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 1,122 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
11616 S Harvard Ave Chicago, IL	3 beds \| 2 baths \| 1,200 sq.ft.	$219,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 7.39% Airbnb Rental Income: $1360 Traditional Rental Income: $1940 Airbnb ROI: 2.61% Traditional ROI: 7.39%
7801 S Ada St Chicago, IL Welcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham...	4 beds \| 3 baths \| 1,200 sq.ft.	$240,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 8.19% Airbnb Rental Income: $659 Traditional Rental Income: $2306 Airbnb ROI: -0.39% Traditional ROI: 8.19%
1432 W Chase Ave Chicago, IL **Seller has accepted an offer in the evening on Fri, March 20. Paperwork still being sign...	4 beds \| 2 baths \| 2,046 sq.ft.	$600,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.19% Airbnb Rental Income: $1439 Traditional Rental Income: $2269 Airbnb ROI: -1.06% Traditional ROI: 1.19%
7216 S Central Park Ave Chicago, IL Well-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi...	4 beds \| 2 baths \| 1,080 sq.ft.	$290,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 6.32% Airbnb Rental Income: $575 Traditional Rental Income: $2371 Airbnb ROI: -1.29% Traditional ROI: 6.32%
3744 N Lockwood Ave Chicago, IL FIRST FLOOR WITH 3 BEDROOMS AND 2 BATHS, INCLUDING MASTER SUITE. UPDATED KITCHEN INCLUDES ...	4 beds \| 3 baths \| N/A	$429,900	Airbnb cash on cash: -0.73% Traditional cash on cash: 5.42% Airbnb Rental Income: $1098 Traditional Rental Income: $3200 Airbnb ROI: -0.73% Traditional ROI: 5.42%
3740 N Pacific Ave Chicago, IL Step into this beautifully updated 5-bedroom, 3-bath raised ranch, offering nearly new-con...	5 beds \| 3 baths \| 3,000 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $3580 Airbnb ROI: N/A Traditional ROI: 3.56%
9328 S Paxton Ave Chicago, IL Welcome to 9328 South Paxton Avenue, a beautifully refreshed home that effortlessly combin...	5 beds \| 2 baths \| N/A	$299,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 5.49% Airbnb Rental Income: $952 Traditional Rental Income: $2048 Airbnb ROI: 0.36% Traditional ROI: 5.49%
306 W 111th St Chicago, IL Beautifully renovated and truly move-in ready, this stylish tri-level home offers 4 bedroo...	4 beds \| 1 baths \| 1,400 sq.ft.	$229,900	Airbnb cash on cash: -0.9% Traditional cash on cash: 6.39% Airbnb Rental Income: $550 Traditional Rental Income: $1855 Airbnb ROI: -0.9% Traditional ROI: 6.39%
9021 S Exchange Ave Chicago, IL Single Family 4 bedrooms, 1 bath home. Updates in 2026 include kitchen, baths, - ceramic t...	4 beds \| 1 baths \| 1,298 sq.ft.	$135,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 10.86% Airbnb Rental Income: $1111 Traditional Rental Income: $1731 Airbnb ROI: 3.19% Traditional ROI: 10.86%
7927 S Burnham Ave Chicago, IL Possible FHA/VA Financing * We are in the area covered by the Cook County DP Assistance Pr...	4 beds \| 2 baths \| 1,124 sq.ft.	$190,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 7.65% Airbnb Rental Income: $1148 Traditional Rental Income: $1775 Airbnb ROI: 2.07% Traditional ROI: 7.65%
7017 S Hermitage Ave Chicago, IL Come and view your new home today in the heart of West Englewood! This fully insulated rem...	7 beds \| 3 baths \| 1,148 sq.ft.	$389,900	Airbnb cash on cash: 0.82% Traditional cash on cash: 3.82% Airbnb Rental Income: $1264 Traditional Rental Income: $1962 Airbnb ROI: 0.82% Traditional ROI: 3.82%
11725 S Morgan St Chicago, IL Experience the perfect blend of comfort and style in this adorable West Pullman home! This...	3 beds \| 2 baths \| 760 sq.ft.	$205,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 7.04% Airbnb Rental Income: $1360 Traditional Rental Income: $1741 Airbnb ROI: 3.04% Traditional ROI: 7.04%
41 E Elm St Chicago, IL Positioned on one of the most desirable blocks in Chicago's Gold Coast, just steps from th...	4 beds \| 5 baths \| 4,200 sq.ft.	$2,499,000	Airbnb cash on cash: -2.1% Traditional cash on cash: 2.67% Airbnb Rental Income: $1342 Traditional Rental Income: $11991 Airbnb ROI: -2.1% Traditional ROI: 2.67%
2424 N Geneva Ter Chicago, IL A rare and distinguished single-family offering in prime East Lincoln Park, this impeccabl...	4 beds \| 2 baths \| N/A	$1,725,000	Airbnb cash on cash: -1.7% Traditional cash on cash: -0.82% Airbnb Rental Income: $1741 Traditional Rental Income: $2676 Airbnb ROI: -1.7% Traditional ROI: -0.82%
1527 W Pearson St Chicago, IL Unique opportunity in amazing West Town/ East Village. Located just two blocks to bustling...	4 beds \| 3 baths \| 3,100 sq.ft.	$1,250,000	Airbnb cash on cash: -1.94% Traditional cash on cash: 0.58% Airbnb Rental Income: $1034 Traditional Rental Income: $3605 Airbnb ROI: -1.94% Traditional ROI: 0.58%
169 N Lorel Ave Chicago, IL Welcome to this beautifully rehabbed 2-story single-family home in the Austin neighborhood...	4 beds \| 1 baths \| 1,800 sq.ft.	$389,999	Airbnb cash on cash: -0.89% Traditional cash on cash: 3.93% Airbnb Rental Income: $565 Traditional Rental Income: $2045 Airbnb ROI: -0.89% Traditional ROI: 3.93%
