| Chicago White Sox vs. Tampa Bay RaysMLB | Tue Jun 1TBA | Rate Field | from $110 | Tickets |
| Chicago White Sox vs. Tampa Bay RaysMLB | Wed Jun 2TBA | Rate Field | from $110 | Tickets |
| Chicago Cubs vs. Los Angeles DodgersMLB | Thu Jun 3TBA | Wrigley Field | from $130 | Tickets |
| Chicago Symphony Orchestra: Lucas & Arthur Jussen - Concerto for Two PianosClassical | Thu Jun 37:30 PM | Symphony Center (Orchestra Hall) | from $54 | Tickets |
| Chicago Cubs vs. Los Angeles DodgersMLB | Fri Jun 4TBA | Wrigley Field | from $130 | Tickets |
| Chicago Symphony Orchestra: Lucas & Arthur Jussen - Concerto for Two PianosClassical | Fri Jun 41:30 PM | Symphony Center (Orchestra Hall) | from $67 | Tickets |
| A Psalm for the Wild-BuiltMusical / Play | Fri Jun 47:30 PM | Lifeline Theatre | from $88 | Tickets |
| Harry StylesPop / Rock | Fri Jun 47:45 PM | Soldier Field | from $105 | Tickets |
| Chucho Valdes 85th Birthday CelebrationJazz / Blues | Fri Jun 48:00 PM | Symphony Center (Orchestra Hall) | from $54 | Tickets |
| Chicago Cubs vs. Los Angeles DodgersMLB | Sat Jun 5TBA | Wrigley Field | from $141 | Tickets |
| A Psalm for the Wild-BuiltMusical / Play | Sat Jun 52:30 PM · 7:30 PM | Lifeline Theatre | from $88 | Tickets |
| Charlie BerensComedy | Sat Jun 57:00 PM | Vic Theatre | from $76 | Tickets |
| Chicago Symphony Orchestra: Lucas & Arthur Jussen - Concerto for Two PianosClassical | Sat Jun 57:30 PM | Symphony Center (Orchestra Hall) | from $67 | Tickets |
| Harry StylesPop / Rock | Sat Jun 57:45 PM | Soldier Field | from $106 | Tickets |
| Chicago Cubs vs. Los Angeles DodgersMLB | Sun Jun 6TBA | Wrigley Field | from $130 | Tickets |
| A Psalm for the Wild-BuiltMusical / Play | Sun Jun 62:30 PM | Lifeline Theatre | from $88 | Tickets |
| Chicago Symphony Orchestra: Lucas & Arthur Jussen - Concerto for Two PianosClassical | Sun Jun 63:00 PM | Symphony Center (Orchestra Hall) | from $67 | Tickets |
| Chicago White Sox vs. Philadelphia PhilliesMLB | Mon Jun 7TBA | Rate Field | from $60 | Tickets |
| Chicago White Sox vs. Philadelphia PhilliesMLB | Tue Jun 8TBA | Rate Field | from $60 | Tickets |
| Chicago White Sox vs. Philadelphia PhilliesMLB | Wed Jun 9TBA | Rate Field | from $60 | Tickets |
| Chicago Symphony Orchestra: Rachmaninov Piano Concerto No. 2Classical | Thu Jun 107:30 PM | Symphony Center (Orchestra Hall) | from $61 | Tickets |
| Chicago Cubs vs. Colorado RockiesMLB | Fri Jun 11TBA | Wrigley Field | from $109 | Tickets |
| Chicago Symphony Orchestra: Rachmaninov Piano Concerto No. 2Classical | Fri Jun 111:30 PM | Symphony Center (Orchestra Hall) | from $75 | Tickets |
| Chicago Cubs vs. Colorado RockiesMLB | Sat Jun 12TBA | Wrigley Field | from $114 | Tickets |
| A Psalm for the Wild-BuiltMusical / Play | Sat Jun 122:30 PM · 7:30 PM | Lifeline Theatre | from $88 | Tickets |
| Chicago Symphony Orchestra: Rachmaninov Piano Concerto No. 2Classical | Sat Jun 127:30 PM | Symphony Center (Orchestra Hall) | from $59 | Tickets |
