The 2021 Chicago Fall Tennis Classic was a WTA tournament organised for female professional tennis players on outdoor hard courts due to the cancellation of the Asian tournaments because of the ongoing COVID-19 pandemic. It was the 1st edition of the event and took place at XS Tennis and Education Foundation in Chicago, United States from 27 September to 3 October 2021.
The following players received wildcard<nowiki>s</nowiki> into the singles main draw:
The following players received entry from the qualifying draw:
The following players received entry as lucky losers:
The following pairs received wildcard<nowiki>s</nowiki> into the doubles main draw:
The following pair received entry into the doubles main draw using a protected ranking: