2023 Chicago Challenger – Singles

Viktoriya Tomova won the title, defeating Claire Liu in the final, 6–1, 6–4.

Clara Tauson was the defending champion from 2021, when the event was last held, but chose to compete in Cleveland instead.

Seeds
• # Arantxa Rus (first round)

• # Elina Avanesyan (first round)

• #🇨🇴 Camila Osorio (first round)

• #🇫🇷 Alizé Cornet (second round)

• #🇮🇹 Lucia Bronzetti (semifinals)

• #🇪🇸 Rebeka Masarova (quarterfinals)

• #🇫🇷 Diane Parry (first round)

• # Kamilla Rakhimova (quarterfinals)

Seeds
• # 🇦🇺 Storm Hunter (qualified)

• # Irina Khromacheva (qualified)

• # 🇯🇵 Eri Hozumi (qualifying competition)

• # 🇳🇴 Ulrikke Eikeri (qualified)

Qualifiers
• # 🇦🇺 Storm Hunter

• # Irina Khromacheva

• # 🇺🇸 Quinn Gleason

• # 🇳🇴 Ulrikke Eikeri

Lucky loser
• # 🇺🇸 Adesuwa Osabuohien