| Yo-Yo Ma & Chicago Symphony Orchestra | 5/1/2023 19:30 | Chicago Symphony Center |
| Storm Large | 5/1/2023 20:00 | City Winery - Chicago |
| Annie DiRusso | 5/1/2023 20:00 | Lincoln Hall |
| Chicago White Sox vs. Minnesota Twins | 5/2/2023 18:10 | Guaranteed Rate Field |
| Into The Woods | 5/2/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| M83 | 5/2/2023 19:30 | Riviera Theatre - IL |
| Felly | 5/2/2023 19:30 | Lincoln Hall |
| Simrit Kaur | 5/2/2023 20:00 | City Winery - Chicago |
| Finch | 5/2/2023 20:00 | House Of Blues - Chicago |
| Alfa Mist | 5/2/2023 20:30 | Thalia Hall |
| Into The Woods | 5/3/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Chicago White Sox vs. Minnesota Twins | 5/3/2023 18:10 | Guaranteed Rate Field |
| Into The Woods | 5/3/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Antonio's Song | 5/3/2023 19:30 | Owen Bruner Goodman Theatre |
| Blue Man Group | 5/3/2023 20:00 | Briar Street Theatre |
| Finch | 5/3/2023 20:00 | House Of Blues - Chicago |
| Khary | 5/3/2023 20:00 | Schubas |
| Cal Scruby | 5/3/2023 20:00 | Subterranean |
| The Vaudettes | 5/3/2023 20:00 | Reggie's Music Joint |
| Overcoats | 5/3/2023 20:00 | Sleeping Village |
| Sawyer Fredericks & Chastity Brown | 5/3/2023 20:00 | City Winery - Chicago |
| Fucked Up | 5/3/2023 20:30 | Thalia Hall |
| Chicago White Sox vs. Minnesota Twins | 5/4/2023 13:10 | Guaranteed Rate Field |
| Hayley Kiyoko | 5/4/2023 18:00 | House Of Blues - Chicago |
| Pouya | 5/4/2023 18:00 | Patio Theater |
| Onyx & R.A. The Rugged Man | 5/4/2023 18:30 | Martyr's |
| Bankrol Hayden | 5/4/2023 19:00 | Subterranean |
| Into The Woods | 5/4/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| Antonio's Song | 5/4/2023 19:30 | Owen Bruner Goodman Theatre |
| Chicago Symphony Orchestra: Giovanni Antonini - Vivaldi Gloria | 5/4/2023 19:30 | Chicago Symphony Center |
| Blue Man Group | 5/4/2023 20:00 | Briar Street Theatre |
| Jackson Wang | 5/4/2023 20:00 | Wintrust Arena |
| Hirs Collective | 5/4/2023 20:00 | Reggie's Music Joint |
| Built To Spill | 5/4/2023 20:30 | Thalia Hall |
| Blue Man Group | 5/5/2023 13:00 | Briar Street Theatre |
| Chicago Cubs vs. Miami Marlins | 5/5/2023 13:20 | Wrigley Field |
| Blue Man Group | 5/5/2023 16:00 | Briar Street Theatre |
| Wage War | 5/5/2023 18:00 | Concord Music Hall |
| Blue Man Group | 5/5/2023 19:00 | Briar Street Theatre |
| Half Alive | 5/5/2023 19:00 | House Of Blues - Chicago |
| Kevin Kaarl | 5/5/2023 19:30 | Vic Theatre |
| Into The Woods | 5/5/2023 19:30 | Nederlander Theatre at Ford Center for the Performing Arts |
| The Flaming Lips | 5/5/2023 20:00 | The Salt Shed - Chicago |
| Antonio's Song | 5/5/2023 20:00 | Owen Bruner Goodman Theatre |
| The New Pornographers | 5/5/2023 20:00 | Thalia Hall |
| Kevin Devine & The New Amsterdams | 5/5/2023 20:00 | Cobra Lounge |
| Enter Shikari | 5/5/2023 20:00 | Bottom Lounge |
| Flatland Cavalry | 5/5/2023 20:00 | Joe's Bar On Weed St. |
