| Event | Venue | Date/Time | |
| Chicago Cubs vs. Miami Marlins | Wrigley Field
Chicago, IL | Thursday
9/24/2026
1:20 PM |  |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Thursday
9/24/2026
2:00 PM | |
| Monsieur Perine | Outset
Chicago, IL | Thursday
9/24/2026
6:30 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Thursday
9/24/2026
7:00 PM | |
| Cliff Cash | Zanies Comedy Club - Chicago
Chicago, IL | Thursday
9/24/2026
7:00 PM | |
| Two Door Cinema Club | The Salt Shed Outdoors - Chicago
Chicago, IL | Thursday
9/24/2026
7:00 PM | |
| Sub Urban | Subterranean
Chicago, IL | Thursday
9/24/2026
7:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Thursday
9/24/2026
7:00 PM | |
| Taylor Tomlinson | Historic Main Stage at Athenaeum Center - IL
Chicago, IL | Thursday
9/24/2026
7:00 PM | |
| Chicago Symphony Orchestra: Klaus Makela - Sibelius & Shostakovich | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Thursday
9/24/2026
7:30 PM | |
| Vape! The Grease Parody | Apollo Theater Main Stage - Chicago
Chicago, IL | Thursday
9/24/2026
7:30 PM | |
| Best of Chicago Comedy | The Foundation Room at House Of Blues - Chicago
Chicago, IL | Thursday
9/24/2026
7:30 PM | |
| Xavier Wulf | Vic Theatre
Chicago, IL | Thursday
9/24/2026
7:30 PM | |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Thursday
9/24/2026
7:30 PM | |
| Yeat | Huntington Bank Pavilion at Northerly Island
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| Culture Wars | Metro Chicago
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| The Secret Sisters | Thalia Hall
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| Cold Waves XIV Chicago Kick-Off Show: The Tear Garden | Bottom Lounge
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| The Takes | Schubas
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| Left Lane Cruiser | Reggie's Music Joint
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| AJ Lee and Blue Summit | Lincoln Hall
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| Phoebe Ryan | Beat Kitchen
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| Joe Rian and the AM Drinkers | Carol's Pub
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| Fox N' Vead | Joe's Bar On Weed St.
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| Brown Eyed Women - Grateful Dead Tribute | Garcias Chicago
Chicago, IL | Thursday
9/24/2026
8:00 PM | |
| Chicago Symphony Orchestra: Klaus Makela - Sibelius & Shostakovich | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Friday
9/25/2026
1:30 PM | |
| Lucy Darling | Studebaker Theater
Chicago, IL | Friday
9/25/2026
5:30 PM | |
| Beyond The Gate: Cate Le Bon & Horsegirl | Bohemian National Cemetery
Chicago, IL | Friday
9/25/2026
6:00 PM | |
| Chicago White Sox vs. Colorado Rockies | Rate Field
Chicago, IL | Friday
9/25/2026
6:40 PM | |
| Teddy Swims | United Center
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Cold Waves XIV Chicago: Stabbing Westward, Pig & Acumen Nation - Friday | Metro Chicago
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Sofi Tukker | Huntington Bank Pavilion at Northerly Island
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Arrows In Action | Bottom Lounge
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Cliff Cash | Zanies Comedy Club - Chicago
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Theo Katzman | Garcias Chicago
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Sun Ra Arkestra | Constellation - Chicago
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Melissa Villasenor | Heath Mainstage At The Den Theatre
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Hannah Cole | Subterranean - Downstairs
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Friday
9/25/2026
7:00 PM | |
| Laura Ramoso | The Chicago Theatre
Chicago, IL | Friday
9/25/2026
7:30 PM | |
| Michael Shannon & Jason Narducy | Riviera Theatre - IL
Chicago, IL | Friday
9/25/2026
7:30 PM | |
| Whipped Cream | Park West
Chicago, IL | Friday
9/25/2026
7:30 PM | |
| Freddie Jackson | City Winery - Chicago
Chicago, IL | Friday
9/25/2026
7:30 PM | |
| Vape! The Grease Parody | Apollo Theater Main Stage - Chicago
Chicago, IL | Friday
9/25/2026
7:30 PM | |
| Topdog/Underdog | Downstairs Theatre At Steppenwolf Theatre - Chicago
Chicago, IL | Friday
9/25/2026
7:30 PM | |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Friday
9/25/2026
7:30 PM | |
| Paula Cole | Thalia Hall
Chicago, IL | Friday
9/25/2026
8:00 PM | |
| Satin Jackets | Outset
Chicago, IL | Friday
9/25/2026
8:00 PM | |
| Nick Hakim | Lincoln Hall
Chicago, IL | Friday
9/25/2026
8:00 PM | |
| Tim Atlas | Schubas
Chicago, IL | Friday
9/25/2026
8:00 PM | |
| Drake White | Joe's Bar On Weed St.
