# 2023 Chicago Men's Challenger – Singles

Roman Safiullin was the defending champion but chose not to defend his title.
Alex Michelsen won the title after defeating Yuta Shimizu 7–5, 6–2 in the final.

## Seeds

* James Duckworth (withdrew)
* Aleksandar Kovacevic (second round)
* Emilio Gómez (first round)
* Shang Juncheng (semifinals)
* Altuğ Çelikbilek (first round)
* Alexis Galarneau (first round)
* Giovanni Mpetshi Perricard (semifinals)
* Steve Johnson (first round)

## 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 |
| | Yuta Shimizu | 7$^7$ | 7$^7$ | | | | |
| 7 | Giovanni Mpetshi Perricard | 6$^5$ | 6$^5$ | | | | |
| 7 | Giovanni Mpetshi Perricard | 6$^5$ | 6$^5$ | | Yuta Shimizu | 5 | 2 |
| | | | | | Alex Michelsen | 7 | 6 |
| 4 | Shang Juncheng | 6 | 5 | 3 | Alex Michelsen | 7 | 6 |
| | Alex Michelsen | 4 | 7 | 6 | | | |

### 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 |
| LL | E Zhu | 2 | 4 | | | | | | | | | | | | | | | |
| | Y Shimizu | 6 | 6 | | | Y Shimizu | 6 | 5 | 6 | | | | | | | | | |
| Q | Y-s Chung | 6 | 6 | | Q | Y-s Chung | 3 | 7 | 3 | | | | | | | | | |
| | A Shelbayh | 3 | 4 | | | | | | | | Y Shimizu | 6 | 7 | | | | | |
| Alt | J Jung | 7 | 6 | | | | | | | Alt | J Jung | 2 | 5 | | | | | |
| Q | B Tomic | 5 | 3 | | Alt | J Jung | 3 | 7$^7$ | 6 | | | | | | | | | |
| | N Basavareddy | 6 | 2 | 6 | | N Basavareddy | 6 | 6$^5$ | 2 | | | | | | | | | |
| 8 | S Johnson | 3 | 6 | 4 | | | | | | | | | | | | Y Shimizu | 7$^7$ | 7$^7$ |
| 3 | E Gómez | 2 | 1 | | | | | | | | | | | | 7 | G Mpetshi Perricard | 6$^5$ | 6$^5$ |
| Alt | Y Uchiyama | 6 | 6 | | Alt | Y Uchiyama | 6 | 2 | 2 | | | | | | | | | |
| | M Lajal | 6 | 6 | | | M Lajal | 4 | 6 | 6 | | | | | | | | | |
| Q | O Jasika | 1 | 4 | | | | | | | | M Lajal | 6$^3$ | 6 | 6$^6$ | | | | |
| WC | E Spizzirri | 2 | 2 | | | | | | | 7 | G Mpetshi Perricard | 7$^7$ | 4 | 7$^8$ | | | | |
| | A Walton | 6 | 6 | | | A Walton | 6$^3$ | 4 | | | | | | | | | | |
| | T Sandgren | 4 | 4 | | 7 | G Mpetshi Perricard | 7$^7$ | 6 | | | | | | | | | | |
| 7 | G Mpetshi Perricard | 6 | 6 | | | | | | | | | | | | | | | |

### Bottom 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 |
| 5 | A Çelikbilek | 4 | 6$^2$ | | | | | | | | | | | | | | | | |
| Q | T Schoolkate | 6 | 7$^7$ | | Q | T Schoolkate | 6 | 3 | 2 | | | | | | | | | | |
| Q | E Escobedo | 6$^6$ | 6 | 4 | WC | E Quinn | 4 | 6 | 6 | | | | | | | | | | |
| WC | E Quinn | 7$^8$ | 0 | 6 | | | | | | WC | E Quinn | 5 | 1 | | | | | | |
| | D Sweeny | 4 | 4 | | | | | | | 4 | J Shang | 7 | 6 | | | | | | |
| Q | I Marchenko | 6 | 6 | | Q | I Marchenko | 5 | 3 | | | | | | | | | | | |
| SE | M Kukushkin | 6$^5$ | 2$^r$ | | 4 | J Shang | 7 | 6 | | | | | | | | | | | |
| 4 | J Shang | 7$^7$ | 3 | | | | | | | | | | | | 4 | J Shang | 6 | 5 | 3 |
| 6 | A Galarneau | 6$^3$ | 1 | | | | | | | | | | | | | A Michelsen | 4 | 7 | 6 |
| WC | K Nishikori | 7$^7$ | 6 | | WC | K Nishikori | 7$^7$ | 6 | | | | | | | | | | | |
| Alt | S Mansouri | 3 | 6 | 6 | Alt | S Mansouri | 6$^1$ | 4 | | | | | | | | | | | |
| Alt | J McCabe | 6 | 4 | 4 | | | | | | WC | K Nishikori | 6$^{13}$ | 6 | 1 | | | | | |
| | L Tu | 6$^3$ | 7$^7$ | 6$^5$ | | | | | | | A Michelsen | 7$^{15}$ | 3 | 6 | | | | | |
| | A Michelsen | 7$^7$ | 6$^5$ | 7$^7$ | | A Michelsen | 6 | 6 | | | | | | | | | | | |
| | B Zhukayev | 3 | 4 | | 2 | A Kovacevic | 4 | 2 | | | | | | | | | | | |
| 2 | A Kovacevic | 6 | 6 | | | | | | | | | | | | | | | | |