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)