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

$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

$134,999
3
bds
|
1
ba
|
880
sqft
|
built
1953
12219 S Throop St, Chicago, IL 60643
$600
Cash flow
23.2%
Cash-on-Cash Return
11.0%
Cap rate
1.5%
Rent to Value Ratio
3,734 out of 4,286 properties for sale in Chicago, IL
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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
|
850
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

$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

$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

$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

$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

$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

$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

$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

Active

$90,500
2
bds
|
1
ba
|
1,106
sqft
|
built
1952
8338 S Ingleside Ave, Chicago, IL 60619
$582
Cash flow
33.6%
Cash-on-Cash Return
13.4%
Cap rate
1.8%
Rent to Value Ratio

Active

$90,500
4
bds
|
2
ba
|
0
sqft
|
built
1898
11854 S Lafayette Ave, Chicago, IL 60628
$452
Cash flow
26.1%
Cash-on-Cash Return
11.7%
Cap rate
1.5%
Rent to Value Ratio

Active

$100,000
2
bds
|
1
ba
|
980
sqft
|
built
1951
2258 E 96th St, Chicago, IL 60617
$575
Cash flow
30.0%
Cash-on-Cash Return
12.6%
Cap rate
1.6%
Rent to Value Ratio

Active

$90,500
3
bds
|
1
ba
|
1,092
sqft
|
built
1968
11641 S Sangamon St, Chicago, IL 60643
$564
Cash flow
32.5%
Cash-on-Cash Return
13.2%
Cap rate
1.8%
Rent to Value Ratio

Active

$80,500
2
bds
|
1
ba
|
1,088
sqft
|
built
1971
355 W 105th Pl, Chicago, IL 60628
$594
Cash flow
38.5%
Cash-on-Cash Return
14.5%
Cap rate
2.0%
Rent to Value Ratio

Active

$159,000
2
bds
|
2
ba
|
1,650
sqft
|
built
1930
10440 S Sangamon St, Chicago, IL 60643
$491
Cash flow
16.1%
Cash-on-Cash Return
9.4%
Cap rate
1.4%
Rent to Value Ratio

Active

$590,000
12
bds
|
6
ba
|
0
sqft
|
built
1889
4735 S Indiana Ave, Chicago, IL 60615
$-2,385
Cash flow
-21.1%
Cash-on-Cash Return
0.8%
Cap rate
0.4%
Rent to Value Ratio

Active

$500,000
6
bds
|
3
ba
|
2,392
sqft
|
built
1896
4205 S Prairie Ave, Chicago, IL 60653
$-655
Cash flow
-6.8%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio

Active

$565,000
2
bds
|
2
ba
|
1,367
sqft
|
built
2004
1717 S Prairie Ave, Chicago, IL 60616
$-1,715
Cash flow
-15.8%
Cash-on-Cash Return
2.0%
Cap rate
0.6%
Rent to Value Ratio

Active

$750,000
3
bds
|
4
ba
|
3,000
sqft
|
built
2015
3407 S Calumet Ave, Chicago, IL 60616
$-417
Cash flow
-2.9%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio

Active

$299,900
4
bds
|
3
ba
|
2,200
sqft
|
built
1959
1409 E 90th St, Chicago, IL 60619
$307
Cash flow
5.3%
Cash-on-Cash Return
6.9%
Cap rate
0.9%
Rent to Value Ratio

Active

$238,500
bds
|
1
ba
|
700
sqft
|
built
1990
401 E Ontario St, Chicago, IL 60611
$-805
Cash flow
-17.6%
Cash-on-Cash Return
1.6%
Cap rate
0.8%
Rent to Value Ratio

Active

$599,000
3
bds
|
2
ba
|
1,770
sqft
|
built
1965
1440 N Lake Shore Dr, Chicago, IL 60610
$-2,257
Cash flow
-19.7%
Cash-on-Cash Return
1.2%
Cap rate
0.8%
Rent to Value Ratio

Active

$299,000
3
bds
|
2
ba
|
0
sqft
|
built
1883
3228 S Paulina St, Chicago, IL 60608
$-160
Cash flow
-2.8%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio

Active

$1,045,000
1
bds
|
3
ba
|
2,230
sqft
|
built
1964
1040 N Lake Shore Dr, Chicago, IL 60611
$-5,093
Cash flow
-25.4%
Cash-on-Cash Return
-0.2%
Cap rate
0.5%
Rent to Value Ratio

Active

$134,999
3
bds
|
1
ba
|
880
sqft
|
built
1953
12219 S Throop St, Chicago, IL 60643
$600
Cash flow
23.2%
Cash-on-Cash Return
11.0%
Cap rate
1.5%
Rent to Value Ratio

Active

$275,000
4
bds
|
2
ba
|
1,440
sqft
|
built
1921
7953 S Avalon Ave, Chicago, IL 60619
$2
Cash flow
0.0%
Cash-on-Cash Return
5.7%
Cap rate
0.8%
Rent to Value Ratio

Active

$279,900
2
bds
|
3
ba
|
0
sqft
|
built
1900
7147 S University Ave, Chicago, IL 60619
$92
Cash flow
1.7%
Cash-on-Cash Return
6.1%
Cap rate
0.8%
Rent to Value Ratio

Active

$235,000
1
bds
|
1
ba
|
840
sqft
|
built
1975
655 W Irving Park Rd, Chicago, IL 60613
$-456
Cash flow
-10.1%
Cash-on-Cash Return
3.3%
Cap rate
1.1%
Rent to Value Ratio

Active

$375,000
4
bds
|
3
ba
|
0
sqft
|
built
1926
6830 S Michigan Ave, Chicago, IL 60637
$-256
Cash flow
-3.6%
Cash-on-Cash Return
4.9%
Cap rate
0.7%
Rent to Value Ratio

Active

$299,000
3
bds
|
3
ba
|
2,252
sqft
|
built
1891
8440 S Peoria St, Chicago, IL 60620
$-217
Cash flow
-3.8%
Cash-on-Cash Return
4.8%
Cap rate
0.6%
Rent to Value Ratio

Active

$225,000
3
bds
|
3
ba
|
1,653
sqft
|
built
1925
7513 S Aberdeen St, Chicago, IL 60620
$144
Cash flow
3.3%
Cash-on-Cash Return
6.4%
Cap rate
1.0%
Rent to Value Ratio

Active

$120,000
1
bds
|
1
ba
|
900
sqft
|
built
1968
6730 S South Shore Dr, Chicago, IL 60649
$-333
Cash flow
-14.5%
Cash-on-Cash Return
2.4%
Cap rate
1.5%
Rent to Value Ratio

Active

$1,084,900
3
bds
|
3
ba
|
2,200
sqft
|
built
2008
1211 S Prairie Ave, Chicago, IL 60605
$-3,523
Cash flow
-16.9%
Cash-on-Cash Return
1.8%
Cap rate
0.7%
Rent to Value Ratio
Active

$275,000
4
bds
|
2
ba
|
2,500
sqft
|
built
1972
4764 S Shields Ave, Chicago, IL 60609
$511
Cash flow
9.7%
Cash-on-Cash Return
7.9%
Cap rate
1.0%
Rent to Value Ratio
Active

$230,000
1
bds
|
1
ba
|
610
sqft
|
built
1925
1645 W Ogden Ave, Chicago, IL 60612
$-437
Cash flow
-9.9%
Cash-on-Cash Return
3.4%
Cap rate
0.8%
Rent to Value Ratio

Active

$150,000
4
bds
|
2
ba
|
0
sqft
|
built
1890
5637 S Green St, Chicago, IL 60621
$463
Cash flow
16.1%
Cash-on-Cash Return
9.4%
Cap rate
1.2%
Rent to Value Ratio

Active

$1,995,000
7
bds
|
6
ba
|
0
sqft
|
built
1881
3035 N Southport Ave, Chicago, IL 60657
$-8,868
Cash flow
-23.2%
Cash-on-Cash Return
0.3%
Cap rate
0.2%
Rent to Value Ratio