| Chicago White Sox vs. Los Angeles AngelsMLB | Sat May 1TBA | Rate Field | from $60 | Tickets |
| Chicago Symphony Orchestra: Hisaishi Conducts HisaishiClassical | Sat May 17:30 PM | Symphony Center (Orchestra Hall) | from $108 | Tickets |
| Idina MenzelPop / Rock | Sat May 17:30 PM | Lyric Opera House | from $126 | Tickets |
| Alonzo King Lines Ballet | Sat May 18:00 PM | Harris Theater | from $55 | Tickets |
| Yuri & LuceroLatin | Sat May 18:00 PM | Rosemont Theatre | from $150 | Tickets |
| Chicago White Sox vs. Los Angeles AngelsMLB | Sun May 2TBA | Rate Field | from $53 | Tickets |
| Alonzo King Lines Ballet | Sun May 22:00 PM | Harris Theater | from $55 | Tickets |
| Sondra Radvanovsky & SeokJong BaekClassical | Sun May 22:00 PM | Lyric Opera House | from $113 | Tickets |
| Chicago White Sox vs. St. Louis CardinalsMLB | Mon May 3TBA | Rate Field | from $54 | Tickets |
| Chicago White Sox vs. St. Louis CardinalsMLB | Tue May 4TBA | Rate Field | from $110 | Tickets |
| HengeHard Rock / Metal | Tue May 48:00 PM | Garcia's Chicago | from $51 | Tickets |
| Chicago White Sox vs. St. Louis CardinalsMLB | Wed May 5TBA | Rate Field | from $54 | Tickets |
| HengeHard Rock / Metal | Wed May 58:00 PM | Garcia's Chicago | from $51 | Tickets |
| Chicago Symphony Orchestra: Honeck Conducts Mahler & Bruckner 9Classical | Thu May 67:30 PM | Symphony Center (Orchestra Hall) | from $40 | Tickets |
| Chicago Cubs vs. Seattle MarinersMLB | Fri May 7TBA | Wrigley Field | from $100 | Tickets |
| Chicago Symphony Orchestra: Honeck Conducts Mahler & Bruckner 9Classical | Fri May 71:30 PM | Symphony Center (Orchestra Hall) | from $54 | Tickets |
| Chicago Cubs vs. Seattle MarinersMLB | Sat May 8TBA | Wrigley Field | from $114 | Tickets |
| Chicago Symphony Orchestra: Honeck Conducts Mahler & Bruckner 9Classical | Sat May 87:30 PM | Symphony Center (Orchestra Hall) | from $59 | Tickets |
| Carsie BlantonCountry / Folk | Sat May 88:00 PM | Lincoln Hall | from $78 | Tickets |
| Chicago Cubs vs. Seattle MarinersMLB | Sun May 9TBA | Wrigley Field | from $98 | Tickets |
| Piotr AnderszewskiClassical | Sun May 93:00 PM | Symphony Center (Orchestra Hall) | from $40 | Tickets |
| The Liminanas RescheduledAlternative | Sun May 99:00 PM | The Empty Bottle | from $970 | Tickets |
| Mass of the Fermenting DregsHard Rock / Metal | Mon May 107:30 PM | Vic Theatre | from $50 | Tickets |
| Chicago Cubs vs. Miami MarlinsMLB | Tue May 11TBA | Wrigley Field | from $72 | Tickets |
| Chicago Cubs vs. Miami MarlinsMLB | Wed May 12TBA | Wrigley Field | from $72 | Tickets |
| Chicago Cubs vs. Miami MarlinsMLB | Thu May 13TBA | Wrigley Field | from $72 | Tickets |
| Sam MillerComedy | Thu May 137:00 PM | Zanies Rosemont | from $81 | Tickets |
| Chicago Symphony Orchestra: Makela, Bariashvili & Sibelius 1Classical | Thu May 137:30 PM | Symphony Center (Orchestra Hall) | from $54 | Tickets |
| Chicago White Sox vs. Miami MarlinsMLB | Fri May 14TBA | Rate Field | from $60 | Tickets |
| Joel RossJazz / Blues | Fri May 148:00 PM | Symphony Center (Orchestra Hall) | from $54 | Tickets |
| Sam MillerComedy | Fri May 149:15 PM | Zanies Chicago (Old Town) | from $59 | Tickets |
| Chicago White Sox vs. Miami MarlinsMLB | Sat May 15TBA | Rate Field | from $65 | Tickets |
| Chicago Symphony Orchestra: Einstein's ImaginationClassical | Sat May 1511:00 AM · 12:45 PM | Symphony Center (Orchestra Hall) | from $21 | Tickets |
| Two FriendsTechno / Electronic | Sat May 156:30 PM | Huntington Bank Pavilion at Northerly Island | from $112 | Tickets |
| Sam MillerComedy | Sat May 157:00 PM · 9:15 PM | Zanies Chicago (Old Town) | from $59 | Tickets |
