| NASCAR Cup Series - 2 Day Pass | 7/1/2023 3:30 | Chicago Street Course |
| The Second City's Improv Brunch | 7/1/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Blue Man Group | 7/1/2023 14:00 | Briar Street Theatre |
| The Who's Tommy | 7/1/2023 14:00 | Albert Ivar Goodman Theatre |
| The Best of The Second City | 7/1/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 7/1/2023 17:00 | Briar Street Theatre |
| Chicago Cubs vs. Cleveland Guardians | 7/1/2023 18:15 | Wrigley Field |
| 46th Revue | 7/1/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 7/1/2023 19:00 | The Lion Theatre - Chicago |
| Lil Louis | 7/1/2023 19:00 | Riviera Theatre - IL |
| Chicago Symphony Orchestra: David Newman - Star Wars Episode VII: The Force Awakens In Concert | 7/1/2023 19:30 | Chicago Symphony Center |
| Erykah Badu & Yasiin Bey (aka) Mos Def | 7/1/2023 19:30 | United Center |
| Blue Man Group | 7/1/2023 20:00 | Briar Street Theatre |
| The Hold Steady | 7/1/2023 20:00 | The Salt Shed - Chicago |
| The Who's Tommy | 7/1/2023 20:00 | Albert Ivar Goodman Theatre |
| Terisa Griffin | 7/1/2023 20:00 | City Winery - Chicago |
| Loma Prieta | 7/1/2023 20:00 | Beat Kitchen |
| Violet Crime | 7/1/2023 20:00 | Subterranean |
| Rebelution | 7/1/2023 20:30 | Byline Bank Aragon Ballroom |
| Joseph - The Band | 7/1/2023 20:30 | Thalia Hall |
| Drunk Shakespeare | 7/1/2023 21:00 | The Lion Theatre - Chicago |
| 46th Revue | 7/1/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Klingande | 7/1/2023 22:00 | PRYSM Nightclub |
| Emo Night Brooklyn | 7/1/2023 22:00 | House Of Blues - Chicago |
| Getter | 7/1/2023 22:00 | Sound-Bar |
| DVBBS | 7/1/2023 22:00 | TAO Nightclub - Chicago |
| The Second City's Improv Brunch | 7/2/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Girls Rock! Chicago | 7/2/2023 12:00 | Thalia Hall |
| Chicago Cubs vs. Cleveland Guardians | 7/2/2023 13:20 | Wrigley Field |
| The Who's Tommy | 7/2/2023 14:00 | Albert Ivar Goodman Theatre |
| The Best of The Second City | 7/2/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 7/2/2023 16:00 | Briar Street Theatre |
| NASCAR Cup Series: Grant Park 220 | 7/2/2023 16:30 | Chicago Street Course |
| Drunk Shakespeare | 7/2/2023 17:00 | The Lion Theatre - Chicago |
| The Karen Hunter Show | 7/2/2023 18:00 | City Winery - Chicago |
| 46th Revue | 7/2/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Les Claypool's Fearless Flying Frog Brigade & Budos Band | 7/2/2023 20:00 | The Salt Shed - Chicago |
| The Rocket Summer & hellogoodbye | 7/2/2023 20:00 | Bottom Lounge |
| Yoko and The Oh No's | 7/2/2023 20:00 | Subterranean |
| The Hold Steady | 7/2/2023 21:00 | The Empty Bottle |
| Blue Man Group | 7/3/2023 20:00 | Briar Street Theatre |
| The Best of The Second City | 7/3/2023 20:00 | Mainstage at Second City - Chicago |
| Tab Benoit | 7/3/2023 20:00 | City Winery - Chicago |
| Chicago White Sox vs. Toronto Blue Jays | 7/4/2023 19:10 | Guaranteed Rate Field |
| Zo! & Tall Black Guy | 7/4/2023 20:00 | City Winery - Chicago |
| Drake & 21 Savage | 7/5/2023 19:00 | United Center |
| Chicago White Sox vs. Toronto Blue Jays | 7/5/2023 19:10 | Guaranteed Rate Field |
| Sparks | 7/5/2023 19:30 | Copernicus Center |
| Drunk Shakespeare | 7/5/2023 19:30 | The Lion Theatre - Chicago |
| LLO | 7/5/2023 19:30 | Cubby Bear |
| Blue Man Group | 7/5/2023 20:00 | Briar Street Theatre |
| Nik West | 7/5/2023 20:00 | City Winery - Chicago |
