Singles
2022 Chicago Men's Challenger
Final
Champion	Roman Safiullin
Runner-up	Ben Shelton
Score	6–3, 4–6, 7–5
Events
Singles Doubles
Chicago Men's Challenger · 2023 →

This was the first edition of the tournament.^[1]

Roman Safiullin won the title after defeating Ben Shelton 6–3, 4–6, 7–5 in the final.

	Semifinals							Final
	5	Radu Albot	5	3
	7	Roman Safiullin	7	6
								7	Roman Safiullin	6	4	7
								WC	Ben Shelton	3	6	5
	WC	Ben Shelton	6	7
		Gijs Brouwer	3	5

	First round							Second round							Quarterfinals							Semifinals
	1	H Laaksonen	6	65	4
		B Gojo	3	77	6				B Gojo	6	61	6
	Alt	M Kukushkin	3	6	6			Alt	M Kukushkin	3	77	1
	WC	G Nanda	6	4	3											B Gojo	6	2	4
		A Escoffier	77	6											5	R Albot	4	6	6
		K Uchida	65	3					A Escoffier	4	2
	Q	E Couacaud	2	3				5	R Albot	6	6
	5	R Albot	6	6																		5	R Albot	5	3
	3	S Kozlov	4	62																		7	R Safiullin	7	6
		E Escobedo	6	77					E Escobedo	4	2
	Q	A McHugh	4	2				LL	Z Svajda	6	6
	LL	Z Svajda	6	6											LL	Z Svajda	3	77	3
		D Svrčina	6	4	3										7	R Safiullin	6	64	6
	Alt	GA Olivieri	4	6	6			Alt	GA Olivieri	4	6	0
		M Krueger	3	3				7	R Safiullin	6	4	6
	7	R Safiullin	6	6

	First round							Second round							Quarterfinals							Semifinals
	Q	B Harris	6	4	6
	WC	A Kovacevic	3	6	3			Q	B Harris	3	2
		D Popko	0	65				WC	B Shelton	6	6
	WC	B Shelton	6	77											WC	B Shelton	714	6
		C Eubanks	65	69											4	J Thompson	612	4
	Q	R Harrison	77	711				Q	R Harrison	3	3
		P Jubb	68	77	3			4	J Thompson	6	6
	4	J Thompson	710	65	6																	WC	B Shelton	6	7
	LL	L Tu	3	2																			G Brouwer	3	5
		L Broady	6	6					L Broady	6	4	6
	Q	B Holt	4	6	6			Q	B Holt	4	6	4
		A Ritschard	6	2	2											L Broady	2	4
	Q	K Smith	3	4												G Brouwer	6	6
		G Brouwer	6	6					G Brouwer	7	6
	LL	E Zhu	3	4				2	C O'Connell	5	4
	2	C O'Connell	6	6

• Main draw
• Qualifying draw