4914 S Washington Park Ct Chicago, IL Completely rehabbed in 2018, this stunning 4-bedroom, 3.5-bath Greystone beautifully blend...	4 beds \| 3 baths \| 3,000 sq.ft.	$660,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.74% Airbnb Rental Income: $1432 Traditional Rental Income: $3539 Airbnb ROI: -0.37% Traditional ROI: 3.74%
7642 S Dante Ave Chicago, IL Beautifully Updated 1.5-Story Home with Modern Upgrades! Welcome to this newly updated 3-b...	3 beds \| 2 baths \| 1,656 sq.ft.	$275,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 7.27% Airbnb Rental Income: $903 Traditional Rental Income: $2376 Airbnb ROI: 0.28% Traditional ROI: 7.27%
12249 S Parnell Ave Chicago, IL Great potential in this spacious home located on oversized Chicago lot with side drive and...	4 beds \| 1 baths \| 1,056 sq.ft.	$120,000	Airbnb cash on cash: -2.26% Traditional cash on cash: 8.99% Airbnb Rental Income: $391 Traditional Rental Income: $1439 Airbnb ROI: -2.26% Traditional ROI: 8.99%
4234 S St Lawrence Ave Chicago, IL STUNNING AND RARE 34' EXTRA WIDE BRONZEVILLE RESIDENCE OFFERING NEARLY 3,000 SQUARE FEET O...	4 beds \| 3 baths \| 3,024 sq.ft.	$695,000	Airbnb cash on cash: -1.75% Traditional cash on cash: 1.2% Airbnb Rental Income: $942 Traditional Rental Income: $2506 Airbnb ROI: -1.75% Traditional ROI: 1.2%
10210 S Bensley Ave Chicago, IL Move-in ready with built-in value! Charming 2-bedroom, 1-bath raised ranch located on Chic...	2 beds \| 1 baths \| 819 sq.ft.	$129,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 9.72% Airbnb Rental Income: $632 Traditional Rental Income: $1562 Airbnb ROI: -0.09% Traditional ROI: 9.72%
11008 S Wallace St Chicago, IL WELCOME HOME TO THIS LOVELY, METICULOSLY MAINTAINED ALL BRICK BUNGALOW ON A QUIET PICTURE-...	5 beds \| 3 baths \| 2,496 sq.ft.	$329,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 10.64% Airbnb Rental Income: $1057 Traditional Rental Income: $3893 Airbnb ROI: 0.31% Traditional ROI: 10.64%
5706 W Dakin St Chicago, IL Amazing 4BR/3.5BA Home in Prime Portage Park Location - 3,500 Sq Ft Don't miss this beauti...	4 beds \| 3 baths \| 3,500 sq.ft.	$699,999	Airbnb cash on cash: -1.77% Traditional cash on cash: 2.75% Airbnb Rental Income: $1098 Traditional Rental Income: $3677 Airbnb ROI: -1.77% Traditional ROI: 2.75%
13415 S Mackinaw Ave Chicago, IL BACK ON MARKET ! NO FAULT TO SELLER! 3-bedrooms & 2-bath home located in the Hegewis...	3 beds \| 2 baths \| 1,793 sq.ft.	$265,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 6.79% Airbnb Rental Income: $894 Traditional Rental Income: $2239 Airbnb ROI: 0.06% Traditional ROI: 6.79%
8229 S Wentworth Ave Chicago, IL Welcome to this beautifully renovated brick single-family home in the heart of Chicago. Th...	4 beds \| 2 baths \| 1,040 sq.ft.	$322,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.53% Airbnb Rental Income: $740 Traditional Rental Income: $1689 Airbnb ROI: -0.64% Traditional ROI: 3.53%
1107 W 101st St Chicago, IL Welcome to this beautifully updated brick 3-bedroom, 2-bath home with a finished basement ...	3 beds \| 2 baths \| 1,200 sq.ft.	$270,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 6.22% Airbnb Rental Income: $1136 Traditional Rental Income: $2148 Airbnb ROI: 0.76% Traditional ROI: 6.22%
34 W 110th Pl Chicago, IL Single family in very good shape ready for a new owner. very nice kitchen and baths	4 beds \| 2 baths \| 1,000 sq.ft.	$227,500	Airbnb cash on cash: -0.47% Traditional cash on cash: 7.96% Airbnb Rental Income: $550 Traditional Rental Income: $2084 Airbnb ROI: -0.47% Traditional ROI: 7.96%
4846 N Hermitage Ave Chicago, IL On a sprawling 165-foot-deep lot stands this brand-new 6-bedroom, 4.5-bath home. From the ...	6 beds \| 4 baths \| 4,800 sq.ft.	$2,350,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 0.05% Airbnb Rental Income: $1756 Traditional Rental Income: $4387 Airbnb ROI: -1.38% Traditional ROI: 0.05%
2037 N Tripp Ave Chicago, IL Turnkey investment opportunity in the Hermosa Neighborhood! This fully rented, income-prod...	4 beds \| 3 baths \| 2,460 sq.ft.	$449,900	Airbnb cash on cash: -0.79% Traditional cash on cash: 5.26% Airbnb Rental Income: $1028 Traditional Rental Income: $3218 Airbnb ROI: -0.79% Traditional ROI: 5.26%
11419 S Fairfield Ave Chicago, IL OPEN SUNDAY 03-29-26 FROM 12:00-3:00 PM. Welcome to this charming, modern brick Georgian t...	4 beds \| 2 baths \| 1,246 sq.ft.	$324,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 5.09% Airbnb Rental Income: $1176 Traditional Rental Income: $2365 Airbnb ROI: -0.07% Traditional ROI: 5.09%
1608 S Throop St Chicago, IL Rare Single-Family Home with Rooftop Deck in the Heart of Pilsen! Opportunities like this ...	3 beds \| 2 baths \| 1,688 sq.ft.	$799,900	Airbnb cash on cash: -1.81% Traditional cash on cash: 1.26% Airbnb Rental Income: $772 Traditional Rental Income: $2747 Airbnb ROI: -1.81% Traditional ROI: 1.26%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chicago, IL