| Masked Wolf | 5/5/2023 20:00 | Park West |
| Chicago Symphony Orchestra: Giovanni Antonini - Vivaldi Gloria | 5/5/2023 20:00 | Chicago Symphony Center |
| Mac Ayres | 5/5/2023 21:00 | Metro Chicago |
| The Kitchen Dwellers | 5/5/2023 21:00 | 1st Ward at Chop Shop |
| Chicago Symphony Orchestra: Scott Speck - Downtown Sounds | 5/6/2023 11:00 | Chicago Symphony Center |
| Chicago Symphony Orchestra: Scott Speck - Downtown Sounds | 5/6/2023 12:45 | Chicago Symphony Center |
| Chicago Cubs vs. Miami Marlins | 5/6/2023 13:20 | Wrigley Field |
| Blue Man Group | 5/6/2023 14:00 | Briar Street Theatre |
| Into The Woods | 5/6/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Blue Man Group | 5/6/2023 17:00 | Briar Street Theatre |
| Luke Combs, Riley Green & Lainey Wilson | 5/6/2023 17:45 | Soldier Field |
| Half Alive | 5/6/2023 19:00 | House Of Blues - Chicago |
| Blink 182 | 5/6/2023 19:30 | United Center |
| Hippie Sabotage | 5/6/2023 19:30 | Riviera Theatre - IL |
| Peter Cat Recording Co. | 5/6/2023 19:30 | Bottom Lounge |
| Peter Cat Recording Co. | 5/6/2023 19:30 | Beat Kitchen |
| Blue Man Group | 5/6/2023 20:00 | Briar Street Theatre |
| Girls Gotta Eat | 5/6/2023 20:00 | The Chicago Theatre |
| Into The Woods | 5/6/2023 20:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Latrice Royale | 5/6/2023 20:00 | Lincoln Hall |
| Antonio's Song | 5/6/2023 20:00 | Owen Bruner Goodman Theatre |
| The New Pornographers | 5/6/2023 20:00 | Thalia Hall |
| Chicago Symphony Orchestra: Giovanni Antonini - Vivaldi Gloria | 5/6/2023 20:00 | Chicago Symphony Center |
| The Crystal Casino Band | 5/6/2023 21:00 | Schubas |
| The Lemon Twigs | 5/6/2023 21:00 | Sleeping Village |
| Amtrac | 5/6/2023 21:30 | 1st Ward at Chop Shop |
| Wuki | 5/6/2023 22:00 | Sound-Bar |
| Chicago Cubs vs. Miami Marlins | 5/7/2023 13:20 | Wrigley Field |
| Into The Woods | 5/7/2023 14:00 | Nederlander Theatre at Ford Center for the Performing Arts |
| Antonio's Song | 5/7/2023 14:00 | Owen Bruner Goodman Theatre |
| Vikingur Olafsson | 5/7/2023 15:00 | Chicago Symphony Center |
| Blue Man Group | 5/7/2023 16:00 | Briar Street Theatre |
| Blink 182 | 5/7/2023 19:30 | United Center |
| Antonio's Song | 5/7/2023 19:30 | Owen Bruner Goodman Theatre |
| Brian Dunne | 5/7/2023 19:30 | Schubas |
| Fever Ray | 5/7/2023 20:00 | The Salt Shed - Chicago |
| Latrice Royale | 5/7/2023 20:00 | Lincoln Hall |
| Gogo Penguin | 5/7/2023 20:00 | Thalia Hall |
| The Lemon Twigs | 5/7/2023 21:00 | Sleeping Village |
| Spiritbox | 5/8/2023 18:00 | House Of Blues - Chicago |
| Chicago Cubs vs. St. Louis Cardinals | 5/8/2023 18:40 | Wrigley Field |
| Against The Current, Trophy Eyes & Yours Truly | 5/8/2023 19:00 | Bottom Lounge |
| Good Kid - Band | 5/8/2023 19:30 | Thalia Hall |
| Jackie Mendoza | 5/8/2023 20:00 | Schubas |
| Metronomy | 5/8/2023 21:00 | Metro Chicago |
| Spiritbox | 5/9/2023 18:00 | House Of Blues - Chicago |
