| Event | Venue | Date/Time | |
| Riot Fest: Tool, Morrissey & Social Distortion - Saturday | Douglass Park
Chicago, IL | Saturday
9/19/2026
11:00 AM |  |
| Bright Star Circus | Stars and Garters Theater
Chicago, IL | Saturday
9/19/2026
12:00 PM | |
| Dirty Dancing | Nederlander Theatre at Ford Center for the Performing Arts
Chicago, IL | Saturday
9/19/2026
2:00 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Saturday
9/19/2026
2:00 PM | |
| Vape! The Grease Parody | Apollo Theater Main Stage - Chicago
Chicago, IL | Saturday
9/19/2026
2:30 PM | |
| Chicago White Sox vs. Detroit Tigers | Rate Field
Chicago, IL | Saturday
9/19/2026
6:10 PM | |
| Candlelight: Tribute to TOOL | Wicker Park Lutheran Church
Chicago, IL | Saturday
9/19/2026
6:30 PM | |
| Role Model | The Salt Shed Outdoors - Chicago
Chicago, IL | Saturday
9/19/2026
7:00 PM | |
| Atsuko Okatsuka | The Chicago Theatre
Chicago, IL | Saturday
9/19/2026
7:00 PM | |
| Ryan Goodcase | The Comedy Bar - Chicago
Chicago, IL | Saturday
9/19/2026
7:00 PM | |
| Hulvey | House Of Blues - Chicago
Chicago, IL | Saturday
9/19/2026
7:00 PM | |
| Alok (Alok Vaid-Menon) | Vic Theatre
Chicago, IL | Saturday
9/19/2026
7:00 PM | |
| Vape! The Grease Parody | Apollo Theater Main Stage - Chicago
Chicago, IL | Saturday
9/19/2026
7:30 PM | |
| Daley | City Winery - Chicago
Chicago, IL | Saturday
9/19/2026
7:30 PM | |
| Dirty Dancing | Nederlander Theatre at Ford Center for the Performing Arts
Chicago, IL | Saturday
9/19/2026
7:30 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Saturday
9/19/2026
7:30 PM | |
| Phoebe Bridgers | United Center
Chicago, IL | Saturday
9/19/2026
7:30 PM | |
| Chicago Symphony Orchestra: Petr Popelka & Hilary Hahn - Schumann, Mendelssohn & Dvorak | Orchestra Hall At Chicago Symphony Center
Chicago, IL | Saturday
9/19/2026
7:30 PM | |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Saturday
9/19/2026
7:30 PM | |
| REZN | Thalia Hall
Chicago, IL | Saturday
9/19/2026
8:00 PM | |
| Kevin Atwater & Jessie Mazin | Lincoln Hall
Chicago, IL | Saturday
9/19/2026
8:00 PM | |
| Booker T. Jones | Garcias Chicago
Chicago, IL | Saturday
9/19/2026
8:00 PM | |
| Beth Hart | Riviera Theatre - IL
Chicago, IL | Saturday
9/19/2026
8:00 PM | |
| 15 Years of A.M. Early Morning | Bookclub
Chicago, IL | Saturday
9/19/2026
8:00 PM | |
| Candlelight: The Best of Hans Zimmer | Wicker Park Lutheran Church
Chicago, IL | Saturday
9/19/2026
8:30 PM | |
| Marty Schwartz | Beat Kitchen
Chicago, IL | Saturday
9/19/2026
8:30 PM | |
| The Good, The Bad, and The Freak | Stars and Garters Theater
Chicago, IL | Saturday
9/19/2026
9:00 PM | |
| Channel Tres | Ramova Theatre
Chicago, IL | Saturday
9/19/2026
9:00 PM | |
| Krewella | Sound-Bar
Chicago, IL | Saturday
9/19/2026
10:00 PM | |
| Daphni | Smart Bar Chicago
Chicago, IL | Saturday
9/19/2026
10:00 PM | |
| LSR/CITY X by Gareth Emery | Radius - IL
Chicago, IL | Saturday
9/19/2026
10:00 PM | |
| Riot Fest Late Night: William Shatner and The *uckers | Park West
Chicago, IL | Saturday
