| Critical Role | 4-10-2025
Thursday
6:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| New Japan Pro Wrestling | 4-11-2025
Friday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| The Millennium Tour: Trey Songz, Omarion, Bow Wow & Boosie BadAzz | 4-17-2025
Thursday
8:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| The Millennium Tour: Trey Songz, Omarion, Bow Wow & Boosie BadAzz | 4-18-2025
Friday
8:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| We Them Ones Comedy Tour: Mike Epps, Kountry Wayne, Karlous Miller & Lil Duval | 4-19-2025
Saturday
8:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Theo Von | 4-24-2025
Thursday
7:30 PM | Wintrust Arena in Chicago, IL | View Tickets |
| WNBA Preseason: Chicago Sky vs. Minnesota Lynx | 5-6-2025
Tuesday
6:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. New York Liberty | 5-22-2025
Thursday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Live Breathe Fight Tour: David and Tamela Mann, Erica Campbell, Tye Tribbett, Karen Clark-Sheard & Kierra Sheard | 5-23-2025
Friday
8:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Dallas Wings | 5-29-2025
Thursday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Washington Mystics | 6-17-2025
Tuesday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| R&B Music Experience: Ashanti, Lil Kim & Mya | 6-19-2025
Thursday
8:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Phoenix Mercury | 6-21-2025
Saturday
12:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Los Angeles Sparks | 6-24-2025
Tuesday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| PFL World Tournament 7: Semifinals | 6-27-2025
Friday
6:30 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Dallas Wings | 7-9-2025
Wednesday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Minnesota Lynx | 7-12-2025
Saturday
12:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Minnesota Lynx | 7-14-2025
Monday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Atlanta Dream | 7-16-2025
Wednesday
11:00 AM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Seattle Storm | 7-24-2025
Thursday
8:30 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Golden State Valkyries | 8-1-2025
Friday
6:30 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Phoenix Mercury | 8-3-2025
Sunday
5:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Washington Mystics | 8-5-2025
Tuesday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Atlanta Dream | 8-7-2025
Thursday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Golden State Valkyries | 8-15-2025
Friday
6:30 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Seattle Storm | 8-19-2025
Tuesday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Connecticut Sun | 8-23-2025
Saturday
3:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Las Vegas Aces | 8-25-2025
Monday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. Connecticut Sun | 9-3-2025
Wednesday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
| Chicago Sky vs. New York Liberty | 9-11-2025
Thursday
7:00 PM | Wintrust Arena in Chicago, IL | View Tickets |
