pm Wicker Park Bucktown Free

Stephen Lynch at Park West

 Thu, 04 Dec at 07:30 pm Park West

Billy Joel Jr. - Album Release

 Wed, 17 Dec at 06:00 pm The Empty Bottle

Chicago Blackhawks vs. Colorado Avalanche

 Thu, 19 Mar at 06:00 pm United Center USD 25 to 744