Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 56 of 92

• 5944 south king drive 1e, Chicago 60637 Active Under Contract $180,000 · 2 bd · 2 ba · 1,300 sqft
• 5901 north naper avenue 1c, Chicago 60631 Active Under Contract $185,000 · 1 bd · 1 ba
• 11104 south avenue o avenue, Chicago 60617 Active Under Contract $239,900 · 3 bd · 2 ba · 1,141 sqft
• 2868 west 84th street, Chicago 60652 Active Under Contract $239,900 · 3 bd · 3 ba · 1,664 sqft
• 5824 south archer avenue 2b, Chicago 60638 Active Under Contract $150,000 · 2 bd · 1 ba · 800 sqft
• 5700 south maplewood avenue, Chicago 60629 Active Under Contract $150,000 · 5 bd · 3 ba · 1,578 sqft
• 2837 south millard avenue, Chicago 60623 Active Under Contract $95,000 · 3 bd · 3 ba · 1,398 sqft
• 7042 west 74th street, Chicago 60638 Active Under Contract $167,000 · 4 bd · 2 ba · 2,227 sqft
• 10513 south avenue east, Chicago 60617 Active Under Contract $225,000 · 3 bd · 2 ba · 1,248 sqft
• 3816 north odell avenue, Chicago 60634 Active Under Contract $299,900 · 3 bd · 1 ba · 660 sqft
• 8035 south oglesby avenue, Chicago 60617 Active Under Contract $209,900 · 4 bd · 2 ba · 1,296 sqft
• 8160 south keating avenue, Chicago 60652 Active Under Contract $174,900 · 3 bd · 1 ba · 998 sqft
• 5306 north cumberland avenue 510, Chicago 60656 Active Under Contract $155,000 · 1 bd · 1 ba
• 12538 south wentworth avenue, Chicago 60628 Active Under Contract $260,000 · 3 bd · 2 ba · 1,502 sqft
• 8821 south eggleston avenue, Chicago 60620 Active Under Contract $250,000 · 2 bd · 2 ba · 1,000 sqft
• 4143 south maplewood avenue, Chicago 60632 Active Under Contract $159,900 · 2 bd · 2 ba · 660 sqft
• 175 east delaware place 4901, Chicago 60611 Active Under Contract $285,000 · 1 bd · 1 ba · 960 sqft
• 2772 east 75th street 2gs, Chicago 60649 Active Under Contract $152,000 · 2 bd · 2 ba · 1,250 sqft
• 6833 north kedzie avenue 914, Chicago 60645 Active Under Contract $178,500 · 1 bd · 1 ba · 986 sqft
• 5432 west windsor avenue 2a, Chicago 60630 Active Under Contract $174,900 · 2 bd · 1 ba · 1,132 sqft
• 7536 south damen avenue, Chicago 60620 Active Under Contract $119,999 · 2 bd · 1 ba · 1,132 sqft
• 5151 north east river road 332d, Chicago 60656 Active Under Contract $214,999 · 2 bd · 2 ba · 1,150 sqft
• 1265 south saint louis avenue, Chicago 60623 Active Under Contract $249,900 · 3 bd · 2 ba · 1,363 sqft
• 1922 west norwood street ga, Chicago 60660 Active Under Contract $120,000 · 2 bd · 1 ba · 1,000 sqft
• 1032 west 88th street, Chicago 60620 Active Under Contract $155,000 · 4 bd · 2 ba · 1,982 sqft
• 2133 west 49th place, Chicago 60609 Active Under Contract $210,000 · 3 bd · 2 ba · 969 sqft
• 5030 north leavitt street 3, Chicago 60625 Active Under Contract $275,000 · 1 bd · 1 ba · 0 sqft
• 3238 west berteau avenue 2e, Chicago 60618 Active Under Contract $250,000 · 2 bd · 1 ba · 836 sqft
• 5416 west windsor avenue 1g, Chicago 60630 Active Under Contract $179,000 · 2 bd · 1 ba · 1,000 sqft
• 30 east division street 15c, Chicago 60610 Active Under Contract $239,900 · 1 bd · 1 ba · 0 sqft
• 4541 south laporte avenue, Chicago 60638 Active Under Contract $259,000 · 3 bd · 1 ba · 912 sqft
• 512 north mcclurg court 4309, Chicago 60611 Active Under Contract $250,000 · 1 ba · 673 sqft
• 10425 south hale avenue 1c, Chicago 60643 Active Under Contract $174,900 · 2 bd · 2 ba · 1,300 sqft
• 5516 west higgins avenue gnw, Chicago 60630 Active Under Contract $169,900 · 1 bd · 1 ba · 0 sqft
• 1525 south sangamon street 610, Chicago 60608 Active Under Contract $249,000 · 1 bd · 1 ba · 988 sqft
• 175 east delaware place 4507, Chicago 60611 Active Under Contract $249,000 · 1 ba · 667 sqft
• 3645 west 116th street, Chicago 60803 Active Under Contract $274,900 · 4 bd · 2 ba · 1,075 sqft
• 4637 south kilpatrick avenue, Chicago 60632 Active Under Contract $129,900 · 2 bd · 1 ba · 1,086 sqft
• 3535 south prairie avenue 2n, Chicago 60653 Active Under Contract $275,000 · 2 bd · 2 ba · 1,300 sqft
• 1415 west lunt avenue 511, Chicago 60626 Active Under Contract $240,000 · 2 bd · 2 ba · 0 sqft
• 6521 south saint lawrence avenue, Chicago 60637 Active Under Contract $210,000 · 4 bd · 3 ba · 1,049 sqft
• 3600 north lake shore drive 2209, Chicago 60613 Active Under Contract $165,000 · 1 ba · 600 sqft
• 6240 south newland avenue 1n, Chicago 60638 Active Under Contract $225,000 · 2 bd · 2 ba · 1,200 sqft
• 4775 north linder avenue 2a, Chicago 60630 Active Under Contract $229,900 · 2 bd · 1 ba · 1,000 sqft
• 5555 north sheridan road 1612, Chicago 60640 Active Under Contract $199,900 · 2 bd · 1 ba · 1,200 sqft
• 8440 south peoria street, Chicago 60620 Off market since Sep 2026 $299,000 · 3 bd · 3 ba · 2,252 sqft
• 6806 south crandon avenue 2, Chicago 60649 Off market since Sep 2026 $150,000 · 3 bd · 3 ba · 2,200 sqft
• 6209 south dorchester avenue 1, Chicago 60637 Off market since Sep 2026 $225,000 · 3 bd · 3 ba · 1,789 sqft
• 8616 south emerald avenue, Chicago 60620 Off market since Sep 2026 $130,000 · 4 bd · 2 ba · 1,246 sqft
• 3008 west flournoy street 3, Chicago 60612 Off market since Sep 2026 $232,999 · 3 bd · 2 ba · 1,200 sqft