| The Who's Tommy | 7/6/2023 14:00 | Albert Ivar Goodman Theatre |
| Craig Owens | 7/6/2023 19:00 | Bottom Lounge |
| Tiny Desk Contest On The Road | 7/6/2023 19:00 | Subterranean |
| Drake & 21 Savage | 7/6/2023 19:00 | United Center |
| Chicago White Sox vs. Toronto Blue Jays | 7/6/2023 19:10 | Guaranteed Rate Field |
| Drunk Shakespeare | 7/6/2023 19:30 | The Lion Theatre - Chicago |
| The Who's Tommy | 7/6/2023 19:30 | Albert Ivar Goodman Theatre |
| Blue Man Group | 7/6/2023 20:00 | Briar Street Theatre |
| 46th Revue | 7/6/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| David Cook | 7/6/2023 20:00 | City Winery - Chicago |
| Taylor Swift Night - Taylor Swift Dance Party | 7/6/2023 20:00 | House Of Blues - Chicago |
| Dancefestopia - Yellow Brick Road Tour | 7/6/2023 20:00 | Cubby Bear |
| Reggae Gold | 7/6/2023 22:00 | Subterranean |
| Dave Matthews Band - 2 Day Pass | 7/7/2023 3:30 | Huntington Bank Pavilion at Northerly Island |
| Chicago Sky vs. Atlanta Dream | 7/7/2023 19:00 | Wintrust Arena |
| We Are The Union | 7/7/2023 19:00 | Bottom Lounge |
| Dirty Heads | 7/7/2023 19:00 | Radius - IL |
| 46th Revue | 7/7/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 7/7/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 7/7/2023 19:00 | The Lion Theatre - Chicago |
| Chicago White Sox vs. St. Louis Cardinals | 7/7/2023 19:10 | Guaranteed Rate Field |
| Dave Matthews Band | 7/7/2023 19:30 | Huntington Bank Pavilion at Northerly Island |
| Blue Man Group | 7/7/2023 20:00 | Briar Street Theatre |
| Dancefestopia - Yellow Brick Road Tour | 7/7/2023 20:00 | Cubby Bear |
| Jenny Lewis | 7/7/2023 20:00 | The Salt Shed - Chicago |
| The Who's Tommy | 7/7/2023 20:00 | Albert Ivar Goodman Theatre |
| Cut The Activist Live! | 7/7/2023 20:00 | City Winery - Chicago |
| Carly Cosgrove | 7/7/2023 20:00 | Beat Kitchen |
| Cabeza de Chivo | 7/7/2023 20:30 | Thalia Hall |
| Drunk Shakespeare | 7/7/2023 21:00 | The Lion Theatre - Chicago |
| Scarface | 7/7/2023 21:00 | House Of Blues - Chicago |
| 46th Revue | 7/7/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Wolfgang Gartner | 7/7/2023 22:00 | Sound-Bar |
| Chosen Few Picnic and Festival | 7/8/2023 3:30 | Jackson Park - Chicago |
| The Second City's Improv Brunch | 7/8/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago White Sox vs. St. Louis Cardinals | 7/8/2023 13:10 | Guaranteed Rate Field |
| Blue Man Group | 7/8/2023 14:00 | Briar Street Theatre |
| The Who's Tommy | 7/8/2023 14:00 | Albert Ivar Goodman Theatre |
| The Best of The Second City | 7/8/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 7/8/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 7/8/2023 17:00 | The Lion Theatre - Chicago |
| 46th Revue | 7/8/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 7/8/2023 19:00 | The Lion Theatre - Chicago |
| Less Than Jake | 7/8/2023 19:00 | Concord Music Hall |
| LustSickPuppy | 7/8/2023 19:00 | Subterranean |
| Dave Matthews Band | 7/8/2023 19:30 | Huntington Bank Pavilion at Northerly Island |
| Gina Yashere | 7/8/2023 19:30 | Thalia Hall |
| Jocko Willink | 7/8/2023 19:30 | Vic Theatre |
| Savage Master | 7/8/2023 19:30 | Reggie's Rock Club |
| Chicago Fire FC vs. Nashville SC | 7/8/2023 19:30 | Soldier Field |
| Blue Man Group | 7/8/2023 20:00 | Briar Street Theatre |
| The Who's Tommy | 7/8/2023 20:00 | Albert Ivar Goodman Theatre |
| 49 Winchester | 7/8/2023 20:00 | Joe's Bar On Weed St. |
| The SteelDrivers | 7/8/2023 20:00 | City Winery - Chicago |
