Chicago Challenger Tennis Draws 2021, Seeds, 2021 Chicago Challenger Winners, Results

Singles

Seeds

1. Belgium Alison Van Uytvanck (First round)
2. Montenegro Danka Kovinić (First round)
3. United States Ann Li
4. Ukraine Anhelina Kalinina (First round)
5. United States Madison Brengle (First round)
6. United States Amanda Anisimova (Second round, retired)
7. Croatia Ana Konjuh (First round)
8. Russia Varvara Gracheva (Second round)

Denmark Clara Tauson def. United Kingdom Emma Raducanu, 6–1, 2–6, 6–4

Doubles

Seeds

1. United States Kaitlyn Christian / Netherlands Lesley Pattinama Kerkhove (First round)
2. Germany Julia Lohoff / Czech Republic Renata Voráčová (First round)
3. United Kingdom Harriet Dart / United States Caroline Dolehide (First round)
4. Italy Sara Errani / Georgia (country) Oksana Kalashnikova (First round)

Japan Eri Hozumi / Thailand Peangtarn Plipuech def. Germany Mona Barthel / Chinese Taipei Hsieh Yu-chieh, 7–5, 6–2