WTA - Chicago 2 - 1R start

First round commenced in Chicago.

2021 Chicago Fall Tennis Classic - a WTA 500 tournament, on Hard, in Chicago, Illinois, USA, 27 September - 3 October 2021.

No defending champion:

This is a new tournament on the WTA calendar.

First round results:

- Qualifier Kateryna Kozlova defeated Marta Kostyuk 6-7(2) 6-3 6-0

- Jessica Pegula (9) defeated qualifier Magdalena Frech 6-3 6-0

- Andrea Petkovic defeated lucky loser Olga Govortsova 6-2 6-2

- Hsieh Su-wei defeated wildcard Kim Clijsters 6-3 5-7 6-3

- Qualifier Maddison Inglis defeated wildcard Caroline Dolehide 4-6 6-2 6-4

- Veronika Kudermetova (12) defeated qualifier Anna Kalinskaya 7-6(8) 4-6 6-2

- Aliaksandra Sasnovich defeated Madison Keys 6-4 2-0 (retired)

- Dayana Yastremska defeated Alizé Cornet 7-5 6-1

- Misaki Doi defeated Marie Bouzkova 6-3 6-7(4) 6-3

- Danielle Collins (10) defeated qualifier Kirsten Flipkens 6-4 6-2

- Marketa Vondrousova defeated Ajla Tomljanovic 6-2 6-1

- Shelby Rogers defeated qualifier Lizette Cabrera 6-2 6-1

- Qualifier Mai Hontama defeated Caroline Garcia 6-3 6-0

- Ann Li defeated Donna Vekic 6-3 6-1