| Kiltro | 7/8/2023 20:00 | Beat Kitchen |
| Davido | 7/8/2023 20:00 | Credit Union 1 Arena |
| Mega64 | 7/8/2023 20:00 | Lincoln Hall |
| Drunk Shakespeare | 7/8/2023 21:00 | The Lion Theatre - Chicago |
| Shrek Rave | 7/8/2023 21:00 | House Of Blues - Chicago |
| Fueled By Emo - Tributes to Fall Out Boy & Paramore | 7/8/2023 21:00 | Bottom Lounge |
| 46th Revue | 7/8/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Ookay | 7/8/2023 22:00 | PRYSM Nightclub |
| He$h | 7/8/2023 22:00 | Sound-Bar |
| The Second City's Improv Brunch | 7/9/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago White Sox vs. St. Louis Cardinals | 7/9/2023 13:10 | Guaranteed Rate Field |
| Blue Man Group | 7/9/2023 14:00 | Briar Street Theatre |
| The Best of The Second City | 7/9/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 7/9/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 7/9/2023 17:00 | The Lion Theatre - Chicago |
| Chicago Sky vs. Atlanta Dream | 7/9/2023 19:00 | Wintrust Arena |
| 46th Revue | 7/9/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| The SteelDrivers | 7/9/2023 19:00 | City Winery - Chicago |
| The Dead South | 7/9/2023 19:30 | Vic Theatre |
| Souls of Mischief | 7/9/2023 20:00 | Metro Chicago |
| Japanese Breakfast | 7/9/2023 20:00 | The Salt Shed - Chicago |
| Superchunk | 7/9/2023 20:00 | Thalia Hall |
| Mal Blum | 7/9/2023 20:00 | Beat Kitchen |
| Blue Man Group | 7/10/2023 20:00 | Briar Street Theatre |
| The Best of The Second City | 7/10/2023 20:00 | Mainstage at Second City - Chicago |
| Japanese Breakfast | 7/10/2023 20:00 | The Salt Shed - Chicago |
| Electric Gradyland - Tribute To Jimi Hendrix | 7/10/2023 20:00 | City Winery - Chicago |
| Etran De L'air | 7/10/2023 20:30 | Constellation - Chicago |
| Stick Figure, Pepper & The Elovaters | 7/11/2023 18:00 | The Salt Shed - Chicago |
| StarBenders | 7/11/2023 19:00 | Subterranean |
| Melanie Martinez | 7/11/2023 19:30 | Byline Bank Aragon Ballroom |
| Blue Man Group | 7/11/2023 20:00 | Briar Street Theatre |
| Home is Where | 7/11/2023 20:00 | Beat Kitchen |
| The Docksiders | 7/11/2023 20:00 | City Winery - Chicago |
| Chicago Sky vs. Connecticut Sun | 7/12/2023 11:00 | Wintrust Arena |
| Drunk Shakespeare | 7/12/2023 19:30 | The Lion Theatre - Chicago |
| Chicago Fire FC vs. CF Montreal | 7/12/2023 19:30 | Soldier Field |
| Just Fine - Mary J. Blige Tribute Band | 7/12/2023 20:00 | City Winery - Chicago |
| Blondshell | 7/12/2023 20:00 | Schubas |
| The Social Animals | 7/12/2023 20:00 | Beat Kitchen |
| Windy City Smokeout: Zach Bryan, Darius Rucker, Luke Bryan & Zac Brown Band - 4 Day Pass | 7/13/2023 3:30 | Windy City Smokeout |
| The Who's Tommy | 7/13/2023 14:00 | Albert Ivar Goodman Theatre |
| Blue Man Group | 7/13/2023 14:00 | Briar Street Theatre |
| Windy City Smokeout: Zach Bryan, Randy Rogers Band & Bailey Zimmerman - Thursday Pass | 7/13/2023 14:00 | Windy City Smokeout |
| Little Jesus | 7/13/2023 19:00 | Bottom Lounge |
| Rock Of Ages | 7/13/2023 19:30 | Mercury Theater - IL |
| Blue Man Group | 7/13/2023 20:00 | Briar Street Theatre |
| Protomartyr | 7/13/2023 20:00 | Thalia Hall |
| 46th Revue | 7/13/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Puddles Pity Party | 7/13/2023 20:00 | City Winery - Chicago |
| Merci | 7/13/2023 20:00 | Subterranean |
| JJ Smith | 7/13/2023 20:00 | Cubby Bear |
| The Crane Wives | 7/13/2023 20:00 | Lincoln Hall |
