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
$65,000
4
bds
|
2
ba
|
1,700
sqft
|
built
1910
5922 S Paulina St, Chicago, IL 60636
$1,172
Cash flow
21.0%
Cash-on-Cash Return
21.6%
Cap rate
2.8%
Rent to Value Ratio
Active under contract
$190,000
3
bds
|
3
ba
|
1,635
sqft
|
built
1927
9940 S Normal Ave, Chicago, IL 60628
$691
Cash flow
19.0%
Cash-on-Cash Return
10.0%
Cap rate
1.3%
Rent to Value Ratio
3,689 out of 4,243 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
$379,900
2
bds
|
2
ba
|
1,226
sqft
|
built
1925
1110 W 15th St, Chicago, IL 60608
$-1,305
Cash flow
-17.9%
Cash-on-Cash Return
1.6%
Cap rate
0.7%
Rent to Value Ratio
Active
$799,000
3
bds
|
3
ba
|
0
sqft
|
built
2002
3353 N Kenmore Ave, Chicago, IL 60657
$-1,641
Cash flow
-10.7%
Cash-on-Cash Return
3.2%
Cap rate
0.6%
Rent to Value Ratio
Active
$240,000
1
bds
|
1
ba
|
850
sqft
|
built
2006
6560 W Diversey Ave, Chicago, IL 60707
$-25
Cash flow
-0.5%
Cash-on-Cash Return
5.6%
Cap rate
0.8%
Rent to Value Ratio
Active
$674,900
3
bds
|
2
ba
|
1,502
sqft
|
built
2008
4043 N Damen Ave, Chicago, IL 60618
$-1,517
Cash flow
-11.7%
Cash-on-Cash Return
3.0%
Cap rate
0.6%
Rent to Value Ratio
Active
$455,500
4
bds
|
3
ba
|
2,400
sqft
|
built
1914
11173 S Hermosa Ave, Chicago, IL 60643
$-678
Cash flow
-7.8%
Cash-on-Cash Return
3.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$255,000
2
bds
|
3
ba
|
3,750
sqft
|
built
2004
5645 W 64th St, Chicago, IL 60638
$536
Cash flow
11.0%
Cash-on-Cash Return
8.2%
Cap rate
1.1%
Rent to Value Ratio
Active under contract
$620,000
2
bds
|
2
ba
|
1,200
sqft
|
built
2003
2700 N Halsted St, Chicago, IL 60614
$-1,394
Cash flow
-11.7%
Cash-on-Cash Return
3.0%
Cap rate
0.6%
Rent to Value Ratio
Active
$388,000
1
bds
|
1
ba
|
1,100
sqft
|
built
1910
1000 W Washington Blvd, Chicago, IL 60607
$-1,143
Cash flow
-15.4%
Cash-on-Cash Return
2.1%
Cap rate
0.8%
Rent to Value Ratio
Active
$499,000
3
bds
|
2
ba
|
984
sqft
|
built
1953
7646 W Myrtle Ave, Chicago, IL 60631
$-898
Cash flow
-9.4%
Cash-on-Cash Return
3.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$298,000
8
bds
|
3
ba
|
0
sqft
|
built
1910
7514 S Dante Ave, Chicago, IL 60619
$-673
Cash flow
-11.8%
Cash-on-Cash Return
3.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$315,000
3
bds
|
2
ba
|
2,556
sqft
|
built
1976
11531 S Avenue J, Chicago, IL 60617
$-180
Cash flow
-3.0%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio
Active under contract
$299,900
1
bds
|
1
ba
|
915
sqft
|
built
1920
726 W Sheridan Rd, Chicago, IL 60613
$-701
Cash flow
-12.2%
Cash-on-Cash Return
2.9%
Cap rate
0.8%
Rent to Value Ratio
Active
$719,000
9
bds
|
6
ba
|
0
sqft
|
built
2008
3341 W Fulton Blvd, Chicago, IL 60624
$-2,292
Cash flow
-16.6%
Cash-on-Cash Return
1.9%
Cap rate
0.3%
Rent to Value Ratio
Active under contract
$389,900
4
bds
|
2
ba
|
1,411
sqft
|
built
1953
3859 W 109th Pl, Chicago, IL 60655
$-190
Cash flow
-2.5%
Cash-on-Cash Return
5.1%
Cap rate
0.7%
Rent to Value Ratio
Active under contract
$475,000
2
bds
|
2
ba
|
0
sqft
|
built
1902
120 E Cullerton St, Chicago, IL 60616
$-1,317
Cash flow
-14.5%
Cash-on-Cash Return
2.4%
Cap rate
0.7%
Rent to Value Ratio
Active
$65,000
4
bds
|
2
ba
|
1,700
sqft
|
built
1910
5922 S Paulina St, Chicago, IL 60636
$1,172
Cash flow
21.0%
Cash-on-Cash Return
21.6%
Cap rate
2.8%
Rent to Value Ratio
Active
$500,000
4
bds
|
2
ba
|
1,700
sqft
|
built
1984
211 E Ohio St, Chicago, IL 60611
$-2,368
Cash flow
-24.7%
Cash-on-Cash Return
0.0%
Cap rate
0.8%
Rent to Value Ratio
Active
$399,900
5
bds
|
3
ba
|
3,078
sqft
|
built
1920
6421 S Mozart St, Chicago, IL 60629
$-967
Cash flow
-12.6%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio
Active under contract
$190,000
3
bds
|
3
ba
|
1,635
sqft
|
built
1927
9940 S Normal Ave, Chicago, IL 60628
$691
Cash flow
