Chicago Fall Tennis Classic 2021
WTA 500HardChicago, United States25 September – 3 October 2021Prize money: 565,530 USD79 matchesAltitude: 179 mCourt: Slow
Champion Garbine Muguruza · Final: 6-7(4) 6-0 7-6(3)
Final rounds
| Final | Garbine Muguruza vs Ons Jabeur | 3-6 6-3 6-0 |
| Semifinal | Ons Jabeur vs Elena Rybakina | 6-4 3-2 ret. |
| Semifinal | Garbine Muguruza vs Marketa Vondrousova | w/o |
| Quarterfinal | Elena Rybakina vs Belinda Bencic | 6-4 3-1 ret. |
| Quarterfinal | Ons Jabeur vs Elina Svitolina | 6-4 6-2 |
| Quarterfinal | Garbine Muguruza vs Mai Hontama | 6-3 6-2 |
| Quarterfinal | Marketa Vondrousova vs Danielle Collins | 6-7(4) 6-0 7-6(3) |
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