| Reggae Gold | 7/13/2023 22:00 | Subterranean |
| Beauty and The Beast | 7/14/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Windy City Smokeout: Darius Rucker, Chris Lane & Jo Dee Messina - Friday Pass | 7/14/2023 14:00 | Windy City Smokeout |
| Zoso - Led Zeppelin Tribute Band | 7/14/2023 18:30 | Concord Music Hall |
| 46th Revue | 7/14/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 7/14/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 7/14/2023 19:00 | The Lion Theatre - Chicago |
| Vivian Green | 7/14/2023 19:00 | City Winery - Chicago |
| Chicago Cubs vs. Boston Red Sox | 7/14/2023 19:05 | Wrigley Field |
| Lauren Spencer Smith | 7/14/2023 19:15 | House Of Blues - Chicago |
| Rock Of Ages | 7/14/2023 19:30 | Mercury Theater - IL |
| Blue Man Group | 7/14/2023 20:00 | Briar Street Theatre |
| Jinkx Monsoon | 7/14/2023 20:00 | The Chicago Theatre |
| Wheatus | 7/14/2023 20:00 | Beat Kitchen |
| The Virus | 7/14/2023 20:00 | Reggie's Rock Club |
| K Camp | 7/14/2023 20:00 | Park West |
| Bonny Doon | 7/14/2023 20:30 | Thalia Hall |
| Deerhoof | 7/14/2023 21:00 | Lincoln Hall |
| Drunk Shakespeare | 7/14/2023 21:00 | The Lion Theatre - Chicago |
| 46th Revue | 7/14/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Vivian Green | 7/14/2023 22:30 | City Winery - Chicago |
| Beauty and The Beast | 7/15/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Second City's Improv Brunch | 7/15/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Soul Brunch | 7/15/2023 12:00 | City Winery - Chicago |
| Windy City Smokeout: Luke Bryan, Dylan Scott & Kameron Marlowe - Saturday Pass | 7/15/2023 13:00 | Windy City Smokeout |
| Chicago Cubs vs. Boston Red Sox | 7/15/2023 13:20 | Wrigley Field |
| Blue Man Group | 7/15/2023 14:00 | Briar Street Theatre |
| The Who's Tommy | 7/15/2023 14:00 | Albert Ivar Goodman Theatre |
| Rock Of Ages | 7/15/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 7/15/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 7/15/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 7/15/2023 17:00 | The Lion Theatre - Chicago |
| 46th Revue | 7/15/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 7/15/2023 19:00 | The Lion Theatre - Chicago |
| Boys of Fall | 7/15/2023 19:00 | Beat Kitchen |
| Ross Mathews | 7/15/2023 19:00 | Athenaeum Theatre - IL |
| Chicago Fire FC vs. Toronto FC | 7/15/2023 19:30 | Soldier Field |
| Kansas - The Band | 7/15/2023 19:30 | The Chicago Theatre |
| Iris DeMent | 7/15/2023 19:30 | Park West |
| Rock Of Ages | 7/15/2023 19:30 | Mercury Theater - IL |
| Blue Man Group | 7/15/2023 20:00 | Briar Street Theatre |
| The Who's Tommy | 7/15/2023 20:00 | Albert Ivar Goodman Theatre |
| True Crime Obsessed | 7/15/2023 20:00 | Vic Theatre |
| John Lodge | 7/15/2023 20:00 | Copernicus Center |
| J. Holiday | 7/15/2023 20:00 | City Winery - Chicago |
| Aleks Syntek | 7/15/2023 20:00 | House Of Blues - Chicago |
| Profanatica | 7/15/2023 20:00 | Reggie's Rock Club |
| Le Tigre & Man On Man | 7/15/2023 20:00 | The Salt Shed - Chicago |
| Altin Gun | 7/15/2023 20:30 | Thalia Hall |
| Drunk Shakespeare | 7/15/2023 21:00 | The Lion Theatre - Chicago |
| Daft Disko - A French House & Disco Party | 7/15/2023 21:00 | Subterranean |
| 46th Revue | 7/15/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Twinsick | 7/15/2023 22:00 | PRYSM Nightclub |
