Chicago 3 WTA 2021 (USA)
(565,530 $, hard, women)
| Start | Round | S | 1 | 2 | 3 | 4 | 5 | H | A | ||
| 26.09. 20:05 | Q-R16 | Flipkens (5) | 2 | 6 | 62 | 6 | 2.87 | 1.39 | info | ||
| Marino (9) | 1 | 4 | 7 | 4 | |||||||
| 26.09. 18:30 | Q-R16 | Haddad Maia (2) | 2 | 6 | 6 | 1.30 | 3.37 | info | |||
| Kawa (10) | 0 | 4 | 2 | ||||||||
| 26.09. 18:25 | Q-R16 | Baindl (6) | 2 | 6 | 64 | 6 | 1.81 | 1.93 | info | ||
| Hon (16) | 1 | 2 | 7 | 3 | |||||||
| 26.09. 18:20 | Q-R16 | Hontama (14) | 2 | 7 | 7 | 2.97 | 1.37 | info | |||
| Dart (8) | 0 | 5 | 63 | ||||||||
| 26.09. 17:15 | Q-R16 | Frech (1) | 2 | 6 | 6 | 1.33 | 3.18 | info | |||
| Mattek | 0 | 2 | 2 | ||||||||
| 26.09. 17:15 | Q-R16 | Inglis (3) | 2 | 62 | 6 | 7 | 2.36 | 1.56 | info | ||
| Muhammad (12) | 1 | 7 | 4 | 63 | |||||||
| 26.09. 17:10 | Q-R16 | Cabrera (11) | 2 | 6 | 6 | 2.09 | 1.71 | info | |||
| Govortsova (4) | 0 | 4 | 0 | ||||||||
| 26.09. 17:10 | Q-R16 | Kalinskaya (7) | 2 | 6 | 6 | 1.62 | 2.23 | info | |||
| Bolkvadze (13) | 0 | 2 | 1 | ||||||||
| 25.09. 23:40 | Q-1R | Haddad Maia (2) | 2 | 6 | 6 | 1.05 | 8.75 | info | |||
| Kichenok | 0 | 1 | 1 | ||||||||
| 25.09. 22:35 | Q-1R | Dart (8) | 2 | 7 | 6 | 1.14 | 5.38 | info | |||
| Gleason | 0 | 5 | 2 | ||||||||
| 25.09. 22:30 | Q-1R | Hon (16) | 2 | 6 | 63 | 6 | 1.24 | 3.91 | info | ||
| Eikeri | 1 | 1 | 7 | 4 | |||||||
| 25.09. 22:15 | Q-1R | Flipkens (5) | 2 | 6 | 6 | 1.01 | 14.88 | info | |||
| Beckham | 0 | 0 | 0 | ||||||||
| 25.09. 21:35 | Q-1R | Marino (9) | 2 | 3 | 6 | 6 | 1.14 | 5.48 | info | ||
| Harrison | 1 | 6 | 3 | 2 | |||||||
| 25.09. 21:05 | Q-1R | Hontama (14) | 2 | 6 | 7 | 1.53 | 2.41 | info | |||
| Bektas | 0 | 2 | 5 | ||||||||
| 25.09. 20:55 | Q-1R | Baindl (6) | 2 | 6 | 6 | 1.12 | 5.35 | info | |||
| Melichar-Martinez | 0 | 4 | 4 | ||||||||
| 25.09. 20:30 | Q-1R | Kawa (10) | 2 | 6 | 6 | 1.11 | 6.31 | info | |||
| Neel | 0 | 3 | 4 | ||||||||
| 25.09. 20:30 | Q-1R | Govortsova (4) | 2 | 6 | 6 | 1.01 | 20.58 | info | |||
| Osabuohien | 0 | 3 | 2 | ||||||||
| 25.09. 19:30 | Q-1R | Bolkvadze (13) | 2 | 6 | 6 | 1.17 | 4.72 | info | |||
| Gatica | 0 | 2 | 1 | ||||||||
| 25.09. 19:10 | Q-1R | Mattek | 2 | 6 | 6 | 1.44 | 2.69 | info | |||
| Parks (15) | 0 | 3 | 4 | ||||||||
| 25.09. 18:40 | Q-1R | Muhammad (12) | 2 | 6 | 6 | 1.36 | 3.02 | info | |||
| Shibahara | 0 | 0 | 4 | ||||||||
