2023 Chicago Men's Challenger

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.

Seeds

 * 1 Rankings as of 3 July 2023.

Other entrants
The following players received wildcards into the singles main draw:
 * 🇯🇵 Kei Nishikori
 * 🇺🇸 Ethan Quinn
 * 🇺🇸 Eliot Spizzirri

The following player received entry into the singles main draw as a special exempt:
 * 🇰🇿 Mikhail Kukushkin

The following players received entry into the singles main draw as alternates:
 * Jason Jung
 * 🇹🇳 Skander Mansouri
 * 🇦🇺 James McCabe
 * 🇯🇵 Yasutaka Uchiyama

The following players received entry from the qualifying draw:
 * 🇰🇷 Chung Yun-seong
 * 🇲🇽 Ernesto Escobedo
 * 🇦🇺 Omar Jasika
 * 🇺🇦 Illya Marchenko
 * 🇦🇺 Tristan Schoolkate
 * 🇦🇺 Bernard Tomic

The following player received entry as a lucky loser:
 * 🇺🇸 Evan Zhu

Singles

 * 🇺🇸 Alex Michelsen def. 🇯🇵 Yuta Shimizu 7–5, 6–2.

Doubles

 * Miķelis Lībietis / 🇹🇳 Skander Mansouri def. 🇰🇷 Chung Yun-seong / 🇦🇺 Andrew Harris 7–6(7–5), 6–3.