Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 53 of 92

• 3033 north sheridan road 403, Chicago 60657 Active Under Contract $269,900 · 1 bd · 1 ba · 723 sqft
• 900 north lake shore drive 1905, Chicago 60611 Active Under Contract $249,000 · 1 ba · 645 sqft
• 835 west lawrence avenue 2n, Chicago 60640 Active Under Contract $235,000 · 1 bd · 1 ba
• 6815 north lakewood avenue 3n, Chicago 60626 Active Under Contract $205,000 · 1 bd · 1 ba · 742 sqft
• 12018 south wentworth avenue, Chicago 60628 Active Under Contract $184,999 · 3 bd · 3 ba · 1,725 sqft
• 1105 west 115th street, Chicago 60643 Active Under Contract $150,000 · 3 bd · 1 ba · 1,000 sqft
• 8423 south wolcott avenue, Chicago 60620 Active Under Contract $195,000 · 2 bd · 1 ba
• 29 west 109th place, Chicago 60628 Active Under Contract $74,700 · 4 bd · 1 ba · 901 sqft
• 18 west 114th street, Chicago 60628 Active Under Contract $80,000 · 3 bd · 2 ba · 1,320 sqft
• 9505 south racine avenue, Chicago 60643 Active Under Contract $120,000 · 2 bd · 2 ba · 1,298 sqft
• 1225 west granville avenue 3a, Chicago 60660 Active Under Contract $244,900 · 1 bd · 1 ba
• 900 north lake shore drive 2308, Chicago 60611 Active Under Contract $275,000 · 1 bd · 1 ba · 887 sqft
• 1345 west greenleaf avenue 3s, Chicago 60626 Active Under Contract $239,900 · 2 bd · 1 ba
• 3900 north lake shore drive 14f, Chicago 60613 Active Under Contract $140,000 · 1 bd · 1 ba · 850 sqft
• 7854 south south shore drive 513, Chicago 60649 Active Under Contract $24,250 · 1 ba · 800 sqft
• 13160 south forrestville avenue, Chicago 60827 Active Under Contract $114,900 · 2 bd · 2 ba · 800 sqft
• 3816 west 84th place, Chicago 60652 Active Under Contract $260,000 · 3 bd · 2 ba · 1,060 sqft
• 5415 north sheridan road 2905, Chicago 60640 Active Under Contract $269,900 · 1 bd · 1 ba · 795 sqft
• 9343 south throop street, Chicago 60620 Active Under Contract $115,000 · 5 bd · 1 ba · 1,317 sqft
• 6325 north sheridan road 2106, Chicago 60660 Active Under Contract $150,000 · 1 bd · 1 ba · 865 sqft
• 2011 west chase avenue 2, Chicago 60645 Active Under Contract $274,500 · 1 bd · 1 ba · 1,142 sqft
• 801 south plymouth court 807, Chicago 60605 Active Under Contract $205,000 · 1 bd · 1 ba · 900 sqft
• 500 south clinton street 632, Chicago 60607 Active Under Contract $239,000 · 1 bd · 1 ba · 872 sqft
• 3650 west 68th street, Chicago 60629 Active Under Contract $260,000 · 2 bd · 1 ba · 1,100 sqft
• 420 west aldine avenue 225, Chicago 60657 Active Under Contract $199,900 · 1 bd · 1 ba · 650 sqft
• 3950 west glenlake avenue a, Chicago 60659 Active Under Contract $175,000 · 3 bd · 2 ba
• 8350 west addison street 202, Chicago 60634 Active Under Contract $209,900 · 1 bd · 1 ba · 950 sqft
• 8534 south vernon avenue, Chicago 60619 Active Under Contract $115,000 · 3 bd · 2 ba · 1,475 sqft
• 400 west ontario street 1404, Chicago 60654 Active Under Contract $250,000 · 1 bd · 1 ba · 900 sqft
• 3923 west ainslie street 1e, Chicago 60625 Active Under Contract $290,000 · 3 bd · 2 ba · 1,400 sqft
• 9130 south indiana avenue, Chicago 60619 Active Under Contract $244,900 · 3 bd · 2 ba · 1,430 sqft
• 474 north lake shore drive 1803, Chicago 60611 Active Under Contract $270,000 · 1 bd · 1 ba · 741 sqft
• 6925 south maplewood avenue, Chicago 60629 Active Under Contract $218,900 · 3 bd · 1 ba · 1,345 sqft
• 1819 west touhy avenue 4, Chicago 60626 Active Under Contract $265,000 · 2 bd · 2 ba · 1,200 sqft
• 8701 west foster avenue 307, Chicago 60656 Active Under Contract $199,900 · 2 bd · 2 ba · 950 sqft
• 6525 north nashville avenue 403d, Chicago 60631 Active Under Contract $249,000 · 2 bd · 2 ba · 930 sqft
• 5551 south kimbark avenue 8, Chicago 60637 Active Under Contract $149,000 · 1 bd · 1 ba · 900 sqft
• 6733 south campbell avenue, Chicago 60629 Active Under Contract $264,900 · 3 bd · 2 ba · 1,083 sqft
• 4719 south kilpatrick avenue, Chicago 60632 Active Under Contract $250,000 · 2 bd · 2 ba · 960 sqft
• 8446 south marshfield avenue, Chicago 60620 Active Under Contract $259,000 · 4 bd · 2 ba · 1,569 sqft
• 1652 west montvale avenue, Chicago 60643 Active Under Contract $195,000 · 3 bd · 2 ba
• 11312 south avenue g, Chicago 60617 Active Under Contract $230,000 · 3 bd · 1 ba · 900 sqft
• 400 north la salle drive 3306, Chicago 60654 Active Under Contract $227,497 · 1 ba · 515 sqft
• 2619 west agatite avenue 2a, Chicago 60625 Active Under Contract $285,000 · 2 bd · 1 ba · 950 sqft
• 2610 west balmoral avenue 103, Chicago 60625 Active Under Contract $148,250 · 1 bd · 1 ba
• 4852 north sacramento avenue g, Chicago 60625 Active Under Contract $207,500 · 2 bd · 1 ba · 1,000 sqft
• 4850 south lake park avenue 2109b, Chicago 60615 Active Under Contract $40,000 · 2 bd · 1 ba
• 8412 south seeley avenue, Chicago 60620 Active Under Contract $215,000 · 3 bd · 2 ba · 1,300 sqft
• 7917 south tripp avenue, Chicago 60652 Active Under Contract $291,900 · 3 bd · 1 ba · 1,024 sqft
• 7653 south honore street, Chicago 60620 Active Under Contract $85,000 · 3 bd · 2 ba · 1,194 sqft