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
$89,900
3
bds
|
2
ba
|
1,000
sqft
|
built
1885
527 N Springfield Ave, Chicago, IL 60624
$839
Cash flow
48.7%
Cash-on-Cash Return
16.9%
Cap rate
2.1%
Rent to Value Ratio
Active
$245,000
4
bds
|
2
ba
|
1,439
sqft
|
built
1898
7227 S Paulina St, Chicago, IL 60636
$582
Cash flow
12.4%
Cash-on-Cash Return
8.5%
Cap rate
1.1%
Rent to Value Ratio
3,769 out of 4,323 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
$799,900
3
bds
|
2
ba
|
1,800
sqft
|
built
1886
3726 N Ashland Ave, Chicago, IL 60613
$-2,150
Cash flow
-14.0%
Cash-on-Cash Return
2.5%
Cap rate
0.5%
Rent to Value Ratio
Active
$159,900
2
bds
|
1
ba
|
950
sqft
|
built
1924
6254 N Richmond St, Chicago, IL 60659
$-11
Cash flow
-0.4%
Cash-on-Cash Return
5.6%
Cap rate
1.1%
Rent to Value Ratio
Active
$1,200,000
4
bds
|
4
ba
|
0
sqft
|
built
1890
2117 W Dickens Ave, Chicago, IL 60647
$-4,442
Cash flow
-19.3%
Cash-on-Cash Return
1.2%
Cap rate
0.3%
Rent to Value Ratio
Active
$599,999
3
bds
|
2
ba
|
1,501
sqft
|
built
1925
1033 W 14th Pl, Chicago, IL 60608
$-1,904
Cash flow
-16.6%
Cash-on-Cash Return
1.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$425,000
2
bds
|
2
ba
|
1,200
sqft
|
built
2001
1242 W Ohio St, Chicago, IL 60642
$-876
Cash flow
-10.8%
Cash-on-Cash Return
3.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$675,000
6
bds
|
3
ba
|
0
sqft
|
built
1982
3430 S Parnell Ave, Chicago, IL 60616
$-2,669
Cash flow
-20.6%
Cash-on-Cash Return
0.9%
Cap rate
0.3%
Rent to Value Ratio
Active
$714,500
9
bds
|
3
ba
|
0
sqft
|
built
1924
6030 N Claremont Ave, Chicago, IL 60659
$-2,066
Cash flow
-15.1%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$192,500
1
bds
|
1
ba
|
0
sqft
|
built
1954
2909 N Sheridan Rd, Chicago, IL 60657
$-551
Cash flow
-14.9%
Cash-on-Cash Return
2.2%
Cap rate
0.9%
Rent to Value Ratio
Active
$211,999
3
bds
|
2
ba
|
1,300
sqft
|
built
1964
11642 S Loomis St, Chicago, IL 60643
$380
Cash flow
9.4%
Cash-on-Cash Return
7.8%
Cap rate
1.0%
Rent to Value Ratio
Active
$2,199,999
6
bds
|
6
ba
|
0
sqft
|
built
1883
1420 W Fulton St, Chicago, IL 60607
$-7,940
Cash flow
-18.8%
Cash-on-Cash Return
1.3%
Cap rate
0.3%
Rent to Value Ratio
Active
$769,000
12
bds
|
7
ba
|
0
sqft
|
built
1920
1531 S Kolin Ave, Chicago, IL 60623
$-2,718
Cash flow
-18.4%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
Active
$435,000
2
bds
|
2
ba
|
1,300
sqft
|
built
1977
405 N Wabash Ave, Chicago, IL 60611
$-1,968
Cash flow
-23.6%
Cash-on-Cash Return
0.3%
Cap rate
0.9%
Rent to Value Ratio
Active
$247,000
2
bds
|
2
ba
|
1,000
sqft
|
built
1974
5332 N Delphia Ave, Chicago, IL 60656
$-196
Cash flow
-4.1%
Cash-on-Cash Return
4.7%
Cap rate
0.8%
Rent to Value Ratio
Active
$470,000
4
bds
|
2
ba
|
0
sqft
|
built
1926
1009 N Harding Ave, Chicago, IL 60651
$-964
Cash flow
-10.7%
Cash-on-Cash Return
3.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$485,000
2
bds
|
2
ba
|
0
sqft
|
built
1974
2144 N Lincoln Park W, Chicago, IL 60614
$-1,860
Cash flow
-20.0%
Cash-on-Cash Return
1.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,685,000
3
bds
|
4
ba
|
2,130
sqft
|
built
2017
540 W Webster Ave, Chicago, IL 60614
$-7,447
Cash flow
-23.1%
Cash-on-Cash Return
0.4%
Cap rate
0.4%
Rent to Value Ratio
Active
$145,000
1
bds
|
1
ba
|
700
sqft
|
built
1950
6833 N Oakley Ave, Chicago, IL 60645
$-181
Cash flow
-6.5%
Cash-on-Cash Return
4.2%
Cap rate
1.0%
Rent to Value Ratio
Active
$225,000
2
bds
|
2
ba
|
792
sqft
|
built
1951
10005 S Calhoun Ave, Chicago, IL 60617
$338
Cash flow
7.8%
Cash-on-Cash Return
7.5%
Cap rate
1.0%
Rent to Value Ratio
Active
$170,000
2
bds
|
1
ba
|
1,082
sqft
|
built
1943
8619 S Jeffery Blvd, Chicago, IL 60617
$423
Cash flow
