Chicago Sky
American WNBA women's professional basketball team
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| 2025 | Drafted Ajša Sivka (10th pick), Hailey Van Lith (11th pick), Maddy Westbeld (16th pick), and Aicha Coulibaly (22nd pick). |
| 2025 | Courtney Paris, Tanisha Wright, and Rena Wakama become assistant coaches for the Chicago Sky. |
| 2025 | The Sky traded their third overall pick in the 2025 WNBA draft to the Mystics in exchange for Ariel Atkins. Vandersloot also returned to the team as a free agent. |
| 2025 | Courtney Paris and Tanisha Wright join the Chicago Sky coaching staff as assistant coaches. |
| 2024 | Angel Reese becomes a Peak Performer in Rebounds and is named to the All-Rookie Team along with Kamilla Cardoso. |
| 2024 | Angel Reese selected as Chicago Sky All-Star representative. |
| 2024 | Achieved highest attendance to date with 8,757 fans per game, ranking 8th in the league and recording 11 sellout games. |
| 2024 | Crystal Robinson, Sydney Johnson, and Tamera Young join the Chicago Sky coaching staff as assistant coaches. |
| 2024 | Jeff Pagliocca becomes the current General Manager of the Chicago Sky |
| 2024 | Teresa Weatherspoon was fired after the season. |
| 2024 | The Sky acquired the third and seventh picks in the 2024 WNBA draft, selecting Kamilla Cardoso and Angel Reese. |
| 2024 | Marina Mabrey was traded to the Sun during the Olympic break. |
| November 3 2024 | Tyler Marsh becomes head coach, succeeding Teresa Weatherspoon |
| August 28 2024 | Skye the Lioness made her debut game appearance at the Wintrust arena, with the Legacy mascot The Sky Guy still supporting the team through the 2024 season. |
| August 26 2024 | The team introduced Skye the Lioness as their new mascot, created under the direction of CMO Tania Haladner and designed by Tom Sapp and Real Characters Inc. |
| 2023 | Drafted Kayana Traylor (23rd pick) and Kseniya Malashka (35th pick). |
| 2023 | Yoann Cabioc'h briefly serves as an assistant coach, while Emre Vatansever and Tonya Edwards conclude their tenure with the Chicago Sky. |
| 2023 | Kahleah Copper selected as Chicago Sky All-Star representative. |
| 2023 | Maintained strong attendance with 7,242 fans per game, ranking 6th in the league. |
| 2023 | Michael J. Alter and Nadia Rawlinson became the owners of the Chicago Sky, taking over ownership of the WNBA team. |
| 2023 | Kahleah Copper ends her tenure with the Chicago Sky, moving to the Phoenix Mercury. |
| October 12 2023 | Teresa Weatherspoon is appointed as head coach of the Chicago Sky |
| September 21 2023 | Emre Vatansever's brief interim coaching period ends |
| July 1 2023 | James Wade steps down, and Emre Vatansever becomes interim head coach |
| 2022 | No draft picks for the Chicago Sky this year. |
| 2022 | James Wade wins Basketball Executive of the Year. Candace Parker is named to the All-WNBA First Team. |
| 2022 | Four Chicago Sky players selected as All-Stars: Kahleah Copper, Emma Meesseman, Candace Parker, and Courtney Vandersloot. |
| 2022 | Attendance began to recover, averaging 7,180 fans per game and ranking 4th in the league. |
| 2022 | Ann Wauters becomes an assistant coach for the Chicago Sky. |
| 2022 | Allie Quigley and Candace Parker conclude their time with the Chicago Sky. |
| 2022 | Chicago Sky finished 2nd in the WNBA with a 26-10 record. James Wade was named Executive of the Year. The team won the First Round playoff series against New York but lost in the Semifinals to Connecticut. |
| 2022 | Posted a strong 26-10 record and earned the second seed in the playoffs. Appeared in the WNBA Commissioner's Cup, hosting but losing to the Las Vegas Aces. |
| 2021 | Drafted Shyla Heal (8th pick) and Natasha Mack (16th pick). |
| 2021 | Three Chicago Sky players selected as All-Stars: Kahleah Copper, Candace Parker, and Courtney Vandersloot. |
| 2021 | Experienced significantly reduced attendance, with an average of 3,187 fans, ranking 2nd lowest in the league. |
| 2021 | Tonya Edwards joins the Chicago Sky coaching staff as an assistant coach. |
| October 19 2021 | Held a parade and rally to celebrate their first WNBA Championship in Chicago. |
| October 17 2021 | Won their first WNBA Championship by defeating the Phoenix Mercury 3-1 in the WNBA Finals. Kahleah Copper was named Finals MVP. |
| February 1 2021 | Signed free agent Candace Parker, a two-time WNBA MVP, who returned to her hometown team after 12 seasons with the Los Angeles Sparks. |
| 2020 | Drafted Ruthy Hebard (8th pick), Japreece Dean (30th pick), and Kiah Gillespie (32nd pick). |
| 2020 | Astou Ndour (from Spain) and Stefanie Dolson represented the Chicago Sky as Olympians in the 2020 Summer Olympics. |
| 2020 | Olaf Lange and Emre Vatansever join the Chicago Sky coaching staff as assistant coaches. |
| 2020 | During the COVID-19 pandemic, the Sky played a shortened season in a bubble in Bradenton, Florida, finishing with a 12-10 record as the sixth seed. |
| 2019 | Drafted Katie Lou Samuelson (4th pick), Chloe Jackson (15th pick), and María Conde (27th pick). |
| 2019 | James Wade wins Coach of the Year. Courtney Vandersloot is named to the All-WNBA First Team and continues as a Peak Performer in Assists. Diamond DeShields is named to the All-WNBA Second Team. |
| 2019 | Three Chicago Sky players selected as All-Stars: Diamond DeShields, Allie Quigley, and Courtney Vandersloot. |
| 2019 | Bridget Pettis becomes an assistant coach for the Chicago Sky, and Carla Morrow concludes her coaching tenure. |
| 2019 | James Wade takes over as General Manager of the Chicago Sky |
| 2019 | Chicago Sky completes a successful season, finishing with a 20-14 record and entering the playoffs as a fifth seed. James Wade was awarded WNBA Coach of the Year. |
| 2019 | Start of the team's second period of success, leading up to their championship run. |
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