Homes under $300K in Chicago, IL

1,323 for sale · 4,569 homes listed · Updated September 29, 2026 · Page 65 of 92

2325 north neva avenue 204b, Chicago 60707 Off market since Sep 2026 $159,000 · 1 bd · 1 ba · 600 sqft
8 west monroe street 1007, Chicago 60603 Off market since Jul 2026 $299,500 · 2 bd · 2 ba · 1,080 sqft
11401 south morgan street, Chicago 60643 Off market since Sep 2026 $210,000 · 3 bd · 2 ba · 1,272 sqft
6700 south crandon avenue 6c, Chicago 60649 Off market since Sep 2026 $185,000 · 3 bd · 3 ba · 1,850 sqft
7139 south winchester avenue, Chicago 60636 Off market since Jul 2026 $87,000 · 4 bd · 2 ba · 2,000 sqft
2342 west adams street 208, Chicago 60612 Off market since Jul 2026 $299,000 · 1 bd · 1 ba · 780 sqft
11265 south may street, Chicago 60643 Off market since Sep 2026 $165,000 · 3 bd · 1 ba · 756 sqft
7535 south vernon avenue, Chicago 60619 Off market since Jul 2026 $174,999 · 4 bd · 2 ba · 1,969 sqft
11534 south princeton avenue, Chicago 60628 Off market since Jul 2026 $69,900 · 3 bd · 1 ba · 1,650 sqft
6933 south michigan avenue 0, Chicago 60637 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,173 sqft
10134 south bensley avenue, Chicago 60617 Off market since Sep 2026 $260,000 · 5 bd · 2 ba · 1,310 sqft
6348 south rhodes avenue, Chicago 60637 Off market since Aug 2026 $235,000 · 3 bd · 2 ba · 2,215 sqft
3001 south michigan avenue 1006, Chicago 60616 Off market since Jul 2026 $110,000 · 1 ba · 600 sqft
8745 south euclid avenue, Chicago 60617 Off market since Aug 2026 $239,900 · 3 bd · 2 ba · 1,248 sqft
3900 north lake shore drive 2b, Chicago 60613 Off market since Jul 2026 $195,000 · 1 bd · 1 ba · 800 sqft
600 south dearborn street 803, Chicago 60605 Off market since Jul 2026 $235,000 · 1 bd · 1 ba · 914 sqft
1451 east 55th street 225n, Chicago 60615 Off market since Aug 2026 $159,000 · 2 bd · 1 ba
8417 south scottsdale avenue, Chicago 60652 Off market since Jul 2026 $251,500 · 4 bd · 1 ba · 1,000 sqft
9823 south drexel avenue, Chicago 60628 Off market since Sep 2026 $240,000 · 2 bd · 2 ba · 779 sqft
222 north columbus drive 2207, Chicago 60601 Off market since Aug 2026 $265,000 · 1 bd · 1 ba · 700 sqft
2342 west adams street 202, Chicago 60612 Off market since Jul 2026 $299,000 · 1 bd · 1 ba · 780 sqft
11243 south vernon avenue, Chicago 60628 Off market since Sep 2026 $210,000 · 3 bd · 3 ba · 1,428 sqft
1712 north washtenaw avenue g, Chicago 60647 Off market since Sep 2026 $215,000 · 2 bd · 1 ba · 700 sqft
253 east delaware place 7h, Chicago 60611 Off market since Sep 2026 $164,900 · 1 ba · 572 sqft
1018 west 104th place, Chicago 60643 Off market since Sep 2026 $149,000 · 3 bd · 2 ba · 1,353 sqft
2205 west highland avenue 1n, Chicago 60659 Off market since Sep 2026 $165,000 · 1 bd · 1 ba · 800 sqft
912 west 87th street, Chicago 60620 Off market since Jul 2026 $69,000 · 4 bd · 2 ba · 1,350 sqft
6316 west montrose avenue 102, Chicago 60634 Off market since Sep 2026 $269,900 · 2 bd · 1 ba · 1,200 sqft
5401 south hyde park boulevard 1101, Chicago 60615 Off market since Sep 2026 $210,000 · 2 bd · 2 ba · 1,000 sqft
3560 south giles avenue g, Chicago 60653 Off market since Aug 2026 $230,000 · 2 bd · 2 ba · 1,200 sqft
4826 south kolin avenue, Chicago 60632 Sold on Jul 17, 2026 $269,900 · 3 bd · 3 ba
545 north dearborn street w3005, Chicago 60654 Off market since Jul 2026 $290,000 · 1 bd · 1 ba · 729 sqft
7949 south manistee avenue, Chicago 60617 Off market since Sep 2026 $159,900 · 3 bd · 2 ba · 1,334 sqft
819 east 98th place, Chicago 60628 Off market since Jul 2026 $285,000 · 4 bd · 2 ba · 1,217 sqft
601 east 32nd street 403, Chicago 60616 Off market since Sep 2026 $129,000 · 1 ba · 420 sqft
7939 south ingleside avenue c, Chicago 60619 Off market since Sep 2026 $115,000 · 2 bd · 2 ba
6301 north sheridan road 18e, Chicago 60660 Off market since Jul 2026 $259,900 · 2 bd · 2 ba · 1,225 sqft
8519 south king drive, Chicago 60619 Off market since Sep 2026 $244,900 · 4 bd · 2 ba · 1,211 sqft
700 west van buren street 602, Chicago 60607 Off market since Sep 2026 $295,000 · 1 bd · 1 ba · 850 sqft
260 east chestnut street 409, Chicago 60611 Off market since Sep 2026 $184,900 · 1 ba
235 west van buren street 2918, Chicago 60607 Off market since Sep 2026 $240,000 · 1 bd · 1 ba
7331 south peoria street, Chicago 60621 Off market since Sep 2026 $59,000 · 3 bd · 1 ba · 1,200 sqft
7000 south eberhart avenue, Chicago 60637 Off market since Sep 2026 $299,900 · 3 bd · 3 ba · 2,000 sqft
6103 south kimbark avenue 3e, Chicago 60637 Off market since Sep 2026 $220,000 · 2 bd · 1 ba · 1,000 sqft
4815 south champlain avenue 2, Chicago 60615 Off market since Aug 2026 $240,000 · 3 bd · 2 ba · 1,600 sqft
3506 south state street 303, Chicago 60609 Off market since Sep 2026 $279,000 · 2 bd · 2 ba · 1,136 sqft
6700 south south shore drive 25k, Chicago 60649 Off market since Aug 2026 $109,900 · 1 ba · 800 sqft
827 east 48th street c, Chicago 60615 Off market since Aug 2026 $164,000 · 2 bd · 1 ba · 1,125 sqft
2481 east 74th street, Chicago 60649 Off market since Sep 2026 $299,000 · 5 bd · 2 ba · 2,400 sqft
10 east ontario street 905, Chicago 60611 Off market since Jul 2026 $285,900 · 1 bd · 1 ba · 995 sqft