| Beauty and The Beast | 7/16/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Second City's Improv Brunch | 7/16/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Windy City Smokeout: Zac Brown Band, Eli Young Band & Larry Fleet - Sunday Pass | 7/16/2023 13:00 | Windy City Smokeout |
| Chicago Cubs vs. Boston Red Sox | 7/16/2023 13:20 | Wrigley Field |
| Blue Man Group | 7/16/2023 14:00 | Briar Street Theatre |
| The Who's Tommy | 7/16/2023 14:00 | Albert Ivar Goodman Theatre |
| Rock Of Ages | 7/16/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 7/16/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 7/16/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 7/16/2023 17:00 | The Lion Theatre - Chicago |
| Underoath, The Ghost Inside, We Came as Romans & Better Lovers | 7/16/2023 18:00 | The Salt Shed - Chicago |
| Red Wanting Blue | 7/16/2023 19:00 | City Winery - Chicago |
| 46th Revue | 7/16/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Cheap Trick | 7/16/2023 19:00 | Metro Chicago |
| When The Sun Sets | 7/16/2023 19:00 | Beat Kitchen |
| Yellowcard, Mayday Parade, Story of the Year, This Wild Life & Emo Night Brooklyn | 7/16/2023 19:00 | Huntington Bank Pavilion at Northerly Island |
| They Are Gutting a Body of Water & Waveform | 7/16/2023 19:00 | Subterranean |
| d4vd | 7/16/2023 19:30 | Bottom Lounge |
| Jeremy Passion, Jesse Barrera, Gabe Bondoc & Albert Posis | 7/16/2023 20:00 | Lincoln Hall |
| Chicago Cubs vs. Washington Nationals | 7/17/2023 19:05 | Wrigley Field |
| Blue Man Group | 7/17/2023 20:00 | Briar Street Theatre |
| The Best of The Second City | 7/17/2023 20:00 | Mainstage at Second City - Chicago |
| Andre Jackson - A Tribute to Teddy Pendergrass | 7/17/2023 20:00 | City Winery - Chicago |
| Lime Cordiale | 7/18/2023 19:00 | Bottom Lounge |
| Chicago Cubs vs. Washington Nationals | 7/18/2023 19:05 | Wrigley Field |
| The Who's Tommy | 7/18/2023 19:30 | Albert Ivar Goodman Theatre |
| Blue Man Group | 7/18/2023 20:00 | Briar Street Theatre |
| Alicia Keys | 7/18/2023 20:00 | United Center |
| Imarhan | 7/18/2023 21:00 | The Empty Bottle |
| Beauty and The Beast | 7/19/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Please Don't Destroy | 7/19/2023 19:00 | Vic Theatre |
| Chicago Cubs vs. Washington Nationals | 7/19/2023 19:05 | Wrigley Field |
| Drunk Shakespeare | 7/19/2023 19:30 | The Lion Theatre - Chicago |
| The Who's Tommy | 7/19/2023 19:30 | Albert Ivar Goodman Theatre |
| Rock Of Ages | 7/19/2023 19:30 | Mercury Theater - IL |
| JD Souther | 7/19/2023 20:00 | City Winery - Chicago |
| Beauty and The Beast | 7/20/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Who's Tommy | 7/20/2023 14:00 | Albert Ivar Goodman Theatre |
| Blue Man Group | 7/20/2023 14:00 | Briar Street Theatre |
| Beauty and The Beast | 7/20/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Please Don't Destroy | 7/20/2023 19:00 | Vic Theatre |
| Chicago Cubs vs. St. Louis Cardinals | 7/20/2023 19:05 | Wrigley Field |
| Drunk Shakespeare | 7/20/2023 19:30 | The Lion Theatre - Chicago |
| The Who's Tommy | 7/20/2023 19:30 | Albert Ivar Goodman Theatre |
| Blue Man Group | 7/20/2023 20:00 | Briar Street Theatre |
| 46th Revue | 7/20/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Louise Post | 7/20/2023 20:00 | Lincoln Hall |
| Damon Williams | 7/20/2023 20:00 | City Winery - Chicago |
| Reggae Gold | 7/20/2023 22:00 | Subterranean |
| Pitchfork Music Festival - 3 Day Pass | 7/21/2023 3:30 | Union Park |
| Pitchfork Music Festival - Friday | 7/21/2023 12:00 | Union Park |
