2025 Chicago Men's Challenger

Country	Player	Rank1	Seed
DEN	August Holmgren	144	1
GBR	Billy Harris	146	2
LBN	Hady Habib	169	3
CHN	Wu Yibing	186	4
KAZ	Beibit Zhukayev	203	5
AUS	Bernard Tomic	211	6
TPE	Hsu Yu-hsiou	217	7
MEX	Rodrigo Pacheco Méndez	220	8

• ¹ Rankings as of 28 July 2025.^[1]

The following players received wildcards into the singles main draw:

• Martin Damm
• Kyle Kang
• Darian King

The following player received entry into the singles main draw using a protected ranking:

• Jason Jung

The following player received entry into the singles main draw through the College Accelerator programme:

• Michael Zheng

The following player received entry into the singles main draw through the Junior Accelerator programme:

• Miguel Tobón

The following players received entry into the singles main draw as alternates:

• Stefan Dostanic
• Andre Ilagan
• Garrett Johns
• Alfredo Perez

The following players received entry from the qualifying draw:

• Samir Banerjee
• Andrew Fenty
• Antoine Ghibaudo
• Huang Tsung-hao
• Joshua Sheehy
• Trevor Svajda

The following player received entry as a lucky loser:

• Giles Hussey

• Michael Zheng def. Hsu Yu-hsiou 6–4, 6–2.

• Mac Kiger / Ryan Seggerman def. Theodore Winegar / Michael Zheng 6–4, 3–6, [10–5].