| 25.09. 17:10 | Q-1R | Frech (1) | 2 | 66 | 7 | 7 | 1.18 | 4.50 | info | ||
| Glatch | 1 | 7 | 65 | 5 | |||||||
| 25.09. 17:10 | Q-1R | Inglis (3) | 2 | 6 | 6 | 1.10 | 6.08 | info | |||
| Lohoff | 0 | 2 | 2 | ||||||||
| 25.09. 17:10 | Q-1R | Cabrera (11) | 2 | 6 | 64 | 6 | 1.39 | 2.82 | info | ||
| Moore | 1 | 1 | 7 | 2 | |||||||
| 25.09. 17:10 | Q-1R | Kalinskaya (7) | 2 | 7 | 6 | 1.12 | 5.46 | info | |||
| Osuigwe | 0 | 67 | 3 | 

1. round
Frech [1]
Parks [15]
Haddad Maia [2]
Neel [WC]
Kawa [10]
Inglis [3]
Lohoff [WC]
Muhammad [12]
Govortsova [4]
Osabuohien [WC]
Cabrera [11]
Flipkens [5]
Beckham [WC]
Marino [9]
Baindl [6]
Hon [16]
Kalinskaya [7]
Bolkvadze [13]
Dart [8]
Hontama [14]
round of 16
Frech [1]
Haddad Maia [2]
Kawa [10]
Inglis [3]
Muhammad [12]
Govortsova [4]
Cabrera [11]
Flipkens [5]
Marino [9]
Baindl [6]
Hon [16]
Kalinskaya [7]
Bolkvadze [13]
Dart [8]
Hontama [14]
Frech [1]
Haddad Maia [2]
Inglis [3]
Cabrera [11]
Flipkens [5]
Baindl [6]
Kalinskaya [7]
Hontama [14]
- Tournament details
| Round | Prize money | Ranking points | 
| 1. round | 3,334 $ | 1 | 
| 2. round | 4,100 $ | 30 | 
| round of 16 | 6,478 $ | 55 | 
| quarterfinal | 12,675 $ | 100 | 
| semifinal | 26,745 $ | 185 | 
| final | 50,130 $ | 305 | 
| winner | 68,570 $ | 470 | 
- This week's tournaments
| Main tournaments | ||||
| Paris | 4 | |||
| Athens | 24 | |||
| Metz | 25 | |||
| Masters Cup WTA | 24 | |||
| Chennai WTA | 4 | |||
| Hong Kong WTA | 3 | |||
| Jiujiang | 3 | |||
| Lower level tournaments | ||||
| Bratislava challenger | 3 | |||
| Seoul challenger | 3 | |||
| Charlottesville challenger | 3 | |||
| Lima challenger | 2 | |||
| Monastir challenger | 3 | |||
| UTR Pro Tennis Series 3 | 229 | |||
| UTR Pro Tennis Series 5 | 57 | |||
| Cali | 2 | |||
| Irapuato ITF | 6 | |||
| Glasgow 2 ITF | 3 | |||
| Toronto ITF | 3 | |||
| Brisbane 4 ITF | 3 | |||
| Istanbul ITF | 3 | |||
| Loule ITF | 3 | |||
| Makinohara ITF | 3 | |||
| Neuquén ITF | 4 | |||
| Villeneuve d'Ascq ITF | 2 | |||
| UTR Pro Tennis Series 5 | 36 | |||
| Bol 15 ITF | 2 | |||
| Malta ITF | 3 | |||
| Monastir 5 ITF | 3 | |||
| Sharm El Sheikh 19 ITF | 3 | |||
| Solarino 3 ITF | 3 | |||
| Sumter 2 ITF | 3 | |||
| Taby ITF | 3 | |||
| Tashkent 4 ITF | 3 | |||
| UTR Pro Match Series | 112 | |||
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