| Chicago Cubs vs. Cincinnati Reds | 8/1/2023 19:05 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/1/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/1/2023 20:00 | Briar Street Theatre |
| Nanna | 8/1/2023 20:00 | Thalia Hall |
| The Stews | 8/1/2023 20:00 | Beat Kitchen |
| Lollapalooza Aftershow: Carly Rae Jepsen | 8/1/2023 21:00 | Metro Chicago |
| Beauty and The Beast | 8/2/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| School Of Rock Allstars | 8/2/2023 18:30 | Reggie's Rock Club |
| Orthodox | 8/2/2023 19:00 | Beat Kitchen |
| Lollapalooza Aftershow: Lovejoy & Junior Mesa | 8/2/2023 19:00 | Bottom Lounge |
| Chicago Cubs vs. Cincinnati Reds | 8/2/2023 19:05 | Wrigley Field |
| Drunk Shakespeare | 8/2/2023 19:30 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/2/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/2/2023 19:30 | Mercury Theater - IL |
| Chelsea FC vs. Borussia Dortmund | 8/2/2023 19:30 | Soldier Field |
| Chantae Cann | 8/2/2023 20:00 | City Winery - Chicago |
| Lollapalooza Aftershow: brakence | 8/2/2023 21:00 | Subterranean |
| Lollapalooza Aftershow: Men I Trust & Husbands | 8/2/2023 21:00 | Thalia Hall |
| Lollapalooza Aftershow: Thirty Seconds to Mars | 8/2/2023 21:00 | House Of Blues - Chicago |
| Lollapalooza Aftershow: Dope Lemon | 8/2/2023 21:00 | Park West |
| Lollapalooza Aftershow: Noah Kahan & Richy Mitch and The Coal Miners | 8/2/2023 21:00 | Vic Theatre |
| Lollapalooza Aftershow: Joy Oladokun & Pony Bradshaw | 8/2/2023 21:00 | Lincoln Hall |
| Lollapalooza Aftershow: Matt Maltese | 8/2/2023 21:00 | Schubas |
| Lollapalooza Aftershow: Franc Moody | 8/2/2023 23:00 | Sleeping Village |
| Lollapalooza Chicago - 4 Day Pass | 8/3/2023 3:30 | Hutchinson Field Grant Park |
| Lollapalooza Chicago - Thursday Only | 8/3/2023 11:00 | Hutchinson Field Grant Park |
| Beauty and The Beast | 8/3/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Blue Man Group | 8/3/2023 14:00 | Briar Street Theatre |
| Beauty and The Beast | 8/3/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Chicago Cubs vs. Cincinnati Reds | 8/3/2023 19:05 | Wrigley Field |
| Drunk Shakespeare | 8/3/2023 19:30 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/3/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/3/2023 19:30 | Mercury Theater - IL |
| Blue Man Group | 8/3/2023 20:00 | Briar Street Theatre |
| 46th Revue | 8/3/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Magic Tuber Stringband | 8/3/2023 20:30 | Constellation - Chicago |
| Reggae Gold | 8/3/2023 22:00 | Subterranean |
| Lollapalooza Aftershow: Ken Carson | 8/3/2023 22:00 | Concord Music Hall |
| Lollapalooza Aftershow: Knocked Loose | 8/3/2023 22:00 | Cobra Lounge |
| Lollapalooza Aftershow: Acraze | 8/3/2023 22:00 | Sound-Bar |
| Lollapalooza Aftershow: Dom Dolla | 8/3/2023 22:00 | Radius - IL |
| Lollapalooza Aftershow: Declan McKenna & Eli Smart | 8/3/2023 23:00 | Bottom Lounge |
| Lollapalooza Aftershow: Band-Maid & Beauty School Dropout | 8/3/2023 23:00 | Park West |
| Lollapalooza Aftershow: Peach Pit & Annie Dirusso | 8/3/2023 23:00 | Vic Theatre |
| Lollapalooza Aftershow: Sabrina Carpenter | 8/3/2023 23:00 | House Of Blues - Chicago |
| Lollapalooza Aftershow: The 502s & Ax and The Hatchetmen | 8/3/2023 23:00 | Lincoln Hall |
| Lollapalooza Aftershow: Morgan Wade | 8/3/2023 23:00 | Reggie's Rock Club |
| Lollapalooza Aftershow: Ekkstacy & Pardyalone | 8/3/2023 23:00 | Schubas |
| Lollapalooza Aftershow: Foals & Friday Pilots Club | 8/3/2023 23:00 | Thalia Hall |
| Lollapalooza Chicago - Friday Only | 8/4/2023 11:00 | Hutchinson Field Grant Park |
| Beauty and The Beast | 8/4/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Chicago Cubs vs. Atlanta Braves | 8/4/2023 13:20 | Wrigley Field |
