| Event | Venue | Date/Time | |
| Loyola Chicago Ramblers vs. George Mason Patriots | Gentile Center
Chicago, IL | Tuesday
1/13/2026
6:00 PM |  |
| Matt Kirshen | Zanies Comedy Club - Chicago
Chicago, IL | Tuesday
1/13/2026
7:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Tuesday
1/13/2026
7:00 PM | |
| Eureka Day | Broadway Playhouse at Water Tower Place
Chicago, IL | Tuesday
1/13/2026
7:00 PM | |
| Paul Chowdhry | Park West
Chicago, IL | Tuesday
1/13/2026
7:30 PM | |
| Chrisette Michele | City Winery - Chicago
Chicago, IL | Tuesday
1/13/2026
7:30 PM | |
| Chicago Underground Comedy | Beat Kitchen
Chicago, IL | Tuesday
1/13/2026
8:00 PM | |
| Stems On Blonde | Schubas
Chicago, IL | Tuesday
1/13/2026
8:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Wednesday
1/14/2026
1:00 PM | |
| Chicago Bulls vs. Utah Jazz | United Center
Chicago, IL | Wednesday
1/14/2026
7:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Wednesday
1/14/2026
7:00 PM | |
| Eureka Day | Broadway Playhouse at Water Tower Place
Chicago, IL | Wednesday
1/14/2026
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Wednesday
1/14/2026
7:00 PM | |
| Crowd Work Wednesday | The Comedy Bar - Chicago
Chicago, IL | Wednesday
1/14/2026
7:00 PM | |
| Chrisette Michele | City Winery - Chicago
Chicago, IL | Wednesday
1/14/2026
7:30 PM | |
| ONEW | Copernicus Center
Chicago, IL | Wednesday
1/14/2026
7:30 PM | |
| Youth Fountain | Subterranean - Downstairs
Chicago, IL | Wednesday
1/14/2026
7:30 PM | |
| Dwayne Neff | Schubas
Chicago, IL | Wednesday
1/14/2026
8:00 PM | |
| Julian Davis Reid & Circle of Trust | Constellation - Chicago
Chicago, IL | Wednesday
1/14/2026
8:30 PM | |
| Jeremy Kahn Trio | Winter's Jazz Club
Chicago, IL | Thursday
1/15/2026
6:30 PM | |
| Nathan Macintosh | Zanies Comedy Club - Chicago
Chicago, IL | Thursday
1/15/2026
7:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Thursday
1/15/2026
7:00 PM | |
| Eureka Day | Broadway Playhouse at Water Tower Place
Chicago, IL | Thursday
1/15/2026
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Thursday
1/15/2026
7:00 PM | |
| Taskmaster Live | Riviera Theatre - IL
Chicago, IL | Thursday
1/15/2026
7:00 PM | |
| OhJay Lamont | The Comedy Bar - Chicago
Chicago, IL | Thursday
1/15/2026
7:00 PM | |
| Chicago Blackhawks vs. Calgary Flames | United Center
Chicago, IL | Thursday
1/15/2026
7:30 PM | |
| Mark Curry | City Winery - Chicago
Chicago, IL | Thursday
1/15/2026
7:30 PM | |
| Wait Wait...Don't Tell Me | Studebaker Theater
Chicago, IL | Thursday
1/15/2026
7:30 PM | |
| Greg Koch | Joe's Bar On Weed St.
Chicago, IL | Thursday
1/15/2026
8:00 PM | |
| Hannah Lacava - Album Release Show | Beat Kitchen
Chicago, IL | Thursday
1/15/2026
8:00 PM | |
| Greenlights Music | Subterranean
Chicago, IL | Thursday
1/15/2026
8:00 PM | |
| Kayo Dot | Reggie's Music Joint
Chicago, IL | Thursday
1/15/2026
8:00 PM | |
| Kenny Reichert Quartet | Constellation - Chicago
Chicago, IL | Thursday
1/15/2026
8:30 PM | |
| M.O.T.O. | The Empty Bottle
Chicago, IL | Thursday
1/15/2026
9:00 PM | |
| Roast Battle Chicago | Zanies Comedy Club - Chicago
Chicago, IL | Thursday
1/15/2026
9:30 PM | |
| Cubs Convention - 3 Day Pass | Sheraton Chicago Hotel & Towers
Chicago, IL | Friday
1/16/2026
TBD | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Friday
1/16/2026
7:00 PM | |
| Eureka Day | Broadway Playhouse at Water Tower Place
Chicago, IL | Friday
1/16/2026
7:00 PM | |
| Freak On A Leash - Korn Tribute | Bottom Lounge
Chicago, IL | Friday
1/16/2026
7:00 PM | |
| Nathan Macintosh | Zanies Comedy Club - Chicago
Chicago, IL | Friday
1/16/2026
7:00 PM | |
| The Lineage | Subterranean - Downstairs
Chicago, IL | Friday
1/16/2026
7:00 PM | |
| Femdot | The Loft at Ramova Theatre
Chicago, IL | Friday
1/16/2026
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Friday
1/16/2026
7:00 PM | |
| DePaul Blue Demons vs. Marquette Golden Eagles | Wintrust Arena
Chicago, IL | Friday
1/16/2026
7:30 PM | |
| Joe Torry | City Winery - Chicago
Chicago, IL | Friday
1/16/2026
7:30 PM | |
| Angel Spiccia | Winter's Jazz Club
Chicago, IL | Friday
1/16/2026
7:30 PM | |
| Trouble Ahead - Grateful Dead Tribute Nite | Garcias Chicago
Chicago, IL | Friday
1/16/2026
8:00 PM | |
| Everything Yes | Beat Kitchen
Chicago, IL | Friday
1/16/2026
8:00 PM | |
| ARMNHMR | The Salt Shed Indoors - Chicago
Chicago, IL | Friday
1/16/2026