9/19/2026
10:30 PM | |
| Riot Fest Late Night: Alkaline Trio | Metro Chicago
Chicago, IL | Saturday
9/19/2026
11:00 PM | |
| PARKING: Chicago Bears vs. Minnesota Vikings | Soldier Field Parking Lot
Chicago, IL | Sunday
9/20/2026
TBD | |
| Riot Fest: Pierce The Veil, Alanis Morissette & Elvis Costello and The Imposters - Sunday | Douglass Park
Chicago, IL | Sunday
9/20/2026
11:00 AM | |
| Chicago Bears vs. Minnesota Vikings | Soldier Field
Chicago, IL | Sunday
9/20/2026
12:00 PM | |
| Beatles Brunch With Phil Angotti | City Winery - Chicago
Chicago, IL | Sunday
9/20/2026
12:00 PM | |
| Dirty Dancing | Nederlander Theatre at Ford Center for the Performing Arts
Chicago, IL | Sunday
9/20/2026
1:00 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Sunday
9/20/2026
1:00 PM | |
| Chicago White Sox vs. Detroit Tigers | Rate Field
Chicago, IL | Sunday
9/20/2026
1:10 PM | |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Sunday
9/20/2026
2:00 PM | |
| Vape! The Grease Parody | Apollo Theater Main Stage - Chicago
Chicago, IL | Sunday
9/20/2026
2:30 PM | |
| ARC At The Lake: Nick Warren | Castaways
Chicago, IL | Sunday
9/20/2026
4:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Sunday
9/20/2026
5:00 PM | |
| Jimmy Dore | Zanies Comedy Club - Chicago
Chicago, IL | Sunday
9/20/2026
6:00 PM | |
| Defining Courage | Historic Main Stage at Athenaeum Center - IL
Chicago, IL | Sunday
9/20/2026
6:00 PM | |
| Role Model | The Salt Shed Outdoors - Chicago
Chicago, IL | Sunday
9/20/2026
6:30 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Sunday
9/20/2026
6:30 PM | |
| Candlelight: Tribute to Adele | Stan Mansion
Chicago, IL | Sunday
9/20/2026
6:30 PM | |
| Cheerleader Roadkill | Subterranean
Chicago, IL | Sunday
9/20/2026
6:30 PM | |
| Cody Smith | The Comedy Bar - Chicago
Chicago, IL | Sunday
9/20/2026
7:00 PM | |
| She And Him | Riviera Theatre - IL
Chicago, IL | Sunday
9/20/2026
7:00 PM | |
| Funky Dineva | City Winery - Chicago
Chicago, IL | Sunday
9/20/2026
7:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Sunday
9/20/2026
7:00 PM | |
| Shoshana Bean | Thalia Hall
Chicago, IL | Sunday
9/20/2026
7:30 PM | |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Sunday
9/20/2026
7:30 PM | |
| Afro Heat Night | Bookclub
Chicago, IL | Sunday
9/20/2026
8:00 PM | |
| Gable Price | Beat Kitchen
Chicago, IL | Sunday
9/20/2026
8:00 PM | |
| Kany Garcia | Auditorium Theatre - IL
Chicago, IL | Sunday
9/20/2026
8:00 PM | |
| Bella Kay | Thalia Hall
Chicago, IL | Monday
9/21/2026
7:00 PM | |
| NHL Preseason: Chicago Blackhawks vs. Minnesota Wild | United Center
Chicago, IL | Monday
9/21/2026
7:00 PM | |
| Twista with Live Band | City Winery - Chicago
Chicago, IL | Monday
9/21/2026
7:30 PM | |
| Soda Blonde | Schubas
Chicago, IL | Monday
9/21/2026
8:00 PM | |
| All Time Low | The Salt Shed Outdoors - Chicago
Chicago, IL | Tuesday
9/22/2026
6:30 PM | |
| Chicago Cubs vs. Miami Marlins | Wrigley Field
Chicago, IL | Tuesday
9/22/2026
6:40 PM | |
| Chicago Sky vs. Toronto Tempo | Wintrust Arena
