2023 Chicago Challenger – Singles
| Singles | |
|---|---|
| 2023 Chicago Challenger | |
| Champion | Viktoriya Tomova |
| Runner-up | Claire Liu |
| Score | 6–1, 6–4 |
| Draw | 32 |
| Seeds | 8 |
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.