Chicago, IL Investment Properties for Sale
Browse homes for sale and investment properties in Chicago, IL. Refine your search by price, property type, or more.
Best cash flowing properties in Chicago, IL
Active
$60,000
3
bds
|
1
ba
|
840
sqft
|
built
1898
10803 S Edbrooke Ave, Chicago, IL 60628
$1,090
Cash flow
21.2%
Cash-on-Cash Return
21.8%
Cap rate
2.8%
Rent to Value Ratio
Active
$214,900
4
bds
|
2
ba
|
1,603
sqft
|
built
1924
1404 W 97th St, Chicago, IL 60643
$756
Cash flow
18.4%
Cash-on-Cash Return
9.9%
Cap rate
1.3%
Rent to Value Ratio
3,742 out of 4,294 properties for sale in Chicago, IL
Limited Results Shown
Create a free account, or log in to reveal all property listings and enjoy the complete experience.
Active under contract
$319,900
2
bds
|
2
ba
|
1,200
sqft
|
built
1989
6430 W Belle Plaine Ave, Chicago, IL 60634
$-512
Cash flow
-8.4%
Cash-on-Cash Return
3.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$420,000
4
bds
|
3
ba
|
3,000
sqft
|
built
1920
7427 S Bennett Ave, Chicago, IL 60649
$125
Cash flow
1.6%
Cash-on-Cash Return
6.0%
Cap rate
0.9%
Rent to Value Ratio
Active
$825,000
6
bds
|
3
ba
|
2,120
sqft
|
built
1918
2231 N Lawndale Ave, Chicago, IL 60647
$-1,952
Cash flow
-12.3%
Cash-on-Cash Return
2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$169,900
1
bds
|
1
ba
|
600
sqft
|
built
1974
4343 N Clarendon Ave, Chicago, IL 60613
$-409
Cash flow
-12.6%
Cash-on-Cash Return
2.8%
Cap rate
1.1%
Rent to Value Ratio
Active
$449,900
2
bds
|
1
ba
|
0
sqft
|
built
1970
1560 N Sandburg Ter, Chicago, IL 60610
$-812
Cash flow
-9.4%
Cash-on-Cash Return
3.5%
Cap rate
0.8%
Rent to Value Ratio
Active
$615,000
6
bds
|
4
ba
|
2,870
sqft
|
built
1902
10628 S Longwood Dr, Chicago, IL 60643
$-945
Cash flow
-8.0%
Cash-on-Cash Return
3.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$349,000
2
bds
|
2
ba
|
1,200
sqft
|
built
2004
1503 S State St, Chicago, IL 60605
$-706
Cash flow
-10.6%
Cash-on-Cash Return
3.3%
Cap rate
0.8%
Rent to Value Ratio
Active
$4,500,000
6
bds
|
9
ba
|
0
sqft
|
built
2010
446 W Huron St, Chicago, IL 60654
$-21,010
Cash flow
-24.4%
Cash-on-Cash Return
0.1%
Cap rate
0.2%
Rent to Value Ratio
Active
$444,900
2
bds
|
1
ba
|
0
sqft
|
built
1974
405 N Wabash Ave, Chicago, IL 60611
$-852
Cash flow
-10.0%
Cash-on-Cash Return
3.4%
Cap rate
0.9%
Rent to Value Ratio
Active
$309,900
2
bds
|
2
ba
|
1,200
sqft
|
built
1991
6433 W Belle Plaine Ave, Chicago, IL 60634
$-551
Cash flow
-9.3%
Cash-on-Cash Return
3.5%
Cap rate
0.7%
Rent to Value Ratio
Active
$459,900
4
bds
|
2
ba
|
1,332
sqft
|
built
1925
4843 W Schubert Ave, Chicago, IL 60639
$-407
Cash flow
-4.6%
Cash-on-Cash Return
4.6%
Cap rate
0.7%
Rent to Value Ratio
Active
$294,900
3
bds
|
2
ba
|
1,234
sqft
|
built
1954
10201 S California Ave, Chicago, IL 60655
$123
Cash flow
2.2%
Cash-on-Cash Return
6.2%
Cap rate
0.9%
Rent to Value Ratio
Active
$445,000
4
bds
|
3
ba
|
2,156
sqft
|
built
1898
3425 W Carroll Ave, Chicago, IL 60624
$-104
Cash flow
-1.2%
Cash-on-Cash Return
5.4%
Cap rate
0.7%
Rent to Value Ratio
Active
$565,000
1
bds
|
2
ba
|
1,244
sqft
|
built
2007
340 E Randolph St, Chicago, IL 60601
$-1,808
Cash flow
-16.7%
Cash-on-Cash Return
1.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$339,000
1
bds
|
1
ba
|
741
sqft
|
built
2003
1255 N Orleans St, Chicago, IL 60610
$-994
Cash flow
-15.3%
Cash-on-Cash Return
2.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$364,900
4
bds
|
3
ba
|
0
sqft
|
built
1923
7755 S Wolcott Ave, Chicago, IL 60620
$-682
Cash flow
-9.8%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$299,900
3
bds
|
2
ba
|
1,000
sqft
|
built
1922
8235 S Woodlawn Ave, Chicago, IL 60619
$-353
Cash flow
-6.1%
Cash-on-Cash Return
4.3%
Cap rate
0.6%
Rent to Value Ratio
Active
$800,000
6
bds
|
3
ba
|
0
sqft
|
built
1898
2909 N Hoyne Ave, Chicago, IL 60618
$-2,758
Cash flow
-18.0%
Cash-on-Cash Return
1.5%
Cap rate
0.4%
Rent to Value Ratio
Active under contract