Chicago, IL | Friday
9/25/2026
8:00 PM | |
| Boleros de Noche | Harris Theater
Chicago, IL | Friday
9/25/2026
8:00 PM | |
| Martin Lawrence | Arie Crown Theater
Chicago, IL | Friday
9/25/2026
8:00 PM | |
| Lucy Darling | Studebaker Theater
Chicago, IL | Friday
9/25/2026
8:30 PM | |
| Reggaeton Y2K | House Of Blues - Chicago
Chicago, IL | Friday
9/25/2026
9:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Friday
9/25/2026
9:00 PM | |
| Pat Egan and The Heavy Hearts | Reggie's Music Joint
Chicago, IL | Friday
9/25/2026
9:00 PM | |
| Echoes of Pompeii - Pink Floyd Tribute | Reggie's Rock Club
Chicago, IL | Friday
9/25/2026
9:00 PM | |
| Lauren Watkins | Carol's Pub
Chicago, IL | Friday
9/25/2026
9:00 PM | |
| Two Runner | Hideout - Chicago
Chicago, IL | Friday
9/25/2026
9:00 PM | |
| Anime Rave | Sound-Bar
Chicago, IL | Friday
9/25/2026
9:00 PM | |
| Cliff Cash | Zanies Comedy Club - Chicago
Chicago, IL | Friday
9/25/2026
9:15 PM | |
| Melissa Villasenor | Heath Mainstage At The Den Theatre
Chicago, IL | Friday
9/25/2026
9:15 PM | |
| Theo Katzman | Garcias Chicago
Chicago, IL | Friday
9/25/2026
9:30 PM | |
| San Holo | Radius - IL
Chicago, IL | Friday
9/25/2026
10:00 PM | |
| Virtual Riot & Blanke | Concord Music Hall
Chicago, IL | Friday
9/25/2026
10:00 PM | |
| Croz Boyce | The Empty Bottle
Chicago, IL | Friday
9/25/2026
10:00 PM | |
| Rising Stars Burlesque Revue | Stars and Garters Theater
Chicago, IL | Friday
9/25/2026
10:00 PM | |
| Soul Brunch: Annual Motown Spectacular | City Winery - Chicago
Chicago, IL | Saturday
9/26/2026
12:00 PM | |
| Bright Star Circus | Stars and Garters Theater
Chicago, IL | Saturday
9/26/2026
12:00 PM | |
| Emily St. John Mandel | Thalia Hall
Chicago, IL | Saturday
9/26/2026
2:00 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Saturday
9/26/2026
2:00 PM | |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Saturday
9/26/2026
2:00 PM | |
| Vape! The Grease Parody | Apollo Theater Main Stage - Chicago
Chicago, IL | Saturday
9/26/2026
2:30 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Saturday
9/26/2026
3:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Saturday
9/26/2026
5:00 PM | |
| Marlon James | Thalia Hall
Chicago, IL | Saturday
9/26/2026
5:30 PM | |
| Lucy Darling | Studebaker Theater
Chicago, IL | Saturday
9/26/2026
5:30 PM | |
| Thee Sacred Souls | The Salt Shed Outdoors - Chicago
Chicago, IL | Saturday
9/26/2026
6:00 PM | |
| Melissa Villasenor | Heath Mainstage At The Den Theatre
Chicago, IL | Saturday
9/26/2026
6:00 PM | |
| Russian Circles | Bohemian National Cemetery
Chicago, IL | Saturday
9/26/2026
6:00 PM | |
| NHL Preseason: Chicago Blackhawks vs. St. Louis Blues | United Center
Chicago, IL | Saturday
9/26/2026
6:00 PM | |
| Chicago White Sox vs. Colorado Rockies | Rate Field
Chicago, IL | Saturday
9/26/2026
6:10 PM | |
| Dusty - Artist | Subterranean - Downstairs
Chicago, IL | Saturday
9/26/2026
6:30 PM | |
| YG | House Of Blues - Chicago
Chicago, IL | Saturday
9/26/2026
6:30 PM | |
| Candlelight: Tribute to Phil Collins | Wicker Park Lutheran Church
Chicago, IL | Saturday
9/26/2026
6:30 PM | |
| Bassem Youssef | The Chicago Theatre
Chicago, IL | Saturday
9/26/2026
7:00 PM | |
| Cold Waves XIV Chicago: TR/ST, Haunt Me & Nghtcrwlr - Saturday | Metro Chicago
Chicago, IL | Saturday
9/26/2026
7:00 PM | |
| Cliff Cash | Zanies Comedy Club - Chicago
Chicago, IL | Saturday
9/26/2026
7:00 PM | |
| BK Dhaliwal | Outset
Chicago, IL | Saturday
9/26/2026
7:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Saturday
9/26/2026
7:00 PM | |
| Chicago Symphony Orchestra: Klaus Makela - Sibelius & Shostakovich | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Saturday
9/26/2026
7:30 PM | |
| Top Gun: Maverick in Concert | Auditorium Theatre - IL
Chicago, IL | Saturday
9/26/2026
7:30 PM | |
| Crashing Out Live | Park West
Chicago, IL | Saturday
9/26/2026
7:30 PM | |
| Cortex | Vic Theatre
Chicago, IL | Saturday
9/26/2026
7:30 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Saturday
9/26/2026
7:30 PM | |
| Charlie Burg | Beat Kitchen
Chicago, IL | Saturday
9/26/2026
7:30 PM | |
| The Garden - The Band | Riviera Theatre - IL
Chicago, IL | Saturday
9/26/2026
7:30 PM | |
| EsDeeKid | Byline Bank Aragon Ballroom
Chicago, IL | Saturday
9/26/2026
7:30 PM | |