| Chicago Cubs vs. St. Louis Cardinals | 5/9/2023 18:40 | Wrigley Field |
| Plini | 5/9/2023 19:00 | Bottom Lounge |
| Obituary | 5/9/2023 19:00 | Metro Chicago |
| Chicago Symphony Orchestra: Giovanni Antonini - Vivaldi Gloria | 5/9/2023 19:30 | Chicago Symphony Center |
| City and Colour | 5/9/2023 20:00 | Riviera Theatre - IL |
| Cobra Man | 5/9/2023 20:30 | Thalia Hall |
| Blue Man Group | 5/10/2023 14:00 | Briar Street Theatre |
| Chicago Cubs vs. St. Louis Cardinals | 5/10/2023 18:40 | Wrigley Field |
| Babyface Ray | 5/10/2023 19:00 | Patio Theater |
| Antonio's Song | 5/10/2023 19:30 | Owen Bruner Goodman Theatre |
| Blue Man Group | 5/10/2023 20:00 | Briar Street Theatre |
| Goth Babe | 5/10/2023 20:00 | The Salt Shed - Chicago |
| Yaeji | 5/10/2023 21:00 | Vic Theatre |
| Antonio's Song | 5/11/2023 19:30 | Owen Bruner Goodman Theatre |
| Chicago Symphony Orchestra: Riccardo Muti - Muti, Montgomery & Rachmaninov 2 | 5/11/2023 19:30 | Chicago Symphony Center |
| Martin Sexton & KT Tunstall | 5/11/2023 19:30 | Thalia Hall |
| Blue Man Group | 5/11/2023 20:00 | Briar Street Theatre |
| The Wood Brothers | 5/11/2023 20:00 | The Salt Shed - Chicago |
| Ler and Lionel - Podcast | 5/11/2023 20:00 | City Winery - Chicago |
| The Silent Comedy | 5/11/2023 20:00 | Reggie's Music Joint |
| Kolby Cooper | 5/11/2023 20:00 | Joe's Bar On Weed St. |
| Blue Man Group | 5/12/2023 13:00 | Briar Street Theatre |
| Chicago Symphony Orchestra: Riccardo Muti - Muti, Montgomery & Rachmaninov 2 | 5/12/2023 13:30 | Chicago Symphony Center |
| Blue Man Group | 5/12/2023 16:00 | Briar Street Theatre |
| Waterparks | 5/12/2023 18:00 | House Of Blues - Chicago |
| Blue Man Group | 5/12/2023 19:00 | Briar Street Theatre |
| Yves Tumor | 5/12/2023 19:00 | Riviera Theatre - IL |
| Rebecca Black | 5/12/2023 19:00 | Bottom Lounge |
| Chicago White Sox vs. Houston Astros | 5/12/2023 19:10 | Guaranteed Rate Field |
| Whose Live Anyway? | 5/12/2023 20:00 | Studebaker Theater |
| Kev Herrera | 5/12/2023 20:00 | City Winery - Chicago |
| Antonio's Song | 5/12/2023 20:00 | Owen Bruner Goodman Theatre |
| Riki Rachtman | 5/12/2023 20:00 | Reggie's Bananna's Comedy Shack |
| Oracle Sisters | 5/12/2023 20:00 | Schubas |
| Bright Eyes | 5/12/2023 20:00 | The Salt Shed - Chicago |
| Dave Holland | 5/12/2023 20:00 | Chicago Symphony Center |
| Josh Ritter & The Royal City Band | 5/12/2023 20:30 | Thalia Hall |
| Moon Boots | 5/12/2023 21:00 | Lincoln Hall |
| Sullivan King | 5/12/2023 22:00 | Radius - IL |
| Chicago Fire FC vs. St. Louis City SC | 5/13/2023 3:30 | Soldier Field |
| Blue Man Group | 5/13/2023 14:00 | Briar Street Theatre |
| Antonio's Song | 5/13/2023 14:00 | Owen Bruner Goodman Theatre |
| Blue Man Group | 5/13/2023 17:00 | Briar Street Theatre |
| Waterparks | 5/13/2023 18:00 | House Of Blues - Chicago |
| Chicago White Sox vs. Houston Astros | 5/13/2023 18:15 | Guaranteed Rate Field |
| Bury Tomorrow | 5/13/2023 18:30 | Park West |