19.0%
Cash-on-Cash Return
10.0%
Cap rate
1.3%
Rent to Value Ratio
Active under contract
$239,000
1
bds
|
1
ba
|
783
sqft
|
built
1964
1460 N Clark St, Chicago, IL 60610
$-511
Cash flow
-11.2%
Cash-on-Cash Return
3.1%
Cap rate
1.0%
Rent to Value Ratio
Active
$535,000
3
bds
|
3
ba
|
3,358
sqft
|
built
1922
2036 N Kilpatrick Ave, Chicago, IL 60639
$-694
Cash flow
-6.8%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$399,000
2
bds
|
2
ba
|
1,183
sqft
|
built
2006
1600 S Indiana Ave, Chicago, IL 60616
$-1,244
Cash flow
-16.3%
Cash-on-Cash Return
1.9%
Cap rate
0.7%
Rent to Value Ratio
Active
$1,349,000
3
bds
|
3
ba
|
2,500
sqft
|
built
2005
1035 N Dearborn St, Chicago, IL 60610
$-8,720
Cash flow
-33.7%
Cash-on-Cash Return
-2.1%
Cap rate
0.2%
Rent to Value Ratio
Active under contract
$1,450,000
3
bds
|
4
ba
|
3,900
sqft
|
built
2007
2336 W Medill Ave, Chicago, IL 60647
$-4,003
Cash flow
-14.4%
Cash-on-Cash Return
2.4%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,600,000
4
bds
|
4
ba
|
4,538
sqft
|
built
2012
2429 W Belden Ave, Chicago, IL 60647
$-4,203
Cash flow
-13.7%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$279,900
3
bds
|
3
ba
|
1,584
sqft
|
built
1938
9754 S Ingleside Ave, Chicago, IL 60628
$-116
Cash flow
-2.2%
Cash-on-Cash Return
5.2%
Cap rate
0.7%
Rent to Value Ratio
Pending
$390,000
1
bds
|
1
ba
|
906
sqft
|
built
2007
450 E Waterside Dr, Chicago, IL 60601
$-766
Cash flow
-10.2%
Cash-on-Cash Return
3.3%
Cap rate
0.8%
Rent to Value Ratio
Active
$345,000
1
bds
|
1
ba
|
883
sqft
|
built
2001
1000 W Adams St, Chicago, IL 60607
$-1,011
Cash flow
-15.3%
Cash-on-Cash Return
2.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$299,000
2
bds
|
1
ba
|
0
sqft
|
built
1891
3117 N Paulina St, Chicago, IL 60657
$-473
Cash flow
-8.3%
Cash-on-Cash Return
3.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$114,000
5
bds
|
3
ba
|
1,044
sqft
|
built
1918
11732 S Yale Ave, Chicago, IL 60628
$505
Cash flow
23.1%
Cash-on-Cash Return
11.0%
Cap rate
1.4%
Rent to Value Ratio
Active
$195,000
3
bds
|
2
ba
|
1,019
sqft
|
built
1943
2129 E 97th St, Chicago, IL 60617
$154
Cash flow
4.1%
Cash-on-Cash Return
6.6%
Cap rate
0.8%
Rent to Value Ratio
Active
$539,000
2
bds
|
2
ba
|
1,260
sqft
|
built
1879
1400 N La Salle Dr, Chicago, IL 60610
$-1,619
Cash flow
-15.7%
Cash-on-Cash Return
2.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$755,000
2
bds
|
2
ba
|
1,624
sqft
|
built
1972
200 E Delaware Pl, Chicago, IL 60611
$-2,346
Cash flow
-16.2%
Cash-on-Cash Return
2.0%
Cap rate
0.8%
Rent to Value Ratio
Active
$2,495,000
3
bds
|
4
ba
|
3,800
sqft
|
built
2004
840 N Lake Shore Dr, Chicago, IL 60611
$-15,180
Cash flow
-31.7%
Cash-on-Cash Return
-1.6%
Cap rate
0.4%
Rent to Value Ratio
Active
$399,000
2
bds
|
2
ba
|
0
sqft
|
built
2006
150 W Superior St, Chicago, IL 60654
$-952
Cash flow
-12.4%
Cash-on-Cash Return
2.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$175,000
1
bds
|
1
ba
|
0
sqft
|
built
1958
33 E Cedar St, Chicago, IL 60611
$-864
Cash flow
-25.8%
Cash-on-Cash Return
-0.2%
Cap rate
1.3%
Rent to Value Ratio
Active
$198,500
4
bds
|
1
ba
|
1,300
sqft
|
built
1925
8129 S Princeton Ave, Chicago, IL 60620
$182
Cash flow
4.8%
Cash-on-Cash Return
6.8%
Cap rate
0.9%
Rent to Value Ratio
Active under contract
$575,000
4
bds
|
3
ba
|
3,037
sqft
|
built
1943
7733 W Rosedale Ave, Chicago, IL 60631
$-383
Cash flow
-3.5%
Cash-on-Cash Return
4.9%
Cap rate
0.8%
Rent to Value Ratio
Active under contract
$275,000
2
bds
|
2
ba
|
0
sqft
|
built
1920
1515 W Pratt Blvd, Chicago, IL 60626
$-520
Cash flow
-9.9%
Cash-on-Cash Return
3.4%
Cap rate
0.7%
Rent to Value Ratio
Active
$399,900
4
bds
|
2
ba
|
0
sqft
|
built
1926
9340 S Elizabeth St, Chicago, IL 60620
$-674
Cash flow
-8.8%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio