CHI Sky

In February 2005, NBA Commissioner David Stern announced that Chicago had been awarded a new WNBA franchise, temporarily named WNBA Chicago. On May 27, 2005, former NBA player and coach Dave Cowens was announced as the team's first head coach and general manager. The team home would be the UIC Pavilion. On September 20, 2005, the team name and logo formally debuted at an introduction event held at the Adler Planetarium. Team President and CEO Margaret Stender explained the team colors of yellow and blue represent "[a] beautiful day in Chicago between the blue sky and bright sunlight to highlight the spectacular skyline." The event was highlighted by the appearance of several star players, including Diana Taurasi, Temeka Johnson, Sue Bird, and Ruth Riley.^[]

In November 2005, the team held an expansion draft to help build its roster of players. Among the notable selections were Brooke Wyckoff from the Connecticut Sun, Bernadette Ngoyisa from the San Antonio Silver Stars, Elaine Powell from the Detroit Shock, and Stacey Dales (who had retired prior to the 2005 season) from the Washington Mystics.

On February 28, 2006, the team announced that two of the minority shareholders of the team are Michelle Williams, from the vocal group Destiny's Child, and Mathew Knowles, father of Destiny's Child lead singer Beyoncé Knowles.

In their first season, the Sky achieved a 5–29 record and finished last in the Eastern Conference. After the season, head coach Dave Cowens resigned to join the coaching staff of the Detroit Pistons. University of Missouri-Kansas City women's head basketball coach Bo Overton was named the Sky's new head coach and general manager on December 12, 2006. The Sky once again recorded a league-worst 5–29 record in 2006. Despite having the highest odds of drawing the first pick in the 2007 WNBA draft lottery, the Sky ended up with the third overall pick, which they used to select Armintie Price. The team was vastly improved in the 2007 season, but still finished with a 14–20 record and were two games behind the final playoff spot in the Eastern Conference. Price was named the 2007 WNBA Rookie of the Year. On March 12, 2008, the Sky announced that Overton had resigned his position of coach/general manager. Assistant coach Steven Key was named head coach/general manager.

With the second overall pick in the 2008 WNBA draft, the Sky selected Sylvia Fowles. In the 2008 season, the Sky would once again fail to make the playoffs, posting a 12–22 record, finishing 5th in the East. Fowles was injured for most of the season (she was, however, selected to play on the winning U.S. team at the 2008 Summer Olympics, where she average 13.4 points and 8.4 rebounds per game). In the 2009 WNBA draft, the Sky selected point guard Kristi Toliver with the third overall pick. Toliver had recently won the NCAA Women's Basketball Championship with the University of Maryland, where she had shot a game-tying three-point basket to send the game into overtime. In the 2009 season, the Sky contended for a playoff position, but finished with a record of 16-18 and lost a three-team tiebreaker to the Washington Mystics for the final playoff position.

Entering the 2010 season, the Sky moved to Allstate Arena in the suburb of Rosemont, Illinois. The team's roster underwent several changes, highlighted by the trading away of Candice Dupree and Kristi Toliver and the acquisition of Shameka Christon and Cathrine Kraayeveld. At one point during the season, they were at .500, just a few games back for the final playoff spot. However, they lost eight of their final ten games and were eliminated from playoff contention, finishing with a 14–20 record. Key resigned as GM and coach, and was replaced on October 28, 2010, by former LSU head coach Pokey Chatman.

In 2011, the Sky were led again by Fowles, who averaged a double-double (20 points and 10.2 rebounds per game). The Sky once again finished the season at 14-20 but were encouraged by going 10-7 at home. The Sky selected Shey Peddy with the 23rd pick and Sydney Carter with the 27th pick in the 2012 WNBA draft. Peddy and Carter were both eventually waived on May 14, 2012. The Sky began the 2012 season 7-1, but finished 14–20 for the third consecutive season. The Sky remained the only WNBA franchise to never make the playoffs.

The 2013 season was a turning point for the Sky. In the draft, they selected Elena Delle Donne with the second overall pick. Delle Donne became the first rookie to lead All-Star voting, averaging 18.1 points per game (fourth in the league) and leading the Sky to a 24-10 record and first place in the Eastern Conference. Delle Donne was named Rookie of the Year, Fowles was named Defensive Player of the Year and led the league in rebounds, and teammate Swin Cash received the Kim Perrot Sportsmanship Award. Chatman finished a close second for Coach of the Year, Delle Donne narrowly missed the MVP award, and Fowles and Delle Donne were named to the All-WNBA first and second teams. Reaching the playoffs for the first time, the Sky lost in the conference semifinals to the Indiana Fever.

