When the WNBA free agency period began, the Chicago Sky took some heavy losses. They lost hometown favorite Candace Parker to the Las Vegas Aces, Courtney Vandersloot to the New York Liberty, Azura Stephens to the Los Angeles Sparks and Allie Quigley decided to sit out the 2023 season. The departures left the Sky with only Kahleah Copper, Dana Evans and Ruthy Hebard from the 2021 championship team and only Copper was a major factor in the rotation. The Sky looked to rebound quickly though in the first couple of days of the WNBA free agency period with a trio of signings in Courtney Williams, Elizabeth Williams and Isabelle Harrison.

In Courtney Williams, the Sky are getting an electric guard who can score from anywhere on the court and can put up points in a hurry. She spent last season with the Connecticut Sun and averaged 11.1 points per game, 4.6 rebounds and 3.3 assists while shooting 42.6 percent from the field and 33.8 percent from the three-point line.

With Elizabeth Williams, the Sky are getting a solid interior defensive player and someone who is active in the paint and on the glass. She spent last season with the Washington Mystics and averaged 5.4 points and 3.8 rebounds in 30 games off the bench while shooting 48.2 percent from the field.

In Isabelle Harrison, the Sky are getting a good forward option who had a solid year for the Dallas Wings last season. She averaged 8.7 points and 4.3 rebounds with shooting splits of 46.6 percent from the field and 86.7 percent from the free-throw line.