Chicago, IL | Tuesday
9/22/2026
7:00 PM | |
| Weezer, The Shins & Silversun Pickups | United Center
Chicago, IL | Tuesday
9/22/2026
7:00 PM | |
| Logic & G-Eazy | Huntington Bank Pavilion at Northerly Island
Chicago, IL | Tuesday
9/22/2026
7:00 PM | |
| Ryan Beatty | House Of Blues - Chicago
Chicago, IL | Tuesday
9/22/2026
7:00 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Tuesday
9/22/2026
7:00 PM | |
| Ilana Glazer | The Chicago Theatre
Chicago, IL | Tuesday
9/22/2026
7:00 PM | |
| Hail The Sun | Metro Chicago
Chicago, IL | Tuesday
9/22/2026
7:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Tuesday
9/22/2026
7:00 PM | |
| The Seven Wonders - Fleetwood Mac Tribute | City Winery - Chicago
Chicago, IL | Tuesday
9/22/2026
7:30 PM | |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Tuesday
9/22/2026
7:30 PM | |
| Igorrr | Vic Theatre
Chicago, IL | Tuesday
9/22/2026
7:30 PM | |
| Vape! The Grease Parody | Apollo Theater Main Stage - Chicago
Chicago, IL | Tuesday
9/22/2026
7:30 PM | |
| The Second City Mainstage 114th Revue | Mainstage at Second City - Chicago
Chicago, IL | Tuesday
9/22/2026
8:00 PM | |
| Wave To Earth | Byline Bank Aragon Ballroom
Chicago, IL | Tuesday
9/22/2026
8:00 PM | |
| Towa Bird | Lincoln Hall
Chicago, IL | Tuesday
9/22/2026
8:00 PM | |
| Shearling | Schubas
Chicago, IL | Tuesday
9/22/2026
8:00 PM | |
| Thundersmack | Garcias Chicago
Chicago, IL | Tuesday
9/22/2026
8:00 PM | |
| Jacques ze Whipper | Thalia Hall
Chicago, IL | Tuesday
9/22/2026
8:00 PM | |
| Dead Pink Radio | Reggie's Music Joint
Chicago, IL | Tuesday
9/22/2026
8:30 PM | |
| Pallbearer | The Empty Bottle
Chicago, IL | Tuesday
9/22/2026
9:00 PM | |
| Play On! | The Yard at Chicago Shakespeare Theatre
Chicago, IL | Wednesday
9/23/2026
1:00 PM | |
| STRFKR | Outset
Chicago, IL | Wednesday
9/23/2026
6:30 PM | |
| Chicago Cubs vs. Miami Marlins | Wrigley Field
Chicago, IL | Wednesday
9/23/2026
6:40 PM | |
| Buffalo Traffic Jam | House Of Blues - Chicago
Chicago, IL | Wednesday
9/23/2026
7:00 PM | |
| Jekyll & Hyde | Broadway Playhouse at Water Tower Place
Chicago, IL | Wednesday
9/23/2026
7:00 PM | |
| Eva Evans | Zanies Comedy Club - Chicago
Chicago, IL | Wednesday
9/23/2026
7:00 PM | |
| Drunk Dracula | The Lion Theatre - Chicago
Chicago, IL | Wednesday
9/23/2026
7:00 PM | |
| Lolo | Bottom Lounge
Chicago, IL | Wednesday
9/23/2026
7:30 PM | |
| Lucy Darling | Studebaker Theater
Chicago, IL | Wednesday
9/23/2026
7:30 PM | |
| Vape! The Grease Parody | Apollo Theater Main Stage - Chicago
Chicago, IL | Wednesday
9/23/2026
7:30 PM | |
| A Winged Victory For The Sullen | Vic Theatre
Chicago, IL | Wednesday
9/23/2026
7:30 PM | |
| Chief Keef | Huntington Bank Pavilion at Northerly Island
Chicago, IL | Wednesday
9/23/2026
7:30 PM | |
| The Attic | Albert Ivar Goodman Theatre
Chicago, IL | Wednesday
9/23/2026
7:30 PM | |
| Topdog/Underdog | Steppenwolf Theatre
Chicago, IL | Wednesday
9/23/2026
7:30 PM | |
| When Chai Met Toast | Lincoln Hall
Chicago, IL | Wednesday
9/23/2026
8:00 PM | |
