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

$68,000
6
bds
|
2
ba
|
2,112
sqft
|
built
1890
7410 S Langley Ave, Chicago, IL 60619
$1,359
Cash flow
23.3%
Cash-on-Cash Return
24.0%
Cap rate
3.2%
Rent to Value Ratio

Active

$50,000
4
bds
|
2
ba
|
1,402
sqft
|
built
1907
12014 S Princeton Ave, Chicago, IL 60628
$1,182
Cash flow
27.5%
Cash-on-Cash Return
28.4%
Cap rate
3.6%
Rent to Value Ratio
3,229 out of 4,711 properties for sale in Chicago, IL
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Active

$829,900
3
bds
|
4
ba
|
3,000
sqft
|
built
1915
4720 N Kenneth Ave, Chicago, IL 60630
$-1,389
Cash flow
-8.7%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio

Active

$109,900
3
bds
|
3
ba
|
2,500
sqft
|
built
1927
6922 S Jeffery Blvd, Chicago, IL 60649
$488
Cash flow
23.2%
Cash-on-Cash Return
11.0%
Cap rate
2.3%
Rent to Value Ratio

Active

$311,900
1
bds
|
1
ba
|
862
sqft
|
built
1900
225 W Huron St, Chicago, IL 60654
$-705
Cash flow
-11.8%
Cash-on-Cash Return
3.0%
Cap rate
0.8%
Rent to Value Ratio

Active

$391,000
4
bds
|
2
ba
|
1,700
sqft
|
built
1952
1327 E 52nd St, Chicago, IL 60615
$-561
Cash flow
-7.5%
Cash-on-Cash Return
4.0%
Cap rate
0.9%
Rent to Value Ratio

Active

$50,000
4
bds
|
2
ba
|
1,402
sqft
|
built
1907
12014 S Princeton Ave, Chicago, IL 60628
$1,182
Cash flow
27.5%
Cash-on-Cash Return
28.4%
Cap rate
3.6%
Rent to Value Ratio

Active

$129,000
3
bds
|
2
ba
|
1,023
sqft
|
built
1885
4254 S Cottage Grove Ave, Chicago, IL 60653
$202
Cash flow
8.2%
Cash-on-Cash Return
7.6%
Cap rate
1.6%
Rent to Value Ratio

Active

$299,999
3
bds
|
2
ba
|
552
sqft
|
built
1908
6207 S Tripp Ave, Chicago, IL 60629
$675
Cash flow
11.7%
Cash-on-Cash Return
8.4%
Cap rate
1.1%
Rent to Value Ratio

Active

$294,900
3
bds
|
3
ba
|
2,100
sqft
|
built
1943
9204 S Perry Ave, Chicago, IL 60620
$295
Cash flow
5.2%
Cash-on-Cash Return
6.9%
Cap rate
0.9%
Rent to Value Ratio

Active

$315,000
2
bds
|
2
ba
|
1,326
sqft
|
built
1904
161 W Harrison St, Chicago, IL 60605
$-605
Cash flow
-10.0%
Cash-on-Cash Return
3.4%
Cap rate
0.9%
Rent to Value Ratio

Active

$995,000
1
bds
|
2
ba
|
1,419
sqft
|
built
2007
401 N Wabash Ave, Chicago, IL 60611
$-4,393
Cash flow
-23.0%
Cash-on-Cash Return
0.4%
Cap rate
0.5%
Rent to Value Ratio

Active

$200,000
5
bds
|
3
ba
|
1,600
sqft
|
built
1888
10456 S Avenue L, Chicago, IL 60617
$536
Cash flow
14.0%
Cash-on-Cash Return
8.9%
Cap rate
1.1%
Rent to Value Ratio

Active

$299,900
1
bds
|
1
ba
|
725
sqft
|
built
1962
300 N State St, Chicago, IL 60654
$-837
Cash flow
-14.6%
Cash-on-Cash Return
2.3%
Cap rate
0.9%
Rent to Value Ratio

