| Event | Venue | Date/Time | |
| The Red Clay Strays | The Salt Shed Outdoors - Chicago
Chicago, IL | Wednesday
9/3/2025
6:30 PM |  |
| Chicago Cubs vs. Atlanta Braves | Wrigley Field
Chicago, IL | Wednesday
9/3/2025
6:40 PM | |
| Chicago Sky vs. Connecticut Sun | Wintrust Arena
Chicago, IL | Wednesday
9/3/2025
7:00 PM | |
| Dungeons & Dragons: The Twenty-Sided Tavern | Broadway Playhouse at Water Tower Place
Chicago, IL | Wednesday
9/3/2025
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Wednesday
9/3/2025
7:00 PM | |
| The Black Keys | Huntington Bank Pavilion at Northerly Island
Chicago, IL | Wednesday
9/3/2025
7:30 PM | |
| 44 - The Unofficial, Unsanctioned Obama Musical | Studebaker Theater
Chicago, IL | Wednesday
9/3/2025
7:30 PM | |
| Finn Wolfhard | Thalia Hall
Chicago, IL | Wednesday
9/3/2025
7:30 PM | |
| Kofi B | City Winery - Chicago
Chicago, IL | Wednesday
9/3/2025
7:30 PM | |
| Caskey | Subterranean
Chicago, IL | Wednesday
9/3/2025
8:00 PM | |
| 3l3d3p | Beat Kitchen
Chicago, IL | Wednesday
9/3/2025
8:00 PM | |
| The Red Clay Strays | The Salt Shed Outdoors - Chicago
Chicago, IL | Thursday
9/4/2025
6:30 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Thursday
9/4/2025
7:00 PM | |
| Do or Die Comedy | The Laugh Factory - Chicago
Chicago, IL | Thursday
9/4/2025
7:00 PM | |
| Dungeons & Dragons: The Twenty-Sided Tavern | Broadway Playhouse at Water Tower Place
Chicago, IL | Thursday
9/4/2025
7:00 PM | |
| Alec Flynn | Zanies Comedy Club - Chicago
Chicago, IL | Thursday
9/4/2025
7:00 PM | |
| The Music of David Sanborn - Tribute | City Winery - Chicago
Chicago, IL | Thursday
9/4/2025
7:30 PM | |
| AJ McQueen | Subterranean
Chicago, IL | Thursday
9/4/2025
8:00 PM | |
| The Steeldrivers | Thalia Hall
Chicago, IL | Thursday
9/4/2025
8:00 PM | |
| Louden Swain | Beat Kitchen
Chicago, IL | Thursday
9/4/2025
8:00 PM | |
| K Camp | Vic Theatre
Chicago, IL | Thursday
9/4/2025
8:00 PM | |
| Clay Street Unit | Garcias Chicago
Chicago, IL | Thursday
9/4/2025
8:00 PM | |
| AJ Lee and Blue Summit & East Nash Grass | Old Town School of Folk Music
Chicago, IL | Thursday
9/4/2025
8:00 PM | |
| Joe Di Zillo | Reggie's Music Joint
Chicago, IL | Thursday
9/4/2025
8:00 PM | |
| Hide - Band | The Empty Bottle
Chicago, IL | Thursday
9/4/2025
9:00 PM | |
| Chicago's Best Stand Up | The Laugh Factory - Chicago
Chicago, IL | Thursday
9/4/2025
9:00 PM | |
| Roast Battle | Zanies Comedy Club - Chicago
Chicago, IL | Thursday
9/4/2025
9:15 PM | |
| Chicago Cubs vs. Washington Nationals | Wrigley Field
Chicago, IL | Friday
9/5/2025
1:20 PM | |
| PUP & Jeff Rosenstock | The Salt Shed Outdoors - Chicago
Chicago, IL | Friday
9/5/2025
6:30 PM | |
| Chris Distefano | The Chicago Theatre
Chicago, IL | Friday
9/5/2025
7:00 PM | |
| Alec Flynn | Zanies Comedy Club - Chicago
Chicago, IL | Friday
9/5/2025
7:00 PM | |
| Clued In - An Improvised Murder Mystery | Donny's Skybox Theatre at Second City - Chicago
Chicago, IL | Friday
9/5/2025
7:00 PM | |
| The Second City e.t.c. 49th Revue | e.t.c. Theater at Second City - Chicago
Chicago, IL | Friday
9/5/2025
7:00 PM | |
