Skip to content
×
Pro Members Get
Full Access!
Get off the sidelines and take action in real estate investing with BiggerPockets Pro. Our comprehensive suite of tools and resources minimize mistakes, support informed decisions, and propel you to success.
Advanced networking features
Market and Deal Finder tools
Property analysis calculators
Landlord Command Center
ANNUAL Save 16%
$32.50 /mo
$390 billed annualy
MONTHLY
$39 /mo
billed monthly
7 day free trial. Cancel anytime

Filters

Price

Price Range

$
  • $0
  • $50,000
  • $100,000
  • $150,000
  • $200,000
  • $250,000
  • $300,000
  • $350,000
  • $400,000
  • $450,000
  • $500,000
  • $550,000
  • $600,000
  • $650,000
  • $700,000
  • $750,000
  • $800,000
  • $850,000
  • $900,000
  • $950,000
  • $1M
  • $1.25M
  • $1.5M
  • $1.75M
  • $2M
  • $2.25M
  • $2.5M
  • $2.75M
  • $3M
  • $4M
  • $5M+
$
  • $0
  • $50,000
  • $100,000
  • $150,000
  • $200,000
  • $250,000
  • $300,000
  • $350,000
  • $400,000
  • $450,000
  • $500,000
  • $550,000
  • $600,000
  • $650,000
  • $700,000
  • $750,000
  • $800,000
  • $850,000
  • $900,000
  • $950,000
  • $1M
  • $1.25M
  • $1.5M
  • $1.75M
  • $2M
  • $2.25M
  • $2.5M
  • $2.75M
  • $3M
  • $4M
  • $5M+
Beds/Baths

Bedrooms

Bathrooms

For Sale

Status

Property Type (6)

Property Type

More

Square Feet

Lot Size

Year Built

Projected Rent

Cash on Cash Return

Monthly Cash Flow

Cap Rate

Copied

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.

3,740 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.

Property photo
Active
MRED

$435,000

2 bds | 2 ba | 1,300 sqft | built 1977
405 N Wabash Ave, Chicago, IL 60611
$-2,187
Cash flow
-26.2%
Cash-on-Cash Return

0.3%
Cap rate
0.9%
Rent to Value Ratio
Property photo
Active
MRED

$247,000

2 bds | 2 ba | 1,000 sqft | built 1974
5332 N Delphia Ave, Chicago, IL 60656
$-320
Cash flow
-6.8%
Cash-on-Cash Return

4.7%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
MRED

$470,000

4 bds | 2 ba | 0 sqft | built 1926
1009 N Harding Ave, Chicago, IL 60651
$-1,201
Cash flow
-13.3%
Cash-on-Cash Return

3.2%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
MRED

$485,000

2 bds | 2 ba | 0 sqft | built 1974
2144 N Lincoln Park W, Chicago, IL 60614
$-2,105
Cash flow
-22.6%
Cash-on-Cash Return

1.1%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
MRED

$1,685,000

3 bds | 4 ba | 2,130 sqft | built 2017
540 W Webster Ave, Chicago, IL 60614
$-8,297
Cash flow
-25.7%
Cash-on-Cash Return

0.4%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
MRED

$145,000

1 bds | 1 ba | 700 sqft | built 1950
6833 N Oakley Ave, Chicago, IL 60645
$-254
Cash flow
-9.1%
Cash-on-Cash Return

4.2%
Cap rate
1.0%
Rent to Value Ratio
Property photo
Active
MRED

$225,000

2 bds | 2 ba | 792 sqft | built 1951
10005 S Calhoun Ave, Chicago, IL 60617
$225
Cash flow
5.2%
Cash-on-Cash Return

7.5%
Cap rate
1.0%
Rent to Value Ratio
Property photo
Active
MRED

$170,000

2 bds | 1 ba | 1,082 sqft | built 1943
8619 S Jeffery Blvd, Chicago, IL 60617
$337
Cash flow
10.3%
Cash-on-Cash Return

