| Event | Venue | Date/Time | |
| Chicago Sky vs. Dallas Wings | Wintrust Arena
Chicago, IL | Wednesday
5/20/2026
8:00 PM | view
tickets |
|
| Chicago Sky vs. Minnesota Lynx | Wintrust Arena
Chicago, IL | Saturday
5/23/2026
12:00 PM | view
tickets |
|
| Chicago Sky vs. Toronto Tempo | Wintrust Arena
Chicago, IL | Wednesday
5/27/2026
7:00 PM | view
tickets |
|
| Chicago Sky vs. Minnesota Lynx | Wintrust Arena
Chicago, IL | Friday
5/29/2026
6:30 PM | view
tickets |
|
| We Them Ones Comedy Tour: Mike Epps, Navv Greene, Karlous Miller & Chico Bean | Wintrust Arena
Chicago, IL | Saturday
5/30/2026
8:00 PM | view
tickets |
|
| Chicago Sky vs. Connecticut Sun | Wintrust Arena
Chicago, IL | Friday
6/5/2026
6:30 PM | view
tickets |
|
| Chicago Sky vs. Atlanta Dream | Wintrust Arena
Chicago, IL | Tuesday
6/9/2026
7:00 PM | view
tickets |
|
| Chicago Sky vs. New York Liberty | Wintrust Arena
Chicago, IL | Wednesday
6/17/2026
7:00 PM | view
tickets |
|
| R&B Music Experience: Tyrese, Tank & Tamar Braxton | Wintrust Arena
Chicago, IL | Saturday
6/20/2026
8:00 PM | view
tickets |
|
| Chicago Sky vs. Portland Fire | Wintrust Arena
Chicago, IL | Wednesday
6/24/2026
8:00 PM | view
tickets |
|
| Chicago Sky vs. Portland Fire | Wintrust Arena
Chicago, IL | Friday
6/26/2026
6:30 PM | view
tickets |
|
| XVII Lithuanian Folk Dance Festival of North America | Wintrust Arena
Chicago, IL | Sunday
7/12/2026
2:00 PM | view
tickets |
|
| Chicago Sky vs. Seattle Storm | Wintrust Arena
Chicago, IL | Wednesday
7/15/2026
11:00 AM | view
tickets |
|
| Chicago Sky vs. Los Angeles Sparks | Wintrust Arena
Chicago, IL | Friday
7/17/2026
6:30 PM | view
tickets |
|
| Big3 Basketball | Wintrust Arena
Chicago, IL | Sunday
7/19/2026
TBD | view
tickets |
|
| WNBA State Farm 3-Point Contest & WNBA Kia Shooting Stars | Wintrust Arena
Chicago, IL | Friday
7/24/2026
7:00 PM | view
tickets |
|
| Chicago Sky vs. Connecticut Sun | Wintrust Arena
Chicago, IL | Thursday
7/30/2026
7:00 PM | view
tickets |
|
| Chicago Sky vs. Las Vegas Aces | Wintrust Arena
Chicago, IL | Saturday
8/1/2026
12:00 PM | view
tickets |
|
| Chicago Sky vs. Phoenix Mercury | Wintrust Arena
Chicago, IL | Monday
8/3/2026
7:00 PM | view
tickets |
|
| Chicago Sky vs. Los Angeles Sparks | Wintrust Arena
Chicago, IL | Wednesday
8/5/2026
8:00 PM | view
tickets |
|
| Mamamoo | Wintrust Arena
Chicago, IL | Saturday
8/15/2026
7:30 PM | view
tickets |
|
| Chicago Sky vs. New York Liberty | Wintrust Arena
Chicago, IL | Tuesday
8/18/2026
8:00 PM | view
tickets |
|
| Chicago Sky vs. Golden State Valkyries | Wintrust Arena
Chicago, IL | Friday
8/21/2026
6:30 PM | view
tickets |
|
| Chicago Sky vs. Indiana Fever | Wintrust Arena
Chicago, IL | Sunday
8/23/2026
6:00 PM | view
tickets |
|
| DePaul Blue Demons Women's Volleyball vs. Nebraska Cornhuskers | Wintrust Arena
Chicago, IL | Friday
9/4/2026
TBD | view
tickets |
|
| Mojo Brookzz | Wintrust Arena
Chicago, IL | Saturday
9/12/2026
8:00 PM | view
tickets |
|
| Mojo Brookzz | Wintrust Arena
Chicago, IL | Sunday
9/13/2026
7:00 PM | view
tickets |
|
| Chicago Sky vs. Washington Mystics | Wintrust Arena
Chicago, IL | Thursday
9/17/2026
7:00 PM | view
tickets |
|
| Chicago Sky vs. Toronto Tempo | Wintrust Arena
Chicago, IL | Tuesday
9/22/2026
7:00 PM | view
tickets |
|
| DePaul Blue Demons vs. Southern Methodist (SMU) Mustangs | Wintrust Arena
Chicago, IL | Saturday
12/5/2026
TBD | view
tickets |
|
