Wed Dec 17, 2025
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 8:00 PM
Featuring: Chicago's Best Stand Up
Thu Dec 18, 2025
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Jim Ryan's Classic Albums Night
Venue: Reggie's Music Joint
Time: 8:00 PM
Featuring: Jim Ryan's Classic Albums Night: Tributes To Weezer, Failure & 311
Funny Music Live - Stand Up Comics
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: Funny Music Live - Stand Up Comics
Roast Battle Chicago
Venue: Zanies Comedy Club - Chicago
Time: 9:15 PM
Featuring: Roast Battle Chicago
Fri Dec 19, 2025
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Clued In - An Improvised Murder Mystery
Venue: Donny's Skybox Theatre at Second City - Chicago
Time: 7:00 PM
Featuring: Clued In - An Improvised Murder Mystery
Where Is The Cool?: Unknown Metal Orchestra, Crumb, & The Black Angels
Venue: Byline Bank Aragon Ballroom
Time: 7:00 PM
Featuring: Unknown Metal Orchestra | Where Is The Cool? | Crumb | Black Angels
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: Merry, Merry Chicago! | Chicago Symphony Orchestra
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Chicago's Best Stand Up
Reverie Stone Country Holiday Extravaganza
Venue: Carol's Pub
Time: 9:30 PM
Featuring: Reverie Stone Country Holiday Extravaganza
Sat Dec 20, 2025
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 11:00 AM
Featuring: Second City Chicago: Rudolph Runs Wild
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 1:00 PM
Featuring: Merry, Merry Chicago! | Chicago Symphony Orchestra
Mannheim Steamroller Christmas
Venue: Nederlander Theatre at Ford Center for the Performing Arts
Time: 3:00 PM
Featuring: Mannheim Steamroller Christmas | Mannheim Steamroller
Ballet Folklorico de Chicago: Tradiciones de Navidad
Venue: Copernicus Center
Time: 5:00 PM
Featuring: Various Artists
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Gods of Chaos Christmas
Venue: Byline Bank Aragon Ballroom
Time: 7:00 PM
Featuring: Gods of Chaos Christmas
Clued In - An Improvised Murder Mystery
Venue: Donny's Skybox Theatre at Second City - Chicago
Time: 7:00 PM
Featuring: Clued In - An Improvised Murder Mystery
Chicago Symphony Orchestra: Klaus Makela & Yunchan Lim
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: Yunchan Lim | Klaus Makela | Chicago Symphony Orchestra
Chicago Philharmonic: The Holiday in Concert
Venue: Auditorium Theatre - IL
Time: 7:30 PM
Featuring: Chicago Philharmonic Orchestra
Mannheim Steamroller Christmas
Venue: Nederlander Theatre at Ford Center for the Performing Arts
Time: 8:00 PM
Featuring: Mannheim Steamroller Christmas | Mannheim Steamroller
Rod Tuffcurls and The Bench Press
Venue: Joe's Bar On Weed St.
Time: 9:00 PM
Featuring: Rod Tuffcurls and The Bench Press
Shaquille O'Neal AKA DJ Diesel
Venue: The Salt Shed Indoors - Chicago
Time: 9:00 PM
Featuring: Shaquille O'Neal AKA DJ Diesel
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Chicago's Best Stand Up
The Nasty Show: Tiny Thickemz
Venue: The Laugh Factory - Chicago
Time: 11:30 PM
Featuring: The Nasty Show: Tiny Thickemz
Sun Dec 21, 2025
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 11:00 AM
Featuring: Second City Chicago: Rudolph Runs Wild
Soul Brunch : Jazz & Soul Christmas Spectacular
Venue: City Winery - Chicago
Time: 12:00 PM
Featuring: Soul Brunch
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 1:00 PM
Featuring: Merry, Merry Chicago! | Chicago Symphony Orchestra
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 4:30 PM
Featuring: Merry, Merry Chicago! | Chicago Symphony Orchestra
The Early Bird Special
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: The Early Bird Special
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: Chicago's Best Stand Up
Angelo Colina - Spanish Performance
Venue: Zanies Comedy Club - Chicago
Time: 9:15 PM
Featuring: Angelo Colina
Mon Dec 22, 2025
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: Merry, Merry Chicago! | Chicago Symphony Orchestra
Stand Ups Sit Down Comedy Showcase
Venue: The Laugh Factory - Chicago
Time: 8:00 PM
Featuring: Stand Ups Sit Down Comedy Showcase
Tue Dec 23, 2025
Winter Solstice Sunrise Concert Series: Drake & Zerang
Venue: Constellation - Chicago
Time: 6:00 AM
Featuring: Winter Solstice Sunrise Concert Series
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 1:00 PM
Featuring: Merry, Merry Chicago! | Chicago Symphony Orchestra
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 4:30 PM
Featuring: Merry, Merry Chicago! | Chicago Symphony Orchestra
Fresh Faces of Chicago
Venue: The Laugh Factory - Chicago
Time: 7:30 PM
Featuring: Fresh Faces of Chicago
Fri Dec 26, 2025
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 11:00 AM
Featuring: Second City Chicago: Rudolph Runs Wild
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 1:30 PM
Featuring: Second City Chicago: Rudolph Runs Wild
First Date Comedy Gameshow
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: First Date Comedy Gameshow
Clued In - An Improvised Murder Mystery
Venue: Donny's Skybox Theatre at Second City - Chicago
Time: 7:00 PM
Featuring: Clued In - An Improvised Murder Mystery
Something Unexpected
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Something Unexpected
Anthony Attalla & Carlo Lio
Venue: PRYSM Nightclub
Time: 10:00 PM
Featuring: Carlo Lio | Anthony Attalla