In the 2014 season, the Sky posted an unimpressive 15-19 regular season record, but qualified for the playoffs as the 4th seed in the Eastern Conference. Guard Allie Quigley, who had grown up in nearby Joliet, Illinois, was named Sixth Woman of the Year. In the playoffs, they won two best-of-three series in the conference semifinals and finals to reach the WNBA Finals for the first time. In the best-of-five series, they were swept by the Phoenix Mercury in three games.

In February 2015, the Sky acquired Chicago native Cappie Pondexter from the New York Liberty in a straight-up trade for Epiphanny Prince. At the end of the 2015 season, they posted a 23-11 record and earned second place in the Eastern Conference. Delle Donne was named the league's Most Valuable Player, point guard Courtney Vandersloot led the league in assists, and Quigley was once again named Sixth Woman of the Year. Despite their improved regular season performance, the Sky fell to the Indiana Fever in the conference semifinals.

In the 2016 season, under the WNBA's new playoff format where teams were seeded regardless of conference, the Sky finished 4th in the league and returned to the playoffs, but lost 3-1 in the semifinals to the Los Angeles Sparks.

The Sky hired Amber Stocks as head coach and general manager, replacing Chatman, on December 6, 2016. During the 2016–17 offseason, in what was called one of the biggest trades in league history, the Sky traded Delle Donne to the Washington Mystics, receiving Kahleah Copper, Stefanie Dolson, and the Mystics' second overall pick in the 2017 WNBA draft. In the 2017 season, the Sky posted a 12–22 record and missed the playoffs for the first time in five seasons. In the ensuing 2018 WNBA draft, they selected Diamond DeShields and Gabby Williams in the first round. In the 2018 season, they posted a 13–21 record and missed the playoffs for a second consecutive season. On August 31, 2018, the Sky relieved Stocks as head coach and general manager. During these seasons, Courtney Vandersloot led the league in assists (setting a new assists-per-game record in 2017) and Allie Quigley won back-to-back Three-Point Contests at the All-Star Game.

In November 2018, the Sky hired James Wade as the team's new head coach and general manager. The Sky selected Katie Lou Samuelson in the first round of the 2019 WNBA draft and traded away Alaina Coates. The 2019 season would be a turnaround for the Sky, as they finished with a 20–14 record and entered the playoffs as a fifth seed. Wade received the WNBA Coach of the Year Award for the regular season, and Courtney Vandersloot exceeded her own assists-per-game record for the second straight season. Vandersloot, Allie Quigley, and Diamond DeShields were all named All-Stars, and DeShields won the All-Star Game Skills Challenge. In the playoffs, they defeated the Phoenix Mercury in the first round, but then lost to the Las Vegas Aces on the road on a buzzer-beater in the final seconds.

In the 2020 season, which was shortened and held in a bubble in Bradenton, Florida due to the COVID-19 pandemic, the Sky showed promise early in the season but battled injuries and ended the season with a sixth-seeded 12–10 record. They lost a first round single-elimination game to the Phoenix Mercury.

On February 1, 2021, the Sky announced the signing of free agent Candace Parker, a two-time WNBA MVP and WNBA Finals MVP. Parker, who had grown up in Naperville, Illinois and played her first 12 seasons in the league with the Los Angeles Sparks, stated that she wanted to return to her hometown team. The Sky had a volatile 2021 season, including a seven-game losing streak and a seven-game winning streak, which they ended with a 16-16 record. They entered the playoffs as the 6th seed, winning two single-elimination games and a semifinals series against the Connecticut Sun on their way to the Finals. On October 17, 2021, the Sky won their first WNBA Championship after defeating the Phoenix Mercury 3-1 in the 2021 WNBA Finals. Kahleah Copper was named the Finals MVP. A parade and rally to celebrate the team were held on October 19, 2021. Since the new playoff format was adopted, the Sky became the lowest-seeded team and first team without a winning record to win the championship.

In the offseason, longtime center Stefanie Dolson left the team in free agency and the Sky added former Finals MVP Emma Meesseman. The team's success continued in the 2022 season, posting a 26–10 record and earning the second seed. The Sky also appeared in the WNBA Commissioner's Cup, hosting the game but losing to the Las Vegas Aces. In the playoffs, the Sky defeated the New York Liberty in the first round, but lost in the semifinals to the Connecticut Sun.

The 2023 season marked a period of significant change for the Sky, with many longtime players departing in free agency, including Courtney Vandersloot, Allie Quigley, Azurá Stevens, and Candace Parker. Centered on Kahleah Copper and new roster additions including Marina Mabrey, Courtney Williams, Elizabeth Williams, and Alanna Smith, the team's record hovered around .500 for much of the season. In July, head coach James Wade announced his resignation to take an assistant coaching position with the NBA's Toronto Raptors. Assistant coach Emre Vatansever served as interim head coach for the remainder of the season. The team finished as the eighth-seed with a 18–22 record and lost in the first round of the playoffs to the eventual champion Las Vegas Aces.