| | | |
| May 17, 2025 | L | Chicago Sky 58 at Indiana Fever 93 | Final |
| May 22, 2025 | L | New York Liberty 99 at Chicago Sky 74 | Final |
| May 25, 2025 | L | Chicago Sky 78 at Los Angeles Sparks 91 | Final |
| May 27, 2025 | L | Chicago Sky 89 at Phoenix Mercury 94 | Final |
| May 29, 2025 | W | Dallas Wings 92 at Chicago Sky 97 | Final |
| May 31, 2025 | W | Chicago Sky 94 at Dallas Wings 83 | Final |
| June 7, 2025 | L | Indiana Fever 79 at Chicago Sky 52 | Final |
| June 10, 2025 | L | Chicago Sky 66 at New York Liberty 85 | Final |
| June 13, 2025 | L | Chicago Sky 70 at Atlanta Dream 88 | Final |
| June 15, 2025 | W | Chicago Sky 78 at Connecticut Sun 66 | Final |
| June 17, 2025 | L | Washington Mystics 79 at Chicago Sky 72 | Final |
| June 21, 2025 | L | Phoenix Mercury 107 at Chicago Sky 86 | Final |
| June 22, 2025 | L | Chicago Sky 80 at Atlanta Dream 93 | Final |
| June 24, 2025 | W | Los Angeles Sparks 86 at Chicago Sky 97 | Final |
| June 27, 2025 | L | Chicago Sky 78 at Golden State Valkyries 83 | Final |
| June 29, 2025 | W | Chicago Sky 92 at Los Angeles Sparks 85 | Final |
| July 6, 2025 | L | Chicago Sky 75 at Minnesota Lynx 80 | Final |
| July 8, 2025 | L | Chicago Sky 79 at Washington Mystics 81 | Final |
| July 9, 2025 | W | Dallas Wings 76 at Chicago Sky 87 | Final |
| July 12, 2025 | W | Minnesota Lynx 81 at Chicago Sky 87 | Final |
| July 14, 2025 | L | Minnesota Lynx 91 at Chicago Sky 78 | Final |
| July 16, 2025 | L | Atlanta Dream 86 at Chicago Sky 49 | Final |
| July 22, 2025 | L | Chicago Sky 68 at Minnesota Lynx 91 | Final |
| July 24, 2025 | L | Seattle Storm 95 at Chicago Sky 57 | Final |
| July 27, 2025 | L | Indiana Fever 93 at Chicago Sky 78 | Final |
| July 29, 2025 | L | Chicago Sky 86 at Washington Mystics 103 | Final |
| August 1, 2025 | L | Golden State Valkyries 73 at Chicago Sky 66 | Final |
| August 3, 2025 | L | Phoenix Mercury 83 at Chicago Sky 67 | Final |
| August 5, 2025 | W | Washington Mystics 64 at Chicago Sky 78 | Final |
| August 7, 2025 | L | Atlanta Dream 86 at Chicago Sky 65 | Final |
| August 9, 2025 | L | Chicago Sky 70 at Indiana Fever 92 | Final |
| August 13, 2025 | | Chicago Sky at Connecticut Sun | 7:00 p.m. |
| August 15, 2025 | | Golden State Valkyries at Chicago Sky | 7:30 p.m. |
| August 19, 2025 | | Seattle Storm at Chicago Sky | 8:00 p.m. |
| August 21, 2025 | | Chicago Sky at New York Liberty | 7:00 p.m. |
| August 23, 2025 | | Connecticut Sun at Chicago Sky | 4:00 p.m. |
| August 25, 2025 | | Las Vegas Aces at Chicago Sky | 8:00 p.m. |
| August 28, 2025 | | Chicago Sky at Phoenix Mercury | 10:00 p.m. |
| August 30, 2025 | | Chicago Sky at Seattle Storm | 9:00 p.m. |
| September 3, 2025 | | Connecticut Sun at Chicago Sky | 8:00 p.m. |
| September 5, 2025 | | Chicago Sky at Indiana Fever | 7:30 p.m. |
| September 7, 2025 | | Chicago Sky at Las Vegas Aces | 9:00 p.m. |
| September 9, 2025 | | Chicago Sky at Las Vegas Aces | 10:00 p.m. |
| September 11, 2025 | | New York Liberty at Chicago Sky | 8:00 p.m. |
Chicago Sky Schedule
