Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 50 of 92

• 6400 north ridge boulevard 402, Chicago 60626 Active Under Contract $225,000 · 2 bd · 2 ba · 1,002 sqft
• 3039 south millard avenue, Chicago 60623 Active Under Contract $299,900 · 3 bd · 3 ba · 1,500 sqft
• 12109 south indiana avenue, Chicago 60628 Active Under Contract $84,900 · 2 bd · 2 ba · 889 sqft
• 4104 north mozart street 2w, Chicago 60618 Active Under Contract $265,000 · 2 bd · 1 ba
• 5701 north sheridan road 12b, Chicago 60660 Active Under Contract $209,999 · 1 bd · 1 ba · 950 sqft
• 2739 west summerdale avenue 2w, Chicago 60625 Active Under Contract $255,000 · 3 bd · 1 ba · 1,000 sqft
• 5000 south east end avenue 2a, Chicago 60615 Active Under Contract $180,000 · 3 bd · 3 ba · 2,600 sqft
• 1354 west greenleaf avenue 1b, Chicago 60626 Active Under Contract $229,000 · 2 bd · 1 ba
• 5415 north sheridan road 5015, Chicago 60640 Active Under Contract $250,000 · 1 bd · 1 ba · 680 sqft
• 1045 west 104th place, Chicago 60643 Active Under Contract $175,000 · 3 bd · 2 ba · 1,045 sqft
• 2323 west pershing road 609, Chicago 60609 Active Under Contract $266,000 · 2 bd · 2 ba · 1,190 sqft
• 6836 south michigan avenue, Chicago 60637 Active Under Contract $240,000 · 4 bd · 3 ba · 1,821 sqft
• 2112 west armitage avenue gs, Chicago 60647 Active Under Contract $299,900 · 2 bd · 1 ba
• 1243 west thorndale avenue 2e, Chicago 60660 Active Under Contract $265,000 · 2 bd · 1 ba · 851 sqft
• 5129 west george avenue, Chicago 60641 Active Under Contract $269,000 · 2 bd · 1 ba · 1,250 sqft
• 5323 south christiana avenue, Chicago 60632 Active Under Contract $239,999 · 4 bd · 3 ba
• 1353 west fargo avenue gw, Chicago 60626 Active Under Contract $250,000 · 2 bd · 1 ba
• 2417 west fitch avenue 1, Chicago 60645 Active Under Contract $199,900 · 2 bd · 1 ba · 811 sqft
• 1426 west cullerton street, Chicago 60608 Active Under Contract $280,000 · 4 bd · 2 ba · 1,561 sqft
• 401 east ontario street 510, Chicago 60611 Active Under Contract $275,000 · 1 bd · 1 ba · 900 sqft
• 3450 west walnut street, Chicago 60624 Active Under Contract $174,900 · 2 bd · 2 ba · 880 sqft
• 7919 south kenwood avenue, Chicago 60619 Active Under Contract $125,900 · 3 bd · 1 ba · 1,248 sqft
• 2115 west farwell avenue 511, Chicago 60645 Active Under Contract $179,900 · 2 bd · 1 ba · 900 sqft
• 7120 north sheridan road 411, Chicago 60626 Active Under Contract $145,000 · 1 bd · 1 ba · 800 sqft
• 1636 north wells street 2907, Chicago 60614 Active Under Contract $299,000 · 1 bd · 1 ba · 750 sqft
• 839 west 54th street, Chicago 60609 Active Under Contract $219,000 · 3 bd · 3 ba · 1,200 sqft
• 7151 south carpenter street, Chicago 60621 Active Under Contract $119,900 · 4 bd · 2 ba · 1,625 sqft
• 7536 north ridge boulevard 3e, Chicago 60645 Active Under Contract $224,900 · 2 bd · 2 ba · 800 sqft
• 6490 north northwest highway 1c, Chicago 60631 Active Under Contract $235,000 · 2 bd · 2 ba · 1,049 sqft
• 238 west 31st street 4w, Chicago 60616 Active Under Contract $249,000 · 3 bd · 1 ba · 1,000 sqft
• 5646 north kenmore avenue 4b, Chicago 60660 Active Under Contract $299,900 · 2 bd · 2 ba
• 8731 south carpenter street, Chicago 60620 Active Under Contract $219,000 · 4 bd · 2 ba · 1,001 sqft
• 7324 south calumet avenue, Chicago 60619 Active Under Contract $175,000 · 3 bd · 2 ba
• 1402 east 76th street, Chicago 60619 Active Under Contract $259,000 · 3 bd · 2 ba · 1,080 sqft
• 9042 south emerald avenue, Chicago 60620 Active Under Contract $265,000 · 3 bd · 2 ba · 1,300 sqft
• 10122 south wallace street, Chicago 60628 Active Under Contract $249,999 · 2 bd · 2 ba · 1,950 sqft
• 4801 south princeton avenue, Chicago 60609 Active Under Contract $34,900 · 4 bd · 2 ba · 1,170 sqft
• 8 west monroe street 2001, Chicago 60603 Active Under Contract $225,000 · 1 bd · 1 ba
• 6912 south woodlawn avenue, Chicago 60637 Active Under Contract $74,900 · 3 bd · 2 ba · 1,338 sqft
• 6142 south kildare avenue, Chicago 60629 Active Under Contract $290,000 · 3 bd · 2 ba · 1,648 sqft
• 1033 east 46th street 406, Chicago 60653 Active Under Contract $275,000 · 2 bd · 2 ba · 1,450 sqft
• 211 east ohio street 2623, Chicago 60611 Active Under Contract $214,900 · 1 ba
• 3804 north hamilton avenue 2n, Chicago 60618 Active Under Contract $255,000 · 1 bd · 1 ba
• 550 west surf street 104, Chicago 60657 Active Under Contract $265,000 · 1 bd · 1 ba
• 17 west 35th street 304, Chicago 60616 Active Under Contract $260,000 · 2 bd · 1 ba · 1,000 sqft
• 731 west bittersweet place 2s, Chicago 60613 Active Under Contract $275,000 · 2 bd · 1 ba · 900 sqft
• 3600 north lake shore drive 2324, Chicago 60613 Active Under Contract $229,000 · 1 bd · 1 ba · 900 sqft
• 10519 south pulaski road, Chicago 60655 Active Under Contract $225,000 · 3 bd · 2 ba · 800 sqft
• 5314 north glenwood avenue 1w, Chicago 60640 Active Under Contract $280,000 · 1 bd · 1 ba · 700 sqft
• 334 west 101st place, Chicago 60628 Active Under Contract $299,900 · 3 bd · 2 ba