| The Gospel At Colonus | 5/13/2023 19:30 | Court Theatre |
| Chase Rice | 5/13/2023 19:30 | Gallagher Way - Chicago |
| Blue Man Group | 5/13/2023 20:00 | Briar Street Theatre |
| Druski | 5/13/2023 20:00 | The Chicago Theatre |
| The World Is A Beautiful Place & I Am No Longer Afraid To Die | 5/13/2023 20:00 | Bottom Lounge |
| Antonio's Song | 5/13/2023 20:00 | Owen Bruner Goodman Theatre |
| Joanne McNally | 5/13/2023 20:00 | Auditorium Theatre - IL |
| Chicago Symphony Orchestra: Riccardo Muti - Muti, Montgomery & Rachmaninov 2 | 5/13/2023 20:00 | Chicago Symphony Center |
| Theo Katzman | 5/13/2023 20:30 | Vic Theatre |
| Okean Elzy | 5/13/2023 20:30 | Riviera Theatre - IL |
| Off! | 5/13/2023 21:00 | Lincoln Hall |
| Chicago White Sox vs. Houston Astros | 5/14/2023 13:10 | Guaranteed Rate Field |
| The Gospel At Colonus | 5/14/2023 14:00 | Court Theatre |
| Antonio's Song | 5/14/2023 14:00 | Owen Bruner Goodman Theatre |
| Renee Fleming & Evgeny Kissin | 5/14/2023 15:00 | Chicago Symphony Center |
| Blue Man Group | 5/14/2023 16:00 | Briar Street Theatre |
| Mother's Day Celebration | 5/14/2023 18:00 | House Of Hope |
| Harakiri for the Sky | 5/14/2023 19:00 | Reggie's Rock Club |
| The Gospel At Colonus | 5/14/2023 19:30 | Court Theatre |
| Hoodoo Gurus | 5/14/2023 20:00 | City Winery - Chicago |
| Bacilos | 5/14/2023 20:00 | House Of Blues - Chicago |
| An Intimate Mother's Day Celebration: Dru Hill & Jagged Edge | 5/14/2023 20:00 | The Chicago Theatre |
| Kali Uchis | 5/15/2023 19:00 | Byline Bank Aragon Ballroom |
| Crowded House | 5/15/2023 19:30 | The Chicago Theatre |
| Avatar | 5/15/2023 19:30 | House Of Blues - Chicago |
| Caroline Polachek | 5/16/2023 19:00 | Riviera Theatre - IL |
| Kali Uchis | 5/16/2023 19:00 | Byline Bank Aragon Ballroom |
| Chicago White Sox vs. Cleveland Guardians | 5/16/2023 19:10 | Guaranteed Rate Field |
| Antonio's Song | 5/16/2023 19:30 | Owen Bruner Goodman Theatre |
| Chicago Symphony Orchestra: Riccardo Muti - Muti, Montgomery & Rachmaninov 2 | 5/16/2023 19:30 | Chicago Symphony Center |
| Muna | 5/16/2023 20:00 | The Salt Shed - Chicago |
| Aladdin | 5/17/2023 14:00 | Cadillac Palace |
| Blue Man Group | 5/17/2023 14:00 | Briar Street Theatre |
| Chicago White Sox vs. Cleveland Guardians | 5/17/2023 19:10 | Guaranteed Rate Field |
| Aladdin | 5/17/2023 19:30 | Cadillac Palace |
| The Gospel At Colonus | 5/17/2023 19:30 | Court Theatre |
| The Walkmen | 5/17/2023 19:30 | Metro Chicago |
| Antonio's Song | 5/17/2023 19:30 | Owen Bruner Goodman Theatre |
| Slater - Band | 5/17/2023 19:30 | Schubas |
| Blue Man Group | 5/17/2023 20:00 | Briar Street Theatre |
| Westerman | 5/17/2023 20:00 | Lincoln Hall |
| Lizzo & Latto | 5/17/2023 20:00 | United Center |
| Lulu Santos | 5/17/2023 20:00 | Vic Theatre |
| Chicago White Sox vs. Cleveland Guardians | 5/18/2023 13:10 | Guaranteed Rate Field |
| Blue Man Group | 5/18/2023 14:00 | Briar Street Theatre |
