# 2022 Chicago Men's Challenger – Singles

This was the first edition of the tournament.
Roman Safiullin won the title after defeating Ben Shelton 6–3, 4–6, 7–5 in the final.

## Seeds

* Henri Laaksonen (first round)
* Christopher O'Connell (second round)
* Stefan Kozlov (first round)
* Jordan Thompson (quarterfinals)
* Radu Albot (semifinals)
* Emilio Gómez (withdrew)
* Roman Safiullin (champion)
* Fernando Verdasco (withdrew)

## 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 | Final | Final | Final | Final | Final |
| 5 | Radu Albot | 5 | 3 | | | | | |
| 7 | Roman Safiullin | 7 | 6 | | | | | |
| 7 | Roman Safiullin | 7 | 6 | 7 | Roman Safiullin | 6 | 4 | 7 |
| | | | | WC | Ben Shelton | 3 | 6 | 5 |
| WC | Ben Shelton | 6 | 7 | WC | Ben Shelton | 3 | 6 | 5 |
| | Gijs Brouwer | 3 | 5 | | | | | |

### 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 |
| 1 | H Laaksonen | 6 | 6$^5$ | 4 | | | | | | | | | | | | | | |
| | B Gojo | 3 | 7$^7$ | 6 | | B Gojo | 6 | 6$^1$ | 6 | | | | | | | | | |
| Alt | M Kukushkin | 3 | 6 | 6 | Alt | M Kukushkin | 3 | 7$^7$ | 1 | | | | | | | | | |
| WC | G Nanda | 6 | 4 | 3 | | | | | | | B Gojo | 6 | 2 | 4 | | | | |
| | A Escoffier | 7$^7$ | 6 | | | | | | | 5 | R Albot | 4 | 6 | 6 | | | | |
| | K Uchida | 6$^5$ | 3 | | | A Escoffier | 4 | 2 | | | | | | | | | | |
| Q | E Couacaud | 2 | 3 | | 5 | R Albot | 6 | 6 | | | | | | | | | | |
| 5 | R Albot | 6 | 6 | | | | | | | | | | | | 5 | R Albot | 5 | 3 |
| 3 | S Kozlov | 4 | 6$^2$ | | | | | | | | | | | | 7 | R Safiullin | 7 | 6 |
| | E Escobedo | 6 | 7$^7$ | | | E Escobedo | 4 | 2 | | | | | | | | | | |
| Q | A McHugh | 4 | 2 | | LL | Z Svajda | 6 | 6 | | | | | | | | | | |
| LL | Z Svajda | 6 | 6 | | | | | | | LL | Z Svajda | 3 | 7$^7$ | 3 | | | | |
| | D Svrčina | 6 | 4 | 3 | | | | | | 7 | R Safiullin | 6 | 6$^4$ | 6 | | | | |
| Alt | GA Olivieri | 4 | 6 | 6 | Alt | GA Olivieri | 4 | 6 | 0 | | | | | | | | | |
| | M Krueger | 3 | 3 | | 7 | R Safiullin | 6 | 4 | 6 | | | | | | | | | |
| 7 | R Safiullin | 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 | Semifinals | Semifinals | Semifinals | Semifinals |
| Q | B Harris | 6 | 4 | 6 | | | | | | | | | | | | | |
| WC | A Kovacevic | 3 | 6 | 3 | Q | B Harris | 3 | 2 | | | | | | | | | |
| | D Popko | 0 | 6$^5$ | | WC | B Shelton | 6 | 6 | | | | | | | | | |
| WC | B Shelton | 6 | 7$^7$ | | | | | | | WC | B Shelton | 7$^{14}$ | 6 | | | | |
| | C Eubanks | 6$^5$ | 6$^9$ | | | | | | | 4 | J Thompson | 6$^{12}$ | 4 | | | | |
| Q | R Harrison | 7$^7$ | 7$^{11}$ | | Q | R Harrison | 3 | 3 | | | | | | | | | |
| | P Jubb | 6$^8$ | 7$^7$ | 3 | 4 | J Thompson | 6 | 6 | | | | | | | | | |
| 4 | J Thompson | 7$^{10}$ | 6$^5$ | 6 | | | | | | | | | | WC | B Shelton | 6 | 7 |
| LL | L Tu | 3 | 2 | | | | | | | | | | | | G Brouwer | 3 | 5 |
| | L Broady | 6 | 6 | | | L Broady | 6 | 4 | 6 | | | | | | | | |
| Q | B Holt | 4 | 6 | 6 | Q | B Holt | 4 | 6 | 4 | | | | | | | | |
| | A Ritschard | 6 | 2 | 2 | | | | | | | L Broady | 2 | 4 | | | | |
| Q | K Smith | 3 | 4 | | | | | | | | G Brouwer | 6 | 6 | | | | |
| | G Brouwer | 6 | 6 | | | G Brouwer | 7 | 6 | | | | | | | | | |
| LL | E Zhu | 3 | 4 | | 2 | C O'Connell | 5 | 4 | | | | | | | | | |
| 2 | C O'Connell | 6 | 6 | | | | | | | | | | | | | | |