| Chicago Cubs vs. St. Louis Cardinals | 7/21/2023 13:20 | Wrigley Field |
| Beauty and The Beast | 7/21/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Sad Summer Festival: Taking Back Sunday, The Maine, Pvris, Hot Mulligan & Mom Jeans | 7/21/2023 14:00 | Huntington Bank Pavilion at Northerly Island |
| Trombone Shorty and Orleans Avenue & Ziggy Marley | 7/21/2023 17:30 | The Salt Shed - Chicago |
| 46th Revue | 7/21/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 7/21/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 7/21/2023 19:00 | The Lion Theatre - Chicago |
| Jay Chandrasekhar | 7/21/2023 19:00 | Thalia Hall |
| Rock Of Ages | 7/21/2023 19:30 | Mercury Theater - IL |
| Blue Man Group | 7/21/2023 20:00 | Briar Street Theatre |
| Karlous Miller | 7/21/2023 20:00 | Riviera Theatre - IL |
| The Big Wu | 7/21/2023 20:00 | City Winery - Chicago |
| The Who's Tommy | 7/21/2023 20:00 | Albert Ivar Goodman Theatre |
| Tears Dry on Their Own | 7/21/2023 20:00 | Reggie's Rock Club |
| Drunk Shakespeare | 7/21/2023 21:00 | The Lion Theatre - Chicago |
| Saymynitti | 7/21/2023 21:00 | Concord Music Hall |
| Vanic | 7/21/2023 22:00 | Sound-Bar |
| 46th Revue | 7/21/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Jay Chandrasekhar | 7/21/2023 22:00 | Thalia Hall |
| Beauty and The Beast | 7/22/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Second City's Improv Brunch | 7/22/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Pitchfork Music Festival - Saturday | 7/22/2023 12:00 | Union Park |
| Chicago Cubs vs. St. Louis Cardinals | 7/22/2023 13:20 | Wrigley Field |
| Blue Man Group | 7/22/2023 14:00 | Briar Street Theatre |
| Beauty and The Beast | 7/22/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 7/22/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 7/22/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 7/22/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 7/22/2023 17:00 | The Lion Theatre - Chicago |
| The Blue Meanies | 7/22/2023 18:00 | Concord Music Hall |
| Destroy Boys | 7/22/2023 18:00 | Metro Chicago |
| Rory Scovel | 7/22/2023 19:00 | Thalia Hall |
| Beyonce | 7/22/2023 19:00 | Soldier Field |
| 46th Revue | 7/22/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 7/22/2023 19:00 | The Lion Theatre - Chicago |
| Matt Bellassai | 7/22/2023 19:00 | City Winery - Chicago |
| Rock Of Ages | 7/22/2023 19:30 | Mercury Theater - IL |
| First Aid Kit | 7/22/2023 20:00 | The Salt Shed - Chicago |
| Blue Man Group | 7/22/2023 20:00 | Briar Street Theatre |
| The Who's Tommy | 7/22/2023 20:00 | Albert Ivar Goodman Theatre |
| Arrows In Action | 7/22/2023 20:00 | Subterranean |
| Leanna Firestone | 7/22/2023 20:00 | Beat Kitchen |
| Drunk Shakespeare | 7/22/2023 21:00 | The Lion Theatre - Chicago |
| 46th Revue | 7/22/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Rory Scovel | 7/22/2023 22:00 | Thalia Hall |
| Bonobo | 7/22/2023 22:00 | Radius - IL |
| The Second City's Improv Brunch | 7/23/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Pitchfork Music Festival - Sunday | 7/23/2023 12:00 | Union Park |
| Chicago Cubs vs. St. Louis Cardinals | 7/23/2023 13:20 | Wrigley Field |
| Blue Man Group | 7/23/2023 14:00 | Briar Street Theatre |
| The Who's Tommy | 7/23/2023 14:00 | Albert Ivar Goodman Theatre |