| Beauty and The Beast | 8/4/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| 46th Revue | 8/4/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 8/4/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 8/4/2023 19:00 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/4/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/4/2023 19:30 | Mercury Theater - IL |
| Blue Man Group | 8/4/2023 20:00 | Briar Street Theatre |
| 46th Revue | 8/4/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Lollapalooza Aftershow: Yung Gravy | 8/4/2023 22:00 | House Of Blues - Chicago |
| Lollapalooza Aftershow: The Knocks - DJ Set | 8/4/2023 22:00 | Sound-Bar |
| Lollapalooza Aftershow: Svdden Death | 8/4/2023 22:00 | Radius - IL |
| Lollapalooza Aftershow: Destroy Lonely & Tiacorine | 8/4/2023 22:00 | Concord Music Hall |
| Lollapalooza Aftershow: Diplo, Major League DJz & Bontan | 8/4/2023 22:00 | The Salt Shed - Chicago |
| Lollapalooza Aftershow: Emo Nite LA | 8/4/2023 22:00 | Subterranean |
| Lollapalooza Aftershow: Spacey Jane & Arcy Drive | 8/4/2023 23:00 | Bottom Lounge |
| Lollapalooza Aftershow: The Happy Fits & Windser | 8/4/2023 23:00 | Schubas |
| Lollapalooza Aftershow: Ivan Cornejo | 8/4/2023 23:00 | Park West |
| Lollapalooza Aftershow: Suki Waterhouse & Ari Abdul | 8/4/2023 23:00 | Lincoln Hall |
| Lollapalooza Aftershow: Portugal. The Man & Usted Senalemelo | 8/4/2023 23:00 | Metro Chicago |
| Lollapalooza Aftershow: The Rose & Isabel Larosa | 8/4/2023 23:00 | Vic Theatre |
| Lollapalooza Aftershow: Morgan Wade | 8/4/2023 23:00 | Reggie's Rock Club |
| Lollapalooza Aftershow: The Garden & Sincere Engineer | 8/4/2023 23:00 | Thalia Hall |
| Lollapalooza Chicago - Saturday | 8/5/2023 11:00 | Hutchinson Field Grant Park |
| Beauty and The Beast | 8/5/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Second City's Improv Brunch | 8/5/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago Cubs vs. Atlanta Braves | 8/5/2023 13:20 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/5/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/5/2023 14:00 | Briar Street Theatre |
| Beauty and The Beast | 8/5/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 8/5/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 8/5/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 8/5/2023 17:00 | Briar Street Theatre |
| 46th Revue | 8/5/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 8/5/2023 19:00 | The Lion Theatre - Chicago |
| Tiera O'Leary | 8/5/2023 19:00 | City Winery - Chicago |
| Rock Of Ages | 8/5/2023 19:30 | Mercury Theater - IL |
| Lionel Richie & Earth, Wind and Fire | 8/5/2023 19:30 | United Center |
| MJ - The Life Story of Michael Jackson | 8/5/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/5/2023 20:00 | Briar Street Theatre |
| Mike and The Moonpies | 8/5/2023 20:00 | Joe's Bar On Weed St. |
| 46th Revue | 8/5/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Lollapalooza Aftershow: AC Slater | 8/5/2023 22:00 | Concord Music Hall |
| Lollapalooza Aftershow: Maisie Peters | 8/5/2023 22:00 | House Of Blues - Chicago |
| Lollapalooza Aftershow: Meduza | 8/5/2023 22:00 | Cermak Hall At Radius - IL |
| Lollapalooza Aftershow: Solardo | 8/5/2023 22:00 | Sound-Bar |
| Lollapalooza Aftershow: Sudan Archives & Harry Edohoukwa | 8/5/2023 23:00 | Bottom Lounge |
| Lollapalooza Aftershow: Michelle & Girl K | 8/5/2023 23:00 | Schubas |
| Lollapalooza Aftershow: Neil Frances | 8/5/2023 23:00 | Lincoln Hall |
| Lollapalooza Aftershow: A Boogie Wit Da Hoodie & Skizzy Mars | 8/5/2023 23:00 | Metro Chicago |
| Lollapalooza Aftershow: Magdalena Bay | 8/5/2023 23:00 | Park West |
| Lollapalooza Aftershow: Bakar | 8/5/2023 23:00 | Reggie's Rock Club |
| Lollapalooza Aftershow: Thee Sacred Souls | 8/5/2023 23:00 | Sleeping Village |
| Lollapalooza Aftershow: Loveless | 8/5/2023 23:00 | Subterranean |
| Lollapalooza Aftershow: L'Imperatrice & Josh Fudge | 8/5/2023 23:00 | Thalia Hall |
