| Event | Venue |  Date/Time | |
| Theo Von | Wintrust Arena
Chicago, IL | Thursday
4/24/2025
7:30 PM |  |
| WNBA Preseason: Chicago Sky vs. Minnesota Lynx | Wintrust Arena
Chicago, IL | Tuesday
5/6/2025
6:00 PM | |
| Chicago Sky vs. New York Liberty | Wintrust Arena
Chicago, IL | Thursday
5/22/2025
7:00 PM | |
| Live Breathe Fight Tour: David and Tamela Mann, Erica Campbell, Tye Tribbett, Karen Clark-Sheard & Kierra Sheard | Wintrust Arena
Chicago, IL | Friday
5/23/2025
8:00 PM | |
| Chicago Sky vs. Dallas Wings | Wintrust Arena
Chicago, IL | Thursday
5/29/2025
7:00 PM | |
| Chicago Sky vs. Washington Mystics | Wintrust Arena
Chicago, IL | Tuesday
6/17/2025
7:00 PM | |
| R&B Music Experience: Ashanti, Lil Kim & Mya | Wintrust Arena
Chicago, IL | Thursday
6/19/2025
8:00 PM | |
| Chicago Sky vs. Phoenix Mercury | Wintrust Arena
Chicago, IL | Saturday
6/21/2025
12:00 PM | |
| Chicago Sky vs. Los Angeles Sparks | Wintrust Arena
Chicago, IL | Tuesday
6/24/2025
7:00 PM | |
| PFL World Tournament 7: Semifinals | Wintrust Arena
Chicago, IL | Friday
6/27/2025
6:30 PM | |
| 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
8:30 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 | |
| Chicago Sky vs. New York Liberty | Wintrust Arena
Chicago, IL | Thursday
9/11/2025
7:00 PM | |