| Beauty and The Beast | 7/23/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 7/23/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 7/23/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 7/23/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 7/23/2023 17:00 | The Lion Theatre - Chicago |
| Beyonce | 7/23/2023 19:00 | Soldier Field |
| 46th Revue | 7/23/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Howie Day | 7/23/2023 19:00 | City Winery - Chicago |
| Belis | 7/23/2023 19:00 | House Of Blues - Chicago |
| Jill Scott | 7/24/2023 19:00 | The Chicago Theatre |
| Blue Man Group | 7/24/2023 20:00 | Briar Street Theatre |
| The Best of The Second City | 7/24/2023 20:00 | Mainstage at Second City - Chicago |
| Des Rocs | 7/24/2023 20:00 | Subterranean |
| Chicago Sky vs. Las Vegas Aces | 7/25/2023 18:00 | Wintrust Arena |
| Matt Watson | 7/25/2023 18:30 | Lincoln Hall |
| Jill Scott | 7/25/2023 19:00 | The Chicago Theatre |
| Chicago White Sox vs. Chicago Cubs | 7/25/2023 19:10 | Guaranteed Rate Field |
| Blue Man Group | 7/25/2023 20:00 | Briar Street Theatre |
| Mike Phillips | 7/25/2023 20:00 | City Winery - Chicago |
| The Juno Show: Juno Birch | 7/25/2023 20:00 | Vic Theatre |
| Beauty and The Beast | 7/26/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Chicago White Sox vs. Chicago Cubs | 7/26/2023 19:10 | Guaranteed Rate Field |
| Drunk Shakespeare | 7/26/2023 19:30 | The Lion Theatre - Chicago |
| Rock Of Ages | 7/26/2023 19:30 | Mercury Theater - IL |
| Grace Kelly | 7/26/2023 20:00 | City Winery - Chicago |
| AJJ | 7/26/2023 20:00 | Thalia Hall |
| Beauty and The Beast | 7/27/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Blue Man Group | 7/27/2023 14:00 | Briar Street Theatre |
| Beauty and The Beast | 7/27/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Chicago White Sox vs. Cleveland Guardians | 7/27/2023 19:10 | Guaranteed Rate Field |
| Drunk Shakespeare | 7/27/2023 19:30 | The Lion Theatre - Chicago |
| Rock Of Ages | 7/27/2023 19:30 | Mercury Theater - IL |
| Glasshouse Owl | 7/27/2023 19:30 | Cubby Bear |
| Blue Man Group | 7/27/2023 20:00 | Briar Street Theatre |
| Reverend Horton Heat | 7/27/2023 20:00 | City Winery - Chicago |
| 46th Revue | 7/27/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Gogol Bordello | 7/27/2023 20:00 | Concord Music Hall |
| Brent Faiyaz | 7/27/2023 20:00 | The Salt Shed - Chicago |
| Lido Pimienta | 7/27/2023 20:00 | Subterranean |
| Javier Rosas | 7/27/2023 20:00 | House Of Blues - Chicago |
| Reggae Gold | 7/27/2023 22:00 | Subterranean |
| Beauty and The Beast | 7/28/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Beauty and The Beast | 7/28/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Slightly Stoopid, Sublime with Rome & Atmosphere | 7/28/2023 17:00 | Huntington Bank Pavilion at Northerly Island |
| 46th Revue | 7/28/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 7/28/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 7/28/2023 19:00 | The Lion Theatre - Chicago |
| Chicago Sky vs. Seattle Storm | 7/28/2023 19:00 | Wintrust Arena |
| Chicago White Sox vs. Cleveland Guardians | 7/28/2023 19:10 | Guaranteed Rate Field |
| Thomas Rhett, Cole Swindell & Nate Smith | 7/28/2023 19:30 | United Center |
| Rock Of Ages | 7/28/2023 19:30 | Mercury Theater - IL |
| Ed Sheeran | 7/28/2023 19:30 | The Chicago Theatre |
| Blue Man Group | 7/28/2023 20:00 | Briar Street Theatre |
| And Then We Had Sex Podcast | 7/28/2023 20:00 | City Winery - Chicago |
| The Home Edit | 7/28/2023 20:00 | Copernicus Center |
