| Event | Date | Venue |
|---|---|---|
| 2023 Chicago Comic and Entertainment Expo - Saturday Pass | 4/1/2023 10:00 | South Building at McCormick Place |
| Once Upon a Symphony: The Elves and The Shoemaker | 4/1/2023 10:00 | Chicago Symphony Center |
| Once Upon a Symphony: The Elves and The Shoemaker | 4/1/2023 11:45 | Chicago Symphony Center |
| Chicago Cubs vs. Milwaukee Brewers | 4/1/2023 13:20 | Wrigley Field |
| TINA - The Tina Turner Musical | 4/1/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Book of Mormon | 4/1/2023 14:00 | Cadillac Palace |
| Blue Man Group | 4/1/2023 14:00 | Briar Street Theatre |
| Layalina | 4/1/2023 14:00 | Owen Bruner Goodman Theatre |
| How Blood Go | 4/1/2023 14:00 | Steppenwolf Theatre |
| The Shaughraun | 4/1/2023 14:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Comedy of Errors | 4/1/2023 14:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Best of The Second City | 4/1/2023 15:00 | Mainstage at Second City - Chicago |
| Freddy Jones Band | 4/1/2023 16:30 | City Winery - Chicago |
| Blue Man Group | 4/1/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 4/1/2023 17:00 | The Lion Theatre - Chicago |
| ComedySportz | 4/1/2023 18:00 | Judy's Beat Lounge at Second City - Chicago |
| Chicago Blackhawks vs. New Jersey Devils | 4/1/2023 19:00 | United Center |
| 46th Revue | 4/1/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| How Blood Go | 4/1/2023 19:00 | Steppenwolf Theatre |
| Do The Right Thing, No Worries If Not | 4/1/2023 19:00 | Mainstage at Second City - Chicago |
| Drunk Shakespeare | 4/1/2023 19:00 | The Lion Theatre - Chicago |
| Microwave & Oso Oso | 4/1/2023 19:00 | Bottom Lounge |
| Stavros Halkias | 4/1/2023 19:30 | Vic Theatre |
| Chicago Fire FC vs. D.C. United | 4/1/2023 19:30 | Soldier Field |
| Comedy of Errors | 4/1/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Last Ten Seconds of Life | 4/1/2023 19:30 | Beat Kitchen |
| Kenny Sebastian | 4/1/2023 19:30 | Park West |
| Giordano Dance Chicago | 4/1/2023 19:30 | Harris Theater |
| The Shaughraun | 4/1/2023 19:30 | Black Box Studio A At Athenaeum Theatre - IL |
| Baby Wants Candy | 4/1/2023 19:30 | Donny's Skybox Theatre at Second City - Chicago |
| Clued In - An Improvised Murder Mystery | 4/1/2023 19:30 | The Blackout Cabaret at Second City - Chicago |
| TINA - The Tina Turner Musical | 4/1/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Book of Mormon | 4/1/2023 20:00 | Cadillac Palace |
| Blue Man Group | 4/1/2023 20:00 | Briar Street Theatre |
| Tedeschi Trucks Band | 4/1/2023 20:00 | The Chicago Theatre |
| Third Eye Blind | 4/1/2023 20:00 | The Salt Shed - Chicago |
| Chiiild | 4/1/2023 20:00 | Schubas |
| The Home Team | 4/1/2023 20:00 | Subterranean |
| Joe DeRosa | 4/1/2023 20:00 | Reggie's Rock Club |
| Layalina | 4/1/2023 20:00 | Owen Bruner Goodman Theatre |
| Los Dos Carnales | 4/1/2023 20:00 | Credit Union 1 Arena |
| Rise Against | 4/1/2023 20:00 | Metro Chicago |
| Freddy Jones Band | 4/1/2023 20:00 | City Winery - Chicago |
| The Cherry Orchard | 4/1/2023 20:00 | Albert Ivar Goodman Theatre |
| Dance Like There Are Black People Watching | 4/1/2023 20:00 | UP Comedy Club at Second City - Chicago |
| Chicago Symphony Orchestra: Bernard Labadie - Boccherini, Vivaldi & Mozart 40 | 4/1/2023 20:00 | Chicago Symphony Center |
| Black Violin | 4/1/2023 20:30 | House Of Blues - Chicago |
| The Heartwreckers | 4/1/2023 20:30 | Golden Dagger |
| Shygirl | 4/1/2023 21:00 | Thalia Hall |
| Manwolves | 4/1/2023 21:00 | Sleeping Village |
| Baby Wants Candy | 4/1/2023 21:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/1/2023 21:00 | The Lion Theatre - Chicago |
| Stavros Halkias | 4/1/2023 21:30 | Vic Theatre |
| Trapped in a Musical | 4/1/2023 21:30 | Judy's Beat Lounge at Second City - Chicago |
| 46th Revue | 4/1/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Dr. Fresch | 4/1/2023 22:00 | Concord Music Hall |
| Cosmic Gate | 4/1/2023 22:00 | Sound-Bar |
| Alok | 4/1/2023 22:00 | PRYSM Nightclub |
| Do The Right Thing, No Worries If Not | 4/1/2023 22:00 | Mainstage at Second City - Chicago |
| Isaiah Collier & The Chosen Few: The World is on Fire | 4/1/2023 22:00 | Jazz Showcase |
| 2023 Chicago White Sox Season Tickets (Includes Tickets To All Regular Season Home Games) | 4/2/2023 3:30 | Guaranteed Rate Field |
| 2023 Chicago Comic and Entertainment Expo - Sunday Pass | 4/2/2023 10:00 | South Building at McCormick Place |
| The Second City's Improv Brunch | 4/2/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Blue Man Group | 4/2/2023 13:00 | Briar Street Theatre |
| Chicago Cubs vs. Milwaukee Brewers | 4/2/2023 13:20 | Wrigley Field |
| Lyric Opera of Chicago: Carmen | 4/2/2023 14:00 | Civic Opera House |
| TINA - The Tina Turner Musical | 4/2/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Book of Mormon | 4/2/2023 14:00 | Cadillac Palace |
| Comedy of Errors | 4/2/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Layalina | 4/2/2023 14:00 | Owen Bruner Goodman Theatre |
| The Cherry Orchard | 4/2/2023 14:00 | Albert Ivar Goodman Theatre |
| The Shaughraun | 4/2/2023 14:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Chicago Bulls vs. Memphis Grizzlies | 4/2/2023 14:30 | United Center |
| Emanuel Ax | 4/2/2023 15:00 | Chicago Symphony Center |
| How Blood Go | 4/2/2023 15:00 | Steppenwolf Theatre |
| Blue Man Group | 4/2/2023 16:00 | Briar Street Theatre |
| Isaiah Collier & The Chosen Few: The World is on Fire | 4/2/2023 16:00 | Jazz Showcase |
| Drunk Shakespeare | 4/2/2023 17:00 | The Lion Theatre - Chicago |
| Blue Man Group | 4/2/2023 19:00 | Briar Street Theatre |
| 46th Revue | 4/2/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Karaoke Storytellers - Improvised Feature Length Comedy | 4/2/2023 19:00 | Beat Kitchen |
| OnlyOneOf | 4/2/2023 19:00 | Park West |
| Wayne Baker Brooks | 4/2/2023 19:00 | City Winery - Chicago |
| Do The Right Thing, No Worries If Not | 4/2/2023 19:00 | Mainstage at Second City - Chicago |
| The Second City Swipes Right | 4/2/2023 19:00 | UP Comedy Club at Second City - Chicago |
| The Book of Mormon | 4/2/2023 19:30 | Cadillac Palace |
| Stavros Halkias | 4/2/2023 19:30 | Vic Theatre |
| The Cherry Orchard | 4/2/2023 19:30 | Albert Ivar Goodman Theatre |
| Ezra Collective | 4/2/2023 20:00 | Lincoln Hall |
