Chicago returned from the Olympic Break with four straight victories over the Dream, Wings, Storm, and Stars, matching their longest winning streak of the season.
The Sky traveled to Washington D.C. to take on the Mystics on September 7. During the first half Elena Delle Donne suffered a thumb injury that would require surgery and leave the Sky without her services for the remainder of the season.
In Delle Donne’s absence, the Sky did not miss a beat. Cappie Pondexter surpassed WNBA legend Lisa Leslie for the fifth-most points in WNBA history with 24 points in a victory over Connecticut on September 11; This began a three-game winning streak for the Sky.
Chicago defeated Minnesota 98-97 in an overtime thriller on September 13 at Allstate Arena in front of special guests 50 Cent and Sophia Bush. Courtney Vandersloot hit two free throws in the closing seconds to force overtime and Pondexter made a go-ahead layup with 21.3 seconds remaining in overtime. Rookie Imani Boyette recorded one block in overtime, which sealed the game for Chicago. In the following game, Chicago defeated New York 92-68 at Allstate Arena. Jessica Breland recorded her 900th career point and Boyette recorded her 200th career point.
Chicago finished the months of August and September with a 7-3 record. The Sky finished the season 18-15, while earning the fourth seed in the playoffs.