| Harbour | 7/28/2023 20:00 | Lincoln Hall |
| Brent Faiyaz | 7/28/2023 20:00 | The Salt Shed - Chicago |
| Dexter and The Moonrocks | 7/28/2023 20:30 | Thalia Hall |
| Drunk Shakespeare | 7/28/2023 21:00 | The Lion Theatre - Chicago |
| Feels So Close - An EDM Golden Era Party | 7/28/2023 21:00 | House Of Blues - Chicago |
| 46th Revue | 7/28/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Beauty and The Beast | 7/29/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Second City's Improv Brunch | 7/29/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Blue Man Group | 7/29/2023 14:00 | Briar Street Theatre |
| Beauty and The Beast | 7/29/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 7/29/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 7/29/2023 15:00 | Mainstage at Second City - Chicago |
| Apollo Showtime | 7/29/2023 16:30 | City Winery - Chicago |
| Blue Man Group | 7/29/2023 17:00 | Briar Street Theatre |
| Cavetown | 7/29/2023 17:00 | The Salt Shed - Chicago |
| Drunk Shakespeare | 7/29/2023 17:00 | The Lion Theatre - Chicago |
| Ed Sheeran & Khalid | 7/29/2023 18:00 | Soldier Field |
| Chicago White Sox vs. Cleveland Guardians | 7/29/2023 18:10 | Guaranteed Rate Field |
| Yung Pinch | 7/29/2023 18:30 | Concord Music Hall |
| MC Magic, Stevie B., Baby Bash & Lil Rob | 7/29/2023 19:00 | Vic Theatre |
| 46th Revue | 7/29/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 7/29/2023 19:00 | The Lion Theatre - Chicago |
| Clutch, Dinosaur Jr. & Red Fang | 7/29/2023 19:30 | Radius - IL |
| Rock Of Ages | 7/29/2023 19:30 | Mercury Theater - IL |
| Neo Reunion | 7/29/2023 19:30 | Metro Chicago |
| Blue Man Group | 7/29/2023 20:00 | Briar Street Theatre |
| Ted Park | 7/29/2023 20:00 | Reggie's Rock Club |
| Apollo Showtime | 7/29/2023 20:00 | City Winery - Chicago |
| Drunk Shakespeare | 7/29/2023 21:00 | The Lion Theatre - Chicago |
| 46th Revue | 7/29/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Speedy Ortiz | 7/29/2023 22:00 | Beat Kitchen |
| The Second City's Improv Brunch | 7/30/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago White Sox vs. Cleveland Guardians | 7/30/2023 13:10 | Guaranteed Rate Field |
| Blue Man Group | 7/30/2023 14:00 | Briar Street Theatre |
| Beauty and The Beast | 7/30/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 7/30/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 7/30/2023 15:00 | Mainstage at Second City - Chicago |
| Chicago Sky vs. Phoenix Mercury | 7/30/2023 15:00 | Wintrust Arena |
| Q101 Piqniq: Incubus, Badflower & Beach Weather | 7/30/2023 16:00 | Huntington Bank Pavilion at Northerly Island |
| Blue Man Group | 7/30/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 7/30/2023 17:00 | The Lion Theatre - Chicago |
| Sevyn Streeter | 7/30/2023 18:00 | City Winery - Chicago |
| 46th Revue | 7/30/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Telekinetic Yeti | 7/30/2023 19:30 | Reggie's Rock Club |
| Baylen Levine | 7/30/2023 20:00 | Vic Theatre |
| Kowloon Walled City | 7/30/2023 20:00 | Beat Kitchen |
| Sevyn Streeter | 7/30/2023 21:30 | City Winery - Chicago |
| Chicago Cubs vs. Cincinnati Reds | 7/31/2023 19:05 | Wrigley Field |
| Blue Man Group | 7/31/2023 20:00 | Briar Street Theatre |
| Candiace Dillard Bassett | 7/31/2023 20:00 | City Winery - Chicago |
| The Best of The Second City | 7/31/2023 20:00 | Mainstage at Second City - Chicago |
| Your Arms Are My Cocoon | 7/31/2023 20:00 | Beat Kitchen |