Active

$274,000
5
bds
|
2
ba
|
0
sqft
|
built
1876
442 N Harding Ave, Chicago, IL 60624
$124
Cash flow
2.4%
Cash-on-Cash Return
6.2%
Cap rate
0.8%
Rent to Value Ratio

Active

$159,000
bds
|
1
ba
|
550
sqft
|
built
1960
3600 N Lake Shore Dr, Chicago, IL 60613
$-143
Cash flow
-4.7%
Cash-on-Cash Return
4.6%
Cap rate
1.1%
Rent to Value Ratio

Active

$246,500
1
bds
|
1
ba
|
700
sqft
|
built
1987
211 E Ohio St, Chicago, IL 60611
$-624
Cash flow
-13.2%
Cash-on-Cash Return
2.6%
Cap rate
0.9%
Rent to Value Ratio

Active

$560,000
3
bds
|
3
ba
|
0
sqft
|
built
1968
2626 N Lakeview Ave, Chicago, IL 60614
$-2,724
Cash flow
-25.4%
Cash-on-Cash Return
-0.2%
Cap rate
0.6%
Rent to Value Ratio

Active

$599,000
8
bds
|
3
ba
|
0
sqft
|
built
1960
1329 N Latrobe Ave, Chicago, IL 60651
$-1,951
Cash flow
-17.0%
Cash-on-Cash Return
1.8%
Cap rate
0.4%
Rent to Value Ratio

Active

$299,000
1
bds
|
1
ba
|
906
sqft
|
built
1906
6 N Michigan Ave, Chicago, IL 60602
$-665
Cash flow
-11.6%
Cash-on-Cash Return
3.0%
Cap rate
0.8%
Rent to Value Ratio

Active

$595,000
2
bds
|
2
ba
|
1,650
sqft
|
built
1964
1325 N State Pkwy, Chicago, IL 60610
$-2,429
Cash flow
-21.3%
Cash-on-Cash Return
0.8%
Cap rate
0.7%
Rent to Value Ratio

Active

$299,999
1
bds
|
1
ba
|
900
sqft
|
built
1969
130 S Canal St, Chicago, IL 60606
$-736
Cash flow
-12.8%
Cash-on-Cash Return
2.7%
Cap rate
0.8%
Rent to Value Ratio

Active

$450,000
1
bds
|
2
ba
|
2,040
sqft
|
built
1898
2342 W Taylor St, Chicago, IL 60612
$-200
Cash flow
-2.3%
Cash-on-Cash Return
5.1%
Cap rate
0.8%
Rent to Value Ratio

Active

$200,000
6
bds
|
3
ba
|
0
sqft
|
built
1881
8410 S Burley Ave, Chicago, IL 60617
$219
Cash flow
5.7%
Cash-on-Cash Return
7.0%
Cap rate
0.9%
Rent to Value Ratio

Active

$590,000
4
bds
|
4
ba
|
3,808
sqft
|
built
1890
638 E 65th St, Chicago, IL 60637
$-1,002
Cash flow
-8.9%
Cash-on-Cash Return
3.6%
Cap rate
0.5%
Rent to Value Ratio

Active

$21,000,000
5
bds
|
6
ba
|
25,000
sqft
|
built
1914
1355 N Astor St, Chicago, IL 60610
$-108,895
Cash flow
-27.1%
Cash-on-Cash Return
-0.5%
Cap rate
0.0%
Rent to Value Ratio

Active

$575,000
1
bds
|
2
ba
|
1,455
sqft
|
built
1984
161 E Chicago Ave, Chicago, IL 60611
$-1,904
Cash flow
-17.3%
Cash-on-Cash Return
1.7%
Cap rate
0.8%
Rent to Value Ratio

Active

$129,000
4
bds
|
3
ba
|
0
sqft
|
built
1888
7505 S Emerald Ave, Chicago, IL 60620
$449
Cash flow
18.2%
Cash-on-Cash Return
9.9%
Cap rate
1.3%
Rent to Value Ratio

