| Event | Venue | Date/Time | |
| Chicago Symphony Orchestra: Pekka Kuusisto - Time Shifting | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Thursday
5/21/2026
7:30 PM |  |
| The Klezmatics | City Winery - Chicago
Chicago, IL | Thursday
5/21/2026
7:30 PM | |
| Concrete Boys | Park West
Chicago, IL | Thursday
5/21/2026
7:30 PM | |
| Fault | The Yard at Chicago Shakespeare Theatre
Chicago, IL | Thursday
5/21/2026
7:30 PM | |
| Clara La San | Riviera Theatre - IL
Chicago, IL | Thursday
5/21/2026
7:30 PM | |
| Windfall | Ensemble Theater At Steppenwolf Theatre
Chicago, IL | Thursday
5/21/2026
7:30 PM | |
| Covenant - Play | Owen Bruner Goodman Theatre
Chicago, IL | Thursday
5/21/2026
7:30 PM | |
| Paige and the Kizers | Lemon Chicago
Chicago, IL | Thursday
5/21/2026
7:30 PM | |
| Greenlights Music | Beat Kitchen
Chicago, IL | Thursday
5/21/2026
8:00 PM | |
| Fightmaster | Lincoln Hall
Chicago, IL | Thursday
5/21/2026
8:00 PM | |
| Twin Peaks | Thalia Hall
Chicago, IL | Thursday
5/21/2026
8:00 PM | |
| Tom Kenny and The Hi-Seas | Reggie's Rock Club
Chicago, IL | Thursday
5/21/2026
8:00 PM | |
| Chicago Cubs vs. Houston Astros | Wrigley Field
Chicago, IL | Friday
5/22/2026
1:20 PM | |
| Chicago Symphony Orchestra: Pekka Kuusisto - Time Shifting | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Friday
5/22/2026
1:30 PM | |
| Solomun | Union Park
Chicago, IL | Friday
5/22/2026
4:00 PM | |
| Black Veil Brides, From Ashes to New & As December Falls | Ramova Theatre
Chicago, IL | Friday
5/22/2026
5:30 PM | |
| Slide Away | Byline Bank Aragon Ballroom
Chicago, IL | Friday
5/22/2026
6:00 PM | |
| Archspire | House Of Blues - Chicago
Chicago, IL | Friday
5/22/2026
6:00 PM | |
| Monty Python's Spamalot | CIBC Theatre
Chicago, IL | Friday
5/22/2026
7:00 PM | |
| Les Miserables | Cadillac Palace
Chicago, IL | Friday
5/22/2026
7:00 PM | |
| La'Trez Anderson | The Comedy Bar - Chicago
Chicago, IL | Friday
5/22/2026
7:00 PM | |
| The Nubile Thangs | Subterranean - Downstairs
Chicago, IL | Friday
5/22/2026
7:00 PM | |
| LOKI - The End of the World Tour | Lifeline Theatre
Chicago, IL | Friday
5/22/2026
7:30 PM | |
| Inept | Beat Kitchen
Chicago, IL | Friday
5/22/2026
7:30 PM | |
| The Kid Laroi | The Salt Shed Outdoors - Chicago
Chicago, IL | Friday
5/22/2026
7:30 PM | |
| The Voices - Tribute to Motown | City Winery - Chicago
Chicago, IL | Friday
5/22/2026
7:30 PM | |
| Fault | The Yard at Chicago Shakespeare Theatre
Chicago, IL | Friday
5/22/2026
7:30 PM | |
| Covenant - Play | Owen Bruner Goodman Theatre
Chicago, IL | Friday
5/22/2026
7:30 PM | |
| Jess Swanson Trio | Lemon Chicago
Chicago, IL | Friday
5/22/2026
7:30 PM | |
| Windfall | Ensemble Theater At Steppenwolf Theatre
Chicago, IL | Friday
5/22/2026
7:30 PM | |
| Heavy Crownz | Lincoln Hall
Chicago, IL | Friday
5/22/2026
8:00 PM | |
| The Orchard | Schubas
Chicago, IL | Friday
5/22/2026
8:00 PM | |
| The Bean Tones | Joe's Bar On Weed St.