8.7%
Cap rate
1.2%
Rent to Value Ratio
Property photo
Active
MRED

$269,000

4 bds | 2 ba | 1,496 sqft | built 1910
6409 S Champlain Ave, Chicago, IL 60637
$122
Cash flow
2.4%
Cash-on-Cash Return

6.8%
Cap rate
0.9%
Rent to Value Ratio
Property photo
Active
MRED

$240,000

1 bds | 1 ba | 875 sqft | built 1911
910 S Michigan Ave, Chicago, IL 60605
$-544
Cash flow
-11.8%
Cash-on-Cash Return

3.6%
Cap rate
1.0%
Rent to Value Ratio
Property photo
Active
MRED

$89,900

3 bds | 2 ba | 1,000 sqft | built 1885
527 N Springfield Ave, Chicago, IL 60624
$793
Cash flow
46.0%
Cash-on-Cash Return

16.9%
Cap rate
2.1%
Rent to Value Ratio
Property photo
Active under contract
MRED

$399,000

3 bds | 2 ba | 1,104 sqft | built 1961
5705 N Oketo Ave, Chicago, IL 60631
$-548
Cash flow
-7.2%
Cash-on-Cash Return

4.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$234,900

3 bds | 2 ba | 1,300 sqft | built 2007
2111 S Fairfield Ave, Chicago, IL 60608
$87
Cash flow
1.9%
Cash-on-Cash Return

6.7%
Cap rate
1.0%
Rent to Value Ratio
Property photo
Active
MRED

$145,000

1 bds | 1 ba | 700 sqft | built 1970
6827 N Oakley Ave, Chicago, IL 60645
$-323
Cash flow
-11.6%
Cash-on-Cash Return

3.6%
Cap rate
0.9%
Rent to Value Ratio
Property photo
Active
MRED

$520,000

3 bds | 2 ba | 2,016 sqft | built 1961
4634 N Hamlin Ave, Chicago, IL 60625
$-663
Cash flow
-6.7%
Cash-on-Cash Return

4.8%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$359,900

3 bds | 2 ba | 1,371 sqft | built 1948
11119 S Maplewood Ave, Chicago, IL 60655
$-496
Cash flow
-7.2%
Cash-on-Cash Return

4.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$815,000

3 bds | 4 ba | 3,600 sqft | built 1921
5141 W Dakin St, Chicago, IL 60641
$-2,140
Cash flow
-13.7%
Cash-on-Cash Return

3.1%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
MRED

$415,000

1 bds | 1 ba | 706 sqft | built 1968
505 N Lake Shore Dr, Chicago, IL 60611
$256
Cash flow
3.2%
Cash-on-Cash Return

7.0%
Cap rate
1.2%
Rent to Value Ratio
Property photo
Active
MRED

$415,000

3 bds | 2 ba | 1,914 sqft | built 1993
5209 S Narragansett Ave, Chicago, IL 60638
$-523
Cash flow
-6.6%
Cash-on-Cash Return

4.8%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$325,000

1 bds | 2 ba | 0 sqft | built 1997
1418 W Cortez St, Chicago, IL 60642
$-470
Cash flow
-7.5%
Cash-on-Cash Return

4.5%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
MRED

$260,000

1 bds | 1 ba | 825 sqft | built 1963
1355 N Clark St, Chicago, IL 60610
$-654
Cash flow
-13.1%
Cash-on-Cash Return

3.3%
Cap rate
1.1%
Rent to Value Ratio
Property photo
Active
MRED

$625,000

1 bds | 2 ba | 1,897 sqft | built 1974
1516 N State Pkwy, Chicago, IL 60610
$-2,436
Cash flow
-20.3%
Cash-on-Cash Return

1.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$319,900

8 bds | 3 ba | 0 sqft | built 1898
6948 S Eberhart Ave, Chicago, IL 60637
$-574
Cash flow
-9.4%
Cash-on-Cash Return

4.1%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
MRED

$389,900

4 bds | 2 ba | 1,107 sqft | built 1923
5941 W Waveland Ave, Chicago, IL 60634
$-464
Cash flow
-6.2%
Cash-on-Cash Return

