[10] In the first round of the 2019 WNBA Playoffs, fifth-seeded Sky hosted the eighth-seeded Phoenix Mercury, whom they defeated 105–76 in a single-elimination game.
After a home loss to the Fever, the Sky faced the league-leading Sun, and surprised their opponents with a blowout 93–75 win.
On a three-game road trip from June 28 to July 2, the Sky lost three games against the Storm, Sparks, and Aces, dropping to a 6–7 record.
[34] Three Sky players—Diamond DeShields, Allie Quigley, and Courtney Vandersloot—were named as reserves in the 2019 WNBA All-Star Game on July 27.
[35] DeShields won the Skills Challenge during All-Star Weekend, but Quigley failed to repeat as Three-Point Contest champion.
During a 101–92 comeback victory against the New York Liberty on August 7, the Chicago Sky scored 42 points in the fourth quarter, the highest of any WNBA team since the league moved to a four-quarter format in 2006.
Their home game against the Aces was marked by officiating controversies and a conflict between Liz Cambage and Cheyenne Parker, which resulted in technical fouls for both players.