| Chicago Symphony Orchestra: Riccardo Muti - Muti, Chen & Mozart Gran Partita | 5/18/2023 19:30 | Chicago Symphony Center |
| Aladdin | 5/18/2023 19:30 | Cadillac Palace |
| The Gospel At Colonus | 5/18/2023 19:30 | Court Theatre |
| The Walkmen | 5/18/2023 19:30 | Metro Chicago |
| Antonio's Song | 5/18/2023 19:30 | Owen Bruner Goodman Theatre |
| The National | 5/18/2023 19:30 | Auditorium Theatre - IL |
| Blue Man Group | 5/18/2023 20:00 | Briar Street Theatre |
| Indigo De Souza | 5/18/2023 20:00 | Thalia Hall |
| Chicago Symphony Orchestra: Riccardo Muti - Muti, Chen & Mozart Gran Partita | 5/19/2023 13:30 | Chicago Symphony Center |
| Blue Man Group | 5/19/2023 16:00 | Briar Street Theatre |
| Set It Off | 5/19/2023 18:30 | House Of Blues - Chicago |
| Blue Man Group | 5/19/2023 19:00 | Briar Street Theatre |
| Chicago White Sox vs. Kansas City Royals | 5/19/2023 19:10 | Guaranteed Rate Field |
| Aladdin | 5/19/2023 19:30 | Cadillac Palace |
| The Gospel At Colonus | 5/19/2023 19:30 | Court Theatre |
| The National | 5/19/2023 19:30 | Auditorium Theatre - IL |
| Loudness | 5/19/2023 20:00 | Reggie's Rock Club |
| Natalie Merchant | 5/19/2023 20:00 | The Chicago Theatre |
| The Walkmen | 5/19/2023 20:00 | Metro Chicago |
| Jeff Tweedy | 5/19/2023 20:00 | Vic Theatre |
| Antonio's Song | 5/19/2023 20:00 | Owen Bruner Goodman Theatre |
| Cursive | 5/19/2023 20:00 | Bottom Lounge |
| Narrow Head | 5/19/2023 21:00 | Lincoln Hall |
| Tom and Collins | 5/19/2023 22:00 | Sound-Bar |
| Once Upon a Symphony: The Elves and The Shoemaker | 5/20/2023 10:00 | Chicago Symphony Center |
| Once Upon a Symphony: The Elves and The Shoemaker | 5/20/2023 11:45 | Chicago Symphony Center |
| Chicago White Sox vs. Kansas City Royals | 5/20/2023 13:10 | Guaranteed Rate Field |
| Aladdin | 5/20/2023 14:00 | Cadillac Palace |
| Blue Man Group | 5/20/2023 14:00 | Briar Street Theatre |
| Antonio's Song | 5/20/2023 14:00 | Owen Bruner Goodman Theatre |
| Blue Man Group | 5/20/2023 17:00 | Briar Street Theatre |
| Aladdin | 5/20/2023 19:30 | Cadillac Palace |
| Ron Pope | 5/20/2023 19:30 | Park West |
| Chicago Fire FC vs. Atlanta United FC | 5/20/2023 19:30 | Soldier Field |
| The National | 5/20/2023 19:30 | Auditorium Theatre - IL |
| Blue Man Group | 5/20/2023 20:00 | Briar Street Theatre |
| The Walkmen | 5/20/2023 20:00 | Metro Chicago |
| Jeff Tweedy | 5/20/2023 20:00 | Vic Theatre |
| Antonio's Song | 5/20/2023 20:00 | Owen Bruner Goodman Theatre |
| Giovannie and The Hired Guns | 5/20/2023 20:00 | Joe's Bar On Weed St. |
| Tina Fey & Amy Poehler | 5/20/2023 20:00 | The Chicago Theatre |
| Chicago Symphony Orchestra: Riccardo Muti - Muti, Chen & Mozart Gran Partita | 5/20/2023 20:00 | Chicago Symphony Center |
| John Butler | 5/20/2023 20:30 | Thalia Hall |
| Y La Bamba | 5/20/2023 21:00 | The Empty Bottle |
| Ben Klock | 5/20/2023 22:00 | Concord Music Hall |
| Aladdin | 5/21/2023 13:00 | Cadillac Palace |
| Chicago White Sox vs. Kansas City Royals | 5/21/2023 13:10 | Guaranteed Rate Field |