| Lollapalooza Chicago - Sunday Only | 8/6/2023 11:00 | Hutchinson Field Grant Park |
| The Second City's Improv Brunch | 8/6/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago Cubs vs. Atlanta Braves | 8/6/2023 13:20 | Wrigley Field |
| Blue Man Group | 8/6/2023 14:00 | Briar Street Theatre |
| MJ - The Life Story of Michael Jackson | 8/6/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Beauty and The Beast | 8/6/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 8/6/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 8/6/2023 15:00 | Mainstage at Second City - Chicago |
| Drunk Shakespeare | 8/6/2023 17:00 | The Lion Theatre - Chicago |
| 46th Revue | 8/6/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Sons of the Never Wrong | 8/6/2023 19:00 | City Winery - Chicago |
| MJ - The Life Story of Michael Jackson | 8/6/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Lollapalooza Aftershow: Gorgon City | 8/6/2023 22:00 | Cermak Hall At Radius - IL |
| Lollapalooza Aftershow: Alan Walker & Telykast | 8/6/2023 22:00 | Radius - IL |
| Lollapalooza Aftershow: Wax Motif | 8/6/2023 22:00 | Concord Music Hall |
| Lollapalooza Aftershow: Matroda | 8/6/2023 22:00 | Sound-Bar |
| Lollapalooza Aftershow: Sylvan Esso & Sarah Kinsley | 8/6/2023 23:00 | Metro Chicago |
| Lollapalooza Aftershow: Dehd & The Hecks | 8/6/2023 23:00 | Thalia Hall |
| Lollapalooza Aftershow: Poolside | 8/6/2023 23:00 | Lincoln Hall |
| Chicago White Sox vs. New York Yankees | 8/7/2023 19:10 | Guaranteed Rate Field |
| Blue Man Group | 8/7/2023 20:00 | Briar Street Theatre |
| The Best of The Second City | 8/7/2023 20:00 | Mainstage at Second City - Chicago |
| The Newest Olympian | 8/7/2023 20:00 | Beat Kitchen |
| Chicago Sky vs. Minnesota Lynx | 8/8/2023 19:00 | Wintrust Arena |
| Chicago White Sox vs. New York Yankees | 8/8/2023 19:10 | Guaranteed Rate Field |
| MJ - The Life Story of Michael Jackson | 8/8/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| To Kill a Mockingbird | 8/8/2023 19:30 | CIBC Theatre |
| Blue Man Group | 8/8/2023 20:00 | Briar Street Theatre |
| The Drums | 8/8/2023 20:00 | Metro Chicago |
| Derrick Hodge | 8/8/2023 20:00 | City Winery - Chicago |
| Nathaniel Rateliff and The Night Sweats - 2 Day Pass | 8/9/2023 3:30 | The Salt Shed - Chicago |
| Beauty and The Beast | 8/9/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| To Kill a Mockingbird | 8/9/2023 14:00 | CIBC Theatre |
| Nathaniel Rateliff and The Night Sweats | 8/9/2023 18:00 | The Salt Shed - Chicago |
| Havok & Toxic Holocaust | 8/9/2023 19:00 | Reggie's Rock Club |
| Cory Henry | 8/9/2023 19:00 | City Winery - Chicago |
| Chicago White Sox vs. New York Yankees | 8/9/2023 19:10 | Guaranteed Rate Field |
| MJ - The Life Story of Michael Jackson | 8/9/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Bruce Springsteen & The E Street Band | 8/9/2023 19:30 | Wrigley Field |
| To Kill a Mockingbird | 8/9/2023 19:30 | CIBC Theatre |
| Drunk Shakespeare | 8/9/2023 19:30 | The Lion Theatre - Chicago |
| Rock Of Ages | 8/9/2023 19:30 | Mercury Theater - IL |
| Madonna | 8/9/2023 20:30 | United Center |
| Sarah Weddle | 8/9/2023 20:30 | Constellation - Chicago |
| Cory Henry | 8/9/2023 22:00 | City Winery - Chicago |
| Beauty and The Beast | 8/10/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Beauty and The Beast | 8/10/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Nathaniel Rateliff and The Night Sweats | 8/10/2023 18:00 | The Salt Shed - Chicago |
| To Kill a Mockingbird | 8/10/2023 19:30 | CIBC Theatre |
| Drunk Shakespeare | 8/10/2023 19:30 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/10/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/10/2023 19:30 | Mercury Theater - IL |
| Super Tease | 8/10/2023 19:30 | Cubby Bear |
| Blue Man Group | 8/10/2023 20:00 | Briar Street Theatre |