| Chicago Cubs vs. Colorado RockiesMLB | Sun Jun 13TBA | Wrigley Field | from $103 | Tickets |
| A Psalm for the Wild-BuiltMusical / Play | Sun Jun 132:30 PM | Lifeline Theatre | from $82 | Tickets |
| Chicago Cubs vs. Cincinnati RedsMLB | Mon Jun 14TBA | Wrigley Field | from $87 | Tickets |
| Chicago Cubs vs. Cincinnati RedsMLB | Tue Jun 15TBA | Wrigley Field | from $87 | Tickets |
| Chicago Cubs vs. Cincinnati RedsMLB | Wed Jun 16TBA | Wrigley Field | from $87 | Tickets |
| Chicago Symphony Orchestra: Makela Conducts Beethoven 9Classical | Thu Jun 177:30 PM | Symphony Center (Orchestra Hall) | from $59 | Tickets |
| Chicago White Sox vs. Minnesota TwinsMLB | Fri Jun 18TBA | Rate Field | from $60 | Tickets |
| Chicago Symphony Orchestra: Makela Conducts Beethoven 9Classical | Fri Jun 187:30 PM | Symphony Center (Orchestra Hall) | from $49 | Tickets |
| Chicago White Sox vs. Minnesota TwinsMLB | Sat Jun 19TBA | Rate Field | from $78 | Tickets |
| Chicago Symphony Orchestra: Makela Conducts Beethoven 9Classical | Sat Jun 197:30 PM | Symphony Center (Orchestra Hall) | from $59 | Tickets |
| Chicago White Sox vs. Minnesota TwinsMLB | Sun Jun 20TBA | Rate Field | from $60 | Tickets |
| Chicago Symphony Orchestra: Makela Conducts Beethoven 9Classical | Sun Jun 203:00 PM | Symphony Center (Orchestra Hall) | from $165 | Tickets |
| Chicago White Sox vs. Texas RangersMLB | Mon Jun 21TBA | Rate Field | from $57 | Tickets |
| Chicago White Sox vs. Texas RangersMLB | Tue Jun 22TBA | Rate Field | from $57 | Tickets |
| Chicago White Sox vs. Texas RangersMLB | Wed Jun 23TBA | Rate Field | from $57 | Tickets |
| Chicago White Sox vs. Kansas City RoyalsMLB | Thu Jun 24TBA | Rate Field | from $57 | Tickets |
| Chicago White Sox vs. Kansas City RoyalsMLB | Fri Jun 25TBA | Rate Field | from $60 | Tickets |
| Chicago Symphony Orchestra: Star Wars' The Empire Strikes Back In ConcertClassical | Fri Jun 257:30 PM | Symphony Center (Orchestra Hall) | from $94 | Tickets |
| Chicago White Sox vs. Kansas City RoyalsMLB | Sat Jun 26TBA | Rate Field | from $65 | Tickets |
| Kenny Chesney, Eric Church, Sheryl Crow & Greylan JamesCountry / Folk | Sat Jun 264:30 PM | Soldier Field | from $99 | Tickets |
| Chicago Symphony Orchestra: Star Wars' The Empire Strikes Back In ConcertClassical | Sat Jun 267:30 PM | Symphony Center (Orchestra Hall) | from $86 | Tickets |
| Chicago White Sox vs. Kansas City RoyalsMLB | Sun Jun 27TBA | Rate Field | from $60 | Tickets |
| Chicago Symphony Orchestra: Star Wars' The Empire Strikes Back In ConcertClassical | Sun Jun 273:00 PM | Symphony Center (Orchestra Hall) | from $92 | Tickets |
| Chicago Cubs vs. San Diego PadresMLB | Mon Jun 28TBA | Wrigley Field | from $83 | Tickets |
| Chicago Cubs vs. San Diego PadresMLB | Tue Jun 29TBA | Wrigley Field | from $83 | Tickets |
| Lizzy McAlpineAlternative | Tue Jun 297:00 PM | United Center | from $134 | Tickets |
| Chicago Cubs vs. San Diego PadresMLB | Wed Jun 30TBA | Wrigley Field | from $83 | Tickets |