| The Gospel At Colonus | 5/21/2023 14:00 | Court Theatre |
| Antonio's Song | 5/21/2023 14:00 | Owen Bruner Goodman Theatre |
| Seong-Jin Cho | 5/21/2023 15:00 | Chicago Symphony Center |
| Blue Man Group | 5/21/2023 16:00 | Briar Street Theatre |
| Aladdin | 5/21/2023 18:30 | Cadillac Palace |
| Blue Man Group | 5/21/2023 19:00 | Briar Street Theatre |
| The Gospel At Colonus | 5/21/2023 19:30 | Court Theatre |
| Antonio's Song | 5/21/2023 19:30 | Owen Bruner Goodman Theatre |
| The National | 5/21/2023 19:30 | Auditorium Theatre - IL |
| Billy Nomates | 5/21/2023 20:00 | Schubas |
| Future Islands | 5/21/2023 20:00 | The Salt Shed - Chicago |
| Tina Fey & Amy Poehler | 5/21/2023 20:00 | The Chicago Theatre |
| John Butler | 5/21/2023 20:30 | Thalia Hall |
| The Carole King & James Taylor Story | 5/22/2023 19:00 | City Winery - Chicago |
| Chicago Cubs vs. New York Mets | 5/23/2023 18:40 | Wrigley Field |
| Ella Mai | 5/23/2023 19:00 | House Of Blues - Chicago |
| Chicago Symphony Orchestra: Riccardo Muti - Muti, Chen & Mozart Gran Partita | 5/23/2023 19:30 | Chicago Symphony Center |
| Blue Man Group | 5/23/2023 20:00 | Briar Street Theatre |
| Aladdin | 5/24/2023 14:00 | Cadillac Palace |
| Blue Man Group | 5/24/2023 14:00 | Briar Street Theatre |
| Cold | 5/24/2023 18:30 | Bottom Lounge |
| Rico Nasty | 5/24/2023 18:30 | Avondale Music Hall |
| Chicago Cubs vs. New York Mets | 5/24/2023 18:40 | Wrigley Field |
| Alestorm | 5/24/2023 19:00 | Vic Theatre |
| Ella Mai | 5/24/2023 19:00 | House Of Blues - Chicago |
| Aladdin | 5/24/2023 19:30 | Cadillac Palace |
| The Gospel At Colonus | 5/24/2023 19:30 | Court Theatre |
| Antonio's Song | 5/24/2023 19:30 | Owen Bruner Goodman Theatre |
| Blue Man Group | 5/24/2023 20:00 | Briar Street Theatre |
| Al Stewart | 5/24/2023 20:00 | City Winery - Chicago |
| Hippo Campus & Gus Dapperton | 5/24/2023 20:00 | The Salt Shed - Chicago |
| Shame | 5/24/2023 20:30 | Thalia Hall |
| Antonio's Song | 5/25/2023 14:00 | Owen Bruner Goodman Theatre |
| Chicago Cubs vs. New York Mets | 5/25/2023 18:40 | Wrigley Field |
| Aladdin | 5/25/2023 19:30 | Cadillac Palace |
| The Gospel At Colonus | 5/25/2023 19:30 | Court Theatre |
| Antonio's Song | 5/25/2023 19:30 | Owen Bruner Goodman Theatre |
| Chicago Symphony Orchestra: Riccardo Muti & David Herbert - Pines of Rome | 5/25/2023 19:30 | Chicago Symphony Center |
| Blue Man Group | 5/25/2023 20:00 | Briar Street Theatre |
| Joan - Band | 5/25/2023 20:00 | Subterranean |
| Fenne Lily & Christian Lee Hutson | 5/25/2023 20:00 | Thalia Hall |
| Chicago Cubs vs. Cincinnati Reds | 5/26/2023 13:20 | Wrigley Field |
| Chicago Symphony Orchestra: Riccardo Muti & David Herbert - Pines of Rome | 5/26/2023 13:30 | Chicago Symphony Center |
| Blue Man Group | 5/26/2023 16:00 | Briar Street Theatre |
| Blue Man Group | 5/26/2023 19:00 | Briar Street Theatre |
| Chicago Sky vs. Washington Mystics | 5/26/2023 19:00 | Wintrust Arena |
