# 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)

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Finals

| Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final |
| 5 | Lucia Bronzetti | 6$^3$ | 6 | 1 | | | |
| | Viktoriya Tomova | 7$^7$ | 3 | 6 | | | |
| | Viktoriya Tomova | 7$^7$ | 3 | 6 | Viktoriya Tomova | 6 | 6 |
| | | | | | Claire Liu | 1 | 4 |
| | Claire Liu | 2 | | | Claire Liu | 1 | 4 |
| | Cristina Bucșa | 1$^r$ | | | | | |

### Top half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 1 | A Rus | 6$^5$ | 3 | | | | | | | | | | | | | | | | |
| | K Baindl | 7$^7$ | 6 | | | K Baindl | 7$^7$ | 6 | | | | | | | | | | | |
| Q | U Eikeri | 6 | 1 | 1 | | S Chang | 6$^1$ | 2 | | | | | | | | | | | |
| | S Chang | 3 | 6 | 6 | | | | | | | K Baindl | | | | | | | | |
| | J Burrage | 7 | 3 | 6$^4$ | | | | | | 5 | L Bronzetti | w/o | | | | | | | |
| Q | Q Gleason | 5 | 6 | 7$^7$ | Q | Q Gleason | 6$^2$ | 2 | | | | | | | | | | | |
| | R Marino | 6$^4$ | 1 | | 5 | L Bronzetti | 7$^7$ | 6 | | | | | | | | | | | |
| 5 | L Bronzetti | 7$^7$ | 6 | | | | | | | | | | | | 5 | L Bronzetti | 6$^3$ | 6 | 1 |
| 4 | A Cornet | 6 | 7 | | | | | | | | | | | | | V Tomova | 7$^7$ | 3 | 6 |
| WC | W Osuigwe | 0 | 5 | | 4 | A Cornet | 4 | 6$^5$ | | | | | | | | | | | |
| | V Tomova | 6 | 6 | | | V Tomova | 6 | 7$^7$ | | | | | | | | | | | |
| LL | A Osabuohien | 0 | 0 | | | | | | | | V Tomova | 7 | 4 | 6 | | | | | |
| | R Anderson | 7$^7$ | 4 | 4 | | | | | | 8 | K Rakhimova | 5 | 6 | 3 | | | | | |
| WC | C Ngounoue | 6$^4$ | 6 | 6 | WC | C Ngounoue | 0 | 7 | 1 | | | | | | | | | | |
| | K Kawa | 1 | 2 | | 8 | K Rakhimova | 6 | 5 | 6 | | | | | | | | | | |
| 8 | K Rakhimova | 6 | 6 | | | | | | | | | | | | | | | | |

### Bottom half

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals |
| 6 | R Masarova | 6 | 6 | | | | | | | | | | | | |
| | P Udvardy | 2 | 4 | 6 | R Masarova | 7$^7$ | 6 | | | | | | | | |
| Q | I Khromacheva | 1 | 0 | | M Brengle | 6$^4$ | 3 | | | | | | | | |
| | M Brengle | 6 | 6 | | | | | | 6 | R Masarova | 5 | 7 | 6$^3$ | | |
| | I Fetecău | 1 | 4 | | | | | | | C Liu | 7 | 5 | 7$^7$ | | |
| | C Liu | 6 | 6 | | C Liu | 6 | 6 | | | | | | | | |
| Q | S Hunter | 6 | 6 | Q | S Hunter | 0 | 4 | | | | | | | | |
| 3 | C Osorio | 2 | 4 | | | | | | | | | | | C Liu | 2 |
| 7 | D Parry | 1 | 4 | | | | | | | | | | | C Bucșa | 1$^r$ |
| | R Peterson | 6 | 6 | | R Peterson | 6 | 1 | 6 | | | | | | | |
| | K Kanepi | 6 | 6 | | K Kanepi | 4 | 6 | 3 | | | | | | | |
| PR | M Betova | 2 | 1 | | | | | | | R Peterson | 6 | 4 | 4 | | |
| WC | K Allen | 0 | 2 | | | | | | | C Bucșa | 3 | 6 | 6 | | |
| | C Bucșa | 6 | 6 | | C Bucșa | w/o | | | | | | | | | |
| WC | V Lepchenko | 6 | 6 | WC | V Lepchenko | | | | | | | | | | |
| 2 | E Avanesyan | 2 | 4 | | | | | | | | | | | | |

## Qualifying
### 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

### Qualifying draw
#### First qualifier

| Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 1 | Storm Hunter | 6 | 6 | |
| WC | Adesuwa Osabuohien | 0 | 2 | |

#### Second qualifier

| Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 2 | Irina Khromacheva | 6 | 6 | |
| WC | Ashley Matz | 2 | 2 | |

#### Third qualifier

| Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 3 | Eri Hozumi | 2 | 2 | |
| | Quinn Gleason | 6 | 6 | |

#### Fourth qualifier

| Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 4 | Ulrikke Eikeri | 6 | 6 | |
| WC | Nia Cooper | 1 | 0 | |