After a banner 2015 season, the team expected to do well again. The club ended the regular season at third place, and played the play-off semi-final at Boyds, Maryland against Washington Spirit on September 30, falling 2–1 and did not reach the championship match.

This season the Red Stars returned to Toyota Park for its home games, where it last played on a regular basis during its 2010 season in Women's Professional Soccer league. In 2016 season, the Red Stars honored the retirements of several long time members; Michelle Lomnicki,Julianne Sitch, Jackie Santacaterina, and Lori Chalupny. The jersey number 17 worn by Chalupny, a 3 year captain, an Olympic gold medalist and a FIFA world champion was retired in honor of her accomplishments.

After the season, National team coach Jill Ellis called up 5 Red Stars, Christen Press, Alyssa Naeher, Arin Gilliland, Casey Short and Danielle Colaprico to national team training camp. On October 7, NWSL announced the voting results of NWSL Best XI and NWSL Second XI; while Press and Gilliland were named to Best XI; 5 Red Stars, Naeher, Julie Johnston, Short, Colaprico and Vanessa DiBernardo were named to NWSL Second XI.

In the off-season 8 Red Stars, the highest number in team history, went to play in Australia on loan to W-League sides; Samantha Johnson to Melbourne Victory; Jen Hoy and Arin Gilliland to Newcastle Jets; Alyssa Mautz and Vannesa DiBernardo to Perth Glory; and Katie Naughton, Danielle Colaprico and Sofia Huerta to Adelaide United. Chicago Red Stars loaned the largest number of players to W-League, 4 more than any other NWSL club.

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