| First Date Comedy Gameshow | The Laugh Factory - Chicago
Chicago, IL | Friday
9/5/2025
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Friday
9/5/2025
7:00 PM | |
| Erthe St. James | City Winery - Chicago
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| Dua Lipa & Cil | United Center
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| TWRP | Thalia Hall
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| 44 - The Unofficial, Unsanctioned Obama Musical | Studebaker Theater
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| 10cc | Park West
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| Dungeons & Dragons: The Twenty-Sided Tavern | Broadway Playhouse at Water Tower Place
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| Le Sserafim | Wintrust Arena
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| George Porter Jr. & Runnin Pardners | Garcias Chicago
Chicago, IL | Friday
9/5/2025
8:00 PM | |
| The Emo Night Tour | Bottom Lounge
Chicago, IL | Friday
9/5/2025
8:00 PM | |
| Mykele Deville | Metro Chicago
Chicago, IL | Friday
9/5/2025
8:00 PM | |
| Christian French | Reggie's Rock Club
Chicago, IL | Friday
9/5/2025
8:00 PM | |
| Sparkle Carcass & Mike Giannini | Carol's Pub
Chicago, IL | Friday
9/5/2025
8:00 PM | |
| Shemekia Copeland | Gary & Laura Maurer Concert Hall at Old Town School of Folk Music
Chicago, IL | Friday
9/5/2025
8:00 PM | |
| Andrew Lucier | Beat Kitchen
Chicago, IL | Friday
9/5/2025
8:00 PM | |
| Shamilton - A Drag Musical Parody | Donny's Skybox Theatre at Second City - Chicago
Chicago, IL | Friday
9/5/2025
8:30 PM | |
| FINGY - The Club Etiquette Release Party | Bookclub
Chicago, IL | Friday
9/5/2025
9:00 PM | |
| Emo Nite | Subterranean
Chicago, IL | Friday
9/5/2025
9:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Friday
9/5/2025
9:00 PM | |
| Alec Flynn | Zanies Comedy Club - Chicago
Chicago, IL | Friday
9/5/2025
9:15 PM | |
| Lowkey Funny Comedy Show | The Laugh Factory - Chicago
Chicago, IL | Friday
9/5/2025
9:15 PM | |
| Apex Martin | Sound-Bar
Chicago, IL | Friday
9/5/2025
10:00 PM | |
| Diox | TAO Nightclub - Chicago
Chicago, IL | Friday
9/5/2025
11:00 PM | |
| Dum and Drummer Comedy Showcase | The Laugh Factory - Chicago
Chicago, IL | Friday
9/5/2025
11:30 PM | |
| The Gospel According To Chicago Brunch | City Winery - Chicago
Chicago, IL | Saturday
9/6/2025
12:00 PM | |
| Chicago Cubs vs. Washington Nationals | Wrigley Field
Chicago, IL | Saturday
9/6/2025
1:20 PM | |
| Dungeons & Dragons: The Twenty-Sided Tavern | Broadway Playhouse at Water Tower Place
Chicago, IL | Saturday
9/6/2025
2:00 PM | |
| 44 - The Unofficial, Unsanctioned Obama Musical | Studebaker Theater
Chicago, IL | Saturday
9/6/2025
2:30 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
9/6/2025
5:00 PM | |
| The 30+ Party | House Of Blues - Chicago
Chicago, IL | Saturday
9/6/2025
5:30 PM | |
| Candlelight: Tribute to Taylor Swift | Stan Mansion
Chicago, IL | Saturday
9/6/2025
6:30 PM | |
| d4vd | The Salt Shed Outdoors - Chicago
Chicago, IL | Saturday
9/6/2025
6:30 PM | |
| Alec Flynn | Zanies Comedy Club - Chicago
Chicago, IL | Saturday
