Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 49 of 92

• 5700 south meade avenue, Chicago 60638 Active Under Contract $299,900 · 4 bd · 1 ba · 1,491 sqft
• 2514 west north shore avenue 1, Chicago 60645 Active Under Contract $219,000 · 2 bd · 1 ba
• 5950 north kenmore avenue 505, Chicago 60660 Active Under Contract $190,000 · 1 bd · 1 ba · 725 sqft
• 555 west cornelia avenue 2012, Chicago 60657 Active Under Contract $235,000 · 1 bd · 1 ba
• 519 south maplewood avenue 4s, Chicago 60612 Active Under Contract $275,000 · 3 bd · 2 ba
• 4023 south calumet avenue 2n, Chicago 60653 Active Under Contract $235,000 · 2 bd · 2 ba · 1,200 sqft
• 1729 west erie street 1n, Chicago 60622 Active Under Contract $299,000 · 1 bd · 1 ba · 1,000 sqft
• 4542 north albany avenue 2, Chicago 60625 Active Under Contract $224,900 · 2 bd · 1 ba
• 13151 south burley avenue, Chicago 60633 Active Under Contract $185,000 · 5 bd · 2 ba · 1,058 sqft
• 974 west 35th place 407, Chicago 60609 Active Under Contract $259,000 · 1 bd · 1 ba · 800 sqft
• 440 north mcclurg court 520, Chicago 60611 Active Under Contract $275,000 · 1 bd · 1 ba · 775 sqft
• 2310 south canal street 217, Chicago 60616 Active Under Contract $240,000 · 1 bd · 2 ba · 977 sqft
• 1151 west grace street 1s, Chicago 60613 Active Under Contract $225,000 · 1 bd · 1 ba
• 13442 south avenue north avenue, Chicago 60633 Active Under Contract $284,900 · 4 bd · 2 ba
• 1070 west 15th street 309, Chicago 60608 Active Under Contract $299,000 · 2 bd · 1 ba
• 2930 north sheridan road 2108, Chicago 60657 Active Under Contract $265,000 · 1 bd · 1 ba
• 7010 south paulina street, Chicago 60636 Active Under Contract $259,900 · 3 bd · 2 ba · 1,800 sqft
• 2610 west balmoral avenue 203, Chicago 60625 Active Under Contract $130,000 · 1 bd · 1 ba
• 5710 south washtenaw avenue, Chicago 60629 Active Under Contract $229,900 · 3 bd · 2 ba · 1,775 sqft
• 1346 5 west estes avenue 1w, Chicago 60626 Active Under Contract $198,000 · 1 bd · 1 ba
• 5230 west 54th street, Chicago 60638 Active Under Contract $230,000 · 3 bd · 2 ba · 1,200 sqft
• 1739 west steuben street, Chicago 60643 Active Under Contract $219,900 · 3 bd · 2 ba · 1,008 sqft
• 1918 south michigan avenue 207, Chicago 60616 Active Under Contract $264,900 · 1 bd · 1 ba · 599 sqft
• 4408 north long avenue 1, Chicago 60630 Active Under Contract $225,000 · 2 bd · 1 ba
• 6046 north francisco avenue 2w, Chicago 60659 Active Under Contract $199,900 · 2 bd · 1 ba
• 6350 south wood street, Chicago 60636 Active Under Contract $280,000 · 4 bd · 3 ba · 2,500 sqft
• 10632 south avenue l, Chicago 60617 Active Under Contract $257,900 · 3 bd · 2 ba · 1,277 sqft
• 1720 south michigan avenue 2805, Chicago 60616 Active Under Contract $270,000 · 1 bd · 1 ba · 750 sqft
• 9207 south greenwood avenue, Chicago 60619 Active Under Contract $219,900 · 2 bd · 2 ba · 1,748 sqft
• 8542 south elizabeth street, Chicago 60620 Active Under Contract $130,000 · 3 bd · 1 ba · 1,077 sqft
• 12200 south yale avenue, Chicago 60628 Active Under Contract $195,000 · 2 bd · 2 ba · 1,218 sqft
• 9010 south parnell avenue, Chicago 60620 Active Under Contract $275,999 · 5 bd · 2 ba · 2,400 sqft
• 9760 south dobson avenue, Chicago 60628 Active Under Contract $195,000 · 2 bd · 2 ba · 1,600 sqft
• 235 west van buren street 1518, Chicago 60607 Active Under Contract $250,000 · 1 bd · 1 ba
• 8060 south kolmar avenue, Chicago 60652 Active Under Contract $294,900 · 3 bd · 3 ba · 1,448 sqft
• 5016 south king drive 1e, Chicago 60615 Active Under Contract $149,900 · 2 bd · 2 ba · 1,100 sqft
• 12716 south saginaw avenue, Chicago 60633 Active Under Contract $250,000 · 3 bd · 1 ba · 1,040 sqft
• 1 east scott street 1811, Chicago 60610 Active Under Contract $179,500 · 1 ba · 518 sqft
• 9926 south wentworth avenue, Chicago 60628 Active Under Contract $149,900 · 3 bd · 2 ba · 999 sqft
• 7141 north kedzie avenue 910, Chicago 60645 Active Under Contract $177,000 · 1 bd · 1 ba · 850 sqft
• 827 west 53rd place, Chicago 60609 Active Under Contract $135,000 · 3 bd · 2 ba · 1,000 sqft
• 630 north state street 1501, Chicago 60654 Active Under Contract $250,000 · 1 bd · 1 ba
• 5616 north kenmore avenue 5c, Chicago 60660 Active Under Contract $119,000 · 1 ba
• 13437 south green bay avenue, Chicago 60633 Active Under Contract $189,900 · 3 bd · 1 ba · 900 sqft
• 3750 north pittsburgh avenue, Chicago 60634 Active Under Contract $299,000 · 2 bd · 2 ba · 1,466 sqft
• 3950 north lake shore drive 1320, Chicago 60611 Active Under Contract $265,000 · 3 bd · 2 ba · 1,200 sqft
• 8018 south michigan avenue, Chicago 60619 Active Under Contract $179,000 · 3 bd · 1 ba · 1,040 sqft
• 5052 north marine drive d3, Chicago 60640 Active Under Contract $167,000 · 2 bd · 1 ba
• 6550 south claremont avenue, Chicago 60636 Active Under Contract $179,000 · 4 bd · 1 ba
• 5320 north sheridan road 1509, Chicago 60640 Active Under Contract $287,500 · 2 bd · 2 ba · 1,100 sqft