| | | |
| May 9, 2026 | W | Chicago Sky 98 at Portland Fire 83 | Final |
| May 13, 2026 | W | Chicago Sky 69 at Golden State Valkyries 63 | Final |
| May 15, 2026 | L | Chicago Sky 83 at Phoenix Mercury 91 | Final |
| May 17, 2026 | W | Chicago Sky 86 at Minnesota Lynx 79 | Final |
| May 20, 2026 | L | Dallas Wings 99 at Chicago Sky 89 | Final |
| May 23, 2026 | L | Minnesota Lynx 85 at Chicago Sky 75 | Final |
| May 27, 2026 | L | Toronto Tempo 111 at Chicago Sky 104 | Final |
| May 29, 2026 | L | Minnesota Lynx 79 at Chicago Sky 58 | Final |
| June 2, 2026 | L | Chicago Sky 72 at Washington Mystics 90 | Final |
| June 5, 2026 | W | Connecticut Sun 80 at Chicago Sky 85 | Final |
| June 7, 2026 | L | Chicago Sky 68 at Toronto Tempo 85 | Final |
| June 9, 2026 | L | Atlanta Dream 82 at Chicago Sky 75 | Final |
| June 11, 2026 | L | Chicago Sky 106 at Indiana Fever 114 | Final (OT) |
| June 17, 2026 | L | New York Liberty 96 at Chicago Sky 95 | Final |
| June 20, 2026 | L | Chicago Sky 92 at Dallas Wings 93 | Final |
| June 22, 2026 | L | Chicago Sky 63 at Connecticut Sun 92 | Final |
| June 24, 2026 | W | Portland Fire 78 at Chicago Sky 101 | Final |
| June 26, 2026 | W | Portland Fire 94 at Chicago Sky 124 | Final |
| June 28, 2026 | L | Las Vegas Aces 107 at Chicago Sky 99 | Final |
| July 3, 2026 | L | Chicago Sky 90 at Las Vegas Aces 98 | Final (OT) |
| July 7, 2026 | W | Chicago Sky 77 at Phoenix Mercury 66 | Final |
| July 10, 2026 | L | Chicago Sky 87 at Los Angeles Sparks 102 | Final |
| July 12, 2026 | L | Chicago Sky 91 at Dallas Wings 96 | Final |
| July 15, 2026 | W | Seattle Storm 90 at Chicago Sky 95 | Final |
| July 17, 2026 | W | Los Angeles Sparks 82 at Chicago Sky 96 | Final |
| July 19, 2026 | L | Chicago Sky 91 at Atlanta Dream 93 | Final |
| July 22, 2026 | L | Chicago Sky 94 at New York Liberty 95 | Final |
| July 30, 2026 | W | Connecticut Sun 88 at Chicago Sky 94 | Final |
| August 1, 2026 | W | Las Vegas Aces 83 at Chicago Sky 84 | Final |
| August 3, 2026 | L | Phoenix Mercury 106 at Chicago Sky 101 | Final |
| August 5, 2026 | W | Los Angeles Sparks 88 at Chicago Sky 95 | Final |
| August 8, 2026 | L | Indiana Fever 90 at Chicago Sky 86 | Final |
| August 10, 2026 | L | Chicago Sky 88 at Seattle Storm 97 | Final |
| August 12, 2026 | L | Chicago Sky 71 at Golden State Valkyries 91 | Final |
| August 16, 2026 | W | Chicago Sky 82 at Seattle Storm 80 | Final |
| August 18, 2026 | W | New York Liberty 86 at Chicago Sky 93 | Final |
| August 21, 2026 | W | Golden State Valkyries 70 at Chicago Sky 73 | Final |
| August 23, 2026 | L | Indiana Fever 113 at Chicago Sky 90 | Final |
| August 25, 2026 | L | Chicago Sky 81 at Connecticut Sun 87 | Final |
| August 29, 2026 | L | Chicago Sky 66 at New York Liberty 85 | Final |
| September 17, 2026 | L | Washington Mystics 110 at Chicago Sky 80 | Final |
| September 19, 2026 | | Chicago Sky at Atlanta Dream | 7:00 p.m. |
| September 22, 2026 | | Toronto Tempo at Chicago Sky | 8:00 p.m. |
| September 24, 2026 | | Chicago Sky at Washington Mystics | 7:30 p.m. |
Chicago Sky Schedule
