Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 51 of 92

• 12344 south union avenue, Chicago 60628 Active Under Contract $99,900 · 4 bd · 2 ba · 1,100 sqft
• 1250 south indiana avenue 307, Chicago 60605 Active Under Contract $299,000 · 1 bd · 1 ba · 881 sqft
• 21 west goethe street 5g, Chicago 60610 Active Under Contract $265,000 · 1 bd · 1 ba · 850 sqft
• 715 west barry avenue 5b, Chicago 60657 Active Under Contract $249,900 · 1 bd · 1 ba · 650 sqft
• 1525 south michigan avenue 212, Chicago 60605 Active Under Contract $245,000 · 1 bd · 1 ba · 1,000 sqft
• 405 north wabash avenue 1801, Chicago 60611 Active Under Contract $249,000 · 1 bd · 1 ba · 725 sqft
• 6328 north bell avenue g, Chicago 60659 Active Under Contract $205,000 · 2 bd · 1 ba · 1,150 sqft
• 6137 north hoyne avenue 2, Chicago 60659 Active Under Contract $190,000 · 2 bd · 1 ba · 900 sqft
• 5700 west montrose avenue 3d, Chicago 60634 Active Under Contract $220,000 · 2 bd · 1 ba · 1,000 sqft
• 8834 south oglesby avenue, Chicago 60617 Active Under Contract $289,900 · 3 bd · 2 ba · 1,114 sqft
• 4338 south mozart street, Chicago 60632 Active Under Contract $269,900 · 4 bd · 2 ba · 1,820 sqft
• 5401 south hyde park boulevard 401, Chicago 60615 Active Under Contract $240,000 · 2 bd · 2 ba · 1,200 sqft
• 4422 north ashland avenue 1e, Chicago 60640 Active Under Contract $225,000 · 1 bd · 1 ba · 650 sqft
• 400 east randolph street 1812, Chicago 60601 Active Under Contract $274,900 · 1 bd · 1 ba
• 4307 north troy street 2, Chicago 60618 Active Under Contract $269,900 · 2 bd · 1 ba · 797 sqft
• 6123 north winchester avenue 2a, Chicago 60660 Active Under Contract $150,000 · 3 bd · 1 ba · 900 sqft
• 11540 south peoria street sfr, Chicago 60643 Active Under Contract $124,999 · 3 bd · 2 ba · 750 sqft
• 6255 west 63rd street 1b, Chicago 60638 Active Under Contract $234,900 · 2 bd · 1 ba · 950 sqft
• 1825 west 115th street, Chicago 60643 Active Under Contract $259,900 · 3 bd · 4 ba · 1,722 sqft
• 2641 west fitch avenue 2, Chicago 60645 Active Under Contract $215,000 · 2 bd · 2 ba · 1,100 sqft
• 6845 south chappel avenue, Chicago 60649 Active Under Contract $260,000 · 4 bd · 3 ba · 1,866 sqft
• 2115 west 68th place, Chicago 60636 Active Under Contract $260,000 · 3 bd · 2 ba · 1,040 sqft
• 2921 south michigan avenue 109, Chicago 60616 Active Under Contract $118,500 · 1 bd · 1 ba · 750 sqft
• 125 south jefferson street 1905, Chicago 60661 Active Under Contract $275,000 · 1 bd · 1 ba · 620 sqft
• 5201 south cornell avenue 27d, Chicago 60615 Active Under Contract $299,900 · 2 bd · 2 ba · 1,700 sqft
• 1300 east 87th street, Chicago 60619 Active Under Contract $109,900 · 2 bd · 2 ba · 1,067 sqft
• 6416 west 64th place 3a, Chicago 60638 Active Under Contract $195,000 · 2 bd · 1 ba · 900 sqft
• 6301 north sheridan road 3d, Chicago 60660 Active Under Contract $125,000 · 1 bd · 1 ba
• 1148 west 115th street, Chicago 60643 Active Under Contract $265,000 · 3 bd · 2 ba · 2,012 sqft
• 5050 south east end avenue 10c, Chicago 60615 Active Under Contract $125,000 · 3 bd · 2 ba
• 5218 north delphia avenue 309, Chicago 60656 Active Under Contract $237,000 · 2 bd · 2 ba · 1,000 sqft
• 253 east delaware place 5e, Chicago 60611 Active Under Contract $155,000 · 1 bd · 1 ba
• 3950 north lake shore drive 2202, Chicago 60613 Active Under Contract $299,500 · 3 bd · 2 ba · 1,100 sqft
• 1629 west north shore avenue 103, Chicago 60626 Active Under Contract $249,000 · 2 bd · 2 ba · 950 sqft
• 5952 north lakewood avenue 2w, Chicago 60660 Active Under Contract $235,000 · 1 bd · 1 ba · 805 sqft
• 7130 south hermitage avenue, Chicago 60636 Active Under Contract $209,900 · 4 bd · 2 ba · 1,450 sqft
• 5445 north sheridan road 2008, Chicago 60640 Active Under Contract $229,900 · 1 bd · 1 ba · 850 sqft
• 10723 south avenue d, Chicago 60617 Active Under Contract $135,000 · 3 bd · 1 ba · 1,008 sqft
• 3544 west 63rd place, Chicago 60629 Active Under Contract $265,000 · 2 bd · 2 ba
• 400 west ontario street 1508, Chicago 60654 Active Under Contract $299,900 · 1 bd · 1 ba · 900 sqft
• 5616 north kenmore avenue 3d, Chicago 60660 Active Under Contract $117,500 · 1 ba
• 5300 south shore drive 59, Chicago 60615 Active Under Contract $139,999 · 2 bd · 2 ba · 1,516 sqft
• 3318 west columbus avenue, Chicago 60652 Active Under Contract $270,000 · 3 bd · 1 ba · 1,020 sqft
• 3434 west leland avenue 3e, Chicago 60625 Active Under Contract $200,000 · 1 bd · 1 ba
• 105 south waller avenue, Chicago 60644 Active Under Contract $150,000 · 4 bd · 4 ba · 2,000 sqft
• 1224 west van buren street 517, Chicago 60607 Active Under Contract $295,000 · 2 bd · 1 ba · 1,000 sqft
• 6410 north hoyne avenue 2w, Chicago 60645 Active Under Contract $274,900 · 3 bd · 2 ba · 1,000 sqft
• 474 north lake shore drive 5509, Chicago 60611 Active Under Contract $289,900 · 1 bd · 1 ba · 750 sqft
• 8001 south oglesby avenue, Chicago 60617 Active Under Contract $289,900 · 4 bd · 4 ba · 3,263 sqft
• 6112 north damen avenue 2, Chicago 60659 Active Under Contract $184,990 · 3 bd · 1 ba · 1,000 sqft