| Helloween | 5/26/2023 19:15 | Riviera Theatre - IL |
| Aladdin | 5/26/2023 19:30 | Cadillac Palace |
| The Gospel At Colonus | 5/26/2023 19:30 | Court Theatre |
| Antonio's Song | 5/26/2023 20:00 | Owen Bruner Goodman Theatre |
| Peter Collins | 5/26/2023 20:00 | City Winery - Chicago |
| Laura Stevenson & Oceanator | 5/26/2023 21:00 | Lincoln Hall |
| Aladdin | 5/27/2023 14:00 | Cadillac Palace |
| Blue Man Group | 5/27/2023 14:00 | Briar Street Theatre |
| The Gospel At Colonus | 5/27/2023 14:00 | Court Theatre |
| Antonio's Song | 5/27/2023 14:00 | Owen Bruner Goodman Theatre |
| Blue Man Group | 5/27/2023 17:00 | Briar Street Theatre |
| Chicago Cubs vs. Cincinnati Reds | 5/27/2023 18:15 | Wrigley Field |
| Aladdin | 5/27/2023 19:30 | Cadillac Palace |
| The Gospel At Colonus | 5/27/2023 19:30 | Court Theatre |
| Seal | 5/27/2023 19:30 | The Chicago Theatre |
| Blue Man Group | 5/27/2023 20:00 | Briar Street Theatre |
| Antonio's Song | 5/27/2023 20:00 | Owen Bruner Goodman Theatre |
| Pedro The Lion | 5/27/2023 20:00 | Thalia Hall |
| Chicago Symphony Orchestra: Riccardo Muti & David Herbert - Pines of Rome | 5/27/2023 20:00 | Chicago Symphony Center |
| Harry Mack | 5/27/2023 20:30 | House Of Blues - Chicago |
| Sickick | 5/27/2023 22:00 | PRYSM Nightclub |
| Aladdin | 5/28/2023 13:00 | Cadillac Palace |
| Chicago Cubs vs. Cincinnati Reds | 5/28/2023 13:20 | Wrigley Field |
| The Gospel At Colonus | 5/28/2023 14:00 | Court Theatre |
| Antonio's Song | 5/28/2023 14:00 | Owen Bruner Goodman Theatre |
| Maria Joao Pires | 5/28/2023 15:00 | Chicago Symphony Center |
| Blue Man Group | 5/28/2023 16:00 | Briar Street Theatre |
| Chicago Sky vs. Dallas Wings | 5/28/2023 17:00 | Wintrust Arena |
| Aladdin | 5/28/2023 18:30 | Cadillac Palace |
| Blue Man Group | 5/28/2023 19:00 | Briar Street Theatre |
| The Gospel At Colonus | 5/28/2023 19:30 | Court Theatre |
| Chicago Cubs vs. Tampa Bay Rays | 5/29/2023 13:20 | Wrigley Field |
| Chicago White Sox vs. Los Angeles Angels | 5/29/2023 19:10 | Guaranteed Rate Field |
| Dark Funeral, Cattle Decapitation, 200 Stab Wounds & Blackbraid | 5/30/2023 19:00 | Metro Chicago |
| Chicago Cubs vs. Tampa Bay Rays | 5/30/2023 19:05 | Wrigley Field |
| Chicago White Sox vs. Los Angeles Angels | 5/30/2023 19:10 | Guaranteed Rate Field |
| Ben Folds & The Chicago Symphony Orchestra | 5/30/2023 19:30 | Chicago Symphony Center |
| Blue Man Group | 5/30/2023 20:00 | Briar Street Theatre |
| Sizzy Rocket | 5/30/2023 20:00 | Schubas |
| Chicago White Sox vs. Los Angeles Angels | 5/31/2023 13:10 | Guaranteed Rate Field |
| Chicago Cubs vs. Tampa Bay Rays | 5/31/2023 13:20 | Wrigley Field |
| Blue Man Group | 5/31/2023 14:00 | Briar Street Theatre |
| Valley - Band | 5/31/2023 19:00 | House Of Blues - Chicago |
| The Gospel At Colonus | 5/31/2023 19:30 | Court Theatre |
| Blue Man Group | 5/31/2023 20:00 | Briar Street Theatre |
| Alex Lahey | 5/31/2023 20:00 | Schubas |