Active

$68,000
6
bds
|
2
ba
|
2,112
sqft
|
built
1890
7410 S Langley Ave, Chicago, IL 60619
$1,359
Cash flow
23.3%
Cash-on-Cash Return
24.0%
Cap rate
3.2%
Rent to Value Ratio

Active

$234,900
3
bds
|
2
ba
|
1,400
sqft
|
built
1954
11318 S Avenue J, Chicago, IL 60617
$103
Cash flow
2.3%
Cash-on-Cash Return
6.2%
Cap rate
0.9%
Rent to Value Ratio

Active

$2,299,000
8
bds
|
5
ba
|
0
sqft
|
built
1894
2128 W Evergreen Ave, Chicago, IL 60622
$-9,638
Cash flow
-21.9%
Cash-on-Cash Return
0.6%
Cap rate
0.3%
Rent to Value Ratio

Active

$225,000
3
bds
|
3
ba
|
1,789
sqft
|
built
1900
6209 S Dorchester Ave, Chicago, IL 60637
$-559
Cash flow
-13.0%
Cash-on-Cash Return
2.7%
Cap rate
0.8%
Rent to Value Ratio

Active

$359,000
1
bds
|
1
ba
|
0
sqft
|
built
1969
512 W Barry Ave, Chicago, IL 60657
$-1,027
Cash flow
-14.9%
Cash-on-Cash Return
2.2%
Cap rate
0.6%
Rent to Value Ratio

Active

$259,000
6
bds
|
2
ba
|
0
sqft
|
built
1888
4823 S Prairie Ave, Chicago, IL 60615
$-177
Cash flow
-3.6%
Cash-on-Cash Return
4.9%
Cap rate
0.8%
Rent to Value Ratio

Active

$550,000
2
bds
|
2
ba
|
1,300
sqft
|
built
1982
360 E Randolph St, Chicago, IL 60601
$-1,810
Cash flow
-17.2%
Cash-on-Cash Return
1.7%
Cap rate
0.7%
Rent to Value Ratio

Active

$950,000
8
bds
|
3
ba
|
0
sqft
|
built
1891
929 N Fairfield Ave, Chicago, IL 60622
$-2,914
Cash flow
-16.0%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio

Active

$390,000
4
bds
|
3
ba
|
2,449
sqft
|
built
1999
8547 S Drake Ave, Chicago, IL 60652
$-94
Cash flow
-1.3%
Cash-on-Cash Return
5.4%
Cap rate
0.8%
Rent to Value Ratio

Active

$2,900,000
3
bds
|
3
ba
|
3,225
sqft
|
built
2000
800 N Michigan Ave, Chicago, IL 60611
$-15,372
Cash flow
-27.7%
Cash-on-Cash Return
-0.7%
Cap rate
0.3%
Rent to Value Ratio

Active

$240,000
3
bds
|
2
ba
|
2,200
sqft
|
built
1921
10240 S State St, Chicago, IL 60628
$700
Cash flow
15.2%
Cash-on-Cash Return
9.2%
Cap rate
1.1%
Rent to Value Ratio

Active

$899,000
4
bds
|
3
ba
|
2,500
sqft
|
built
1963
2400 N Lakeview Ave, Chicago, IL 60614
$-2,589
Cash flow
-15.0%
Cash-on-Cash Return
2.2%
Cap rate
0.9%
Rent to Value Ratio

Active

$2,950,000
4
bds
|
6
ba
|
4,800
sqft
|
built
2025
1342 W Wellington Ave, Chicago, IL 60657
$-7,658
Cash flow
-13.5%
Cash-on-Cash Return
2.6%
Cap rate
0.4%
Rent to Value Ratio

Active

$239,000
6
bds
|
3
ba
|
2,600
sqft
|
built
1903
6916 S Lowe Ave, Chicago, IL 60621
$179
Cash flow
3.9%
Cash-on-Cash Return
6.6%
Cap rate
0.8%
Rent to Value Ratio