| Stay Outside | 4/2/2023 20:00 | Schubas |
| Maggie Lindemann | 4/2/2023 20:00 | Thalia Hall |
| White Sox Opening Day Bash | 4/3/2023 11:00 | Reggie's Music Joint |
| Chicago White Sox vs. San Francisco Giants - Home Opener | 4/3/2023 15:10 | Guaranteed Rate Field |
| Bubbe and Zayde Save Passover | 4/3/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Archer Oh | 4/3/2023 19:30 | Schubas |
| The Murder Capital | 4/3/2023 19:30 | Lincoln Hall |
| Attack The Sound | 4/3/2023 20:00 | City Winery - Chicago |
| The Best of The Second City | 4/3/2023 20:00 | Mainstage at Second City - Chicago |
| Michelle Zauner | 4/4/2023 19:00 | Music Box Theatre - IL |
| Chicago Bulls vs. Atlanta Hawks | 4/4/2023 19:00 | United Center |
| A Soldier's Play | 4/4/2023 19:30 | CIBC Theatre |
| The Book of Mormon | 4/4/2023 19:30 | Cadillac Palace |
| Comedy of Errors | 4/4/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| Chicago Symphony Orchestra: Bernard Labadie - Boccherini, Vivaldi & Mozart 40 | 4/4/2023 19:30 | Chicago Symphony Center |
| Andi - Artist | 4/4/2023 20:00 | Beat Kitchen |
| Coco and Clair Clair | 4/4/2023 20:00 | Lincoln Hall |
| Milk & Bone | 4/4/2023 20:00 | Schubas |
| One Of These Nights - A Tribute To The Eagles | 4/4/2023 20:00 | City Winery - Chicago |
| Emma Ruth Rundle | 4/4/2023 20:30 | Thalia Hall |
| Chicago White Sox vs. San Francisco Giants | 4/5/2023 13:10 | Guaranteed Rate Field |
| Lyric Opera of Chicago: Proximity | 4/5/2023 14:00 | Civic Opera House |
| A Soldier's Play | 4/5/2023 14:00 | CIBC Theatre |
| The Book of Mormon | 4/5/2023 14:00 | Cadillac Palace |
| Blue Man Group | 4/5/2023 14:00 | Briar Street Theatre |
| Nate Smith | 4/5/2023 18:00 | Harris Theater |
| Vader | 4/5/2023 19:00 | Reggie's Rock Club |
| A Soldier's Play | 4/5/2023 19:30 | CIBC Theatre |
| The Book of Mormon | 4/5/2023 19:30 | Cadillac Palace |
| Depeche Mode | 4/5/2023 19:30 | United Center |
| Comedy of Errors | 4/5/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Cherry Orchard | 4/5/2023 19:30 | Albert Ivar Goodman Theatre |
| Describe The Night | 4/5/2023 19:30 | Steppenwolf Theatre |
| Drunk Shakespeare | 4/5/2023 19:30 | The Lion Theatre - Chicago |
| Blue Man Group | 4/5/2023 20:00 | Briar Street Theatre |
| Jackie Greene | 4/5/2023 20:00 | Lincoln Hall |
| Caitlin Krisko and The Broadcast | 4/5/2023 20:00 | Bourbon On Division |
| Jamo Laurice | 4/5/2023 20:00 | City Winery - Chicago |
| Combo Chimbita | 4/5/2023 20:30 | Thalia Hall |
| Chicago White Sox vs. San Francisco Giants | 4/6/2023 13:10 | Guaranteed Rate Field |
| Blue Man Group | 4/6/2023 14:00 | Briar Street Theatre |
| How Blood Go | 4/6/2023 19:00 | Steppenwolf Theatre |
| League Night | 4/6/2023 19:00 | Judy's Beat Lounge at Second City - Chicago |
| A Soldier's Play | 4/6/2023 19:30 | CIBC Theatre |
| The Book of Mormon | 4/6/2023 19:30 | Cadillac Palace |
| Comedy of Errors | 4/6/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| Shen Yun Performing Arts | 4/6/2023 19:30 | Auditorium Theatre - IL |
| The Cherry Orchard | 4/6/2023 19:30 | Albert Ivar Goodman Theatre |
| Drunk Shakespeare | 4/6/2023 19:30 | The Lion Theatre - Chicago |
| Chicago Symphony Orchestra: Thomas Ades - Gerstein | 4/6/2023 19:30 | Chicago Symphony Center |
| I Guess So | 4/6/2023 19:30 | Cubby Bear |
| Blue Man Group | 4/6/2023 20:00 | Briar Street Theatre |
| 46th Revue | 4/6/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| The Heavy Heavy | 4/6/2023 20:00 | Lincoln Hall |
| David Cross | 4/6/2023 20:00 | Thalia Hall |
| BJ Barham | 4/6/2023 20:00 | Schubas |
| High Vis | 4/6/2023 20:00 | Cobra Lounge |
| Smells Like Nirvana - Nirvana Tribute | 4/6/2023 20:00 | City Winery - Chicago |
| Under the Rug | 4/6/2023 20:00 | Reggie's Music Joint |
| The Second City Swipes Right | 4/6/2023 20:00 | UP Comedy Club at Second City - Chicago |
| Chicago Cubs vs. Texas Rangers | 4/7/2023 13:20 | Wrigley Field |
| Chicago Symphony Orchestra: Thomas Ades - Gerstein | 4/7/2023 13:30 | Chicago Symphony Center |
| Blue Man Group | 4/7/2023 16:00 | Briar Street Theatre |
| Static X | 4/7/2023 17:30 | House Of Blues - Chicago |
| Lyric Opera of Chicago: Carmen | 4/7/2023 19:00 | Civic Opera House |
| Blue Man Group | 4/7/2023 19:00 | Briar Street Theatre |
| 46th Revue | 4/7/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| How Blood Go | 4/7/2023 19:00 | Steppenwolf Theatre |
| Coached Ensembles | 4/7/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/7/2023 19:00 | The Lion Theatre - Chicago |
| A Soldier's Play | 4/7/2023 19:30 | CIBC Theatre |
| The Book of Mormon | 4/7/2023 19:30 | Cadillac Palace |
| Comedy of Errors | 4/7/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| Shen Yun Performing Arts | 4/7/2023 19:30 | Auditorium Theatre - IL |
| Nick Lutsko | 4/7/2023 19:30 | Park West |
| Jo Koy | 4/7/2023 20:00 | United Center |
| Tennis - The Band | 4/7/2023 20:00 | Riviera Theatre - IL |
| David Cross | 4/7/2023 20:00 | Thalia Hall |
| Wheelwright | 4/7/2023 20:00 | Golden Dagger |
| Donovan Woods | 4/7/2023 20:00 | Lincoln Hall |
| Old Gods of Appalachia | 4/7/2023 20:00 | Vic Theatre |
| Keith Washington | 4/7/2023 20:00 | City Winery - Chicago |
| The Cherry Orchard | 4/7/2023 20:00 | Albert Ivar Goodman Theatre |
| The Silver Palms | 4/7/2023 20:00 | Beat Kitchen |
| ComedySportz | 4/7/2023 20:00 | Judy's Beat Lounge at Second City - Chicago |
| Zakir Hussain & The Masters of Percussion | 4/7/2023 20:00 | Chicago Symphony Center |
| Magic Giant | 4/7/2023 20:30 | Reggie's Rock Club |
| Shamilton, The Improvised Hip-Hop American Musical | 4/7/2023 20:30 | Donny's Skybox Theatre at Second City - Chicago |
| Avey Tare | 4/7/2023 21:00 | Sleeping Village |
| Drunk Shakespeare | 4/7/2023 21:00 | The Lion Theatre - Chicago |
| Emo Nite | 4/7/2023 21:00 | Subterranean |
| 46th Revue | 4/7/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Ilan Bluestone | 4/7/2023 22:00 | Sound-Bar |
| Chloe Caillet | 4/7/2023 22:00 | PRYSM Nightclub |
| House Party Comedy - The Late Night Game Show | 4/7/2023 22:00 | Judy's Beat Lounge at Second City - Chicago |
| Babelon 5 | 4/8/2023 12:00 | City Winery - Chicago |
| A Soldier's Play | 4/8/2023 14:00 | CIBC Theatre |
| The Book of Mormon | 4/8/2023 14:00 | Cadillac Palace |
| Blue Man Group | 4/8/2023 14:00 | Briar Street Theatre |
