| Event | Venue | Date/Time | |
| Chicago Sky vs. Dallas Wings | Wintrust Arena
Chicago, IL | Wednesday
7/9/2025
7:00 PM |  |
| Chicago Sky vs. Minnesota Lynx | Wintrust Arena
Chicago, IL | Saturday
7/12/2025
12:00 PM | |
| Chicago Sky vs. Minnesota Lynx | Wintrust Arena
Chicago, IL | Monday
7/14/2025
7:00 PM | |
| Chicago Sky vs. Atlanta Dream | Wintrust Arena
Chicago, IL | Wednesday
7/16/2025
11:00 AM | |
| Chicago Sky vs. Seattle Storm | Wintrust Arena
Chicago, IL | Thursday
7/24/2025
7:30 PM | |
| Chicago Sky vs. Golden State Valkyries | Wintrust Arena
Chicago, IL | Friday
8/1/2025
6:30 PM | |
| Chicago Sky vs. Phoenix Mercury | Wintrust Arena
Chicago, IL | Sunday
8/3/2025
5:00 PM | |
| Chicago Sky vs. Washington Mystics | Wintrust Arena
Chicago, IL | Tuesday
8/5/2025
7:00 PM | |
| Chicago Sky vs. Atlanta Dream | Wintrust Arena
Chicago, IL | Thursday
8/7/2025
7:00 PM | |
| Chicago Sky vs. Golden State Valkyries | Wintrust Arena
Chicago, IL | Friday
8/15/2025
6:30 PM | |
| Chicago Sky vs. Seattle Storm | Wintrust Arena
Chicago, IL | Tuesday
8/19/2025
7:00 PM | |
| Chicago Sky vs. Connecticut Sun | Wintrust Arena
Chicago, IL | Saturday
8/23/2025
3:00 PM | |
| Chicago Sky vs. Las Vegas Aces | Wintrust Arena
Chicago, IL | Monday
8/25/2025
7:00 PM | |
| Chicago Sky vs. Connecticut Sun | Wintrust Arena
Chicago, IL | Wednesday
9/3/2025
7:00 PM | |
| Le Sserafim | Wintrust Arena
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| Chicago Sky vs. New York Liberty | Wintrust Arena
Chicago, IL | Thursday
9/11/2025
7:00 PM | |
| Sweetest Day Comedy Jam: Lavell Crawford, Bill Bellamy, & T.I. (TIP Harris) | Wintrust Arena
Chicago, IL | Saturday
10/18/2025
8:00 PM | |
| Exhibition: DePaul Blue Demons vs. Loyola Chicago Ramblers | Wintrust Arena
Chicago, IL | Monday
10/20/2025
TBD | |
| GRiZ - 2 Day Pass | Wintrust Arena
Chicago, IL | Friday
10/31/2025
TBD | |
| GRiZ | Wintrust Arena
Chicago, IL | Friday
10/31/2025
7:00 PM | |
| GRiZ | Wintrust Arena
Chicago, IL | Saturday
11/1/2025
7:00 PM | |
| DePaul Blue Demons vs. Chicago State Cougars | Wintrust Arena
Chicago, IL | Monday
11/3/2025
TBD | |
| DePaul Blue Demons vs. Stonehill Skyhawks | Wintrust Arena
Chicago, IL | Friday
11/7/2025
TBD | |
| DePaul Blue Demons vs. Northwestern Wildcats | Wintrust Arena
Chicago, IL | Friday
11/14/2025
TBD | |
| Depaul Blue Demons Vs. Gardner-webb Runnin' Bulldogs | Wintrust Arena
Chicago, IL | Tuesday
11/18/2025
TBD | |
| DePaul Blue Demons vs. Detroit Mercy Titans | Wintrust Arena
Chicago, IL | Sunday
11/23/2025
TBD | |
| The 85 South Show | Wintrust Arena
Chicago, IL | Friday
11/28/2025
8:00 PM | |
| DePaul Blue Demons vs. Arkansas-Pine Bluff Golden Lions | Wintrust Arena
Chicago, IL | Saturday
12/6/2025
TBD | |
| DePaul Blue Demons vs. Morgan State Bears | Wintrust Arena
Chicago, IL | Tuesday
12/9/2025
TBD | |
