5 Bedroom Homes in Chicago, IL

192 for sale · 407 homes listed · Updated September 27, 2026 · Page 5 of 9

• 6330 north paulina street, Chicago 60660 Pending $895,000 · 5 bd · 3 ba
• 11727 south normal avenue, Chicago 60628 Active Under Contract $90,000 · 5 bd · 1 ba
• 1201 east 56th street, Chicago 60637 Active Under Contract $1,495,000 · 5 bd · 4 ba · 3,564 sqft
• 7549 south michigan avenue, Chicago 60619 Active Under Contract $350,000 · 5 bd · 2 ba · 945 sqft
• 5643 north glenwood avenue, Chicago 60660 Active Under Contract $2,500,000 · 5 bd · 4 ba · 4,800 sqft
• 1838 north burling street, Chicago 60614 Active Under Contract $7,750,000 · 5 bd · 5 ba · 6,031 sqft
• 5247 south neva avenue, Chicago 60638 Active Under Contract $496,000 · 5 bd · 2 ba · 1,992 sqft
• 4827 north harding avenue, Chicago 60625 Active Under Contract $767,700 · 5 bd · 3 ba · 3,472 sqft
• 1816 north hudson avenue, Chicago 60614 Active Under Contract $2,875,000 · 5 bd · 5 ba · 4,308 sqft
• 5415 west rice street, Chicago 60651 Active Under Contract $449,900 · 5 bd · 3 ba · 2,200 sqft
• 7047 south eberhart avenue, Chicago 60637 Active Under Contract $124,900 · 5 bd · 3 ba · 2,400 sqft
• 2531 west morse avenue, Chicago 60645 Active Under Contract $635,000 · 5 bd · 3 ba · 2,398 sqft
• 7317 west myrtle avenue, Chicago 60631 Active Under Contract $649,000 · 5 bd · 3 ba · 3,900 sqft
• 5530 south merrimac avenue, Chicago 60638 Active Under Contract $450,000 · 5 bd · 3 ba · 2,750 sqft
• 8106 south burnham avenue, Chicago 60617 Active Under Contract $105,000 · 5 bd · 2 ba · 1,080 sqft
• 7616 south langley avenue, Chicago 60619 Active Under Contract $435,000 · 5 bd · 3 ba · 1,612 sqft
• 8641 south kingston avenue, Chicago 60617 Active Under Contract $329,900 · 5 bd · 3 ba
• 4326 west washington boulevard, Chicago 60624 Active Under Contract $385,000 · 5 bd · 3 ba · 1,600 sqft
• 1201 east madison park drive 3, Chicago 60615 Active Under Contract $799,900 · 5 bd · 3 ba · 3,200 sqft
• 473 north clinton street, Chicago 60654 Active Under Contract $1,499,900 · 5 bd · 4 ba · 3,447 sqft
• 6108 south bishop street, Chicago 60636 Active Under Contract $169,900 · 5 bd · 2 ba · 1,176 sqft
• 10708 south avenue east, Chicago 60617 Active Under Contract $330,000 · 5 bd · 2 ba · 3,300 sqft
• 8844 south pleasant avenue, Chicago 60643 Active Under Contract $1,200,000 · 5 bd · 6 ba · 5,000 sqft
• 12242 south normal avenue, Chicago 60628 Active Under Contract $200,000 · 5 bd · 1 ba · 2,551 sqft
• 6429 south tripp avenue, Chicago 60629 Active Under Contract $499,900 · 5 bd · 3 ba · 1,232 sqft
• 7541 south merrill avenue, Chicago 60649 Active Under Contract $199,000 · 5 bd · 2 ba · 1,800 sqft
• 1518 north laramie avenue, Chicago 60651 Active Under Contract $334,900 · 5 bd · 2 ba · 1,178 sqft
• 5898 north caldwell avenue, Chicago 60646 Active Under Contract $1,299,000 · 5 bd · 5 ba · 4,791 sqft
• 12410 south stewart avenue, Chicago 60628 Active Under Contract $319,000 · 5 bd · 3 ba · 1,680 sqft
• 5311 west cuyler avenue, Chicago 60641 Active Under Contract $685,000 · 5 bd · 3 ba · 3,000 sqft
• 6142 south champlain avenue, Chicago 60637 Active Under Contract $349,900 · 5 bd · 2 ba · 3,000 sqft
• 6013 south natchez avenue, Chicago 60638 Active Under Contract $599,999 · 5 bd · 3 ba · 2,250 sqft
• 10001 south wentworth avenue, Chicago 60628 Active Under Contract $224,900 · 5 bd · 2 ba · 2,879 sqft
• 5730 south washtenaw avenue, Chicago 60629 Active Under Contract $280,000 · 5 bd · 2 ba · 836 sqft
• 6828 south champlain avenue, Chicago 60637 Active Under Contract $385,000 · 5 bd · 3 ba · 2,300 sqft
• 6551 north maplewood avenue, Chicago 60645 Active Under Contract $700,000 · 5 bd · 2 ba · 2,700 sqft
• 5038 north nagle avenue, Chicago 60630 Active Under Contract $450,000 · 5 bd · 3 ba · 2,253 sqft
• 9250 south ada street, Chicago 60620 Active Under Contract $195,000 · 5 bd · 3 ba · 1,318 sqft
• 2251 west berwyn avenue, Chicago 60625 Active Under Contract $1,650,000 · 5 bd · 4 ba · 3,344 sqft
• 4507 south prairie avenue, Chicago 60653 Active Under Contract $635,000 · 5 bd · 3 ba · 5,500 sqft
• 5310 north lockwood avenue, Chicago 60630 Active Under Contract $665,000 · 5 bd · 3 ba
• 1931 north whipple street, Chicago 60647 Active Under Contract $1,595,000 · 5 bd · 4 ba · 4,000 sqft
• 5144 north kolmar avenue, Chicago 60630 Active Under Contract $700,000 · 5 bd · 3 ba
• 5227 west berteau avenue, Chicago 60641 Active Under Contract $599,900 · 5 bd · 3 ba · 2,483 sqft
• 2835 west wellington avenue 2, Chicago 60618 Active Under Contract $450,000 · 5 bd · 2 ba
• 5725 south wolcott avenue, Chicago 60636 Active Under Contract $215,000 · 5 bd · 2 ba · 3,720 sqft
• 5801 south blackstone avenue, Chicago 60637 Active Under Contract $1,595,000 · 5 bd · 5 ba · 4,580 sqft
• 6501 south claremont avenue, Chicago 60636 Active Under Contract $329,000 · 5 bd · 3 ba · 1,400 sqft
• 8140 south elizabeth street, Chicago 60620 Active Under Contract $299,000 · 5 bd · 3 ba · 2,200 sqft
• 2229 west farragut avenue, Chicago 60625 Active Under Contract $1,650,000 · 5 bd · 5 ba · 4,200 sqft