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.[1]
See main article: article and 2021 Chicago Fall Tennis Classic – Singles.
Garbiñe Muguruza def. 
Ons Jabeur, 3–6, 6–3, 6–0See main article: article and 2021 Chicago Fall Tennis Classic – Doubles.
Květa Peschke / Andrea Petkovic def. 
Caroline Dolehide / CoCo Vandeweghe, 6–3, 6–1The following players received wildcards into the singles main draw:
The following players received entry from the qualifying draw:
The following players received entry as lucky losers:
Sorana Cîrstea → replaced by Hsieh Su-wei Coco Gauff → replaced by Ann Li
Daria Kasatkina → replaced by Amanda Anisimova Sofia Kenin → replaced by Andrea Petkovic
Johanna Konta → replaced by Madison Brengle Petra Kvitová → replaced by 
Misaki Doi
Camila Osorio Harriet Dart Karolína Plíšková → replaced by 
Kaia Kanepi Alison Riske → replaced by 
Jasmine Paolini
Aryna Sabalenka → replaced by Sloane Stephens Olga Govortsova Elena Vesnina → replaced by Marie BouzkováThe following pairs received wildcards into the doubles main draw:
The following pair received entry into the doubles main draw using a protected ranking:
Lyudmyla Kichenok / Jeļena Ostapenko → replaced by 
Magdalena Fręch / Katarzyna Kawa Marta Kostyuk / Dayana Yastremska → replaced by Lyudmyla Kichenok / Marta Kostyuk Jamie Loeb / 
Tereza Mihalíková → replaced by Harriet Dart / Tereza Mihalíková
Kazakhstan
Belgium
Canada
Mexico