| Shen Yun Performing Arts | 4/8/2023 14:00 | Auditorium Theatre - IL |
| The Cherry Orchard | 4/8/2023 14:00 | Albert Ivar Goodman Theatre |
| How Blood Go | 4/8/2023 14:00 | Steppenwolf Theatre |
| Comedy of Errors | 4/8/2023 14:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Best of The Second City | 4/8/2023 15:00 | Mainstage at Second City - Chicago |
| Chicago Cubs vs. Texas Rangers | 4/8/2023 15:05 | Wrigley Field |
| Blue Man Group | 4/8/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 4/8/2023 17:00 | The Lion Theatre - Chicago |
| Dwele | 4/8/2023 18:00 | City Winery - Chicago |
| ComedySportz | 4/8/2023 18:00 | Judy's Beat Lounge at Second City - Chicago |
| Kankan | 4/8/2023 18:30 | Avondale Music Hall |
| Unknown Mortal Orchestra | 4/8/2023 19:00 | Radius - IL |
| Spencer Sutherland | 4/8/2023 19:00 | House Of Blues - Chicago |
| 46th Revue | 4/8/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Chelcie Lynn | 4/8/2023 19:00 | Vic Theatre |
| Varietopia | 4/8/2023 19:00 | Lincoln Hall |
| How Blood Go | 4/8/2023 19:00 | Steppenwolf Theatre |
| Drunk Shakespeare | 4/8/2023 19:00 | The Lion Theatre - Chicago |
| Aly & AJ | 4/8/2023 19:30 | Riviera Theatre - IL |
| Chicago Fire FC vs. Minnesota United FC | 4/8/2023 19:30 | Soldier Field |
| Comedy of Errors | 4/8/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| Shen Yun Performing Arts | 4/8/2023 19:30 | Auditorium Theatre - IL |
| Baby Wants Candy | 4/8/2023 19:30 | Donny's Skybox Theatre at Second City - Chicago |
| Clued In - An Improvised Murder Mystery | 4/8/2023 19:30 | The Blackout Cabaret at Second City - Chicago |
| Western Bisexual | 4/8/2023 19:30 | Bottom Lounge |
| Lyric Opera of Chicago: Proximity | 4/8/2023 19:30 | Civic Opera House |
| A Soldier's Play | 4/8/2023 20:00 | CIBC Theatre |
| The Book of Mormon | 4/8/2023 20:00 | Cadillac Palace |
| Chicago Symphony Orchestra: Thomas Ades - Gerstein | 4/8/2023 20:00 | Chicago Symphony Center |
| Blue Man Group | 4/8/2023 20:00 | Briar Street Theatre |
| The Sloppy Boys | 4/8/2023 20:00 | Beat Kitchen |
| R&B Only | 4/8/2023 20:00 | Byline Bank Aragon Ballroom |
| Black Belt Eagle Scout | 4/8/2023 20:00 | Subterranean |
| The Cherry Orchard | 4/8/2023 20:00 | Albert Ivar Goodman Theatre |
| D.R.I. (Dirty Rotten Imbeciles) | 4/8/2023 20:00 | Reggie's Rock Club |
| The Snozzberries | 4/8/2023 20:00 | Bourbon On Division |
| Jukebox the Ghost | 4/8/2023 20:30 | Thalia Hall |
| Will Joseph Cook | 4/8/2023 21:00 | Schubas |
| Boot Scoot USA | 4/8/2023 21:00 | Joe's Bar On Weed St. |
| Baby Wants Candy | 4/8/2023 21:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/8/2023 21:00 | The Lion Theatre - Chicago |
| Dwele | 4/8/2023 21:30 | City Winery - Chicago |
| Trapped in a Musical | 4/8/2023 21:30 | Judy's Beat Lounge at Second City - Chicago |
| 46th Revue | 4/8/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Biscits & Goodboys | 4/8/2023 22:00 | PRYSM Nightclub |
| Cray | 4/8/2023 22:00 | Sound-Bar |
| The Second City's Improv Brunch | 4/9/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago Bulls vs. Detroit Pistons | 4/9/2023 12:00 | United Center |
| Shen Yun Performing Arts | 4/9/2023 13:00 | Auditorium Theatre - IL |
| Chicago Cubs vs. Texas Rangers | 4/9/2023 13:20 | Wrigley Field |
| A Soldier's Play | 4/9/2023 14:00 | CIBC Theatre |
| The Book of Mormon | 4/9/2023 14:00 | Cadillac Palace |
| Comedy of Errors | 4/9/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Cherry Orchard | 4/9/2023 14:00 | Albert Ivar Goodman Theatre |
| How Blood Go | 4/9/2023 14:00 | Steppenwolf Theatre |
| Tim Woodson and The Heirs Gospel Brunch | 4/9/2023 14:00 | City Winery - Chicago |
| Blue Man Group | 4/9/2023 16:00 | Briar Street Theatre |
| VV - Ville Valo | 4/9/2023 19:00 | House Of Blues - Chicago |
| 46th Revue | 4/9/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Varietopia | 4/9/2023 19:00 | Lincoln Hall |
| The Second City Swipes Right | 4/9/2023 19:00 | UP Comedy Club at Second City - Chicago |
| Drunk Shakespeare | 4/9/2023 19:00 | The Lion Theatre - Chicago |
| A Soldier's Play | 4/9/2023 19:30 | CIBC Theatre |
| Lil Wayne | 4/9/2023 20:00 | Radius - IL |
| George Willborn | 4/9/2023 20:00 | City Winery - Chicago |
| Chicago Cubs vs. Seattle Mariners | 4/10/2023 18:40 | Wrigley Field |
| VV - Ville Valo | 4/10/2023 19:00 | House Of Blues - Chicago |
| Bubbe and Zayde Save Passover | 4/10/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Chicago Blackhawks vs. Minnesota Wild | 4/10/2023 20:00 | United Center |
| Public Announcement | 4/10/2023 20:00 | City Winery - Chicago |
| The Best of The Second City | 4/10/2023 20:00 | Mainstage at Second City - Chicago |
| NBA Playoffs Play-In Tournament: Chicago Bulls vs. TBD - Game 1 (Date: TBD - If Necessary) | 4/11/2023 3:30 | United Center |
| Chicago Cubs vs. Seattle Mariners | 4/11/2023 18:40 | Wrigley Field |
| Enslaved & Insomnium | 4/11/2023 19:00 | House Of Blues - Chicago |
| Chloe | 4/11/2023 19:00 | Riviera Theatre - IL |
| Jagged Little Pill | 4/11/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| A Soldier's Play | 4/11/2023 19:30 | CIBC Theatre |
| The Book of Mormon | 4/11/2023 19:30 | Cadillac Palace |
| Comedy of Errors | 4/11/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| Chicago Symphony Orchestra: Thomas Ades - Gerstein | 4/11/2023 19:30 | Chicago Symphony Center |
| Unwritten Law | 4/11/2023 20:00 | Bottom Lounge |
| Begonia | 4/11/2023 20:00 | Schubas |
| Paraleven | 4/11/2023 20:00 | Subterranean |
| Maui The Poet | 4/11/2023 20:00 | City Winery - Chicago |
| Chicago Underground Comedy | 4/11/2023 21:00 | Beat Kitchen |
| Chicago Cubs vs. Seattle Mariners | 4/12/2023 13:20 | Wrigley Field |
| The Book of Mormon | 4/12/2023 14:00 | Cadillac Palace |
| A Soldier's Play | 4/12/2023 14:00 | CIBC Theatre |
| A Soldier's Play | 4/12/2023 19:30 | CIBC Theatre |
| The Book of Mormon | 4/12/2023 19:30 | Cadillac Palace |
| Jagged Little Pill | 4/12/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Drunk Shakespeare | 4/12/2023 19:30 | The Lion Theatre - Chicago |
| Blue Man Group | 4/12/2023 20:00 | Briar Street Theatre |
| Newski | 4/12/2023 20:00 | Golden Dagger |
| Ron Gallo | 4/12/2023 20:00 | Schubas |
| Heart to Gold | 4/12/2023 20:00 | Beat Kitchen |
| Last Night and the Night Before | 4/12/2023 20:00 | Steppenwolf Theatre |
| Michael Glabicki & Dirk Miller | 4/12/2023 20:00 | City Winery - Chicago |
| Blue Man Group | 4/13/2023 14:00 | Briar Street Theatre |
| The Cherry Orchard | 4/13/2023 14:00 | Albert Ivar Goodman Theatre |
| City Morgue | 4/13/2023 19:00 | Riviera Theatre - IL |
| How Blood Go | 4/13/2023 19:00 | Steppenwolf Theatre |
| Neema Naz | 4/13/2023 19:00 | House Of Blues - Chicago |
| League Night | 4/13/2023 19:00 | Judy's Beat Lounge at Second City - Chicago |
| Jagged Little Pill | 4/13/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| A Soldier's Play | 4/13/2023 19:30 | CIBC Theatre |
| The Book of Mormon | 4/13/2023 19:30 | Cadillac Palace |
| Chicago Symphony Orchestra: Mikko Franck & Hilary Hahn | 4/13/2023 19:30 | Chicago Symphony Center |
| Morgan James | 4/13/2023 19:30 | City Winery - Chicago |
| Comedy of Errors | 4/13/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Cherry Orchard | 4/13/2023 19:30 | Albert Ivar Goodman Theatre |
| Vial | 4/13/2023 19:30 | Subterranean |
| Drunk Shakespeare | 4/13/2023 19:30 | The Lion Theatre - Chicago |
| Chicago Blackhawks vs. Philadelphia Flyers | 4/13/2023 19:30 | United Center |
| The Piano Guys | 4/13/2023 20:00 | Athenaeum Theatre - IL |
| John Mellencamp | 4/13/2023 20:00 | The Chicago Theatre |
| Blue Man Group | 4/13/2023 20:00 | Briar Street Theatre |
| Fruit Bats | 4/13/2023 20:00 | Thalia Hall |
| Cipha Sounds | 4/13/2023 20:00 | Zanies Comedy Club - Chicago |
| Haunt Me | 4/13/2023 20:00 | Beat Kitchen |
| Stars | 4/13/2023 20:00 | Lincoln Hall |
| The Second City Swipes Right | 4/13/2023 20:00 | UP Comedy Club at Second City - Chicago |
| 46th Revue | 4/13/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Adi Oasis | 4/13/2023 21:00 | Sleeping Village |
| NBA Playoffs Play-In Tournament: Chicago Bulls vs. TBD - Game 2 (Date: TBD - If Necessary) | 4/14/2023 3:30 | United Center |
| Blue Man Group | 4/14/2023 13:00 | Briar Street Theatre |
| Chicago Symphony Orchestra: Mikko Franck & Hilary Hahn | 4/14/2023 13:30 | Chicago Symphony Center |
| Blue Man Group | 4/14/2023 16:00 | Briar Street Theatre |
| Chicago White Sox vs. Baltimore Orioles | 4/14/2023 18:10 | Guaranteed Rate Field |
| Blue Man Group | 4/14/2023 19:00 | Briar Street Theatre |
| Yeat | 4/14/2023 19:00 | Byline Bank Aragon Ballroom |
| Cipha Sounds | 4/14/2023 19:00 | Zanies Comedy Club - Chicago |
| How Blood Go | 4/14/2023 19:00 | Steppenwolf Theatre |
| 46th Revue | 4/14/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 4/14/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/14/2023 19:00 | The Lion Theatre - Chicago |
| A Soldier's Play | 4/14/2023 19:30 | CIBC Theatre |
| Jagged Little Pill | 4/14/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Book of Mormon | 4/14/2023 19:30 | Cadillac Palace |
| American Ballet Theatre | 4/14/2023 19:30 | Auditorium Theatre - IL |
| Scary Pockets | 4/14/2023 19:30 | Thalia Hall |
| Comedy of Errors | 4/14/2023 19:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| Monterey Jazz Festival On Tour | 4/14/2023 20:00 | Chicago Symphony Center |
| John Mellencamp | 4/14/2023 20:00 | The Chicago Theatre |
| Marcia Ball & Tinsley Ellis | 4/14/2023 20:00 | City Winery - Chicago |
| Goose | 4/14/2023 20:00 | The Salt Shed - Chicago |
| Little Stranger | 4/14/2023 20:00 | Beat Kitchen |
| Boy Named Banjo | 4/14/2023 20:00 | Joe's Bar On Weed St. |
| Sertab Erener | 4/14/2023 20:00 | Copernicus Center |
| Trouble Ahead - Grateful Dead Tribute Nite | 4/14/2023 20:00 | Cubby Bear |
| The Cherry Orchard | 4/14/2023 20:00 | Albert Ivar Goodman Theatre |
| Hits! The Musical | 4/14/2023 20:00 | Harris Theater |
| ComedySportz | 4/14/2023 20:00 | Judy's Beat Lounge at Second City - Chicago |
| Straight Up With Stassi | 4/14/2023 20:00 | Vic Theatre |
| Kem, Ledisi & Musiq Soulchild | 4/14/2023 20:00 | Credit Union 1 Arena |
| R&B Music Experience: Xscape, Brian McKnight, 112 & Silk | 4/14/2023 20:00 | Wintrust Arena |
| Shamilton, The Improvised Hip-Hop American Musical | 4/14/2023 20:30 | Donny's Skybox Theatre at Second City - Chicago |
| Michigander | 4/14/2023 21:00 | Lincoln Hall |
| Sugar - The Nu-Metal Party | 4/14/2023 21:00 | House Of Blues - Chicago |
| Drunk Shakespeare | 4/14/2023 21:00 | The Lion Theatre - Chicago |
| Luzcid | 4/14/2023 22:00 | Sound-Bar |
| Deathpact | 4/14/2023 22:00 | Concord Music Hall |
| DVBBS | 4/14/2023 22:00 | TAO Nightclub - Chicago |
| Bedouin | 4/14/2023 22:00 | PRYSM Nightclub |
| 46th Revue | 4/14/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| House Party Comedy - The Late Night Game Show | 4/14/2023 22:00 | Judy's Beat Lounge at Second City - Chicago |
| DJ Logic and Friends | 4/14/2023 23:55 | Bourbon On Division |
| NBA Eastern Conference First Round: Chicago Bulls vs. TBD - Home Game 1 (Date: TBD - If Necessary) | 4/15/2023 3:30 | United Center |
| Brunch & Beats: Mr. Dave | 4/15/2023 11:00 | City Winery - Chicago |
| Chicago White Sox vs. Baltimore Orioles | 4/15/2023 13:10 | Guaranteed Rate Field |
| A Soldier's Play | 4/15/2023 14:00 | CIBC Theatre |
| Jagged Little Pill | 4/15/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Book of Mormon | 4/15/2023 14:00 | Cadillac Palace |
| Blue Man Group | 4/15/2023 14:00 | Briar Street Theatre |
| The Cherry Orchard | 4/15/2023 14:00 | Albert Ivar Goodman Theatre |
| How Blood Go | 4/15/2023 14:00 | Steppenwolf Theatre |
| Comedy of Errors | 4/15/2023 14:30 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Best of The Second City | 4/15/2023 15:00 | Mainstage at Second City - Chicago |
| Nicodemus | 4/15/2023 16:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Blue Man Group | 4/15/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 4/15/2023 17:00 | The Lion Theatre - Chicago |
| ComedySportz | 4/15/2023 18:00 | Judy's Beat Lounge at Second City - Chicago |
| North Star Boys | 4/15/2023 18:30 | Avondale Music Hall |
| Noahfinnce | 4/15/2023 19:00 | Bottom Lounge |
| Sunny Day Real Estate | 4/15/2023 19:00 | Metro Chicago |
| Ryan Davis | 4/15/2023 19:00 | House Of Blues - Chicago |
| How Blood Go | 4/15/2023 19:00 | Steppenwolf Theatre |
| Sonja Morgan | 4/15/2023 19:00 | City Winery - Chicago |
| 46th Revue | 4/15/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 4/15/2023 19:00 | The Lion Theatre - Chicago |
| American Ballet Theatre | 4/15/2023 19:30 | Auditorium Theatre - IL |
| Kishi Bashi | 4/15/2023 19:30 | Harris Theater |
| Baby Wants Candy | 4/15/2023 19:30 | Donny's Skybox Theatre at Second City - Chicago |
| Clued In - An Improvised Murder Mystery | 4/15/2023 19:30 | The Blackout Cabaret at Second City - Chicago |
| Chicago Fire FC vs. Philadelphia Union | 4/15/2023 19:30 | Soldier Field |
| Jagged Little Pill | 4/15/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| A Soldier's Play | 4/15/2023 20:00 | CIBC Theatre |
| The Book of Mormon | 4/15/2023 20:00 | Cadillac Palace |
| Chicago Symphony Orchestra: Mikko Franck & Hilary Hahn | 4/15/2023 20:00 | Chicago Symphony Center |
| Blue Man Group | 4/15/2023 20:00 | Briar Street Theatre |
| Daisy The Great | 4/15/2023 20:00 | Beat Kitchen |
| Goose | 4/15/2023 20:00 | The Salt Shed - Chicago |
| John Mellencamp | 4/15/2023 20:00 | The Chicago Theatre |
| Pink Talking Fish - A Tribute to Pink Floyd, The Talking Heads & Phish | 4/15/2023 20:00 | Park West |
| Wormwitch | 4/15/2023 20:00 | Reggie's Music Joint |
| The Cherry Orchard | 4/15/2023 20:00 | Albert Ivar Goodman Theatre |
| Nicodemus | 4/15/2023 20:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Straight Up With Stassi | 4/15/2023 20:00 | Vic Theatre |
| Yolanda Del Rio | 4/15/2023 20:30 | Copernicus Center |
| Field Guide | 4/15/2023 21:00 | Schubas |
| The Nude Party | 4/15/2023 21:00 | Lincoln Hall |
| Baby Wants Candy | 4/15/2023 21:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/15/2023 21:00 | The Lion Theatre - Chicago |
| Cipha Sounds | 4/15/2023 21:15 | Zanies Comedy Club - Chicago |
| Ryan Davis | 4/15/2023 21:30 | House Of Blues - Chicago |
| Sixteen Candles | 4/15/2023 21:30 | Joe's Bar On Weed St. |
| Trapped in a Musical | 4/15/2023 21:30 | Judy's Beat Lounge at Second City - Chicago |
| Boiler Room | 4/15/2023 22:00 | Radius - IL |
| Minnesota | 4/15/2023 22:00 | Concord Music Hall |
| Doctor P. | 4/15/2023 22:00 | Sound-Bar |
| Noizu | 4/15/2023 22:00 | PRYSM Nightclub |
| 46th Revue | 4/15/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| DJ Logic and Friends | 4/15/2023 23:55 | Bourbon On Division |
| Winter Warm Up Blues Brunch | 4/16/2023 11:00 | Reggie's Music Joint |
| The Second City's Improv Brunch | 4/16/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Beatles Brunch With Phil Angotti and Friends | 4/16/2023 12:00 | City Winery - Chicago |
| Chicago White Sox vs. Baltimore Orioles | 4/16/2023 13:10 | Guaranteed Rate Field |
| A Soldier's Play | 4/16/2023 14:00 | CIBC Theatre |
| Jagged Little Pill | 4/16/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Book of Mormon | 4/16/2023 14:00 | Cadillac Palace |
| American Ballet Theatre | 4/16/2023 14:00 | Auditorium Theatre - IL |
| Comedy of Errors | 4/16/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Cherry Orchard | 4/16/2023 14:00 | Albert Ivar Goodman Theatre |
| Evgeny Kissin | 4/16/2023 15:00 | Chicago Symphony Center |
| Nicodemus | 4/16/2023 15:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Blue Man Group | 4/16/2023 16:00 | Briar Street Theatre |
| Drunk Shakespeare | 4/16/2023 17:00 | The Lion Theatre - Chicago |
| Lenny Schmidt | 4/16/2023 19:00 | Zanies Comedy Club - Chicago |
| Marquis Hill | 4/16/2023 19:00 | City Winery - Chicago |
| The Second City Swipes Right | 4/16/2023 19:00 | UP Comedy Club at Second City - Chicago |
| 46th Revue | 4/16/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Jagged Little Pill | 4/16/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| A Soldier's Play | 4/16/2023 19:30 | CIBC Theatre |
| The Cherry Orchard | 4/16/2023 19:30 | Albert Ivar Goodman Theatre |
| Gable Price and Friends | 4/16/2023 19:30 | Subterranean |
| The Criticals | 4/16/2023 20:00 | Lincoln Hall |
| Chicago White Sox vs. Philadelphia Phillies | 4/17/2023 18:10 | Guaranteed Rate Field |
| The Academic | 4/17/2023 19:30 | Lincoln Hall |
| A Tribute To A Tribe Called Quest | 4/17/2023 20:00 | City Winery - Chicago |
| The Best of The Second City | 4/17/2023 20:00 | Mainstage at Second City - Chicago |
| NBA Eastern Conference First Round: Chicago Bulls vs. TBD - Home Game 2 (Date: TBD - If Necessary) | 4/18/2023 3:30 | United Center |
| Chicago White Sox vs. Philadelphia Phillies | 4/18/2023 18:10 | Guaranteed Rate Field |
| Carcass | 4/18/2023 19:00 | Metro Chicago |
| Jagged Little Pill | 4/18/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Built To Spill | 4/18/2023 19:30 | Athenaeum Theatre - IL |
| Two Another | 4/18/2023 20:00 | Schubas |
| Fly By Midnight | 4/18/2023 20:00 | Beat Kitchen |
| Mames Babegenush | 4/18/2023 20:00 | City Winery - Chicago |
| Last Night and the Night Before | 4/18/2023 20:00 | Steppenwolf Theatre |
| Smash Into Pieces & Citizen Soldier | 4/18/2023 20:00 | Subterranean |
| Chicago White Sox vs. Philadelphia Phillies | 4/19/2023 13:10 | Guaranteed Rate Field |
| Jagged Little Pill | 4/19/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Jagged Little Pill | 4/19/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Kinneret | 4/19/2023 19:30 | Schubas |
| The Cherry Orchard | 4/19/2023 19:30 | Albert Ivar Goodman Theatre |
| Drunk Shakespeare | 4/19/2023 19:30 | The Lion Theatre - Chicago |
| Joffrey Ballet: The Little Mermaid | 4/19/2023 19:30 | Civic Opera House |
| Blue Man Group | 4/19/2023 20:00 | Briar Street Theatre |
| Lewis Capaldi | 4/19/2023 20:00 | Byline Bank Aragon Ballroom |
| Bongzilla | 4/19/2023 20:00 | Beat Kitchen |
| Band of Heathens | 4/19/2023 20:00 | Lincoln Hall |
| Talbott Brothers | 4/19/2023 20:00 | City Winery - Chicago |
| Last Night and the Night Before | 4/19/2023 20:00 | Steppenwolf Theatre |
| The Cherry Orchard | 4/20/2023 14:00 | Albert Ivar Goodman Theatre |
| Chicago Cubs vs. Los Angeles Dodgers | 4/20/2023 18:40 | Wrigley Field |
| Lolo Zouai | 4/20/2023 19:00 | Subterranean |
| 100 Gecs & Machine Girl | 4/20/2023 19:00 | Byline Bank Aragon Ballroom |
| Covet | 4/20/2023 19:00 | Bottom Lounge |
| How Blood Go | 4/20/2023 19:00 | Steppenwolf Theatre |
| League Night | 4/20/2023 19:00 | Judy's Beat Lounge at Second City - Chicago |
| Lady A | 4/20/2023 19:30 | The Chicago Theatre |
| Jagged Little Pill | 4/20/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Redveil | 4/20/2023 19:30 | Lincoln Hall |
