Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 41 of 92

• 3418 west 82nd place, Chicago 60652 Active Under Contract $237,000 · 2 bd · 2 ba · 1,202 sqft
• 7614 south carpenter street, Chicago 60620 Active Under Contract $224,900 · 3 bd · 2 ba · 1,296 sqft
• 9023 south cornell avenue, Chicago 60617 Active Under Contract $160,000 · 3 bd · 2 ba · 904 sqft
• 1460 north sandburg terrace 803a, Chicago 60610 Active Under Contract $275,000 · 2 bd · 1 ba
• 11149 south green bay avenue, Chicago 60617 Active Under Contract $290,000 · 3 bd · 2 ba · 1,040 sqft
• 1555 north sandburg terrace 517, Chicago 60610 Active Under Contract $240,000 · 1 bd · 1 ba · 825 sqft
• 405 north wabash avenue 4101, Chicago 60611 Active Under Contract $259,900 · 1 bd · 1 ba · 725 sqft
• 8215 west forest preserve avenue, Chicago 60634 Active Under Contract $239,900 · 4 bd · 2 ba · 1,146 sqft
• 5052 south blackstone avenue 2, Chicago 60615 Active Under Contract $249,000 · 3 bd · 1 ba · 1,000 sqft
• 7928 south winchester avenue, Chicago 60620 Active Under Contract $299,000 · 3 bd · 2 ba · 1,508 sqft
• 5353 south princeton avenue, Chicago 60609 Active Under Contract $195,000 · 2 bd · 2 ba · 1,150 sqft
• 7337 south south shore drive 211, Chicago 60649 Active Under Contract $55,000 · 1 ba · 500 sqft
• 4323 south saint louis avenue, Chicago 60632 Active Under Contract $299,000 · 3 bd · 2 ba · 1,388 sqft
• 1663 west pratt boulevard 2, Chicago 60626 Active Under Contract $225,000 · 2 bd · 1 ba · 900 sqft
• 6108 south kimbark avenue 2e, Chicago 60637 Active Under Contract $199,500 · 3 bd · 1 ba · 1,600 sqft
• 2 south leavitt street 308, Chicago 60612 Active Under Contract $235,000 · 1 bd · 1 ba · 795 sqft
• 900 south wabash avenue 206, Chicago 60605 Active Under Contract $250,000 · 1 bd · 1 ba
• 11955 south prairie avenue, Chicago 60628 Active Under Contract $234,000 · 3 bd · 2 ba · 1,080 sqft
• 1150 north lake shore drive 9j, Chicago 60611 Active Under Contract $154,900 · 1 ba
• 6253 north magnolia avenue g, Chicago 60660 Active Under Contract $285,000 · 2 bd · 2 ba · 1,300 sqft
• 1454 north central avenue, Chicago 60651 Active Under Contract $250,000 · 2 bd · 1 ba · 814 sqft
• 2851 south saint louis avenue, Chicago 60623 Active Under Contract $240,000 · 3 bd · 2 ba · 1,050 sqft
• 480 north mcclurg court 911, Chicago 60611 Active Under Contract $299,000 · 1 bd · 1 ba · 806 sqft
• 10122 south luella avenue, Chicago 60617 Active Under Contract $149,900 · 3 bd · 1 ba · 1,181 sqft
• 10553 south calumet avenue, Chicago 60628 Active Under Contract $155,000 · 2 bd · 2 ba · 1,095 sqft
• 7190 west dickens avenue 1e, Chicago 60707 Active Under Contract $166,000 · 2 bd · 1 ba
• 10001 south wentworth avenue, Chicago 60628 Active Under Contract $224,900 · 5 bd · 2 ba · 2,879 sqft
• 1255 south state street 708, Chicago 60605 Active Under Contract $250,000 · 1 bd · 1 ba · 880 sqft
• 10055 south oglesby avenue, Chicago 60617 Active Under Contract $222,999 · 3 bd · 2 ba · 1,152 sqft
• 3930 north pine grove avenue 909, Chicago 60613 Active Under Contract $250,000 · 1 bd · 1 ba
• 2740 north pine grove avenue 6c, Chicago 60614 Active Under Contract $239,900 · 1 bd · 1 ba · 600 sqft
• 3930 north pine grove avenue 1708, Chicago 60613 Active Under Contract $199,900 · 1 bd · 1 ba
• 474 north lake shore drive 3609, Chicago 60611 Active Under Contract $299,000 · 1 bd · 1 ba
• 421 west huron street 1207, Chicago 60654 Active Under Contract $279,900 · 1 bd · 1 ba · 784 sqft
• 7048 west 72nd place, Chicago 60638 Active Under Contract $275,000 · 4 bd · 2 ba · 2,011 sqft
• 5730 south washtenaw avenue, Chicago 60629 Active Under Contract $280,000 · 5 bd · 2 ba · 836 sqft
• 1426 west 112th place, Chicago 60643 Active Under Contract $129,900 · 2 bd · 2 ba · 876 sqft
• 1122 north clark street 2302, Chicago 60610 Active Under Contract $199,000 · 1 ba
• 4819 west race avenue, Chicago 60644 Active Under Contract $189,900 · 3 bd · 2 ba · 1,100 sqft
• 780 south federal street 405, Chicago 60605 Active Under Contract $185,000 · 1 bd · 1 ba
• 1446 east 71st place, Chicago 60619 Active Under Contract $199,900 · 4 bd · 2 ba · 1,700 sqft
• 4850 south lake park avenue 1201, Chicago 60615 Active Under Contract $75,000 · 3 bd · 2 ba · 1,500 sqft
• 3217 west bryn mawr avenue 201, Chicago 60659 Active Under Contract $270,000 · 2 bd · 2 ba · 1,200 sqft
• 3930 north pine grove avenue 2708, Chicago 60613 Active Under Contract $210,000 · 1 bd · 1 ba · 775 sqft
• 2307 west haddon avenue a, Chicago 60622 Active Under Contract $220,000 · 1 bd · 1 ba
• 1511 south karlov avenue, Chicago 60623 Active Under Contract $295,000 · 3 bd · 2 ba · 1,588 sqft
• 535 north michigan avenue 3211, Chicago 60611 Active Under Contract $259,900 · 1 bd · 1 ba · 755 sqft
• 3460 north harlem avenue 1b, Chicago 60634 Active Under Contract $238,000 · 2 bd · 2 ba
• 1209 east 53rd street 1, Chicago 60615 Active Under Contract $240,000 · 2 bd · 2 ba
• 645 north kingsbury street 1207, Chicago 60610 Active Under Contract $249,999 · 1 bd · 1 ba · 650 sqft