| 46th Revue | 8/10/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Bully | 8/10/2023 20:00 | Thalia Hall |
| Josh Joplin | 8/10/2023 20:00 | City Winery - Chicago |
| Madonna | 8/10/2023 20:30 | United Center |
| Cindy Lee | 8/10/2023 20:30 | Constellation - Chicago |
| Reggae Gold | 8/10/2023 22:00 | Subterranean |
| Beauty and The Beast | 8/11/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Beauty and The Beast | 8/11/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| MJ - The Life Story of Michael Jackson | 8/11/2023 19:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| 46th Revue | 8/11/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 8/11/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 8/11/2023 19:00 | The Lion Theatre - Chicago |
| Lil Durk, Kodak Black & NLE Choppa | 8/11/2023 19:00 | United Center |
| Chicago White Sox vs. Milwaukee Brewers | 8/11/2023 19:10 | Guaranteed Rate Field |
| Bruce Springsteen & The E Street Band | 8/11/2023 19:30 | Wrigley Field |
| To Kill a Mockingbird | 8/11/2023 19:30 | CIBC Theatre |
| Rock Of Ages | 8/11/2023 19:30 | Mercury Theater - IL |
| Summer Block Party: Jodeci, SWV & Dru Hill | 8/11/2023 19:30 | Arie Crown Theater |
| Blue Man Group | 8/11/2023 20:00 | Briar Street Theatre |
| Nicotine Dolls | 8/11/2023 20:00 | Beat Kitchen |
| Drunk Shakespeare | 8/11/2023 21:00 | The Lion Theatre - Chicago |
| CircuitMOM | 8/11/2023 21:00 | House Of Blues - Chicago |
| Plaid | 8/11/2023 21:00 | Sleeping Village |
| 46th Revue | 8/11/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| M.E.A.T. | 8/11/2023 22:00 | Radius - IL |
| Beauty and The Beast | 8/12/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Second City's Improv Brunch | 8/12/2023 12:00 | UP Comedy Club at Second City - Chicago |
| NFL Preseason: Chicago Bears vs. Tennessee Titans | 8/12/2023 12:00 | Soldier Field |
| Soul Brunch | 8/12/2023 12:00 | City Winery - Chicago |
| PARKING: NFL Preseason - Chicago Bears vs. Tennessee Titans | 8/12/2023 12:00 | Soldier Field Parking Lot |
| MJ - The Life Story of Michael Jackson | 8/12/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/12/2023 14:00 | Briar Street Theatre |
| To Kill a Mockingbird | 8/12/2023 14:00 | CIBC Theatre |
| Beauty and The Beast | 8/12/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 8/12/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 8/12/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 8/12/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 8/12/2023 17:00 | The Lion Theatre - Chicago |
| Blessthefall | 8/12/2023 18:00 | House Of Blues - Chicago |
| Chicago White Sox vs. Milwaukee Brewers | 8/12/2023 18:15 | Guaranteed Rate Field |
| Pink, Pat Benatar, Neil Giraldo & Grouplove | 8/12/2023 18:30 | Wrigley Field |
| 46th Revue | 8/12/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 8/12/2023 19:00 | The Lion Theatre - Chicago |
| Lil Durk, Kodak Black & NLE Choppa | 8/12/2023 19:00 | United Center |
| Rock Of Ages | 8/12/2023 19:30 | Mercury Theater - IL |
| Mariachi Los Camperos | 8/12/2023 19:30 | Athenaeum Theatre - IL |
| MJ - The Life Story of Michael Jackson | 8/12/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/12/2023 20:00 | Briar Street Theatre |
| Small Town Murder Podcast | 8/12/2023 20:00 | Auditorium Theatre - IL |
| To Kill a Mockingbird | 8/12/2023 20:00 | CIBC Theatre |
| Pelican | 8/12/2023 20:00 | Metro Chicago |
| Ruger | 8/12/2023 20:00 | Park West |
| Devin Drobka Trio | 8/12/2023 20:30 | Constellation - Chicago |
| Drunk Shakespeare | 8/12/2023 21:00 | The Lion Theatre - Chicago |
| CircuitMOM | 8/12/2023 21:00 | Byline Bank Aragon Ballroom |
| 46th Revue | 8/12/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Nurko | 8/12/2023 22:00 | Concord Music Hall |
| Myles O'Neal | 8/12/2023 22:00 | Sound-Bar |
