Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 64 of 92

9133 south halsted street, Chicago 60620 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,017 sqft
7717 south luella avenue, Chicago 60649 Off market since Aug 2026 $245,000 · 3 bd · 2 ba · 1,571 sqft
1053 west 104th place, Chicago 60643 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 924 sqft
5445 north sheridan road 3805, Chicago 60640 Off market since Sep 2026 $165,000 · 1 ba · 725 sqft
6843 south carpenter street, Chicago 60621 Off market since Jul 2026 $274,999 · 7 bd · 3 ba · 1,970 sqft
11432 south wentworth avenue, Chicago 60628 Off market since Sep 2026 $115,000 · 3 bd · 2 ba · 1,200 sqft
11116 south longwood drive 202, Chicago 60643 Off market since Sep 2026 $153,900 · 2 bd · 2 ba · 850 sqft
10201 south princeton avenue, Chicago 60628 Off market since Sep 2026 $125,000 · 2 bd · 1 ba · 1,020 sqft
1755 east 55th street 605, Chicago 60615 Off market since Sep 2026 $109,900 · 1 bd · 1 ba · 850 sqft
5701 north sheridan road 6d, Chicago 60660 Off market since Sep 2026 $152,500 · 1 ba · 550 sqft
2859 north kostner avenue 1, Chicago 60641 Off market since Jul 2026 $260,000 · 3 bd · 2 ba · 1,282 sqft
6101 north sheridan road 11e, Chicago 60660 Off market since Jul 2026 $184,900 · 1 bd · 1 ba · 800 sqft
320 east 21st street 807, Chicago 60616 Off market since Jul 2026 $275,000 · 1 bd · 1 ba · 832 sqft
6171 north sheridan road 1112, Chicago 60660 Off market since Jul 2026 $269,000 · 2 bd · 2 ba · 1,400 sqft
10933 south avenue f, Chicago 60617 Off market since Sep 2026 $259,900 · 3 bd · 2 ba · 1,066 sqft
6118 north sheridan road 506, Chicago 60660 Off market since Aug 2026 $149,000 · 1 ba · 550 sqft
6118 north sheridan road 106, Chicago 60660 Off market since Aug 2026 $168,000 · 1 bd · 1 ba · 750 sqft
10841 south vernon avenue, Chicago 60628 Off market since Sep 2026 $199,500 · 3 bd · 2 ba · 1,000 sqft
3600 north lake shore drive 1814, Chicago 60613 Off market since Jul 2026 $294,900 · 1 bd · 2 ba · 900 sqft
6735 south oglesby avenue 101, Chicago 60649 Off market since Jul 2026 $265,000 · 3 bd · 2 ba · 2,400 sqft
5516 west higgins avenue gnw, Chicago 60630 Off market since Sep 2026 $169,900 · 1 bd · 1 ba
7302 south dorchester avenue a, Chicago 60619 Off market since Sep 2026 $79,000 · 2 bd · 1 ba · 960 sqft
1550 north lake shore drive 23e, Chicago 60610 Off market since Aug 2026 $299,950 · 1 bd · 1 ba · 800 sqft
8533 south rhodes avenue, Chicago 60619 Off market since Aug 2026 $284,900 · 5 bd · 3 ba · 801 sqft
659 west randolph street 1711, Chicago 60661 Off market since Sep 2026 $275,000 · 1 bd · 1 ba · 655 sqft
6007 south la salle street, Chicago 60621 Off market since Sep 2026 $61,500 · 4 bd · 2 ba · 2,718 sqft
6926 south paxton avenue 2s, Chicago 60649 Off market since Sep 2026 $165,000 · 2 bd · 2 ba
500 east 92nd street, Chicago 60619 Off market since Jul 2026 $225,000 · 2 bd · 2 ba · 1,200 sqft
1525 south sangamon street 610, Chicago 60608 Off market since Aug 2026 $260,000 · 1 bd · 1 ba · 988 sqft
8613 south colfax avenue, Chicago 60617 Off market since Jul 2026 $277,900 · 3 bd · 2 ba · 1,808 sqft
265 west 107th street, Chicago 60628 Off market since Sep 2026 $159,000 · 4 bd · 2 ba · 1,050 sqft
8319 south crandon avenue, Chicago 60617 Off market since Aug 2026 $199,900 · 3 bd · 2 ba · 1,024 sqft
10 east ontario street 2509, Chicago 60611 Off market since Sep 2026 $274,000 · 1 bd · 1 ba · 995 sqft
444 west fullerton parkway 1010, Chicago 60614 Off market since Aug 2026 $285,000 · 1 bd · 1 ba
3600 north lake shore drive 1217, Chicago 60613 Sold on Jul 17, 2026 $184,900 · 1 ba · 590 sqft
40 east delaware place 1204, Chicago 60611 Off market since Jul 2026 $245,000 · 1 bd · 1 ba
1600 south indiana avenue 1401, Chicago 60616 Off market since Sep 2026 $288,000 · 1 bd · 1 ba · 800 sqft
4417 south calumet avenue 2s, Chicago 60653 Off market since Aug 2026 $250,000 · 2 bd · 2 ba · 1,200 sqft
2600 west balmoral avenue 402, Chicago 60625 Off market since Aug 2026 $145,000 · 1 bd · 1 ba · 700 sqft
2930 north sheridan road 702, Chicago 60657 Off market since Jul 2026 $299,900 · 2 bd · 1 ba · 720 sqft
738 west 129th place, Chicago 60628 Off market since Jul 2026 $274,500 · 3 bd · 2 ba · 1,500 sqft
5009 west chicago avenue, Chicago 60651 Off market since Aug 2026 $179,900 · 4 bd · 1 ba · 924 sqft
2316 west rosemont avenue 3, Chicago 60659 Off market since Sep 2026 $220,000 · 2 bd · 2 ba
7714 south marquette avenue, Chicago 60649 Off market since Sep 2026 $274,000 · 4 bd · 3 ba · 1,587 sqft
5303 south winchester avenue, Chicago 60609 Off market since Jul 2026 $225,000 · 3 bd · 1 ba · 1,120 sqft
1145 east 90th street, Chicago 60619 Off market since Jul 2026 $260,000 · 3 bd · 2 ba · 1,850 sqft
8156 south king drive, Chicago 60619 Off market since Jul 2026 $179,900 · 2 bd · 1 ba · 700 sqft
9815 south clyde avenue, Chicago 60617 Off market since Sep 2026 $105,000 · 2 bd · 1 ba · 956 sqft
11326 south union avenue, Chicago 60628 Off market since Sep 2026 $160,000 · 2 bd · 1 ba · 1,480 sqft
4313 west 77th place, Chicago 60652 Sold on Jul 15, 2026 $280,000 · 3 bd · 1 ba · 1,049 sqft