| Singles | |
|---|---|
| 2024 Chicago Men's Challenger | |
| Champion |  Gabriel Diallo |
| Runner-up |  Bu Yunchaokete |
| Score | 6–3, 7–6(7–3) |
Alex Michelsen was the defending champion [1] but chose not to defend his title.
Gabriel Diallo won the title after defeating Bu Yunchaokete 6–3, 7–6(7–3) in the final.
Térence Atmane (second round) Benjamin Bonzi (first round) Hugo Grenier (quarterfinals) Gabriel Diallo (champion) Alexis Galarneau (first round) Bu Yunchaokete (final)
Coleman Wong (first round)
Hong Seong-chan (quarterfinals)| Semifinals | Final | ||||||||||||
| Q |  Jacob Fearnley | 2 | 3 | ||||||||||
| 4 | Gabriel Diallo | 6 | 6 | ||||||||||
| 4 | Gabriel Diallo | 6 | 77 | ||||||||||
| 6 | Bu Yunchaokete | 3 | 63 | ||||||||||
| 6 | Bu Yunchaokete | 6 | 7 | ||||||||||
| WC |  Learner Tien | 4 | 5 | ||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1/SE | T Atmane | 77 | 77 | ||||||||||||||||||||||||
| Micah Braswell | 64 | 65 | 1/SE | T Atmane | 2 | 6 | 63 | ||||||||||||||||||||
| Q | J Fearnley | 6 | 6 | Q | J Fearnley | 6 | 1 | 77 | |||||||||||||||||||
 L Tu | 4 | 3 | Q | J Fearnley | 6 | 6 | |||||||||||||||||||||
| Alt | B Holt | 6 | 77 | Alt | B Holt | 3 | 2 | ||||||||||||||||||||
| WC | Andrew Fenty | 1 | 64 | Alt | B Holt | 6 | 77 | ||||||||||||||||||||
| M Polmans | 2 | 77 | 6 | M Polmans | 4 | 64 | |||||||||||||||||||||
| 5 | A Galarneau | 6 | 65 | 4 | Q | J Fearnley | 2 | 3 | |||||||||||||||||||
| 4 | G Diallo | 6 | 6 | 4 | G Diallo | 6 | 6 | ||||||||||||||||||||
| Q |  J Trotter | 4 | 2 | 4 | G Diallo | 77 | 6 | ||||||||||||||||||||
 J Fonseca | 6 | 6 | J Fonseca | 61 | 1 | ||||||||||||||||||||||
| Y Shimizu | 3 | 4 | 4 | G Diallo | 6 | 6 | |||||||||||||||||||||
| M Krueger | 6 | 6 | M Krueger | 3 | 2 | ||||||||||||||||||||||
| Arthur Gea | 4 | 4 | M Krueger | 6 | 6 | ||||||||||||||||||||||
| P Sekulic | 6 | 6 | P Sekulic | 4 | 2 | ||||||||||||||||||||||
| 7 | C Wong | 2 | 1 | ||||||||||||||||||||||||
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 6 | Y Bu | 6 | 6 | ||||||||||||||||||||||||
| Q | Michael Zheng | 4 | 4 | 6 | Y Bu | 6 | 6 | ||||||||||||||||||||
| Q |  T-l Wu | 4 | 6 | 1 | P Jubb | 3 | 3 | ||||||||||||||||||||
| P Jubb | 6 | 2 | 6 | 6 | Y Bu | 6 | 69 | 6 | |||||||||||||||||||
| WC | N Basavareddy | 2 | 78 | 7 | 3 | H Grenier | 2 | 711 | 1 | ||||||||||||||||||
| Q |  M Lajal | 6 | 66 | 5 | WC | N Basavareddy | 4 | 0 | |||||||||||||||||||
| B Tomic | 2 | 4 | 3 | H Grenier | 6 | 6 | |||||||||||||||||||||
| 3 | H Grenier | 6 | 6 | 6 | Y Bu | 6 | 7 | ||||||||||||||||||||
| 8 | S-c Hong | 6 | 6 | WC | L Tien | 4 | 5 | ||||||||||||||||||||
| A Bolt | 4 | 3 | 8 | S-c Hong | 6 | 64 | 6 | ||||||||||||||||||||
| S Shimabukuro | 77 | 2 | 65 | C Broom | 3 | 77 | 4 | ||||||||||||||||||||
| C Broom | 64 | 6 | 77 | 8 | S-c Hong | 3 | 1 | ||||||||||||||||||||
 JP Ficovich | 4 | 6 | 5 | WC | L Tien | 6 | 6 | ||||||||||||||||||||
| Q | A Mayo | 6 | 3 | 7 | Q | A Mayo | 3 | 77 | 3 | ||||||||||||||||||
| WC | L Tien | 6 | 6 | WC | L Tien | 6 | 64 | 6 | |||||||||||||||||||
| 2 | B Bonzi | 4 | 4 | ||||||||||||||||||||||||
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