8:00 PM | |
| Glamor Mirage | Reggie's Music Joint
Chicago, IL | Friday
1/16/2026
9:00 PM | |
| Doug Shorts | Reggie's Rock Club
Chicago, IL | Friday
1/16/2026
9:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Friday
1/16/2026
9:00 PM | |
| Brady Matthews | The Comedy Bar - Chicago
Chicago, IL | Friday
1/16/2026
9:00 PM | |
| Austra | Sleeping Village
Chicago, IL | Friday
1/16/2026
9:00 PM | |
| Real Estate | Metro Chicago
Chicago, IL | Friday
1/16/2026
9:00 PM | |
| Nathan Macintosh | Zanies Comedy Club - Chicago
Chicago, IL | Friday
1/16/2026
9:15 PM | |
| Broadway Rave | Subterranean
Chicago, IL | Friday
1/16/2026
9:30 PM | |
| Hannah Geiser | Carol's Pub
Chicago, IL | Friday
1/16/2026
9:30 PM | |
| Cheat Codes | Sound-Bar
Chicago, IL | Friday
1/16/2026
10:00 PM | |
| ALLEYCVT | Concord Music Hall
Chicago, IL | Friday
1/16/2026
10:00 PM | |
| Nora En Pure | Cermak Hall At Radius - IL
Chicago, IL | Friday
1/16/2026
10:00 PM | |
| Quinn Dale | Avondale Music Hall
Chicago, IL | Friday
1/16/2026
10:00 PM | |
| North by North | The Empty Bottle
Chicago, IL | Friday
1/16/2026
10:00 PM | |
| Xandra | TAO Nightclub - Chicago
Chicago, IL | Friday
1/16/2026
11:00 PM | |
| Chicago State Cougars vs. Le Moyne Dolphins | Jones Convocation Center
Chicago, IL | Saturday
1/17/2026
1:00 PM | |
| DePaul Blue Demons Women's Basketball vs. Seton Hall Pirates | Wintrust Arena
Chicago, IL | Saturday
1/17/2026
2:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Saturday
1/17/2026
2:00 PM | |
| Eureka Day | Broadway Playhouse at Water Tower Place
Chicago, IL | Saturday
1/17/2026
2:00 PM | |
| Illinois-Chicago Flames vs. Drake Bulldogs | Credit Union 1 Arena
Chicago, IL | Saturday
1/17/2026
2:00 PM | |
| Several States | Ramova Theatre
Chicago, IL | Saturday
1/17/2026
2:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
1/17/2026
3:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
1/17/2026
5:00 PM | |
| Chicago Blackhawks vs. Boston Bruins | United Center
Chicago, IL | Saturday
1/17/2026
7:00 PM | |
| Nathan Macintosh | Zanies Comedy Club - Chicago
Chicago, IL | Saturday
1/17/2026
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
1/17/2026
7:00 PM | |
| Brady Matthews | The Comedy Bar - Chicago
Chicago, IL | Saturday
1/17/2026
7:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Saturday
1/17/2026
7:30 PM | |
| Eureka Day | Broadway Playhouse at Water Tower Place
Chicago, IL | Saturday
1/17/2026
7:30 PM | |
| Ban Paterson Trio | Winter's Jazz Club
Chicago, IL | Saturday
1/17/2026
7:30 PM | |
| Brian Regan | The Chicago Theatre
Chicago, IL | Saturday
1/17/2026
8:00 PM | |
| Rebirth Brass Band | Thalia Hall
Chicago, IL | Saturday
1/17/2026
8:00 PM | |
| Garry Princeton and The Flyover Country Band | Beat Kitchen
Chicago, IL | Saturday
1/17/2026
8:00 PM | |
| Henry Holden | Reggie's Music Joint
Chicago, IL | Saturday
1/17/2026
8:30 PM | |
| Dee Dee Bridgewater & Bill Charlap | City Winery - Chicago
Chicago, IL | Saturday
1/17/2026
8:30 PM | |
| Modern Nature | Constellation - Chicago
Chicago, IL | Saturday
1/17/2026
8:30 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
1/17/2026
9:00 PM | |
| Brady Matthews | The Comedy Bar - Chicago
Chicago, IL | Saturday
1/17/2026
9:00 PM | |
| Whiskey Friends - Tribute to Morgan Wallen | Joe's Bar On Weed St.
Chicago, IL | Saturday
1/17/2026
9:00 PM | |
| Hatis Noit | The Empty Bottle
Chicago, IL | Saturday
1/17/2026
9:00 PM | |
| Nathan Macintosh | Zanies Comedy Club - Chicago
Chicago, IL | Saturday
1/17/2026
9:15 PM | |
| Ferry Corsten | Sound-Bar
Chicago, IL | Saturday
1/17/2026
10:00 PM | |
| ALLEYCVT | Concord Music Hall
Chicago, IL | Saturday
1/17/2026
10:00 PM | |
| Dj Five | TAO Nightclub - Chicago
Chicago, IL | Saturday
1/17/2026
11:00 PM | |
| PARKING: NFC Divisional Home Game: Chicago Bears vs. Los Angeles Rams | Soldier Field Parking Lot
Chicago, IL | Sunday
1/18/2026
TBD | |
| NFC Divisional Home Game: Chicago Bears vs. Los Angeles Rams | Soldier Field
Chicago, IL | Sunday
1/18/2026
TBD | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Sunday
1/18/2026
1:00 PM | |
| Eureka Day | Broadway Playhouse at Water Tower Place
Chicago, IL | Sunday
1/18/2026
2:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Sunday
1/18/2026
3:00 PM | |
| Orquesta Sinfonica De Mineria | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Sunday
1/18/2026
3:00 PM | |
