WTA - Chicago 2 - 2R complete

Second round completed and round of sixteen set 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.

Second round results:

- Elina Svitolina (1) defeated Amanda Anisimova 6-4 6-3

- Elena-Gabriela Ruse defeated qualifier Kateryna Kozlova 7-5 6-2

- Jessica Pegula (9) defeated Andrea Petkovic 6-2 7-5

- Belinda Bencic (3) defeated qualifier Maddison Inglis 5-7 6-1 6-0

- Tereza Martincova defeated Tamara Zidansek (13) 6-2 7-5

- Veronika Kudermetova (12) defeated lucky loser Harriet Dart 6-3 6-4

- Elena Rybakina (5) defeated Aliaksandra Sasnovich 6-4 6-4

- Jil Teichmann (16) defeated Magda Linette 6-2 6-4

- Marketa Vondrousova defeated Anastasia Pavlyuchenkova (4) 6-3 6-2

- Shelby Rogers defeated Bianca Andreescu (8) 6-4 7-5

- Qualifier Mai Hontama received a walkover from Anett Kontaveit (11)

- Victoria Azarenka (14) defeated wildcard Hailey Baptiste 6-2 4-6 6-3

Round of sixteen match ups 

Elina Svitolina (1) v Elena-Gabriela Ruse

Jessica Pegula (9) v Ons Jabeur (6)

Belinda Bencic (3) v Tereza Martincova 

Veronika Kudermetova (12) v Elena Rybakina (5)

Elise Mertens (7) v Danielle Collins (10)

Jil Teichmann (16) v Marketa Vondrousova 

Shelby Rogers v qualifier Mai Hontama

Victoria Azarenka (14) v Garbiñe Muguruza (2)