13.0%
Cash-on-Cash Return
8.7%
Cap rate
1.2%
Rent to Value Ratio
Active
$269,000
4
bds
|
2
ba
|
1,496
sqft
|
built
1910
6409 S Champlain Ave, Chicago, IL 60637
$258
Cash flow
5.0%
Cash-on-Cash Return
6.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$240,000
1
bds
|
1
ba
|
875
sqft
|
built
1911
910 S Michigan Ave, Chicago, IL 60605
$-423
Cash flow
-9.2%
Cash-on-Cash Return
3.6%
Cap rate
1.0%
Rent to Value Ratio
Active
$89,900
3
bds
|
2
ba
|
1,000
sqft
|
built
1885
527 N Springfield Ave, Chicago, IL 60624
$839
Cash flow
48.7%
Cash-on-Cash Return
16.9%
Cap rate
2.1%
Rent to Value Ratio
Active
$399,000
3
bds
|
2
ba
|
1,104
sqft
|
built
1961
5705 N Oketo Ave, Chicago, IL 60631
$-347
Cash flow
-4.5%
Cash-on-Cash Return
4.6%
Cap rate
0.7%
Rent to Value Ratio
Active
$234,900
3
bds
|
2
ba
|
1,300
sqft
|
built
2007
2111 S Fairfield Ave, Chicago, IL 60608
$205
Cash flow
4.6%
Cash-on-Cash Return
6.7%
Cap rate
1.0%
Rent to Value Ratio
Active
$145,000
1
bds
|
1
ba
|
700
sqft
|
built
1970
6827 N Oakley Ave, Chicago, IL 60645
$-250
Cash flow
-9.0%
Cash-on-Cash Return
3.6%
Cap rate
0.9%
Rent to Value Ratio
Active
$520,000
3
bds
|
2
ba
|
2,016
sqft
|
built
1961
4634 N Hamlin Ave, Chicago, IL 60625
$-401
Cash flow
-4.0%
Cash-on-Cash Return
4.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$359,900
3
bds
|
2
ba
|
1,371
sqft
|
built
1948
11119 S Maplewood Ave, Chicago, IL 60655
$-314
Cash flow
-4.6%
Cash-on-Cash Return
4.6%
Cap rate
0.7%
Rent to Value Ratio
Active
$815,000
3
bds
|
4
ba
|
3,600
sqft
|
built
1921
5141 W Dakin St, Chicago, IL 60641
$-1,729
Cash flow
-11.1%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$415,000
1
bds
|
1
ba
|
706
sqft
|
built
1968
505 N Lake Shore Dr, Chicago, IL 60611
$465
Cash flow
5.8%
Cash-on-Cash Return
7.0%
Cap rate
1.2%
Rent to Value Ratio
Active
$415,000
3
bds
|
2
ba
|
1,914
sqft
|
built
1993
5209 S Narragansett Ave, Chicago, IL 60638
$-314
Cash flow
-3.9%
Cash-on-Cash Return
4.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$325,000
1
bds
|
2
ba
|
0
sqft
|
built
1997
1418 W Cortez St, Chicago, IL 60642
$-306
Cash flow
-4.9%
Cash-on-Cash Return
4.5%
Cap rate
0.8%
Rent to Value Ratio
Active
$260,000
1
bds
|
1
ba
|
825
sqft
|
built
1963
1355 N Clark St, Chicago, IL 60610
$-522
Cash flow
-10.5%
Cash-on-Cash Return
3.3%
Cap rate
1.1%
Rent to Value Ratio
Active
$625,000
1
bds
|
2
ba
|
1,897
sqft
|
built
1974
1516 N State Pkwy, Chicago, IL 60610
$-2,121
Cash flow
-17.7%
Cash-on-Cash Return
1.6%
Cap rate
0.7%
Rent to Value Ratio
Active
$319,900
8
bds
|
3
ba
|
0
sqft
|
built
1898
6948 S Eberhart Ave, Chicago, IL 60637
$-413
Cash flow
-6.7%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$389,900
4
bds
|
2
ba
|
1,107
sqft
|
built
1923
5941 W Waveland Ave, Chicago, IL 60634
$-267
Cash flow
-3.6%
Cash-on-Cash Return
4.9%
Cap rate
0.7%
Rent to Value Ratio
Active
$145,000
1
bds
|
1
ba
|
796
sqft
|
built
1982
4800 S Chicago Beach Dr, Chicago, IL 60615
$-315
Cash flow
-11.3%
Cash-on-Cash Return
3.1%
Cap rate
1.4%
Rent to Value Ratio
Active
$304,999
4
bds
|
2
ba
|
1,312
sqft
|
built
1956
4918 S Luna Ave, Chicago, IL 60638
$-200
Cash flow
-3.4%
Cash-on-Cash Return
4.9%
Cap rate
0.8%
Rent to Value Ratio
Active
$245,000
4
bds
|
2
ba
|
1,439
sqft
|
built
1898
7227 S Paulina St, Chicago, IL 60636
$582
Cash flow
12.4%
Cash-on-Cash Return
8.5%
Cap rate
1.1%
Rent to Value Ratio
Active
$385,000
2
bds
|
2
ba
|
1,165
sqft
|
built
1989
200 N Dearborn St, Chicago, IL 60601
$-1,459
Cash flow
-19.8%
Cash-on-Cash Return
1.1%
Cap rate
0.8%
Rent to Value Ratio
Active
$249,900
5
bds
|
2
ba
|
2,065
sqft
|
built
1963
250 W 119th St, Chicago, IL 60628
$-324
Cash flow
-6.8%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio