Stadium: Stadium Round: 29 Ground: Hardcourt outdoor
| WTA Chicago WD | 2021/08/20 17:50 | Minnen/Van Uytvanck v Hozumi/Plipuech | 7-5,3-6,4-10 |
| WTA Chicago WD | 2021/08/19 16:00 | Hozumi/Plipuech v Galfi/Rakhimova | 5-7,6-4,11-9 |
| WTA Chicago WD | 2021/08/17 23:15 | Errani/Kalashnikova v Hozumi/Plipuech | 6-0,3-6,6-10 |
| WTA Chicago WD | 2021/08/20 16:00 | Burel/Mladenovic v Barthel/Hsieh | 4-6,7-6,10-12 |
| WTA Chicago WD | 2021/08/19 16:00 | Barthel/Hsieh v Gorgodze/Raina | 7-5,6-2 |
| WTA Chicago WD | 2021/08/17 23:35 | Kung/Marozava v Barthel/Hsieh | 6-7,3-6 |