| The Second City's Improv Brunch | 8/13/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Girls Rock! Chicago | 8/13/2023 12:00 | Thalia Hall |
| Chicago White Sox vs. Milwaukee Brewers | 8/13/2023 13:10 | Guaranteed Rate Field |
| MJ - The Life Story of Michael Jackson | 8/13/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/13/2023 14:00 | Briar Street Theatre |
| To Kill a Mockingbird | 8/13/2023 14:00 | CIBC Theatre |
| Beauty and The Beast | 8/13/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 8/13/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 8/13/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 8/13/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 8/13/2023 17:00 | The Lion Theatre - Chicago |
| 46th Revue | 8/13/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Poptropicaslutz | 8/13/2023 19:00 | Beat Kitchen |
| Erthe St. James | 8/13/2023 19:00 | City Winery - Chicago |
| Horsegirl & Lifeguard | 8/13/2023 19:30 | Thalia Hall |
| MJ - The Life Story of Michael Jackson | 8/13/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Have Mercy | 8/13/2023 20:00 | Subterranean |
| LL Cool J, The Roots & DJ Jazzy Jeff | 8/13/2023 20:00 | United Center |
| CircuitMOM | 8/13/2023 21:00 | Byline Bank Aragon Ballroom |
| Mat Kerekes | 8/14/2023 19:30 | Beat Kitchen |
| The Best of The Second City | 8/14/2023 20:00 | Mainstage at Second City - Chicago |
| Chicago Cubs vs. Chicago White Sox | 8/15/2023 19:05 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/15/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Ghost & Amon Amarth | 8/15/2023 19:30 | Huntington Bank Pavilion at Northerly Island |
| Sam Smith | 8/15/2023 20:00 | United Center |
| Arthur Verocai | 8/15/2023 20:00 | Thalia Hall |
| The Clientele | 8/15/2023 20:00 | Lincoln Hall |
| Beauty and The Beast | 8/16/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| MJ - The Life Story of Michael Jackson | 8/16/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Jimmy Eat World & Manchester Orchestra | 8/16/2023 19:00 | The Salt Shed - Chicago |
| Chicago Cubs vs. Chicago White Sox | 8/16/2023 19:05 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/16/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Drunk Shakespeare | 8/16/2023 19:30 | The Lion Theatre - Chicago |
| Rock Of Ages | 8/16/2023 19:30 | Mercury Theater - IL |
| Hobo Johnson | 8/16/2023 20:00 | Lincoln Hall |
| Great Southern | 8/16/2023 20:00 | City Winery - Chicago |
| Will Paquin | 8/16/2023 20:00 | Beat Kitchen |
| Beauty and The Beast | 8/17/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Beauty and The Beast | 8/17/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Primal Moon | 8/17/2023 19:00 | Cubby Bear |
| Richard Marx | 8/17/2023 19:00 | Auditorium Theatre - IL |
| Hermitage Green | 8/17/2023 19:30 | Schubas |
| Drunk Shakespeare | 8/17/2023 19:30 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/17/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/17/2023 20:00 | Briar Street Theatre |
| 46th Revue | 8/17/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Gavin DeGraw | 8/17/2023 20:00 | House Of Blues - Chicago |
| Reggae Gold | 8/17/2023 22:00 | Subterranean |
| Beauty and The Beast | 8/18/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Chicago Cubs vs. Kansas City Royals | 8/18/2023 13:20 | Wrigley Field |
| Beauty and The Beast | 8/18/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Life Of Agony & Sick of It All | 8/18/2023 18:00 | Cobra Lounge |
| 46th Revue | 8/18/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 8/18/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 8/18/2023 19:00 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/18/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/18/2023 19:30 | Mercury Theater - IL |
| Blue Man Group | 8/18/2023 20:00 | Briar Street Theatre |
| Jidenna | 8/18/2023 20:00 | Vic Theatre |
