The 2016 Chicago Sky season was the franchise's 11th season in the Women's National Basketball Association (WNBA). The season began on May 14th, at home against the Connecticut Sun.

The Sky began the season with a win, but could not sustain that momentum and lost their next four games. They finished May with a win and extended their streak with three wins to start June. However, they only won one of their final five games in June to finish the first two months of the season with a 6–9 record. The Sky split a home and away matchup with Washington to begin July and lost two of their next three. The won three of their last four to end the month with a 5–4 record. The Sky came out of the Olympic break strongly, winning both their games in August and their first two in September. They lost their next two, before winning three in a row. They could not overcome Seattle on the final day of the season and finished with an 18–16 regular season record.

Their record was good enough for second place in the Eastern Conference and the fourth overall seed in the 2016 WNBA Playoffs. They earned a bye into the Second Round where they defeated sixth-seed Atlanta 108–98 and advanced to the Semfinals. There they matched-up against the Los Angeles Sparks. The Sparks defeated the Sky 3 games to 1 and would go on to finish as WNBA Champions.

Round	Pick	Player	Nationality	School/team/country
1	10	Imani Boyette	United States	Texas
3	34	Jordan Jones	United States	Texas A&M

2016 Chicago Sky Roster
Players	Coaches
Pos. # Nat. Name Ht. Wt. From C 34 Boyette, Imani 6 ft 7 in (2.01 m) 195 lb (88 kg) (1994-10-11)October 11, 1994 (aged 21) Texas F 51 Breland, Jessica 6 ft 3 in (1.91 m) 170 lb (77 kg) (1988-02-23)February 23, 1988 (aged 28) North Carolina F/C 41 de Souza, Érika 6 ft 5 in (1.96 m) 190 lb (86 kg) (1982-03-03)March 3, 1982 (aged 34) Brazil G/F 11 Delle Donne, Elena 6 ft 5 in (1.96 m) 188 lb (85 kg) (1989-09-05)September 5, 1989 (aged 26) Delaware C 8 dos Santos, Clarissa 6 ft 1 in (1.85 m) 196 lb (89 kg) (1988-03-10)March 10, 1988 (aged 28) Brazil G 21 Faulkner, Jamierra 5 ft 6 in (1.68 m) 141 lb (64 kg) (1992-03-09)March 9, 1992 (aged 24) Southern Miss G/F 44 Laney, Betnijah 6 ft 0 in (1.83 m) 160 lb (73 kg) (1993-10-29)October 29, 1993 (aged 22) Rutgers F 32 Parker, Cheyenne 6 ft 4 in (1.93 m) 190 lb (86 kg) (1992-08-22)August 22, 1992 (aged 23) Middle Tennessee G 23 Pondexter, Cappie 5 ft 9 in (1.75 m) 160 lb (73 kg) (1983-01-07)January 7, 1983 (aged 33) Rutgers G 14 Quigley, Allie 5 ft 10 in (1.78 m) 140 lb (64 kg) (1986-06-20)June 20, 1986 (aged 29) DePaul G 22 Vandersloot, Courtney 5 ft 8 in (1.73 m) 145 lb (66 kg) (1989-02-08)February 8, 1989 (aged 27) Gonzaga F 1 Young, Tamera 6 ft 2 in (1.88 m) 170 lb (77 kg) (1986-10-30)October 30, 1986 (aged 29) James Madison	Head coach Pokey Chatman (LSU) Assistant coaches Jonah Herscu (Lake Forest College) Christie Sides (Louisiana Tech) Athletic trainer Heidi Wlezien Strength and conditioning coach Ann Crosby (Western Michigan) Legend (C) Team captain (FA) Free agent (IN) Inactive (S) Suspended Injured Notes Age of player is as of the start of the regular season.

Notes

# – Playoff seed

e – Eliminated from playoffs

The Sky's 18–16 regular season record was good for second in the Eastern Conference and fourth overall in the WNBA. This standing led to Chicago being seeded fourth and being granted an automatic bye from the first of two single elimination rounds. In the second single elimination round, the Sky drew sixth-seeded Atlanta, defeating the Dream 108–98 and advancing to the best-of-five semifinal round. The Sky fell to second-seeded Los Angeles in the semifinals, losing in four games.

Note: Teams re-seeded after second round and semi-finals.