9/6/2025
7:00 PM | |
| Clued In - An Improvised Murder Mystery | Donny's Skybox Theatre at Second City - Chicago
Chicago, IL | Saturday
9/6/2025
7:00 PM | |
| The Second City e.t.c. 49th Revue | e.t.c. Theater at Second City - Chicago
Chicago, IL | Saturday
9/6/2025
7:00 PM | |
| Talking Sopranos - A Conversation with Michael Imerioli and Steve Schirripa | Historic Main Stage at Athenaeum Center - IL
Chicago, IL | Saturday
9/6/2025
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
9/6/2025
7:00 PM | |
| Chicago's Best Stand Up | The Laugh Factory - Chicago
Chicago, IL | Saturday
9/6/2025
7:00 PM | |
| Uncle Charlie's R&B Cookout: Charlie Wilson, Babyface & K-Ci | Huntington Bank Pavilion at Northerly Island
Chicago, IL | Saturday
9/6/2025
7:15 PM | |
| Dua Lipa & Cil | United Center
Chicago, IL | Saturday
9/6/2025
7:30 PM | |
| Ashland Avenue | Albert Ivar Goodman Theatre
Chicago, IL | Saturday
9/6/2025
7:30 PM | |
| Dungeons & Dragons: The Twenty-Sided Tavern | Broadway Playhouse at Water Tower Place
Chicago, IL | Saturday
9/6/2025
7:30 PM | |
| 44 - The Unofficial, Unsanctioned Obama Musical | Studebaker Theater
Chicago, IL | Saturday
9/6/2025
7:30 PM | |
| Sounds Of Blackness | City Winery - Chicago
Chicago, IL | Saturday
9/6/2025
7:30 PM | |
| Pink Turns Blue | Bottom Lounge
Chicago, IL | Saturday
9/6/2025
8:00 PM | |
| Andres Parra | Copernicus Center
Chicago, IL | Saturday
9/6/2025
8:00 PM | |
| Kruder and Dorfmeister | Auditorium Theatre - IL
Chicago, IL | Saturday
9/6/2025
8:00 PM | |
| George Porter Jr. & Runnin Pardners | Garcias Chicago
Chicago, IL | Saturday
9/6/2025
8:00 PM | |
| Blue Heaven | Black Ensemble Theater
Chicago, IL | Saturday
9/6/2025
8:00 PM | |
| Madison Ryann Ward | Vic Theatre
Chicago, IL | Saturday
9/6/2025
8:00 PM | |
| Baby Wants Candy | Donny's Skybox Theatre at Second City - Chicago
Chicago, IL | Saturday
9/6/2025
8:30 PM | |
| Joe Wortell and His Country Band | Carol's Pub
Chicago, IL | Saturday
9/6/2025
9:00 PM | |
| Music for the Masses: Dark 80s New Wave Nite | Beat Kitchen
Chicago, IL | Saturday
9/6/2025
9:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
9/6/2025
9:00 PM | |
| Telula | Reggie's Music Joint
Chicago, IL | Saturday
9/6/2025
9:00 PM | |
| El Circo | Joe's Bar On Weed St.
Chicago, IL | Saturday
9/6/2025
9:00 PM | |
| Sam Evian | The Empty Bottle
Chicago, IL | Saturday
9/6/2025
9:00 PM | |
| Satin Jackets | Subterranean
Chicago, IL | Saturday
9/6/2025
9:00 PM | |
| Alec Flynn | Zanies Comedy Club - Chicago
Chicago, IL | Saturday
9/6/2025
9:15 PM | |
| Chicago's Best Stand Up | The Laugh Factory - Chicago
Chicago, IL | Saturday
9/6/2025
9:15 PM | |
| Binge the Fringe | Io Theater
Chicago, IL | Saturday
9/6/2025
9:30 PM | |
| The Taylor Party | House Of Blues - Chicago
Chicago, IL | Saturday
9/6/2025
9:30 PM | |
| Uncle Waffles | Ramova Theatre
Chicago, IL | Saturday
9/6/2025
9:30 PM | |
| MCR-T | Smart Bar Chicago
Chicago, IL | Saturday
9/6/2025
10:00 PM | |
| Jerome Isma-Ae | Sound-Bar
Chicago, IL | Saturday
9/6/2025
10:00 PM | |
| BRESH | Radius - IL
Chicago, IL | Saturday
9/6/2025
10:00 PM | |
