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.
Champions
Singles
Garbiñe Muguruza def. Ons Jabeur, 3–6, 6–3, 6–0
Doubles
Květa Peschke / Andrea Petkovic def. Caroline Dolehide / CoCo Vandeweghe, 6–3, 6–1
Singles main draw entrants
Seeds
Rankings are as of September 20, 2021.
Other entrants
The following players received wildcards into the singles main draw: Hailey Baptiste Kim Clijsters Caroline Dolehide CoCo Vandeweghe
The following players received entry from the qualifying draw: Lizette Cabrera Kirsten Flipkens Magdalena Fręch Beatriz Haddad Maia Mai Hontama Maddison Inglis Anna Kalinskaya Kateryna Kozlova
The following players received entry as lucky losers: Harriet Dart Olga Govortsova
Withdrawals
Before the tournament
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
Petra Martić → replaced by María Camila Osorio Serrano
Jeļena Ostapenko → replaced by Harriet Dart
Karolína Plíšková → replaced by Kaia Kanepi
Alison Riske → replaced by Jasmine Paolini
Aryna Sabalenka → replaced by Sloane Stephens
Maria Sakkari → replaced by Olga Govortsova
Elena Vesnina → replaced by Marie Bouzková
During the tournament
Victoria Azarenka
Anett Kontaveit
Markéta Vondroušová
Doubles main draw entrants
Seeds
1 Rankings as of September 20, 2021.
Other entrants
The following pairs received wildcards into the doubles main draw: Hailey Baptiste / Whitney Osuigwe Kim Clijsters / Kirsten Flipkens Caroline Dolehide / CoCo Vandeweghe
The following pair received entry into the doubles main draw using a protected ranking: Ingrid Neel / Anastasia Rodionova
Withdrawals
Before the tournament
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