Real Estate Investment Properties for Sale in Chicago, IL

Looking for investment property in Chicago, IL with high ROI ?

Explore a variety of short-term homes & houses in Chicago, IL. Invest wisely with VRBO & Chicago, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Chicago, IL

Search for Single Family Residential for Sale in Chicago, Illinois. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 2,773 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
7240 S Oakley Avenue Chicago, IL BRING YOUR CLIENTS! THIS BEAUTHY LOOKS LITTLE BUT IS ENORMOUS! WITH PLANE OF ROOMS IDEAL F...	4 beds \| 2 baths \| 1,016 sq.ft.	$314,990	Airbnb cash on cash: -0.35% Traditional cash on cash: 5.31% Airbnb Rental Income: $761 Traditional Rental Income: $2121 Airbnb ROI: -0.35% Traditional ROI: 5.31%
1722 N Keeler Avenue Chicago, IL Hot Hermosa location! Updated single family home on a great block. House went through ext...	3 beds \| 1 baths \| 842 sq.ft.	$315,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 3.35% Airbnb Rental Income: $1756 Traditional Rental Income: $1632 Airbnb ROI: 2.14% Traditional ROI: 3.35%
40 E 9th Street #1516 Chicago, IL Discover a unique gem within the South Loop's prominent high-rise community-a stunning thr...	3 beds \| 3 baths \| 2,000 sq.ft.	$400,000	Airbnb cash on cash: -4.13% Traditional cash on cash: 2.44% Airbnb Rental Income: $2210 Traditional Rental Income: $4117 Airbnb ROI: -4.13% Traditional ROI: 2.44%
7228 N Rogers Avenue Chicago, IL This is a 3 Bedroom, 1.5 Bath, 2 story, frame Coach House with 1 Deeded Parking Space. It ...	2 beds \| 3 baths \| 1,600 sq.ft.	$435,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 4.04% Airbnb Rental Income: $1850 Traditional Rental Income: $2651 Airbnb ROI: 0.86% Traditional ROI: 4.04%
6929 S Loomis Boulevard Chicago, IL This house has everything your client requested. 5 bedrooms, 3 full bathrooms, Full finis...	4 beds \| 3 baths \| 1,000 sq.ft.	$259,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 7.88% Airbnb Rental Income: $872 Traditional Rental Income: $2322 Airbnb ROI: 0.6% Traditional ROI: 7.88%
7216 S CENTRAL PARK Avenue Chicago, IL Well-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi...	3 beds \| 2 baths \| N/A	$304,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 5.98% Airbnb Rental Income: $1139 Traditional Rental Income: $2371 Airbnb ROI: 0.36% Traditional ROI: 5.98%
7205 S HAMLIN Avenue Chicago, IL Maintenance free 4 bedroom ranch with finished basement. 3 bedrooms on the main and one in...	3 beds \| 2 baths \| 1,080 sq.ft.	$379,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 3.88% Airbnb Rental Income: $1438 Traditional Rental Income: $1877 Airbnb ROI: 1.45% Traditional ROI: 3.88%
3036 N Luna Avenue Chicago, IL Spacious & Stylish 5-Bedroom Home with Modern Upgrades! Welcome to your new home-offering...	3 beds \| 3 baths \| 2,532 sq.ft.	$535,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 4.51% Airbnb Rental Income: $1372 Traditional Rental Income: $3396 Airbnb ROI: -0.37% Traditional ROI: 4.51%
5814 S Massasoit Ave Chicago, IL 5814 S Massasoit Ave, Chicago, IL 60638 \| Single Family Residential	3 beds \| 1 baths \| 1,017 sq.ft.	$359,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 1.35% Airbnb Rental Income: $1409 Traditional Rental Income: $1643 Airbnb ROI: -0.6% Traditional ROI: 1.35%
175 E Delaware Place #7204 Chicago, IL Welcome to your home in the sky, offering breathtaking North-facing views from the 72nd fl...	2 beds \| 2 baths \| 1,470 sq.ft.	$720,000	Airbnb cash on cash: -2.84% Traditional cash on cash: -1.79% Airbnb Rental Income: $2213 Traditional Rental Income: $2363 Airbnb ROI: -2.84% Traditional ROI: -1.79%
401 E Ontario Street #1805 Chicago, IL Lovely junior one bedroom in desirable Streeterville neighborhood located steps from the l...	1 beds \| 1 baths \| 700 sq.ft.	$265,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 1.37% Airbnb Rental Income: $1957 Traditional Rental Income: $1767 Airbnb ROI: 0.07% Traditional ROI: 1.37%
3558 W Belle Plaine Avenue #3 Chicago, IL Bright and full of personality, this two-bedroom Irving Park condo offers stylish comfort ...	2 beds \| 1 baths \| 1,000 sq.ft.	$255,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 2.72% Airbnb Rental Income: $1795 Traditional Rental Income: $1787 Airbnb ROI: 0.73% Traditional ROI: 2.72%
9356 S Union Avenue Chicago, IL Beautifully updated 3-bedroom, 2-bath brick ranch with a full finished basement. Ideally l...	3 beds \| 2 baths \| 1,097 sq.ft.	$289,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 4.21% Airbnb Rental Income: $1535 Traditional Rental Income: $1788 Airbnb ROI: 1.65% Traditional ROI: 4.21%
4531 S Lawler Avenue Chicago, IL Pristine 3bed/2bath raised ranch ready for move-in. Spacious layout with finished baseme...	3 beds \| 2 baths \| 1,008 sq.ft.	$329,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 4.04% Airbnb Rental Income: $1475 Traditional Rental Income: $1920 Airbnb ROI: 1.19% Traditional ROI: 4.04%
4442 N Melvina Avenue Chicago, IL If you're dreaming of a fully renovated home with a massive yard, without leaving the city...	4 beds \| 3 baths \| 2,398 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $3231 Airbnb ROI: N/A Traditional ROI: 3.38%
21 E Huron Street #706 Chicago, IL When Parisian charm meets New York Edge in the heart of Chicago - Unlike Anything You've S...	2 beds \| 2 baths \| 1,771 sq.ft.	$1,650,000	Airbnb cash on cash: -2.05% Traditional cash on cash: -1.38% Airbnb Rental Income: $2213 Traditional Rental Income: $2683 Airbnb ROI: -2.05% Traditional ROI: -1.38%
630 N State Street #1406 Chicago, IL Back on the market due to buyer unable to sell their property. Experience refined urban li...	2 beds \| 2 baths \| 1,241 sq.ft.	$469,000	Airbnb cash on cash: -2.07% Traditional cash on cash: 0.31% Airbnb Rental Income: $2213 Traditional Rental Income: $2698 Airbnb ROI: -2.07% Traditional ROI: 0.31%
401 E Ontario Street #809 Chicago, IL LOCATION, LOCATION, LOCATION! This OVERSIZED CORNER unit with gorgeous city and lake views...	2 beds \| 2 baths \| 1,200 sq.ft.	$399,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 0.49% Airbnb Rental Income: $2534 Traditional Rental Income: $2619 Airbnb ROI: -1.37% Traditional ROI: 0.49%
2244 W IRVING PARK Road Chicago, IL PRIME CANDIDATE FOR OWNER OCCUPANT, FHA 203K BUYER! Single family home located in high tr...	3 beds \| 2 baths \| N/A	$624,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 1.56% Airbnb Rental Income: $1985 Traditional Rental Income: $2696 Airbnb ROI: -0.55% Traditional ROI: 1.56%
6005 W Waveland Ave Chicago, IL 6005 W Waveland Ave, Chicago, IL 60634 \| Single Family Residential	7 beds \| 3 baths \| 2,769 sq.ft.	$629,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 2.27% Airbnb Rental Income: $2673 Traditional Rental Income: $3333 Airbnb ROI: 0.06% Traditional ROI: 2.27%
9021 S Exchange Avenue Chicago, IL Single Family 4 bedrooms, 1 bath home. Updates in 2019 include kitchen, baths, - ceramic t...	4 beds \| 1 baths \| 1,298 sq.ft.	$125,000	Airbnb cash on cash: 7.77% Traditional cash on cash: 11.77% Airbnb Rental Income: $1726 Traditional Rental Income: $1731 Airbnb ROI: 7.77% Traditional ROI: 11.77%
1819 S Michigan Avenue #406 Chicago, IL South Loop Stunner with Two Private Balconies - Bright and spacious 2BD/2BA with floor-to-...	2 beds \| 2 baths \| 1,205 sq.ft.	$362,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.4% Airbnb Rental Income: $1936 Traditional Rental Income: $1873 Airbnb ROI: -0.92% Traditional ROI: 0.4%
222 N Columbus Drive #4606 Chicago, IL Luxury, convenience and affordability! 46th floor one bedroom at the Park Millenium! Unobs...	1 beds \| 1 baths \| 685 sq.ft.	$279,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.3% Airbnb Rental Income: $1889 Traditional Rental Income: $1863 Airbnb ROI: -0.52% Traditional ROI: 1.3%
7017 S Hermitage Avenue Chicago, IL Come and view your new home today in the heart of West Englewood! This fully insulated re...	5 beds \| 3 baths \| 1,148 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $1962 Airbnb ROI: N/A Traditional ROI: 3.82%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chicago, IL

7240 S Oakley Avenue

Chicago, IL

4 beds | 2 baths | 1,016 sq.ft.

$314,990

Airbnb cash on cash: -0.35%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $761

Traditional Rental Income: $2121

Airbnb ROI: -0.35%

Traditional ROI: 5.31%

1722 N Keeler Avenue

Chicago, IL

3 beds | 1 baths | 842 sq.ft.

$315,000

Airbnb cash on cash: 2.14%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $1756

Traditional Rental Income: $1632

Airbnb ROI: 2.14%

Traditional ROI: 3.35%

40 E 9th Street #1516

Chicago, IL

3 beds | 3 baths | 2,000 sq.ft.

$400,000

Airbnb cash on cash: -4.13%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $2210

Traditional Rental Income: $4117

Airbnb ROI: -4.13%

Traditional ROI: 2.44%

7228 N Rogers Avenue

Chicago, IL

2 beds | 3 baths | 1,600 sq.ft.

$435,000

Airbnb cash on cash: 0.86%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $1850

Traditional Rental Income: $2651

Airbnb ROI: 0.86%

Traditional ROI: 4.04%

6929 S Loomis Boulevard

Chicago, IL

4 beds | 3 baths | 1,000 sq.ft.

$259,900

Airbnb cash on cash: 0.6%

Traditional cash on cash: 7.88%

Airbnb Rental Income: $872

Traditional Rental Income: $2322

Airbnb ROI: 0.6%

Traditional ROI: 7.88%

7216 S CENTRAL PARK Avenue

Chicago, IL

3 beds | 2 baths | N/A

$304,900

Airbnb cash on cash: 0.36%

Traditional cash on cash: 5.98%

Airbnb Rental Income: $1139

Traditional Rental Income: $2371

Airbnb ROI: 0.36%

Traditional ROI: 5.98%

7205 S HAMLIN Avenue

Chicago, IL

3 beds | 2 baths | 1,080 sq.ft.

$379,900

Airbnb cash on cash: 1.45%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $1438

Traditional Rental Income: $1877

Airbnb ROI: 1.45%

Traditional ROI: 3.88%

3036 N Luna Avenue

Chicago, IL

3 beds | 3 baths | 2,532 sq.ft.

$535,000

Airbnb cash on cash: -0.37%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $1372

Traditional Rental Income: $3396

Airbnb ROI: -0.37%