11616 S Harvard Ave

Chicago, IL

3 beds | 2 baths | 1,200 sq.ft.

$219,900

Airbnb cash on cash: 2.61%

Traditional cash on cash: 7.39%

Airbnb Rental Income: $1360

Traditional Rental Income: $1940

Airbnb ROI: 2.61%

Traditional ROI: 7.39%

7801 S Ada St

Chicago, IL

4 beds | 3 baths | 1,200 sq.ft.

$240,000

Airbnb cash on cash: -0.39%

Traditional cash on cash: 8.19%

Airbnb Rental Income: $659

Traditional Rental Income: $2306

Airbnb ROI: -0.39%

Traditional ROI: 8.19%

1432 W Chase Ave

Chicago, IL

4 beds | 2 baths | 2,046 sq.ft.

$600,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $1439

Traditional Rental Income: $2269

Airbnb ROI: -1.06%

Traditional ROI: 1.19%

7216 S Central Park Ave

Chicago, IL

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

$290,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $575

Traditional Rental Income: $2371

Airbnb ROI: -1.29%

Traditional ROI: 6.32%

3744 N Lockwood Ave

Chicago, IL

4 beds | 3 baths | N/A

$429,900

Airbnb cash on cash: -0.73%

Traditional cash on cash: 5.42%

Airbnb Rental Income: $1098

Traditional Rental Income: $3200

Airbnb ROI: -0.73%

Traditional ROI: 5.42%

3740 N Pacific Ave

Chicago, IL

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

$580,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.56%

Airbnb Rental Income: $null

Traditional Rental Income: $3580

Airbnb ROI: N/A

Traditional ROI: 3.56%

9328 S Paxton Ave

Chicago, IL

5 beds | 2 baths | N/A

$299,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $952

Traditional Rental Income: $2048

Airbnb ROI: 0.36%

Traditional ROI: 5.49%

306 W 111th St

Chicago, IL

4 beds | 1 baths | 1,400 sq.ft.

$229,900

Airbnb cash on cash: -0.9%

Traditional cash on cash: 6.39%

Airbnb Rental Income: $550

Traditional Rental Income: $1855

Airbnb ROI: -0.9%