Sat Dec 6, 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'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
WGCI Big Jam: GloRilla, Sexyy Red, Tink, BossMan Dlow & Big Boogie
Venue: United Center
Time: 7:00 PM
Featuring: WGCI Big Jam
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 7, 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
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Samantha Fish, Cedric Burnside & Jon Spencer
Venue: House Of Blues - Chicago
Time: 7:00 PM
Featuring: Samantha Fish
Daniel Villarreal - Artist
Venue: The Promontory
Time: 9:00 PM
Featuring: Daniel Villarreal - Artist
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: Chicago's Best Stand Up
Mon Dec 8, 2025
Tue Dec 9, 2025
Twisted 2025 (Includes Ticket to AJR, Cake, Third Eye Blind & Sublime Shows) - 4 Day Pass
Venue: Byline Bank Aragon Ballroom
Time: To Be Announced
Featuring: Twisted 2025
Gwen Rose and Allies
Venue: Zanies Comedy Club - Chicago
Time: 7:00 PM
Featuring: Gwen Rose and Allies
A Chanticleer Christmas
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: A Chanticleer Christmas
Home For The Yeehawlidays
Venue: The Empty Bottle
Time: 9:00 PM
Featuring: Home For The Yeehawlidays
Wed Dec 10, 2025
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 8:00 PM
Featuring: Chicago's Best Stand Up
Thu Dec 11, 2025
Third Eye Blind & Yellowcard
Venue: Byline Bank Aragon Ballroom
Time: 7:00 PM
Featuring: Third Eye Blind | Yellowcard
Whose Lie Is It Anyway
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Whose Lie Is It Anyway
Chicago Symphony Orchestra: Gianandrea Noseda - Debussy & Prokofiev
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: Chicago Symphony Orchestra | Prokofiev | Gianandrea Noseda | Debussy
What Could Go Wrong Comedy Show
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: What Could Go Wrong Comedy Show
Fri Dec 12, 2025
Chicago Symphony Orchestra: Gianandrea Noseda - Debussy & Prokofiev
Venue: Orchestra Hall At Chicago Symphony Center
Time: 1:30 PM
Featuring: Chicago Symphony Orchestra | Prokofiev | Gianandrea Noseda | Debussy
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
Something Unexpected
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Something Unexpected
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 11:30 PM
Featuring: Chicago's Best Stand Up
Sat Dec 13, 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 Sound Collective
Venue: Reggie's Music Joint
Time: 1:00 PM
Featuring: Chicago Sound Collective
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 1:30 PM
Featuring: Second City Chicago: Rudolph Runs Wild
Hip Hop and R&B Bingo With Tom Swoope
Venue: City Winery - Chicago
Time: 6:00 PM
Featuring: Hip Hop and R&B Bingo With Tom Swoope
City Wide Symphony Holiday Concert
Venue: Copernicus Center
Time: 7:00 PM
Featuring: City Wide Symphony
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's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Chicago Symphony Orchestra: Gianandrea Noseda - Debussy & Prokofiev
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: Chicago Symphony Orchestra | Prokofiev | Gianandrea Noseda | Debussy
A Soulful Motown Christmas
Venue: Harris Theater
Time: 7:30 PM
Featuring: A Soulful Motown Christmas
Brendan Bayliss & Jake Cinninger
Venue: Park West
Time: 8:00 PM
Featuring: Jake cinninger | Brendan Bayliss
Galapagos4 Holiday Reunion Party: Qwel, Robust & Offwhyte
Venue: Reggie's Rock Club
Time: 9:00 PM
Featuring: Qwel | Offwhyte | Galapagos4 Holiday Reunion Party | Robust
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Chicago's Best Stand Up
Hip Hop and R&B Bingo With Tom Swoope
Venue: City Winery - Chicago
Time: 9:30 PM
Featuring: Hip Hop and R&B Bingo With Tom Swoope
The Nasty Show: Tiny Thickemz
Venue: The Laugh Factory - Chicago
Time: 11:30 PM
Featuring: The Nasty Show: Tiny Thickemz
Sun Dec 14, 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
Chicago Symphony Orchestra: Home Alone In Concert
Venue: Orchestra Hall At Chicago Symphony Center
Time: 3:00 PM
Featuring: Chicago Symphony Orchestra | Home Alone in Concert
Candlelight: Tribute to Queen
Venue: Stan Mansion
Time: 6:30 PM
Featuring: Candlelight: A Tribute to Queen
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: Chicago's Best Stand Up
The Throw Gala: A Red Carpet Affair - DJ Skinny
Venue: The Promontory
Time: 10:00 PM
Featuring: A Red Carpet Affair
Mon Dec 15, 2025
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 8:00 PM
Featuring: Chicago's Best Stand Up
Tue Dec 16, 2025
Carl Payne & Reginald Ballard
Venue: City Winery - Chicago
Time: 7:30 PM
Featuring: Carl Payne | Reginald Ballard!