Chicago, IL | Friday
5/22/2026
8:00 PM | |
| Hot Like Mars | Garcias Chicago
Chicago, IL | Friday
5/22/2026
8:00 PM | |
| Shamilton, The Improvised Hip-Hop American Musical | Donny's Skybox Theatre at Second City - Chicago
Chicago, IL | Friday
5/22/2026
8:30 PM | |
| AirOtic Soiree - A Circus-Style Burlesque Show | Experience 868 Events
Chicago, IL | Friday
5/22/2026
8:30 PM | |
| Yailin | V Live- Chicago
Chicago, IL | Friday
5/22/2026
9:00 PM | |
| A Night of Bob Dylan Music | Reggie's Music Joint
Chicago, IL | Friday
5/22/2026
9:00 PM | |
| La'Trez Anderson | The Comedy Bar - Chicago
Chicago, IL | Friday
5/22/2026
9:00 PM | |
| The Brokes - The Strokes Experience | Reggie's Rock Club
Chicago, IL | Friday
5/22/2026
9:00 PM | |
| Broadway Rave | Subterranean
Chicago, IL | Friday
5/22/2026
9:30 PM | |
| Yoi Toki | Bottom Lounge
Chicago, IL | Friday
5/22/2026
10:00 PM | |
| Cole DeGenova | Lemon Chicago
Chicago, IL | Friday
5/22/2026
10:30 PM | |
| Forever Mine Music Festival - 2 Day Pass | Union Park
Chicago, IL | Saturday
5/23/2026
TBD | |
| Suenos Music Festival - 2 Day Pass | Hutchinson Field Grant Park
Chicago, IL | Saturday
5/23/2026
TBD | |
| Chicago Sky vs. Minnesota Lynx | Wintrust Arena
Chicago, IL | Saturday
5/23/2026
12:00 PM | |
| Chicago Cubs vs. Houston Astros | Wrigley Field
Chicago, IL | Saturday
5/23/2026
1:20 PM | |
| Warm Love Cool Dreams: The Jesus and Mary Chain, Tortoise & Smerz - Saturday | The Salt Shed Outdoors - Chicago
Chicago, IL | Saturday
5/23/2026
2:00 PM | |
| Monty Python's Spamalot | CIBC Theatre
Chicago, IL | Saturday
5/23/2026
2:00 PM | |
| Les Miserables | Cadillac Palace
Chicago, IL | Saturday
5/23/2026
2:00 PM | |
| LOKI - The End of the World Tour | Lifeline Theatre
Chicago, IL | Saturday
5/23/2026
2:30 PM | |
| Fault | The Yard at Chicago Shakespeare Theatre
Chicago, IL | Saturday
5/23/2026
2:30 PM | |
| Windfall | Ensemble Theater At Steppenwolf Theatre
Chicago, IL | Saturday
5/23/2026
3:00 PM | |
| Slide Away | Byline Bank Aragon Ballroom
Chicago, IL | Saturday
5/23/2026
6:00 PM | |
| Fallout Funny Comedy Tour | City Winery - Chicago
Chicago, IL | Saturday
5/23/2026
6:00 PM | |
| Decibel Magazine Tour: Cryptopsy, Necrot, Fulci & Blood Monolith | Bottom Lounge
Chicago, IL | Saturday
5/23/2026
7:00 PM | |
| Kurt Rosenwinkel | Garcias Chicago
Chicago, IL | Saturday
5/23/2026
7:00 PM | |
| Inept | Beat Kitchen
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| The Dialogue of Memories | Studebaker Theater
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| LOKI - The End of the World Tour | Lifeline Theatre
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Chicago Fire FC vs. Toronto FC | Soldier Field
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Chicago Symphony Orchestra: Pekka Kuusisto - Time Shifting | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Les Miserables | Cadillac Palace
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Monty Python's Spamalot | CIBC Theatre
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Covenant - Play | Owen Bruner Goodman Theatre
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Windfall | Ensemble Theater At Steppenwolf Theatre