| The Cherry Orchard | 4/20/2023 19:30 | Albert Ivar Goodman Theatre |
| Drunk Shakespeare | 4/20/2023 19:30 | The Lion Theatre - Chicago |
| Chicago Symphony Orchestra: Fabien Gabel - Trifonov Plays Rachmaninov Piano Concerto No. 3 | 4/20/2023 19:30 | Chicago Symphony Center |
| Blue Man Group | 4/20/2023 20:00 | Briar Street Theatre |
| Darren Hayes | 4/20/2023 20:00 | House Of Blues - Chicago |
| Bendigo Fletcher | 4/20/2023 20:00 | Schubas |
| Snow Tha Product | 4/20/2023 20:00 | Riviera Theatre - IL |
| Lyrics Born | 4/20/2023 20:00 | City Winery - Chicago |
| Gully Boys | 4/20/2023 20:00 | Beat Kitchen |
| The Second City Swipes Right | 4/20/2023 20:00 | UP Comedy Club at Second City - Chicago |
| 46th Revue | 4/20/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Blue Man Group | 4/21/2023 13:00 | Briar Street Theatre |
| Chicago Cubs vs. Los Angeles Dodgers | 4/21/2023 13:20 | Wrigley Field |
| Blue Man Group | 4/21/2023 16:00 | Briar Street Theatre |
| Blue Man Group | 4/21/2023 19:00 | Briar Street Theatre |
| Felipe Esparza | 4/21/2023 19:00 | Vic Theatre |
| How Blood Go | 4/21/2023 19:00 | Steppenwolf Theatre |
| 46th Revue | 4/21/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 4/21/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/21/2023 19:00 | The Lion Theatre - Chicago |
| Jagged Little Pill | 4/21/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Joffrey Ballet: The Little Mermaid | 4/21/2023 19:30 | Civic Opera House |
| Lizzy McAlpine | 4/21/2023 19:30 | Riviera Theatre - IL |
| Ionnalee | 4/21/2023 20:00 | Metro Chicago |
| Placebo | 4/21/2023 20:00 | The Salt Shed - Chicago |
| Ripe | 4/21/2023 20:00 | House Of Blues - Chicago |
| The Wldlfe | 4/21/2023 20:00 | Subterranean |
| Trevor Hall | 4/21/2023 20:00 | Gary & Laura Maurer Concert Hall |
| U.S. Girls | 4/21/2023 20:00 | Lincoln Hall |
| Phoneboy | 4/21/2023 20:00 | Beat Kitchen |
| And Then We Had Sex Podcast | 4/21/2023 20:00 | City Winery - Chicago |
| The Cherry Orchard | 4/21/2023 20:00 | Albert Ivar Goodman Theatre |
| Nicodemus | 4/21/2023 20:00 | Black Box Studio A At Athenaeum Theatre - IL |
| ComedySportz | 4/21/2023 20:00 | Judy's Beat Lounge at Second City - Chicago |
| Caroline Rose | 4/21/2023 20:30 | Thalia Hall |
| Shamilton, The Improvised Hip-Hop American Musical | 4/21/2023 20:30 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/21/2023 21:00 | The Lion Theatre - Chicago |
| Felipe Esparza | 4/21/2023 22:00 | Vic Theatre |
| Space Laces | 4/21/2023 22:00 | Concord Music Hall |
| Destructo | 4/21/2023 22:00 | Sound-Bar |
| Luttrell - DJ | 4/21/2023 22:00 | PRYSM Nightclub |
| Joel Corry | 4/21/2023 22:00 | TAO Nightclub - Chicago |
| 46th Revue | 4/21/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| House Party Comedy - The Late Night Game Show | 4/21/2023 22:00 | Judy's Beat Lounge at Second City - Chicago |
| The Reunion - An Interactive Office Fan Convention - Weekend Pass | 4/22/2023 3:30 | Festival Hall A At Navy Pier |
| The Reunion - An Interactive Office Fan Convention - Saturday | 4/22/2023 12:00 | Festival Hall A At Navy Pier |
| Chicago Cubs vs. Los Angeles Dodgers | 4/22/2023 13:20 | Wrigley Field |
| Jagged Little Pill | 4/22/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Joffrey Ballet: The Little Mermaid | 4/22/2023 14:00 | Civic Opera House |
| Blue Man Group | 4/22/2023 14:00 | Briar Street Theatre |
| The Cherry Orchard | 4/22/2023 14:00 | Albert Ivar Goodman Theatre |
| How Blood Go | 4/22/2023 14:00 | Steppenwolf Theatre |
| The Best of The Second City | 4/22/2023 15:00 | Mainstage at Second City - Chicago |
| Nicodemus | 4/22/2023 16:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Blue Man Group | 4/22/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 4/22/2023 17:00 | The Lion Theatre - Chicago |
| Pop Evil | 4/22/2023 17:30 | Concord Music Hall |
| ComedySportz | 4/22/2023 18:00 | Judy's Beat Lounge at Second City - Chicago |
| Schaffer the Darklord | 4/22/2023 18:30 | Subterranean |
| Pat McGann | 4/22/2023 19:00 | The Chicago Theatre |
| Chelsea Grin & Carnifex | 4/22/2023 19:00 | Bottom Lounge |
| How Blood Go | 4/22/2023 19:00 | Steppenwolf Theatre |
| 46th Revue | 4/22/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 4/22/2023 19:00 | The Lion Theatre - Chicago |
| Dorrance Dance | 4/22/2023 19:30 | Auditorium Theatre - IL |
| Tom Papa | 4/22/2023 19:30 | Vic Theatre |
| BareFace | 4/22/2023 19:30 | Harris Theater |
| Baby Wants Candy | 4/22/2023 19:30 | Donny's Skybox Theatre at Second City - Chicago |
| Clued In - An Improvised Murder Mystery | 4/22/2023 19:30 | The Blackout Cabaret at Second City - Chicago |
| Joffrey Ballet: The Little Mermaid | 4/22/2023 19:30 | Civic Opera House |
| Jagged Little Pill | 4/22/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 4/22/2023 20:00 | Briar Street Theatre |
| Bikini Kill | 4/22/2023 20:00 | The Salt Shed - Chicago |
| Louder Now | 4/22/2023 20:00 | Cubby Bear |
| Worry Club | 4/22/2023 20:00 | Subterranean |
| The Cherry Orchard | 4/22/2023 20:00 | Albert Ivar Goodman Theatre |
| Passafire & Crooked Coast | 4/22/2023 20:00 | Beat Kitchen |
| Nicodemus | 4/22/2023 20:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Chicago Symphony Orchestra: Fabien Gabel - Trifonov Plays Rachmaninov Piano Concerto No. 3 | 4/22/2023 20:00 | Chicago Symphony Center |
| Wild Child - Band | 4/22/2023 20:30 | Thalia Hall |
| Mo Lowda and The Humble | 4/22/2023 21:00 | Lincoln Hall |
| Black Tiger Sex Machine | 4/22/2023 21:00 | Riviera Theatre - IL |
| Baby Wants Candy | 4/22/2023 21:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/22/2023 21:00 | The Lion Theatre - Chicago |
| Trapped in a Musical | 4/22/2023 21:30 | Judy's Beat Lounge at Second City - Chicago |
| Pat McGann | 4/22/2023 22:00 | The Chicago Theatre |
| Gioli & Assia | 4/22/2023 22:00 | PRYSM Nightclub |
| Hood Politics Showcase | 4/22/2023 22:00 | Sound-Bar |
| 46th Revue | 4/22/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| The Reunion - An Interactive Office Fan Convention - Sunday | 4/23/2023 12:00 | Festival Hall A At Navy Pier |
| Bubbles and Beauties's Drag Brunch | 4/23/2023 12:00 | City Winery - Chicago |