| Glaive | 8/18/2023 20:00 | Metro Chicago |
| Sweeping Promises | 8/18/2023 20:00 | Lincoln Hall |
| The Collection | 8/18/2023 20:00 | Subterranean |
| Fueled By Emo - Tributes to Fall Out Boy & Paramore | 8/18/2023 20:00 | Cubby Bear |
| The Swell Season: Glen Hansard & Marketa Irglova | 8/18/2023 20:00 | The Salt Shed - Chicago |
| Molly Tuttle | 8/18/2023 20:30 | Thalia Hall |
| Drunk Shakespeare | 8/18/2023 21:00 | The Lion Theatre - Chicago |
| 46th Revue | 8/18/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Dirt Monkey | 8/18/2023 22:00 | Sound-Bar |
| Beauty and The Beast | 8/19/2023 11:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Second City's Improv Brunch | 8/19/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago Cubs vs. Kansas City Royals | 8/19/2023 13:20 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/19/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/19/2023 14:00 | Briar Street Theatre |
| Beauty and The Beast | 8/19/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| Rock Of Ages | 8/19/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 8/19/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 8/19/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 8/19/2023 17:00 | The Lion Theatre - Chicago |
| 46th Revue | 8/19/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 8/19/2023 19:00 | The Lion Theatre - Chicago |
| Tony Hinchcliffe | 8/19/2023 19:00 | The Chicago Theatre |
| Neal Brennan | 8/19/2023 19:30 | Vic Theatre |
| Rock Of Ages | 8/19/2023 19:30 | Mercury Theater - IL |
| MJ - The Life Story of Michael Jackson | 8/19/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/19/2023 20:00 | Briar Street Theatre |
| Chance The Rapper | 8/19/2023 20:00 | United Center |
| Kings Kaleidoscope | 8/19/2023 20:00 | House Of Blues - Chicago |
| The Righteous Babes | 8/19/2023 20:00 | City Winery - Chicago |
| The Old 97's | 8/19/2023 20:30 | Thalia Hall |
| Drunk Shakespeare | 8/19/2023 21:00 | The Lion Theatre - Chicago |
| Neal Brennan | 8/19/2023 22:00 | Vic Theatre |
| 46th Revue | 8/19/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Paul Van Dyk | 8/19/2023 22:00 | Sound-Bar |
| The Second City's Improv Brunch | 8/20/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago Cubs vs. Kansas City Royals | 8/20/2023 13:20 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/20/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Beauty and The Beast | 8/20/2023 14:00 | Courtyard Theater at Chicago Shakespeare Theatre |
| The Best of The Second City | 8/20/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 8/20/2023 17:00 | Briar Street Theatre |
| Chicago Sky vs. Connecticut Sun | 8/20/2023 17:00 | Wintrust Arena |
| Drunk Shakespeare | 8/20/2023 17:00 | The Lion Theatre - Chicago |
| 46th Revue | 8/20/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Bettye LaVette | 8/20/2023 19:00 | City Winery - Chicago |
| Jeff Goldblum and The Mildred Snitzer Orchestra | 8/20/2023 19:30 | Vic Theatre |
| Chicago Fire FC vs. Orlando City SC | 8/20/2023 19:30 | Soldier Field |
| MJ - The Life Story of Michael Jackson | 8/20/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rose Wollman | 8/20/2023 20:30 | Constellation - Chicago |
| Carla Morrison | 8/21/2023 3:30 | Jay Pritzker Pavilion |
| Chicago White Sox vs. Seattle Mariners | 8/21/2023 19:10 | Guaranteed Rate Field |
| The Best of The Second City | 8/21/2023 20:00 | Mainstage at Second City - Chicago |
| Goo Goo Dolls & O.A.R. | 8/22/2023 19:00 | Huntington Bank Pavilion at Northerly Island |
| Chicago Sky vs. Seattle Storm | 8/22/2023 19:00 | Wintrust Arena |
| Chicago White Sox vs. Seattle Mariners | 8/22/2023 19:10 | Guaranteed Rate Field |
| MJ - The Life Story of Michael Jackson | 8/22/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Fontaines D.C. | 8/22/2023 20:00 | Metro Chicago |