$599,900
6
bds
|
3
ba
|
0
sqft
|
built
1923
5236 W Nelson St, Chicago, IL 60641
$-977
Cash flow
-8.5%
Cash-on-Cash Return
3.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$214,900
4
bds
|
2
ba
|
1,603
sqft
|
built
1924
1404 W 97th St, Chicago, IL 60643
$756
Cash flow
18.4%
Cash-on-Cash Return
9.9%
Cap rate
1.3%
Rent to Value Ratio
Active
$849,999
3
bds
|
4
ba
|
4,100
sqft
|
built
1904
4825 W Ainslie St, Chicago, IL 60630
$-2,376
Cash flow
-14.6%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$250,000
2
bds
|
1
ba
|
1,035
sqft
|
built
1900
3348 N Narragansett Ave, Chicago, IL 60634
$278
Cash flow
5.8%
Cash-on-Cash Return
7.0%
Cap rate
1.0%
Rent to Value Ratio
Active
$60,000
3
bds
|
1
ba
|
840
sqft
|
built
1898
10803 S Edbrooke Ave, Chicago, IL 60628
$1,090
Cash flow
21.2%
Cash-on-Cash Return
21.8%
Cap rate
2.8%
Rent to Value Ratio
Active under contract
$380,000
3
bds
|
2
ba
|
1,261
sqft
|
built
1978
7141 W 72nd St, Chicago, IL 60638
$-364
Cash flow
-5.0%
Cash-on-Cash Return
4.5%
Cap rate
0.7%
Rent to Value Ratio
Active under contract
$499,900
4
bds
|
2
ba
|
2,098
sqft
|
built
1940
3836 N Pioneer Ave, Chicago, IL 60634
$-647
Cash flow
-6.8%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$560,000
3
bds
|
5
ba
|
2,600
sqft
|
built
2012
4355 S Lake Park Ave, Chicago, IL 60653
$-1,151
Cash flow
-10.7%
Cash-on-Cash Return
3.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$575,000
3
bds
|
2
ba
|
1,500
sqft
|
built
2018
3037 W Belmont Ave, Chicago, IL 60618
$-614
Cash flow
-5.6%
Cash-on-Cash Return
4.4%
Cap rate
0.8%
Rent to Value Ratio
Active
$919,000
8
bds
|
6
ba
|
0
sqft
|
built
1911
4933 S Wabash Ave, Chicago, IL 60615
$-1,516
Cash flow
-8.6%
Cash-on-Cash Return
3.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,350,000
4
bds
|
3
ba
|
3,200
sqft
|
built
2015
2503 N Maplewood Ave, Chicago, IL 60647
$-4,516
Cash flow
-17.5%
Cash-on-Cash Return
1.7%
Cap rate
0.4%
Rent to Value Ratio
Active under contract
$420,000
3
bds
|
2
ba
|
1,132
sqft
|
built
1921
1205 W Sherwin Ave, Chicago, IL 60626
$-1,916
Cash flow
-23.8%
Cash-on-Cash Return
0.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$675,000
3
bds
|
4
ba
|
2,763
sqft
|
built
1890
1940 S Racine Ave, Chicago, IL 60608
$-1,771
Cash flow
-13.7%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$384,999
2
bds
|
1
ba
|
1,000
sqft
|
built
2003
1435 N Mohawk St, Chicago, IL 60610
$-780
Cash flow
-10.6%
Cash-on-Cash Return
3.2%
Cap rate
0.6%
Rent to Value Ratio
Active under contract
$339,000
2
bds
|
2
ba
|
1,000
sqft
|
built
1941
2916 N Melvina Ave, Chicago, IL 60634
$-363
Cash flow
-5.6%
Cash-on-Cash Return
4.4%
Cap rate
0.7%
Rent to Value Ratio
Pending
$344,900
1
bds
|
1
ba
|
0
sqft
|
built
2001
600 N Dearborn St, Chicago, IL 60654
$-1,002
Cash flow
-15.2%
Cash-on-Cash Return
2.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$550,000
3
bds
|
3
ba
|
1,337
sqft
|
built
1960
5654 N Manor Ln, Chicago, IL 60631
$-1,001
Cash flow
-9.5%
Cash-on-Cash Return
3.5%
Cap rate
0.6%
Rent to Value Ratio
Active under contract
$399,900
3
bds
|
2
ba
|
1,800
sqft
|
built
2008
5010 W Lawrence Ave, Chicago, IL 60630
$-864
Cash flow
-11.3%
Cash-on-Cash Return
3.1%
Cap rate
0.7%
Rent to Value Ratio
Active
$149,000
2
bds
|
2
ba
|
1,092
sqft
|
built
1925
8723 S Hermitage Ave, Chicago, IL 60620
$671
Cash flow
23.5%
Cash-on-Cash Return
11.1%
Cap rate
1.5%
Rent to Value Ratio
Active
$330,000
1
bds
|
1
ba
|
600
sqft
|
built
1997
1645 W School St, Chicago, IL 60657
$-213
Cash flow
-3.4%
Cash-on-Cash Return
4.9%
Cap rate
0.8%
Rent to Value Ratio
Active
$349,900
3
bds
|
3
ba
|
900
sqft
|
built
1912
5512 W Wrightwood Ave, Chicago, IL 60639
$-361
Cash flow
-5.4%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
Rent to Value Ratio
Active under contract
$310,000
4
bds
|
3
ba
|
2,476
sqft
|
built
1925
6721 S Ada St, Chicago, IL 60636
$-630
Cash flow
-10.6%
Cash-on-Cash Return
3.2%
Cap rate
0.4%
Rent to Value Ratio