Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 44 of 92

• 10508 south bensley avenue, Chicago 60617 Active Under Contract $249,900 · 3 bd · 2 ba · 1,032 sqft
• 7500 west addison street 1-s, Chicago 60634 Active Under Contract $242,000 · 2 bd · 2 ba · 1,000 sqft
• 6000 south narragansett avenue, Chicago 60638 Active Under Contract $299,000 · 3 bd · 2 ba · 1,128 sqft
• 450 west briar place 8n, Chicago 60657 Active Under Contract $260,000 · 1 bd · 1 ba
• 1601 south michigan avenue 405, Chicago 60616 Active Under Contract $220,000 · 1 bd · 1 ba
• 212 west washington street 1406, Chicago 60606 Active Under Contract $259,000 · 1 bd · 1 ba · 750 sqft
• 5402 south marshfield avenue, Chicago 60609 Active Under Contract $240,000 · 3 bd · 2 ba · 1,586 sqft
• 5515 north winthrop avenue 2a, Chicago 60640 Active Under Contract $200,000 · 1 bd · 1 ba · 900 sqft
• 3848 west 47th street 1sw, Chicago 60632 Active Under Contract $157,000 · 2 bd · 1 ba · 950 sqft
• 735 east 105th street, Chicago 60628 Active Under Contract $200,000 · 2 bd · 2 ba · 1,197 sqft
• 5646 north kenmore avenue 2a, Chicago 60660 Active Under Contract $299,900 · 2 bd · 2 ba · 1,100 sqft
• 1347 north greenview avenue 1f, Chicago 60642 Active Under Contract $200,000 · 1 bd · 1 ba · 750 sqft
• 633 south plymouth court 301, Chicago 60605 Active Under Contract $215,000 · 1 bd · 1 ba
• 5056 north marine drive 4a, Chicago 60640 Active Under Contract $169,900 · 1 bd · 1 ba · 850 sqft
• 8059 south sawyer avenue, Chicago 60652 Active Under Contract $275,000 · 2 bd · 2 ba · 1,764 sqft
• 8057 south saint louis avenue, Chicago 60652 Active Under Contract $250,000 · 2 bd · 1 ba · 1,000 sqft
• 1631 south michigan avenue 502, Chicago 60616 Active Under Contract $269,900 · 1 bd · 1 ba · 900 sqft
• 2320 north nordica avenue 410d, Chicago 60707 Active Under Contract $160,000 · 1 bd · 1 ba · 800 sqft
• 1030 north state street 40f, Chicago 60610 Active Under Contract $245,000 · 1 ba · 627 sqft
• 3747 east 112th street, Chicago 60617 Active Under Contract $240,000 · 3 bd · 2 ba · 1,051 sqft
• 2310 south canal street 215, Chicago 60616 Active Under Contract $240,000 · 1 bd · 2 ba · 1,030 sqft
• 9552 south greenwood avenue, Chicago 60628 Active Under Contract $150,000 · 2 bd · 1 ba · 915 sqft
• 10806 south avenue o, Chicago 60617 Active Under Contract $295,000 · 3 bd · 2 ba · 1,600 sqft
• 233 east erie street 1110, Chicago 60611 Active Under Contract $219,000 · 1 bd · 1 ba
• 10508 south forest avenue, Chicago 60628 Active Under Contract $145,000 · 3 bd · 3 ba · 1,426 sqft
• 417 south jefferson street 102b, Chicago 60607 Active Under Contract $288,000 · 1 bd · 1 ba · 850 sqft
• 1044 west 115th street, Chicago 60643 Active Under Contract $24,900 · 3 bd · 2 ba · 1,500 sqft
• 8746 south kenwood avenue, Chicago 60619 Active Under Contract $249,900 · 4 bd · 3 ba · 1,500 sqft
• 7006 south calumet avenue, Chicago 60637 Active Under Contract $239,999 · 4 bd · 2 ba · 1,800 sqft
• 33 west delaware place 22h, Chicago 60610 Active Under Contract $290,000 · 1 bd · 1 ba
• 10416 south sangamon street, Chicago 60643 Active Under Contract $204,900 · 3 bd · 2 ba · 1,463 sqft
• 6118 north sheridan road 310, Chicago 60660 Active Under Contract $149,000 · 1 bd · 1 ba · 561 sqft
• 11442 south normal avenue, Chicago 60628 Active Under Contract $99,900 · 3 bd · 1 ba · 1,085 sqft
• 1504 west 73rd street, Chicago 60636 Active Under Contract $259,000 · 4 bd · 3 ba · 1,500 sqft
• 7021 north greenview avenue 3n, Chicago 60626 Active Under Contract $299,900 · 2 bd · 1 ba · 1,070 sqft
• 7209 north damen avenue 3, Chicago 60626 Active Under Contract $229,900 · 2 bd · 2 ba · 900 sqft
• 6922 south rockwell street, Chicago 60629 Active Under Contract $249,900 · 4 bd · 2 ba · 1,483 sqft
• 2901 south michigan avenue 1610, Chicago 60616 Active Under Contract $125,000 · 1 bd · 1 ba · 800 sqft
• 8444 west wilson avenue 208-s, Chicago 60656 Active Under Contract $179,000 · 1 bd · 1 ba · 620 sqft
• 1819 north mcvicker avenue, Chicago 60639 Active Under Contract $275,000 · 2 bd · 1 ba · 1,150 sqft
• 8433 south wolcott avenue, Chicago 60620 Active Under Contract $85,000 · 2 bd · 2 ba · 1,242 sqft
• 5455 north sheridan road 2207, Chicago 60640 Active Under Contract $160,000 · 1 ba
• 12628 south state street, Chicago 60628 Active Under Contract $220,000 · 4 bd · 2 ba · 888 sqft
• 9640 south morgan street, Chicago 60643 Active Under Contract $160,000 · 3 bd · 2 ba · 1,433 sqft
• 5455 north sheridan road 2509, Chicago 60640 Active Under Contract $155,000 · 1 ba · 600 sqft
• 8517 west catherine avenue 181, Chicago 60656 Active Under Contract $220,000 · 2 bd · 1 ba · 1,000 sqft
• 4324 west division street, Chicago 60651 Active Under Contract $144,900 · 4 bd · 2 ba · 1,180 sqft
• 6101 north sheridan road 10c, Chicago 60660 Active Under Contract $229,000 · 2 bd · 1 ba
• 8117 south michigan avenue, Chicago 60619 Active Under Contract $255,000 · 3 bd · 2 ba · 940 sqft
• 1146 west 88th street, Chicago 60620 Active Under Contract $135,000 · 3 bd · 2 ba · 1,168 sqft