| The Second City's Improv Brunch | 4/23/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago Cubs vs. Los Angeles Dodgers | 4/23/2023 13:20 | Wrigley Field |
| Jagged Little Pill | 4/23/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Joffrey Ballet: The Little Mermaid | 4/23/2023 14:00 | Civic Opera House |
| The Cherry Orchard | 4/23/2023 14:00 | Albert Ivar Goodman Theatre |
| How Blood Go | 4/23/2023 14:00 | Steppenwolf Theatre |
| Nicodemus | 4/23/2023 15:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Chicago Symphony Orchestra: Fabien Gabel - Trifonov Plays Rachmaninov Piano Concerto No. 3 | 4/23/2023 15:00 | Chicago Symphony Center |
| Blue Man Group | 4/23/2023 16:00 | Briar Street Theatre |
| Drunk Shakespeare | 4/23/2023 17:00 | The Lion Theatre - Chicago |
| Night of the SuperWrestlers | 4/23/2023 18:00 | Concord Music Hall |
| Ann Hampton Callaway | 4/23/2023 19:00 | City Winery - Chicago |
| Tink | 4/23/2023 19:00 | The Chicago Theatre |
| The Second City Swipes Right | 4/23/2023 19:00 | UP Comedy Club at Second City - Chicago |
| 46th Revue | 4/23/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Nils Frahm | 4/23/2023 20:00 | The Salt Shed - Chicago |
| Boulet Brothers' Dragula Titans | 4/23/2023 20:00 | Vic Theatre |
| Joe P. | 4/23/2023 20:00 | Beat Kitchen |
| Pinback | 4/23/2023 20:30 | Thalia Hall |
| MALONE | 4/23/2023 22:00 | PRYSM Nightclub |
| NBA Eastern Conference First Round: Chicago Bulls vs. TBD - Home Game 3 (Date: TBD - If Necessary) | 4/24/2023 3:30 | United Center |
| Saint Motel | 4/24/2023 19:00 | Metro Chicago |
| Kill Alters | 4/24/2023 19:00 | Subterranean |
| Radwimps | 4/24/2023 19:30 | Vic Theatre |
| Radwimps | 4/24/2023 19:30 | Riviera Theatre - IL |
| Nico Hoerner & Patrick Wisdom | 4/24/2023 20:00 | Lincoln Hall |
| Evan Dando | 4/24/2023 20:00 | City Winery - Chicago |
| Ambre | 4/24/2023 20:00 | Reggie's Rock Club |
| The Best of The Second City | 4/24/2023 20:00 | Mainstage at Second City - Chicago |
| Chicago Cubs vs. San Diego Padres | 4/25/2023 18:40 | Wrigley Field |
| Whitechapel | 4/25/2023 19:00 | House Of Blues - Chicago |
| Into The Woods | 4/25/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Wilder Woods | 4/25/2023 19:30 | Lincoln Hall |
| FLO Live | 4/25/2023 19:30 | Thalia Hall |
| The Cherry Orchard | 4/25/2023 19:30 | Albert Ivar Goodman Theatre |
| Bruce-O-Rama: Bruce Campbell | 4/25/2023 19:30 | Vic Theatre |
| Graham Nash | 4/25/2023 20:00 | Old Town School of Folk Music |
| Last Night and the Night Before | 4/25/2023 20:00 | Steppenwolf Theatre |
| Gene Noble | 4/25/2023 20:00 | City Winery - Chicago |
| Chicago Underground Comedy | 4/25/2023 21:00 | Beat Kitchen |
| Blue Man Group | 4/26/2023 14:00 | Briar Street Theatre |
| Chicago Cubs vs. San Diego Padres | 4/26/2023 18:40 | Wrigley Field |
| Meg Myers | 4/26/2023 19:00 | Park West |
| Into The Woods | 4/26/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Cherry Orchard | 4/26/2023 19:30 | Albert Ivar Goodman Theatre |
| Drunk Shakespeare | 4/26/2023 19:30 | The Lion Theatre - Chicago |
| Blue Man Group | 4/26/2023 20:00 | Briar Street Theatre |
| Brooks Nielsen | 4/26/2023 20:00 | Bottom Lounge |
| Tamino | 4/26/2023 20:00 | Thalia Hall |
| Graham Nash | 4/26/2023 20:00 | Old Town School of Folk Music |
| Last Night and the Night Before | 4/26/2023 20:00 | Steppenwolf Theatre |
| NBA Eastern Conference First Round: Chicago Bulls vs. TBD - Home Game 4 (Date: TBD - If Necessary) | 4/27/2023 3:30 | United Center |
| Chicago Cubs vs. San Diego Padres | 4/27/2023 13:20 | Wrigley Field |
| The Cherry Orchard | 4/27/2023 14:00 | Albert Ivar Goodman Theatre |
| Chicago Bears Draft Day Party | 4/27/2023 18:00 | Soldier Field |
| Chicago White Sox vs. Tampa Bay Rays | 4/27/2023 18:10 | Guaranteed Rate Field |
| G Perico | 4/27/2023 19:00 | Avondale Music Hall |
| League Night | 4/27/2023 19:00 | Judy's Beat Lounge at Second City - Chicago |
| Into The Woods | 4/27/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Cherry Orchard | 4/27/2023 19:30 | Albert Ivar Goodman Theatre |
| Drunk Shakespeare | 4/27/2023 19:30 | The Lion Theatre - Chicago |
| Joffrey Ballet: The Little Mermaid | 4/27/2023 19:30 | Civic Opera House |
| Chicago Symphony Orchestra: Vladimir Jurowski - Jurowski, Helmchen & Shostakovich 8 | 4/27/2023 19:30 | Chicago Symphony Center |
| Blue Man Group | 4/27/2023 20:00 | Briar Street Theatre |
| Marcello Hernandez | 4/27/2023 20:00 | Zanies Comedy Club - Chicago |
| July Talk | 4/27/2023 20:00 | Subterranean |
| Hiatus Kaiyote | 4/27/2023 20:00 | Riviera Theatre - IL |
| Last Night and the Night Before | 4/27/2023 20:00 | Steppenwolf Theatre |
| The Second City Swipes Right | 4/27/2023 20:00 | UP Comedy Club at Second City - Chicago |
| 46th Revue | 4/27/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Tanukichan | 4/27/2023 21:00 | Sleeping Village |
| Blue Man Group | 4/28/2023 13:00 | Briar Street Theatre |
| Blue Man Group | 4/28/2023 16:00 | Briar Street Theatre |
| Chicago White Sox vs. Tampa Bay Rays | 4/28/2023 18:10 | Guaranteed Rate Field |
| Blue Man Group | 4/28/2023 19:00 | Briar Street Theatre |
| The Summer Set & Grayscale | 4/28/2023 19:00 | House Of Blues - Chicago |
| Marcello Hernandez | 4/28/2023 19:00 | Zanies Comedy Club - Chicago |
| String Cheese Incident | 4/28/2023 19:00 | Riviera Theatre - IL |
| Nicodemus | 4/28/2023 19:00 | Black Box Studio A At Athenaeum Theatre - IL |
| 46th Revue | 4/28/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 4/28/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/28/2023 19:00 | The Lion Theatre - Chicago |
| Joffrey Ballet: The Little Mermaid | 4/28/2023 19:30 | Civic Opera House |
| Into The Woods | 4/28/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Khemmis | 4/28/2023 19:30 | Reggie's Rock Club |
| Perpetual Flame | 4/28/2023 19:30 | Thalia Hall |
| Delta Rae | 4/28/2023 20:00 | Lincoln Hall |
| Antonio's Song | 4/28/2023 20:00 | Owen Bruner Goodman Theatre |
| Graham Nash | 4/28/2023 20:00 | Old Town School of Folk Music |
| Griffin House | 4/28/2023 20:00 | City Winery - Chicago |
| Randall King | 4/28/2023 20:00 | Joe's Bar On Weed St. |
| The Cherry Orchard | 4/28/2023 20:00 | Albert Ivar Goodman Theatre |
| Last Night and the Night Before | 4/28/2023 20:00 | Steppenwolf Theatre |
| ComedySportz | 4/28/2023 20:00 | Judy's Beat Lounge at Second City - Chicago |
