RotoWire this summer is exploring the WNBA's 50+ defining moments across its 30-year history, including spotlights on individual franchises. Below, we take a look at the 
Chicago Sky and their rise in the league on the court and across cultural and business milestones.
In a city filled with historic franchises, Chicago's most recent championship among the four major sports belongs to the Chicago Sky, who won their first title in 2021.
From Early Struggles To Finals Contenders
The Sky began play in 2006 and faced growing pains early on, going 5-29 in their inaugural season. Head coach Dave Cowens left for the NBA following the campaign, and the team improved to 14-20 under new head coach Bo Overton. Overton resigned ahead of the 2008 season, but the Sky selected Sylvia Fowles with the second overall pick in the 2008 WNBA Draft to play under new head coach and general manager, Steven Key.
Fowles missed 17 games during her rookie season, and the Sky finished the year with a 12-22 record, but she was a young cornerstone who the team could build around. After spending their first four seasons at UIC Pavilion, the Sky moved to Allstate Arena in Rosemont, Illinois, ahead of the 2010 campaign. Key resigned as general manager and head coach following the 2010 season, and Pokey Chatman replaced him in both positions.
The 2011 season brought some stability for the franchise that underwent plenty of change early in its existence. Chatman began a six-year coaching tenure with the team, which remains the longest stint in franchise history. The Sky also selected Courtney Vandersloot with the third overall pick in the 2011 WNBA Draft, providing a talented guard to complement Fowles' frontcourt presence.
The Sky drafted another future superstar in the 2013 WNBA Draft by selecting Elena Delle Donne with the second overall pick. After seven consecutive losing seasons to begin their time in the league, the Sky went 24-10 in 2013 and won the Eastern Conference. Delle Donne finished third in MVP voting, but the team was eliminated from the playoffs in the conference semifinals. The following season, the Sky had a losing record but made the playoffs and qualified for the WNBA Finals for the first time in franchise history, where they were swept by the Mercury.
Ahead of the 2015 campaign, Fowles demanded a trade and sat out the first half of the year until a deal was made. The Sky remained a playoff team in the following two seasons but traded Delle Donne to the Mystics ahead of the 2017 campaign in exchange for Kahleah Copper -- who went on to be the 2021 WNBA Finals MVP -- as well as Stefanie Dolson and the second overall pick in the 2017 WNBA Draft. After ending a four-year playoff streak in 2017, the Sky moved to Wintrust Arena in 2018, where they play to this day.
Candace Parker's Homecoming & Chicago's First WNBA Title
The Sky reached the summit of WNBA success for the first time in storybook fashion, as Candace Parker -- who grew up in Naperville, Illinois and was a two-time WNBA MVP -- returned home ahead of the 2021 campaign to play for Chicago after spending the first 13 years of her career in Los Angeles. While the Sky finished the regular season 16-16 that year, they earned the No. 6 seed in the playoffs and advanced to the WNBA Finals.
While the Phoenix Mercury had home-court advantage for the Finals as the 5-seed, the Sky claimed Game 1 in Phoenix before losing Game 2 in overtime. However, Chicago bounced back with a 36-point win in Game 3 and won Game 4 to clinch the series and secure the team's first-ever title and the city's first championship since the Cubs ended their 108-year drought in 2016.
The Post-Title Reset & A New Chicago Era
The Sky kept most of their core intact for the year following their first title, and the team went 26-10 in 2022 and made it to the semifinals in the playoffs before falling to the Connecticut Sun. Chicago's history of turbulence picked back up ahead of the 2023 season, when the team lost Vandersloot, Parker, Allie Quigley and others. Head coach and general manager James Wade also announced that he was leaving for the NBA midway through the season.
The Sky traded Copper before the 2024 season and Marina Mabrey during the All-Star break. However, the team drafted Kamilla Cardoso and Angel Reese before going 13-27 that season and firing head coach Teresa Weatherspoon after just one year.
Vandersloot rejoined the team ahead of the 2025 campaign, but she missed most of the year due to a knee injury, while Reese expressed her frustrations in the organization during a late-season interview before being suspended half a game due to "statements detrimental to the team." Reese was traded to the Atlanta Dream ahead of the 2026 season.
Although the Chicago Bulls are unaffiliated with the Sky, the two franchises share some similarities in their story of Chicago basketball. Each team has a long list of superstars who have donned the uniform, some of whom parted ways with the organization in a relatively abrupt fashion. However, each franchise has withstood turbulence to achieve success.
While Reese is no longer with the team, her popularity on and off the court helped the team revitalize its brand, including a pair of sellout games at the United Center, home of the Bulls. The team's ownership has also begun construction on a new training facility in Bedford Park, Illinois. Chicago was selected to host the WNBA All-Star Game during the league's 30th anniversary season in 2026, signaling that the city's basketball culture has remained integral to the league's success even as the Sky have withstood changes over the past two decades.
