| Event | Venue | Date/Time | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Friday
1/2/2026
1:00 PM |  |
| Chicago State Cougars vs. Wagner Seahawks | Jones Convocation Center
Chicago, IL | Friday
1/2/2026
6:00 PM | |
| Chicago Bulls vs. Orlando Magic | United Center
Chicago, IL | Friday
1/2/2026
7:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Friday
1/2/2026
7:00 PM | |
| Correy Bell | The Comedy Bar - Chicago
Chicago, IL | Friday
1/2/2026
7:00 PM | |
| Umphrey's McGee | The Salt Shed Indoors - Chicago
Chicago, IL | Friday
1/2/2026
7:30 PM | |
| The Voices Trilogy | City Winery - Chicago
Chicago, IL | Friday
1/2/2026
7:30 PM | |
| Joe Marcinek Band | Garcias Chicago
Chicago, IL | Friday
1/2/2026
8:30 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Friday
1/2/2026
9:00 PM | |
| Correy Bell | The Comedy Bar - Chicago
Chicago, IL | Friday
1/2/2026
9:00 PM | |
| Loyola Chicago Ramblers vs. Dayton Flyers | Gentile Center
Chicago, IL | Saturday
1/3/2026
1:00 PM | |
| DePaul Blue Demons vs. Xavier Musketeers | Wintrust Arena
Chicago, IL | Saturday
1/3/2026
1:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Saturday
1/3/2026
2:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
1/3/2026
3:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
1/3/2026
5:00 PM | |
| Chicago Bulls vs. Charlotte Hornets | United Center
Chicago, IL | Saturday
1/3/2026
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
1/3/2026
7:00 PM | |
| Loyola Chicago Ramblers Women's Basketball vs. Rhode Island Rams | Gentile Center
Chicago, IL | Saturday
1/3/2026
7:00 PM | |
| Correy Bell | The Comedy Bar - Chicago
Chicago, IL | Saturday
1/3/2026
7:00 PM | |
| Moonbird | Subterranean - Downstairs
Chicago, IL | Saturday
1/3/2026
7:00 PM | |
| Umphrey's McGee | The Salt Shed Indoors - Chicago
Chicago, IL | Saturday
1/3/2026
7:30 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Saturday
1/3/2026
7:30 PM | |
| Animal Panic | Subterranean
Chicago, IL | Saturday
1/3/2026
7:30 PM | |
| Railheart | Garcias Chicago
Chicago, IL | Saturday
1/3/2026
8:00 PM | |
| Speed Therapy | Schubas
Chicago, IL | Saturday
1/3/2026
8:30 PM | |
| Daniel Knox | Constellation - Chicago
Chicago, IL | Saturday
1/3/2026
8:30 PM | |
| Correy Bell | The Comedy Bar - Chicago
Chicago, IL | Saturday
1/3/2026
9:00 PM | |
| Bowie Ball | Metro Chicago
Chicago, IL | Saturday
1/3/2026
9:00 PM | |
| Riot! At the Disco | Beat Kitchen
Chicago, IL | Saturday
1/3/2026
9:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Saturday
1/3/2026
9:00 PM | |
| Spice Factory | Subterranean - Downstairs
Chicago, IL | Saturday
1/3/2026
10:00 PM | |
| PARKING: Chicago Bears vs. Detroit Lions | Soldier Field Parking Lot
Chicago, IL | Sunday
1/4/2026
TBD | |
| Tailgreeter Tailgate: Chicago Bears vs. Detroit Lions | Tailgreeter All-Inclusive Tailgate - Soldier Field
Chicago, IL | Sunday
1/4/2026
TBD | |
| Chicago State Cougars vs. Long Island University Sharks | Jones Convocation Center
Chicago, IL | Sunday
1/4/2026
1:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Sunday
1/4/2026
1:00 PM | |
| Illinois-Chicago Flames Women's Basketball vs. Indiana State Sycamores | Credit Union 1 Arena
Chicago, IL | Sunday
1/4/2026
2:00 PM | |
| DePaul Blue Demons Women's Basketball vs. Providence Friars | Wintrust Arena
Chicago, IL | Sunday
1/4/2026
2:00 PM | |
| Chicago Bears vs. Detroit Lions | Soldier Field
Chicago, IL | Sunday
1/4/2026
3:25 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Sunday
1/4/2026
5:00 PM | |
| Chicago Blackhawks vs. Vegas Golden Knights | United Center
Chicago, IL | Sunday
1/4/2026
6:00 PM | |
| The Collideoscopes | Subterranean
Chicago, IL | Sunday
1/4/2026
7:00 PM | |
| Draggy Tingz | Subterranean - Downstairs
Chicago, IL | Sunday
1/4/2026
8:00 PM | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Monday
1/5/2026
6:00 PM | |
| Super Six Showcase | Zanies Comedy Club - Chicago
Chicago, IL | Monday
1/5/2026
7:00 PM | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Monday
1/5/2026
9:30 PM | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Tuesday
1/6/2026
6:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Tuesday
1/6/2026
7:00 PM | |
| DePaul Blue Demons vs. Georgetown Hoyas | Wintrust Arena
Chicago, IL | Tuesday
1/6/2026
7:00 PM | |
| Chloe La Branche | Zanies Comedy Club - Chicago
Chicago, IL | Tuesday
1/6/2026
7:00 PM | |
| Giant Pit of Glass | Schubas