Fresh Faces of Chicago
Venue: The Laugh Factory - Chicago
Time: 7:30 PM
Featuring: Fresh Faces of Chicago
Chicago Symphony Orchestra Brass
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: Chicago Symphony Orchestra Brass
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
Chicago Symphony Orchestra: Klaus Makela & Yunchan Lim
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: Chicago Symphony Orchestra | Yunchan Lim | Klaus Makela
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
Candlelight: Tribute to Queen
Venue: Stan Mansion
Time: 6:30 PM
Featuring: Candlelight: A Tribute to Queen
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: Black Angels | Unknown Metal Orchestra | Where Is The Cool? | Crumb
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 7:30 PM
Featuring: Chicago Symphony Orchestra | Merry, Merry Chicago!
American English - Beatles Tribute
Venue: The WC Social Club
Time: 8:00 PM
Featuring: American English - Beatles Tribute
Candlelight: Tribute to Taylor Swift
Venue: Stan Mansion
Time: 8:45 PM
Featuring: Candlelight: A Tribute to Taylor Swift
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: Chicago Symphony Orchestra | Merry, Merry Chicago!
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: Chicago Symphony Orchestra | Yunchan Lim | Klaus Makela
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: Chicago Symphony Orchestra | Merry, Merry Chicago!
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 4:30 PM
Featuring: Chicago Symphony Orchestra | Merry, Merry Chicago!
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: Chicago Symphony Orchestra | Merry, Merry Chicago!
Winter Solstice Sunrise Concert Series: Drake & Zerang
Venue: Constellation - Chicago
Time: 8:00 PM
Featuring: Winter Solstice Sunrise Concert Series
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: Chicago Symphony Orchestra | Merry, Merry Chicago!
Chicago Symphony Orchestra: Merry, Merry Chicago!
Venue: Orchestra Hall At Chicago Symphony Center
Time: 4:30 PM
Featuring: Chicago Symphony Orchestra | Merry, Merry Chicago!
Fresh Faces of Chicago
Venue: The Laugh Factory - Chicago
Time: 7:30 PM
Featuring: Fresh Faces of Chicago
Thu Dec 25, 2025
Fri Dec 26, 2025
Pier Pressure - 2 Day Pass
Venue: Aon Grand Ballroom Navy Pier
Time: To Be Announced
Featuring: Pier Pressure
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
Pier Pressure: Subtronics, Muzz & OkayJake - Night 1
Venue: Aon Grand Ballroom Navy Pier
Time: 7:00 PM
Featuring: Subtronics | Pier Pressure | Muzz
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: Anthony Attalla | Carlo Lio
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 11:30 PM
Featuring: Chicago's Best Stand Up
Sat Dec 27, 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
Pier Pressure: Alison Wonderland & San Holo Wholseom Riddim Set - Night 2
Venue: Aon Grand Ballroom Navy Pier
Time: 7:00 PM
Featuring: Alison Wonderland | San Holo | Pier Pressure
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
Holiday Of Horror 2025 Edition
Venue: Reggie's Rock Club
Time: 7:00 PM
Featuring: The Annual Holiday of Horror
Candlelight: Tribute to Taylor Swift
Venue: Stan Mansion
Time: 8:45 PM
Featuring: Candlelight: A Tribute to Taylor Swift
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Chicago's Best Stand Up
The Last Dance: LGBTQ Pre NYE Party
Venue: The Promontory
Time: 10:00 PM
Featuring: The Last Dance: LGBTQ Pre NYE Party
Bart Skils & Pleasurekraft
Venue: PRYSM Nightclub
Time: 10:00 PM
Featuring: Pleasurekraft | Bart Skils
The Nasty Show: Tiny Thickemz
Venue: The Laugh Factory - Chicago
Time: 11:30 PM
Featuring: The Nasty Show: Tiny Thickemz
Sun Dec 28, 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
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: Chicago's Best Stand Up
Mon Dec 29, 2025
Stand Ups Sit Down Comedy Showcase
Venue: The Laugh Factory - Chicago
Time: 8:00 PM
Featuring: Stand Ups Sit Down Comedy Showcase
Tue Dec 30, 2025
Fresh Faces of Chicago
Venue: The Laugh Factory - Chicago
Time: 7:30 PM
Featuring: Fresh Faces of Chicago
Karl Denson's Tiny Universe
Venue: Garcias Chicago
Time: 8:00 PM
Featuring: Karl Denson's Tiny Universe