| Charly Bliss | 4/28/2023 20:00 | Subterranean |
| Chicago Symphony Orchestra: Vladimir Jurowski - Jurowski, Helmchen & Shostakovich 8 | 4/28/2023 20:00 | Chicago Symphony Center |
| Mana | 4/28/2023 20:30 | United Center |
| Shamilton, The Improvised Hip-Hop American Musical | 4/28/2023 20:30 | Donny's Skybox Theatre at Second City - Chicago |
| DeeOhGee | 4/28/2023 21:00 | Reggie's Music Joint |
| Drunk Shakespeare | 4/28/2023 21:00 | The Lion Theatre - Chicago |
| Marcello Hernandez | 4/28/2023 21:15 | Zanies Comedy Club - Chicago |
| Kyle Watson | 4/28/2023 22:00 | Sound-Bar |
| Alesso | 4/28/2023 22:00 | TAO Nightclub - Chicago |
| 46th Revue | 4/28/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| House Party Comedy - The Late Night Game Show | 4/28/2023 22:00 | Judy's Beat Lounge at Second City - Chicago |
| SLS Chicago - Street League Skateboarding | 4/29/2023 3:30 | Wintrust Arena |
| Once Upon a Symphony: The Elves and The Shoemaker | 4/29/2023 10:00 | Chicago Symphony Center |
| Once Upon a Symphony: The Elves and The Shoemaker | 4/29/2023 11:45 | Chicago Symphony Center |
| Joffrey Ballet: The Little Mermaid | 4/29/2023 14:00 | Civic Opera House |
| Blue Man Group | 4/29/2023 14:00 | Briar Street Theatre |
| Into The Woods | 4/29/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Cherry Orchard | 4/29/2023 14:00 | Albert Ivar Goodman Theatre |
| Last Night and the Night Before | 4/29/2023 15:00 | Steppenwolf Theatre |
| The Best of The Second City | 4/29/2023 15:00 | Mainstage at Second City - Chicago |
| Nicodemus | 4/29/2023 16:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Blue Man Group | 4/29/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 4/29/2023 17:00 | The Lion Theatre - Chicago |
| Melanie Fiona | 4/29/2023 18:00 | City Winery - Chicago |
| ComedySportz | 4/29/2023 18:00 | Judy's Beat Lounge at Second City - Chicago |
| Chicago White Sox vs. Tampa Bay Rays | 4/29/2023 18:10 | Guaranteed Rate Field |
| August Burns Red | 4/29/2023 18:30 | Concord Music Hall |
| Kountry Wayne | 4/29/2023 19:00 | The Chicago Theatre |
| Marcello Hernandez | 4/29/2023 19:00 | Zanies Comedy Club - Chicago |
| String Cheese Incident | 4/29/2023 19:00 | Riviera Theatre - IL |
| 46th Revue | 4/29/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 4/29/2023 19:00 | The Lion Theatre - Chicago |
| Christina P | 4/29/2023 19:30 | Park West |
| Eddie B | 4/29/2023 19:30 | Vic Theatre |
| Chicago Fire FC vs. New York Red Bulls | 4/29/2023 19:30 | Soldier Field |
| Perpetual Flame | 4/29/2023 19:30 | Thalia Hall |
| La La Land: Green Velvet | 4/29/2023 19:30 | The Salt Shed - Chicago |
| Baby Wants Candy | 4/29/2023 19:30 | Donny's Skybox Theatre at Second City - Chicago |
| Clued In - An Improvised Murder Mystery | 4/29/2023 19:30 | The Blackout Cabaret at Second City - Chicago |
| Joffrey Ballet: The Little Mermaid | 4/29/2023 19:30 | Civic Opera House |
| Blue Man Group | 4/29/2023 20:00 | Briar Street Theatre |
| Into The Woods | 4/29/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Antonio's Song | 4/29/2023 20:00 | Owen Bruner Goodman Theatre |
| Graham Nash | 4/29/2023 20:00 | Old Town School of Folk Music |
| Sasha Velour - The Big Reveal Live Show | 4/29/2023 20:00 | Broadway Playhouse at Water Tower Place |
| Ruston Kelly | 4/29/2023 20:00 | House Of Blues - Chicago |
| The Cherry Orchard | 4/29/2023 20:00 | Albert Ivar Goodman Theatre |
| Last Night and the Night Before | 4/29/2023 20:00 | Steppenwolf Theatre |
| Fireworks | 4/29/2023 20:00 | Bottom Lounge |
| Nicodemus | 4/29/2023 20:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Direct Hit! | 4/29/2023 20:00 | Beat Kitchen |
| Caitlyn Smith | 4/29/2023 20:00 | Avondale Music Hall |
| Chicago Symphony Orchestra: Vladimir Jurowski - Jurowski, Helmchen & Shostakovich 8 | 4/29/2023 20:00 | Chicago Symphony Center |
| Mana | 4/29/2023 20:30 | United Center |
| Weval | 4/29/2023 21:00 | Lincoln Hall |
| Baby Wants Candy | 4/29/2023 21:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 4/29/2023 21:00 | The Lion Theatre - Chicago |
| Marcello Hernandez | 4/29/2023 21:15 | Zanies Comedy Club - Chicago |
| Melanie Fiona | 4/29/2023 21:30 | City Winery - Chicago |
| Trapped in a Musical | 4/29/2023 21:30 | Judy's Beat Lounge at Second City - Chicago |
| Dnmo | 4/29/2023 22:00 | Sound-Bar |
| Gareth Emery | 4/29/2023 22:00 | PRYSM Nightclub |
| 46th Revue | 4/29/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| The Second City's Improv Brunch | 4/30/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago White Sox vs. Tampa Bay Rays | 4/30/2023 13:10 | Guaranteed Rate Field |
| Joffrey Ballet: The Little Mermaid | 4/30/2023 14:00 | Civic Opera House |
| Into The Woods | 4/30/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Antonio's Song | 4/30/2023 14:00 | Owen Bruner Goodman Theatre |
| The Reverend Kristin Hayter | 4/30/2023 14:00 | Thalia Hall |
| The Cherry Orchard | 4/30/2023 14:00 | Albert Ivar Goodman Theatre |
| National Geographic Live: Coral Kingdom and Empires of Ice | 4/30/2023 14:00 | Auditorium Theatre - IL |
| Jerusalem Quartet, Pinchas Zukerman & Amanda Forsyth | 4/30/2023 15:00 | Chicago Symphony Center |
| Last Night and the Night Before | 4/30/2023 15:00 | Steppenwolf Theatre |
| Nicodemus | 4/30/2023 15:00 | Black Box Studio A At Athenaeum Theatre - IL |
| Blue Man Group | 4/30/2023 16:00 | Briar Street Theatre |
| Drunk Shakespeare | 4/30/2023 17:00 | The Lion Theatre - Chicago |
| The Interrupters | 4/30/2023 18:00 | House Of Blues - Chicago |
| Anita Wilson | 4/30/2023 19:00 | City Winery - Chicago |
| Graham Nash | 4/30/2023 19:00 | Old Town School of Folk Music |
| The Reverend Kristin Hayter | 4/30/2023 19:00 | Thalia Hall |
| Sasha Velour - The Big Reveal Live Show | 4/30/2023 19:00 | Broadway Playhouse at Water Tower Place |
| The Second City Swipes Right | 4/30/2023 19:00 | UP Comedy Club at Second City - Chicago |
| 46th Revue | 4/30/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Transviolet | 4/30/2023 19:30 | Schubas |
| Into The Woods | 4/30/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Antonio's Song | 4/30/2023 19:30 | Owen Bruner Goodman Theatre |
| Perpetual Flame | 4/30/2023 21:30 | Thalia Hall |
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