Chicago, IL | Tuesday
1/6/2026
7:30 PM | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Tuesday
1/6/2026
9:30 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Wednesday
1/7/2026
1:00 PM | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Wednesday
1/7/2026
6:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Wednesday
1/7/2026
7:00 PM | |
| Joey Villagomez | Zanies Comedy Club - Chicago
Chicago, IL | Wednesday
1/7/2026
7:00 PM | |
| Illinois-Chicago Flames vs. Southern Illinois Salukis | Credit Union 1 Arena
Chicago, IL | Wednesday
1/7/2026
7:00 PM | |
| Moo Court | Studebaker Theater
Chicago, IL | Wednesday
1/7/2026
7:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Wednesday
1/7/2026
7:00 PM | |
| Carter Ward | Schubas
Chicago, IL | Wednesday
1/7/2026
7:30 PM | |
| Loyola Chicago Ramblers vs. Davidson Wildcats | Gentile Center
Chicago, IL | Wednesday
1/7/2026
8:00 PM | |
| Chicago Blackhawks vs. St. Louis Blues | United Center
Chicago, IL | Wednesday
1/7/2026
8:30 PM | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Wednesday
1/7/2026
9:30 PM | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Thursday
1/8/2026
6:00 PM | |
| Chicago State Cougars Women's Basketball vs. Fairleigh Dickinson Knights | Jones Convocation Center
Chicago, IL | Thursday
1/8/2026
6:00 PM | |
| Carmen Stokes Quartet | Winter's Jazz Club
Chicago, IL | Thursday
1/8/2026
6:30 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Thursday
1/8/2026
7:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Thursday
1/8/2026
7:00 PM | |
| Chicago Bulls vs. Miami Heat | United Center
Chicago, IL | Thursday
1/8/2026
7:00 PM | |
| Chanel Ali | Zanies Comedy Club - Chicago
Chicago, IL | Thursday
1/8/2026
7:00 PM | |
| Wait Wait...Don't Tell Me | Studebaker Theater
Chicago, IL | Thursday
1/8/2026
7:30 PM | |
| And I, You | Beat Kitchen
Chicago, IL | Thursday
1/8/2026
7:30 PM | |
| Gorilla Tuesday | Reggie's Music Joint
Chicago, IL | Thursday
1/8/2026
8:00 PM | |
| Future Nobodies | Schubas
Chicago, IL | Thursday
1/8/2026
8:00 PM | |
| Roast Battle Chicago | Zanies Comedy Club - Chicago
Chicago, IL | Thursday
1/8/2026
9:30 PM | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Thursday
1/8/2026
9:30 PM | |
| Led Zeppelin 2 - Tribute Band - 2 Day Pass | House Of Blues - Chicago
Chicago, IL | Friday
1/9/2026
TBD | |
| Robert Glasper | City Winery - Chicago
Chicago, IL | Friday
1/9/2026
6:00 PM | |
| The Phantom of the Opera | Cadillac Palace
Chicago, IL | Friday
1/9/2026
7:00 PM | |
| Chicago Blackhawks vs. Washington Capitals | United Center
Chicago, IL | Friday
1/9/2026
7:00 PM | |
| Chanel Ali | Zanies Comedy Club - Chicago
Chicago, IL | Friday
1/9/2026
7:00 PM | |
| State Champs | The Salt Shed Indoors - Chicago
Chicago, IL | Friday
1/9/2026
7:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Friday
1/9/2026
7:00 PM | |
| Chicago Symphony Orchestra: 2001: A Space Odyssey In Concert | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Friday
1/9/2026
7:30 PM | |
| Moo Court | Studebaker Theater
Chicago, IL | Friday
1/9/2026
7:30 PM | |
| Woody Guthrie's American Song | Mercury Theater - IL
Chicago, IL | Friday
1/9/2026
7:30 PM | |
| Chicago Soul Jazz Collective | Winter's Jazz Club
Chicago, IL | Friday
1/9/2026
7:30 PM | |
| Led Zeppelin 2 - Tribute Band | House Of Blues - Chicago
Chicago, IL | Friday
1/9/2026
8:00 PM | |
| Mother Soki | Schubas
Chicago, IL | Friday
1/9/2026
8:00 PM | |
| Six Foot Blonde | Lincoln Hall
Chicago, IL | Friday
1/9/2026
8:00 PM | |
| Rock & Rye - Tribute to Grateful Dead | Garcias Chicago
Chicago, IL | Friday
1/9/2026
8:00 PM | |
| Bill Murray and His Blood Brothers | Thalia Hall
Chicago, IL | Friday
1/9/2026
8:00 PM | |
| The Yacht Rock-ettes | Beat Kitchen
Chicago, IL | Friday
1/9/2026
8:00 PM | |
| Discus | The Loft at Ramova Theatre
Chicago, IL | Friday
1/9/2026
8:00 PM | |
| Farseer | Reggie's Music Joint
Chicago, IL | Friday
1/9/2026
8:30 PM | |
| Candlelight: Tribute to Queen | Stan Mansion
Chicago, IL | Friday
1/9/2026
8:45 PM | |
| Emo Nite | Subterranean
Chicago, IL | Friday
1/9/2026
9:00 PM | |
| Lil M.U. | Reggie's Rock Club
Chicago, IL | Friday
1/9/2026
9:00 PM | |
| Drunk Shakespeare | The Lion Theatre - Chicago
Chicago, IL | Friday
1/9/2026
9:00 PM | |
| Swamp Dogg | Metro Chicago
Chicago, IL | Friday
1/9/2026
9:00 PM | |
| Taylor Rave | Concord Music Hall
Chicago, IL | Friday
1/9/2026
9:00 PM | |