| Paradise Fears | 8/22/2023 20:00 | Subterranean |
| Paradise Fears | 8/22/2023 20:00 | Beat Kitchen |
| Damon Williams | 8/22/2023 20:00 | City Winery - Chicago |
| Angel - Glam Band | 8/22/2023 20:00 | Reggie's Rock Club |
| Chicago White Sox vs. Seattle Mariners | 8/23/2023 13:10 | Guaranteed Rate Field |
| MJ - The Life Story of Michael Jackson | 8/23/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| 5 Seconds of Summer | 8/23/2023 19:00 | Huntington Bank Pavilion at Northerly Island |
| Drunk Shakespeare | 8/23/2023 19:30 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/23/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/23/2023 19:30 | Mercury Theater - IL |
| Late Night Drive Home | 8/23/2023 19:30 | Lincoln Hall |
| Melissa Ferrick | 8/23/2023 20:00 | City Winery - Chicago |
| Beach Bunny | 8/24/2023 17:00 | The Salt Shed - Chicago |
| Guns N' Roses & The Pretenders | 8/24/2023 17:30 | Wrigley Field |
| Chicago Sky vs. Las Vegas Aces | 8/24/2023 19:00 | Wintrust Arena |
| Kamelot | 8/24/2023 19:00 | Vic Theatre |
| Lil Baby, The Kid Laroi & GloRilla | 8/24/2023 19:00 | United Center |
| Chicago White Sox vs. Oakland Athletics | 8/24/2023 19:10 | Guaranteed Rate Field |
| Drunk Shakespeare | 8/24/2023 19:30 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/24/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Have a Nice Life | 8/24/2023 19:30 | House Of Blues - Chicago |
| Blue Man Group | 8/24/2023 20:00 | Briar Street Theatre |
| 46th Revue | 8/24/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Dominic Fike | 8/24/2023 20:00 | Huntington Bank Pavilion at Northerly Island |
| Euro Nights USA: Liz Mitchel, Samantha Fox & Bad Boys Blue | 8/24/2023 20:00 | Copernicus Center |
| Reggae Gold | 8/24/2023 22:00 | Subterranean |
| 46th Revue | 8/25/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Coached Ensembles | 8/25/2023 19:00 | Donny's Skybox Theatre at Second City - Chicago |
| Drunk Shakespeare | 8/25/2023 19:00 | The Lion Theatre - Chicago |
| Matt Braunger | 8/25/2023 19:00 | Lincoln Hall |
| Chicago White Sox vs. Oakland Athletics | 8/25/2023 19:10 | Guaranteed Rate Field |
| MJ - The Life Story of Michael Jackson | 8/25/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/25/2023 19:30 | Mercury Theater - IL |
| Jonas Brothers | 8/25/2023 19:30 | Wrigley Field |
| Blue Man Group | 8/25/2023 20:00 | Briar Street Theatre |
| Malik Yusef | 8/25/2023 20:00 | City Winery - Chicago |
| The Heavy Heavy | 8/25/2023 20:30 | Thalia Hall |
| Los Amantes Perfectos | 8/25/2023 20:30 | Copernicus Center |
| Drunk Shakespeare | 8/25/2023 21:00 | The Lion Theatre - Chicago |
| 46th Revue | 8/25/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Miss Nine | 8/25/2023 22:00 | Sound-Bar |
| The Second City's Improv Brunch | 8/26/2023 12:00 | UP Comedy Club at Second City - Chicago |
| NFL Preseason: Chicago Bears vs. Buffalo Bills | 8/26/2023 12:00 | Soldier Field |
| PARKING: NFL Preseason - Chicago Bears vs. Buffalo Bills | 8/26/2023 12:00 | Soldier Field Parking Lot |
| MJ - The Life Story of Michael Jackson | 8/26/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/26/2023 14:00 | Briar Street Theatre |
| The Best of The Second City | 8/26/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 8/26/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 8/26/2023 17:00 | The Lion Theatre - Chicago |
| Chicago White Sox vs. Oakland Athletics | 8/26/2023 18:10 | Guaranteed Rate Field |
| Cox n Crendor Podcast | 8/26/2023 18:30 | Bottom Lounge |
| 46th Revue | 8/26/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Drunk Shakespeare | 8/26/2023 19:00 | The Lion Theatre - Chicago |
| Leanne Morgan | 8/26/2023 19:00 | The Chicago Theatre |
| Motel Breakfast | 8/26/2023 19:00 | Metro Chicago |
| Rock Of Ages | 8/26/2023 19:30 | Mercury Theater - IL |