4.9%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$145,000

1 bds | 1 ba | 796 sqft | built 1982
4800 S Chicago Beach Dr, Chicago, IL 60615
$-388
Cash flow
-14.0%
Cash-on-Cash Return

3.1%
Cap rate
1.4%
Rent to Value Ratio
Property photo
Active
MRED

$304,999

4 bds | 2 ba | 1,312 sqft | built 1956
4918 S Luna Ave, Chicago, IL 60638
$-354
Cash flow
-6.1%
Cash-on-Cash Return

4.9%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
MRED

$245,000

4 bds | 2 ba | 1,439 sqft | built 1898
7227 S Paulina St, Chicago, IL 60636
$458
Cash flow
9.8%
Cash-on-Cash Return

8.5%
Cap rate
1.1%
Rent to Value Ratio
Property photo
Active
MRED

$385,000

2 bds | 2 ba | 1,165 sqft | built 1989
200 N Dearborn St, Chicago, IL 60601
$-1,653
Cash flow
-22.4%
Cash-on-Cash Return

1.1%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
MRED

$249,900

5 bds | 2 ba | 2,065 sqft | built 1963
250 W 119th St, Chicago, IL 60628
$-450
Cash flow
-9.4%
Cash-on-Cash Return

4.1%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
MRED

$549,900

2 bds | 2 ba | 1,240 sqft | built 1983
10 E Ontario St, Chicago, IL 60611
$-2,332
Cash flow
-22.1%
Cash-on-Cash Return

1.2%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Pending
MRED

$549,900

10 bds | 4 ba | 0 sqft | built 1895
1533 E 65th Pl, Chicago, IL 60637
$-1,540
Cash flow
-14.6%
Cash-on-Cash Return

2.9%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
MRED

$949,999

3 bds | 3 ba | 0 sqft | built 2005
2411 W Walton St, Chicago, IL 60622
$-2,444
Cash flow
-13.4%
Cash-on-Cash Return

3.2%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$389,999

5 bds | 2 ba | 0 sqft | built 1910
5726 S Elizabeth St, Chicago, IL 60636
$-603
Cash flow
-8.1%
Cash-on-Cash Return

4.4%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
MRED

$292,000

1 bds | 1 ba | 850 sqft | built 2005
545 N Dearborn St, Chicago, IL 60654
$-943
Cash flow
-16.8%
Cash-on-Cash Return

2.4%
Cap rate
0.9%
Rent to Value Ratio
Property photo
Active
MRED

$499,900

3 bds | 3 ba | 3,400 sqft | built 1929
10215 S Charles St, Chicago, IL 60643
$-603
Cash flow
-6.3%
Cash-on-Cash Return

4.8%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$2,795,000

6 bds | 6 ba | 6,500 sqft | built 1890
2124 N Cleveland Ave, Chicago, IL 60614
$-13,883
Cash flow
-25.9%
Cash-on-Cash Return

0.3%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Active
MRED

$575,000

4 bds | 5 ba | 2,954 sqft | built 1956
9139 S Oakley Ave, Chicago, IL 60643
$-763
Cash flow
-6.9%
Cash-on-Cash Return

4.7%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
MRED

$1,675,000

5 bds | 4 ba | 4,200 sqft | built 2019
2131 W Huron St, Chicago, IL 60612
$-4,035
Cash flow
-12.6%
Cash-on-Cash Return

3.4%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
MRED

$269,000

11 bds | 5 ba | 0 sqft | built 1884
8822 S Exchange Ave, Chicago, IL 60617
$-428
Cash flow
-8.3%
Cash-on-Cash Return

4.4%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
MRED

$330,000

2 bds | 2 ba | 980 sqft | built 1920
1001 W 15th St, Chicago, IL 60608
$-956
Cash flow
-15.1%
Cash-on-Cash Return

2.8%
Cap rate
0.8%
Rent to Value Ratio