| Date: | 10–16 July |
| Edition: | 2nd |
| Surface: | Hard |
| Location: | Chicago, United States |
| Champs: |  Alex Michelsen |
| Champd: | Miķelis Lībietis /  Skander Mansouri |
The 2023 Chicago Men's Challenger was a professional tennis tournament played on hard courts. It was the second edition of the tournament which was part of the 2023 ATP Challenger Tour. It took place in Chicago, United States between July 10 and July 16, 2023.
| Country | Player | Rank1 | Seed | |
|---|---|---|---|---|
 Australia | ||||
| United States | Aleksandar Kovacevic | 120 | 2 | |
 Ecuador | Emilio Gómez | 127 | 3 | |
 China | Shang Juncheng | 155 | 4 | |
 Turkey | Altuğ Çelikbilek | 211 | 5 | |
 Canada | Alexis Galarneau | 215 | 6 | |
 France | Giovanni Mpetshi Perricard | 218 | 7 | |
| United States | Steve Johnson | 219 | 8 |
The following players received wildcards into the singles main draw:
The following player received entry into the singles main draw as a special exempt:
The following players received entry into the singles main draw as alternates:
The following players received entry from the qualifying draw:
The following player received entry as a lucky loser:
See main article: 2023 Chicago Men's Challenger – Singles.
Alex Michelsen def. 
Yuta Shimizu 7–5, 6–2.See main article: 2023 Chicago Men's Challenger – Doubles.
Skander Mansouri def. 
Chung Yun-seong / Andrew Harris 7–6(7–5), 6–3.