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Yves | Copernicus Center
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Fault | The Yard at Chicago Shakespeare Theatre
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| Biologica y Su Combo | Lemon Chicago
Chicago, IL | Saturday
5/23/2026
7:30 PM | |
| The Bishop's Daredevil Stunt Club | Reggie's Music Joint
Chicago, IL | Saturday
5/23/2026
8:00 PM | |
| Trap Bingo | House Of Blues - Chicago
Chicago, IL | Saturday
5/23/2026
8:00 PM | |
| AirOtic Soiree - A Circus-Style Burlesque Show | Experience 868 Events
Chicago, IL | Saturday
5/23/2026
8:30 PM | |
| Candlelight: Neo-Soul Favorites | Wicker Park Lutheran Church
Chicago, IL | Saturday
5/23/2026
8:30 PM | |
| D.R.I. (Dirty Rotten Imbeciles) | Reggie's Rock Club
Chicago, IL | Saturday
5/23/2026
8:30 PM | |
| Pleasures - An R&B Party | Schubas
Chicago, IL | Saturday
5/23/2026
9:00 PM | |
| Recession Indicatior: Recession Pop Dance Party | Lincoln Hall
Chicago, IL | Saturday
5/23/2026
9:00 PM | |
| Fallout Funny Comedy Tour | City Winery - Chicago
Chicago, IL | Saturday
5/23/2026
9:30 PM | |
| Kurt Rosenwinkel | Garcias Chicago
Chicago, IL | Saturday
5/23/2026
9:30 PM | |
| BRESH | Cermak Hall At Radius - IL
Chicago, IL | Saturday
5/23/2026
10:00 PM | |
| Furball | Metro Chicago
Chicago, IL | Saturday
5/23/2026
11:30 PM | |
| Forever Mine Music Festival - Sunday | Union Park
Chicago, IL | Sunday
5/24/2026
TBD | |
| Monty Python's Spamalot | CIBC Theatre
Chicago, IL | Sunday
5/24/2026
1:00 PM | |
| Les Miserables | Cadillac Palace
Chicago, IL | Sunday
5/24/2026
1:00 PM | |
| Chicago Cubs vs. Houston Astros | Wrigley Field
Chicago, IL | Sunday
5/24/2026
1:20 PM | |
| Covenant - Play | Owen Bruner Goodman Theatre
Chicago, IL | Sunday
5/24/2026
2:00 PM | |
| Warm Love Cool Dreams: Courtney Barnett, Toro y Moi & Whitney - Sunday | The Salt Shed Outdoors - Chicago
Chicago, IL | Sunday
5/24/2026
2:00 PM | |
| LOKI - The End of the World Tour | Lifeline Theatre
Chicago, IL | Sunday
5/24/2026
2:30 PM | |
| Fault | The Yard at Chicago Shakespeare Theatre
Chicago, IL | Sunday
5/24/2026
2:30 PM | |
| The Dialogue of Memories | Studebaker Theater
Chicago, IL | Sunday
5/24/2026
3:00 PM | |
| Hilary Hahn | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Sunday
5/24/2026
3:00 PM | |
| ARC At The Lake: Sistek | Castaways
Chicago, IL | Sunday
5/24/2026
4:00 PM | |
| Thornhill | Vic Theatre
Chicago, IL | Sunday
5/24/2026
6:00 PM | |
| Monty Python's Spamalot | CIBC Theatre
Chicago, IL | Sunday
5/24/2026
6:30 PM | |
| Murphy Lee and Kyjuan | City Winery - Chicago
Chicago, IL | Sunday
5/24/2026
7:00 PM | |
| Em Brown | Zanies Comedy Club - Chicago
Chicago, IL | Sunday
5/24/2026
7:00 PM | |
| Chicago's Best Comedy Show | The Comedy Bar - Chicago
Chicago, IL | Sunday
5/24/2026
7:00 PM | |
| Diva Bleach | Beat Kitchen
Chicago, IL | Sunday
5/24/2026
7:30 PM | |
| Covenant - Play | Owen Bruner Goodman Theatre
Chicago, IL | Sunday
5/24/2026
7:30 PM | |
| Johnny Kilroy | Reggie's Music Joint
Chicago, IL | Sunday
5/24/2026
8:00 PM | |
| Snowcuffs | The Empty Bottle
Chicago, IL | Sunday
5/24/2026
9:00 PM | |