| Tony Baker & KevOnStage | 8/26/2023 19:30 | Harris Theater |
| MJ - The Life Story of Michael Jackson | 8/26/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 8/26/2023 20:00 | Briar Street Theatre |
| JVKE | 8/26/2023 20:00 | House Of Blues - Chicago |
| Greg Howe | 8/26/2023 20:00 | Reggie's Rock Club |
| Drunk Shakespeare | 8/26/2023 21:00 | The Lion Theatre - Chicago |
| 46th Revue | 8/26/2023 22:00 | e.t.c. Theater at Second City - Chicago |
| Spag Heddy | 8/26/2023 22:00 | Concord Music Hall |
| Midnight Tyrannosaurus | 8/26/2023 22:00 | Radius - IL |
| The Second City's Improv Brunch | 8/27/2023 12:00 | UP Comedy Club at Second City - Chicago |
| Chicago White Sox vs. Oakland Athletics | 8/27/2023 13:10 | Guaranteed Rate Field |
| MJ - The Life Story of Michael Jackson | 8/27/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/27/2023 14:30 | Mercury Theater - IL |
| The Best of The Second City | 8/27/2023 15:00 | Mainstage at Second City - Chicago |
| Blue Man Group | 8/27/2023 17:00 | Briar Street Theatre |
| Drunk Shakespeare | 8/27/2023 17:00 | The Lion Theatre - Chicago |
| 46th Revue | 8/27/2023 19:00 | e.t.c. Theater at Second City - Chicago |
| Midnight Sun - A Tribute to Earth, Wind and Fire | 8/27/2023 19:00 | City Winery - Chicago |
| James Bay | 8/27/2023 19:30 | Riviera Theatre - IL |
| Edith Marquez | 8/27/2023 19:30 | Copernicus Center |
| MJ - The Life Story of Michael Jackson | 8/27/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Arctic Monkeys | 8/27/2023 20:00 | United Center |
| Ocean Alley | 8/27/2023 20:30 | Thalia Hall |
| Musiq Soulchild | 8/28/2023 19:00 | City Winery - Chicago |
| Chicago Cubs vs. Milwaukee Brewers | 8/28/2023 19:05 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/28/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Best of The Second City | 8/28/2023 20:00 | Mainstage at Second City - Chicago |
| The Body, Troller & Dead Times | 8/28/2023 20:30 | Sleeping Village |
| Musiq Soulchild | 8/28/2023 22:30 | City Winery - Chicago |
| Musiq Soulchild | 8/29/2023 19:00 | City Winery - Chicago |
| Chicago Cubs vs. Milwaukee Brewers | 8/29/2023 19:05 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/29/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Yoke Lore | 8/29/2023 19:30 | Metro Chicago |
| Musiq Soulchild | 8/29/2023 22:30 | City Winery - Chicago |
| Chicago Cubs vs. Milwaukee Brewers | 8/30/2023 13:20 | Wrigley Field |
| MJ - The Life Story of Michael Jackson | 8/30/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Pixies & Modest Mouse | 8/30/2023 18:00 | The Salt Shed - Chicago |
| Toosii | 8/30/2023 19:00 | House Of Blues - Chicago |
| Chicago Fire FC vs. Vancouver Whitecaps FC | 8/30/2023 19:30 | Soldier Field |
| Drunk Shakespeare | 8/30/2023 19:30 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/30/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Rock Of Ages | 8/30/2023 19:30 | Mercury Theater - IL |
| The Hippies | 8/30/2023 19:30 | Cubby Bear |
| Pixies & Modest Mouse | 8/31/2023 18:00 | The Salt Shed - Chicago |
| Prerex | 8/31/2023 18:30 | Cubby Bear |
| Beck & Phoenix | 8/31/2023 18:30 | Huntington Bank Pavilion at Northerly Island |
| Musiq Soulchild | 8/31/2023 19:00 | City Winery - Chicago |
| Toosii | 8/31/2023 19:00 | House Of Blues - Chicago |
| Drunk Shakespeare | 8/31/2023 19:30 | The Lion Theatre - Chicago |
| MJ - The Life Story of Michael Jackson | 8/31/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Corey Taylor | 8/31/2023 19:30 | Riviera Theatre - IL |
| Blue Man Group | 8/31/2023 20:00 | Briar Street Theatre |
| 46th Revue | 8/31/2023 20:00 | e.t.c. Theater at Second City - Chicago |
| Jimmie's Chicken Shack | 8/31/2023 20:00 | Beat Kitchen |
| Murder By Death | 8/31/2023 21:00 | Metro Chicago |
| Reggae Gold | 8/31/2023 22:00 | Subterranean |
| Musiq Soulchild | 8/31/2023 22:30 | City Winery - Chicago |
