Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 40 of 92

• 4800 south chicago beach drive 709s, Chicago 60615 Active Under Contract $120,000 · 1 ba · 514 sqft
• 4800 south lake park avenue 2005, Chicago 60615 Active Under Contract $80,000 · 2 bd · 1 ba · 1,500 sqft
• 1707 west wallen avenue 3h, Chicago 60626 Active Under Contract $129,900 · 2 bd · 1 ba
• 606 east woodland park avenue 306, Chicago 60616 Active Under Contract $127,000 · 2 bd · 2 ba · 1,038 sqft
• 4229 north keystone avenue 3h, Chicago 60641 Active Under Contract $259,900 · 2 bd · 1 ba · 1,000 sqft
• 4326 north keystone avenue 2c, Chicago 60641 Active Under Contract $224,900 · 2 bd · 1 ba · 1,100 sqft
• 405 north wabash avenue 1905, Chicago 60611 Active Under Contract $237,000 · 1 bd · 1 ba · 573 sqft
• 3307 east 136th street, Chicago 60633 Active Under Contract $239,900 · 3 bd · 2 ba · 1,084 sqft
• 6245 south damen avenue, Chicago 60636 Active Under Contract $264,900 · 5 bd · 3 ba · 2,100 sqft
• 7337 south south shore drive 1030, Chicago 60649 Active Under Contract $112,000 · 2 bd · 1 ba · 700 sqft
• 850 north dewitt place 20a, Chicago 60611 Active Under Contract $259,000 · 1 bd · 1 ba
• 555 east 105th street, Chicago 60628 Active Under Contract $275,000 · 3 bd · 2 ba · 1,790 sqft
• 8238 south prairie avenue, Chicago 60619 Active Under Contract $99,999 · 2 bd · 2 ba · 1,200 sqft
• 5455 north sheridan road 1908, Chicago 60640 Active Under Contract $225,000 · 1 bd · 1 ba · 850 sqft
• 8219 south muskegon avenue, Chicago 60617 Active Under Contract $299,900 · 3 bd · 2 ba · 2,304 sqft
• 650 east 105th place, Chicago 60628 Active Under Contract $69,900 · 2 bd · 1 ba · 864 sqft
• 5148 north monitor avenue 303, Chicago 60630 Active Under Contract $225,000 · 2 bd · 1 ba
• 5000 north marine drive 12e, Chicago 60640 Active Under Contract $149,900 · 1 bd · 1 ba · 1,000 sqft
• 1255 west 108th place, Chicago 60643 Active Under Contract $139,900 · 4 bd · 2 ba · 1,600 sqft
• 5333 south ellis avenue 3a, Chicago 60615 Active Under Contract $159,000 · 2 bd · 1 ba · 800 sqft
• 1 east 114th street, Chicago 60628 Active Under Contract $229,900 · 6 bd · 3 ba
• 1071 west 15th street 314, Chicago 60608 Active Under Contract $299,999 · 1 bd · 1 ba · 880 sqft
• 512 north mcclurg court 2402, Chicago 60611 Active Under Contract $225,000 · 1 ba · 650 sqft
• 7410 south wentworth avenue, Chicago 60621 Active Under Contract $75,000 · 3 bd · 2 ba · 1,288 sqft
• 780 south federal street 201, Chicago 60605 Active Under Contract $155,900 · 1 ba · 520 sqft
• 7527 south perry avenue, Chicago 60620 Active Under Contract $259,900 · 4 bd · 3 ba · 2,300 sqft
• 10066 south van vlissingen road, Chicago 60617 Active Under Contract $150,000 · 4 bd · 2 ba · 1,414 sqft
• 6612 north harlem avenue 2w, Chicago 60631 Active Under Contract $199,900 · 2 bd · 1 ba · 900 sqft
• 819 east 98th place, Chicago 60628 Active Under Contract $289,000 · 4 bd · 2 ba · 1,217 sqft
• 440 north mcclurg court 407s, Chicago 60611 Active Under Contract $179,000 · 1 ba · 550 sqft
• 600 north dearborn street 1705, Chicago 60610 Active Under Contract $289,900 · 1 bd · 1 ba
• 3440 north lake shore drive 12b, Chicago 60657 Active Under Contract $240,000 · 1 bd · 1 ba · 800 sqft
• 1550 north lake shore drive 23f, Chicago 60610 Active Under Contract $299,900 · 1 bd · 1 ba
• 7919 south wabash avenue, Chicago 60619 Active Under Contract $139,900 · 3 bd · 2 ba · 1,566 sqft
• 2342 west adams street 208, Chicago 60612 Active Under Contract $285,000 · 1 bd · 1 ba · 780 sqft
• 3809 west 86th street, Chicago 60652 Active Under Contract $230,000 · 4 bd · 2 ba · 1,385 sqft
• 924 north oakley boulevard gn, Chicago 60622 Active Under Contract $249,000 · 2 bd · 1 ba
• 2901 south michigan avenue 403, Chicago 60616 Active Under Contract $95,000 · 1 ba · 500 sqft
• 111 west maple street 912, Chicago 60610 Active Under Contract $189,900 · 1 ba · 550 sqft
• 405 north wabash avenue 4712, Chicago 60611 Active Under Contract $269,900 · 1 bd · 1 ba · 725 sqft
• 1110 west 15th street 316, Chicago 60608 Active Under Contract $299,999 · 2 bd · 1 ba · 840 sqft
• 5457 south ingleside avenue 1e, Chicago 60615 Active Under Contract $210,000 · 2 bd · 1 ba
• 1217 west granville avenue 2b, Chicago 60660 Active Under Contract $189,900 · 1 bd · 1 ba
• 11427 south longwood drive, Chicago 60643 Active Under Contract $287,000 · 3 bd · 2 ba · 1,443 sqft
• 3660 north lake shore drive 909, Chicago 60613 Active Under Contract $265,000 · 1 bd · 1 ba · 712 sqft
• 5701 north sheridan road 30f, Chicago 60660 Active Under Contract $188,800 · 1 bd · 1 ba · 850 sqft
• 4004 north monitor avenue 3s, Chicago 60634 Active Under Contract $275,000 · 2 bd · 2 ba · 895 sqft
• 6 north michigan avenue 806, Chicago 60602 Active Under Contract $295,000 · 1 bd · 1 ba · 900 sqft
• 9631 south jeffery avenue, Chicago 60617 Active Under Contract $159,900 · 2 bd · 1 ba · 944 sqft
• 6215 north oakley avenue g, Chicago 60659 Active Under Contract $215,000 · 2 bd · 2 ba · 1,200 sqft