| Chicago Symphony Orchestra: Makela, Bariashvili & Sibelius 1Classical | Sat May 157:30 PM | Symphony Center (Orchestra Hall) | from $61 | Tickets |
| Banda MS RescheduledLatin | Sat May 158:00 PM | Allstate Arena | from $95 | Tickets |
| Chicago White Sox vs. Miami MarlinsMLB | Sun May 16TBA | Rate Field | from $138 | Tickets |
| Chicago Symphony Orchestra: Makela, Bariashvili & Sibelius 1Classical | Sun May 163:00 PM | Symphony Center (Orchestra Hall) | from $54 | Tickets |
| Chicago White Sox vs. Cleveland GuardiansMLB | Mon May 17TBA | Rate Field | from $110 | Tickets |
| Chicago White Sox vs. Cleveland GuardiansMLB | Tue May 18TBA | Rate Field | from $110 | Tickets |
| Kissin, Vengerov & CapuconClassical | Tue May 187:30 PM | Symphony Center (Orchestra Hall) | from $80 | Tickets |
| Chicago White Sox vs. Cleveland GuardiansMLB | Wed May 19TBA | Rate Field | from $110 | Tickets |
| Josh BlueComedy | Thu May 207:00 PM | Zanies Rosemont | from $97 | Tickets |
| Chicago Symphony Orchestra: Tan Dun - Water Concerto & Marco PoloClassical | Thu May 207:30 PM | Symphony Center (Orchestra Hall) | from $40 | Tickets |
| Chicago Cubs vs. Washington NationalsMLB | Fri May 21TBA | Wrigley Field | from $103 | Tickets |
| Chicago Symphony Orchestra: Tan Dun - Water Concerto & Marco PoloClassical | Fri May 211:30 PM | Symphony Center (Orchestra Hall) | from $61 | Tickets |
| Josh BlueComedy | Fri May 217:00 PM · 9:15 PM | Zanies Rosemont | from $97 | Tickets |
| Chicago Cubs vs. Washington NationalsMLB | Sat May 22TBA | Wrigley Field | from $122 | Tickets |
| Chicago Symphony Orchestra: Tan Dun - Water Concerto & Marco PoloClassical | Sat May 227:30 PM | Symphony Center (Orchestra Hall) | from $54 | Tickets |
| Chicago Cubs vs. Washington NationalsMLB | Sun May 23TBA | Wrigley Field | from $103 | Tickets |
| Valery Meladze | Sun May 237:00 PM | Riviera Theatre | from $146 | Tickets |
| Chicago Symphony Orchestra: Two Pianos - Who Could Ask for Anthing More?Classical | Mon May 247:30 PM | Symphony Center (Orchestra Hall) | from $80 | Tickets |
| Chicago Cubs vs. Kansas City RoyalsMLB | Tue May 25TBA | Wrigley Field | from $82 | Tickets |
| Chicago Cubs vs. Kansas City RoyalsMLB | Wed May 26TBA | Wrigley Field | from $83 | Tickets |
| The Airborne Toxic Event RescheduledAlternative | Wed May 267:30 PM | Vic Theatre | from $51 | Tickets |
| Chicago Cubs vs. Kansas City RoyalsMLB | Thu May 27TBA | Wrigley Field | from $83 | Tickets |
| Chicago Symphony Orchestra: Esa-Pekka Salonen & Yunchan LimClassical | Thu May 277:30 PM | Symphony Center (Orchestra Hall) | from $76 | Tickets |
| FKJTechno / Electronic | Thu May 278:00 PM | The Salt Shed (Outdoors) | from $66 | Tickets |
| Chicago White Sox vs. Seattle MarinersMLB | Fri May 28TBA | Rate Field | from $55 | Tickets |
| Chicago Symphony Orchestra: Esa-Pekka Salonen & Yunchan LimClassical | Fri May 281:30 PM | Symphony Center (Orchestra Hall) | from $81 | Tickets |
| Harry StylesPop / Rock | Fri May 287:45 PM | Soldier Field | from $83 | Tickets |
| Chicago White Sox vs. Seattle MarinersMLB | Sat May 29TBA | Rate Field | from $60 | Tickets |
| Suenos Music Festival - 2 Day PassFestival / Tour | Sat May 29TBA | Hutchinson Field Grant Park | from $577 | Tickets |
| Harry StylesPop / Rock | Sat May 297:45 PM | Soldier Field | from $95 | Tickets |
| Chicago White Sox vs. Seattle MarinersMLB | Sun May 30TBA | Rate Field | from $55 | Tickets |
| Chicago White Sox vs. Tampa Bay RaysMLB | Mon May 31TBA | Rate Field | from $110 | Tickets |
| Harry StylesPop / Rock | Mon May 317:45 PM | Soldier Field | from $91 | Tickets |
