| Major. | 5-26-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Christian McBride & Ursa Major | 6-6-2026
Saturday
9:30 PM | Garcias Chicago in Chicago, IL | View Tickets |
| Major League Rugby Championship | 6-21-2026
Sunday
7:00 PM | SeatGeek Stadium in Bridgeview, IL | View Tickets |
| Major League Pickleball Chicago - Thursday (Time: TBD) | 7-23-2026
Thursday
12:00 PM | Life Time North Shore Sport and Racquet in Northbrook, IL | View Tickets |
| Major League Pickleball Chicago - Friday (Time: TBD) | 7-24-2026
Friday
12:00 PM | Life Time North Shore Sport and Racquet in Northbrook, IL | View Tickets |
| Major League Pickleball Chicago - Saturday (Time: TBD) | 7-25-2026
Saturday
12:00 PM | Life Time North Shore Sport and Racquet in Northbrook, IL | View Tickets |
| Major League Pickleball Chicago - Sunday (Time: TBD) | 7-26-2026
Sunday
12:00 PM | Life Time North Shore Sport and Racquet in Northbrook, IL | View Tickets |
| Lollapalooza - 4 Day Pass | 7-30-2026
Thursday
TBD | Hutchinson Field Grant Park in Chicago, IL | View Tickets |
| Lollapalooza - 2 Day Pass (Thursday & Saturday) | 7-30-2026
Thursday
7:30 AM | Hutchinson Field Grant Park in Chicago, IL | View Tickets |
| Major League Wrestling: Azteca Lucha | 11-7-2026
Saturday
7:30 PM | Cicero Stadium - IL in Cicero, IL | View Tickets |
