2021 Chicago Challenger – Singles

Petra Martić was the defending champion, but chose to compete at the 2021 Western & Southern Open instead.

Singles
2021 Chicago Challenger
Champion	Clara Tauson
Runner-up	Emma Raducanu
Score	6–1, 2–6, 6–4
Draw	32
Seeds	8

Main article: 2021 Chicago Challenger

Clara Tauson won the title, defeating wildcard Emma Raducanu in the final, 6–1, 2–6, 6–4.

Seeds

1. Alison Van Uytvanck (first round)
2. Danka Kovinić (first round)
3. Ann Li (semifinals)
4. Anhelina Kalinina (first round)
5. Madison Brengle (first round)
6. Amanda Anisimova (second round, retired)
7. Ana Konjuh (first round)
8. Varvara Gracheva (second round)

Draw

Key

• Q = Qualifier
• WC = Wild card
• LL = Lucky loser
• Alt = Alternate
• SE = Special exempt
• PR = Protected ranking
• ITF = ITF entry
• JE = Junior exempt
• w/o = Walkover
• r = Retired
• d = Defaulted
• SR = Special ranking

Finals

	Semifinals							Final
	WC	Emma Raducanu	77	4	6
		Claire Liu	63	6	1
								WC	Emma Raducanu	1	6	4
									Clara Tauson	6	2	6
	3	Ann Li	65	1
		Clara Tauson	77	6

Top half

	First round							Second round							Quarterfinals							Semifinals
	1	A Van Uytvanck	67	3
	WC	E Raducanu	79	6				WC	E Raducanu	6	7
		C Burel	7	3					C Burel	2	5
	PR	I Jorović	5	2r											WC	E Raducanu	77	0
		J Niemeier	6	6												J Niemeier	64	0r
		G Minnen	2	2					J Niemeier	3	6	4
		N Párrizas Díaz	6	2	4			6	A Anisimova	6	3	0r
	6	A Anisimova	3	6	6																	WC	E Raducanu	77	4	6
	4	A Kalinina	2	4																			C Liu	63	6	1
		A Kalinskaya	6	6				A Kalinskaya		4	6	3
		C Liu	6	6				C Liu		6	4	6
		Y Bonaventure	3	2												C Liu	6	6
	PR	K Kozlova	5	6	77										Q	V Diatchenko	2	3
	Q	M Zanevska	7	4	62			PR	K Kozlova	5	6	4
	Q	V Diatchenko	77	6				Q	V Diatchenko	7	1	6
	7	A Konjuh	64	3

Bottom half

	First round							Second round							Quarterfinals							Semifinals
	5	M Brengle	77	65	4
		Z Diyas	62	77	6			Z Diyas		6	1	6
		H Tan	4	6	3			S Errani		3	6	4
		S Errani	6	2	6											Z Diyas	4	6	3
	WC	C Vandeweghe	63	4											3	A Li	6	2	6
		O Dodin	77	6					O Dodin	3	1
	WC	W Osuigwe	3	4				3	A Li	6	6
	3	A Li	6	6																		3	A Li	65	1
	8	V Gracheva	4	6	6																		C Tauson	77	6
		M Doi	6	4	4			8	V Gracheva	7	3	4
	Q	C Dolehide	3	6	2				S Sanders	5	6	6
		S Sanders	6	4	6										S Sanders		5	3
	Q	H Dart	1	77	2										C Tauson		7	6
		C Tauson	6	62	6				C Tauson	6	3	6
	WC	H Baptiste	6	6				WC	H Baptiste	2	6	3
	2	D Kovinić	3	4

Qualifying

Seeds

1. Kristína Kučová (qualifying competition)
2. Maryna Zanevska (qualified)
3. Harmony Tan (moved to main draw)
4. Vitalia Diatchenko (qualified)

Qualifiers

1. Harriet Dart
2. Maryna Zanevska
3. Caroline Dolehide
4. Vitalia Diatchenko

Draw

First qualifier

	Qualifying competition
	1	Kristína Kučová	6	4	4
	Alt	Harriet Dart	2	6	6

Second qualifier

	Qualifying competition
	2	Maryna Zanevska	6	6
		Dalma Gálfi	2	2

Third qualifier

	Qualifying competition
	Alt	Lesley Pattinama Kerkhove	6	2	3
	WC	Caroline Dolehide	2	6	6

Fourth qualifier

	Qualifying competition
	4	Vitalia Diatchenko	77	6
	WC	Dalayna Hewitt	65	3

External links

• Main Draw
• Qualifying Draw