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 1,167 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
13223 S Buffalo Ave Chicago, IL Nicely updated Bungalow with Basement in a Great Location in Hegewisch! Features a sun-fil...	3 beds \| 2 baths \| 1,100 sq.ft.	$199,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 7.5% Airbnb Rental Income: $830 Traditional Rental Income: $1876 Airbnb ROI: 0.23% Traditional ROI: 7.5%
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: -0.23% Traditional cash on cash: 8.19% Airbnb Rental Income: $704 Traditional Rental Income: $2306 Airbnb ROI: -0.23% Traditional ROI: 8.19%
5705 S Nottingham Ave Chicago, IL 5705 S Nottingham Ave, Chicago, IL 60638 \| Single Family Residential	2 beds \| 2 baths \| 929 sq.ft.	$399,900	Airbnb cash on cash: -2.18% Traditional cash on cash: 1.26% Airbnb Rental Income: $819 Traditional Rental Income: $1782 Airbnb ROI: -2.18% Traditional ROI: 1.26%
10139 S May St Chicago, IL 10139 S May St, Chicago, IL 60643 \| Single Family Residential	4 beds \| 2 baths \| 1,013 sq.ft.	$258,900	Airbnb cash on cash: -1.26% Traditional cash on cash: 3.94% Airbnb Rental Income: $917 Traditional Rental Income: $1847 Airbnb ROI: -1.26% Traditional ROI: 3.94%
9020 S Carpenter St Chicago, IL COME TAKE A LOOK AT THIS BEAUTIFUL NEWLY REMODELED 4 BEDROOM 2 BATH HOME IN WASHINGTON HEI...	3 beds \| 2 baths \| 1,400 sq.ft.	$219,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 6.44% Airbnb Rental Income: $1148 Traditional Rental Income: $1757 Airbnb ROI: 1.69% Traditional ROI: 6.44%
1220 N Damen Ave Chicago, IL 1220 N Damen Ave, Chicago, IL 60622 \| Single Family Residential	4 beds \| 4 baths \| 5,000 sq.ft.	$2,300,000	Airbnb cash on cash: -2.75% Traditional cash on cash: -1.55% Airbnb Rental Income: $1652 Traditional Rental Income: $3739 Airbnb ROI: -2.75% Traditional ROI: -1.55%
3310 N Harding Ave Chicago, IL Situated in the vibrant Avondale/Old Irving Park neighborhood, this stunning 2022 new cons...	5 beds \| 3 baths \| 4,000 sq.ft.	$1,249,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.01% Airbnb Rental Income: $null Traditional Rental Income: $4227 Airbnb ROI: N/A Traditional ROI: 1.01%
4834 N Mulligan Ave Chicago, IL 4834 N Mulligan Ave, Chicago, IL 60630 \| Single Family Residential	3 beds \| 2 baths \| 1,800 sq.ft.	$526,900	Airbnb cash on cash: -1.37% Traditional cash on cash: 1.5% Airbnb Rental Income: $1450 Traditional Rental Income: $2435 Airbnb ROI: -1.37% Traditional ROI: 1.5%
3859 N Cumberland Ave Chicago, IL Welcome to this beautiful 3-bedroom, 1-bathroom ranch home! Walk into a bright and open-co...	3 beds \| 1 baths \| 1,128 sq.ft.	$310,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.62% Airbnb Rental Income: $1316 Traditional Rental Income: $1922 Airbnb ROI: 0.14% Traditional ROI: 3.62%
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.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $3580 Airbnb ROI: N/A Traditional ROI: 3.6%
1228 W 96th St Chicago, IL Charming 5-bedroom, 2-bath brick bungalow offering plenty of space for a growing or multi-...	5 beds \| 2 baths \| 1,632 sq.ft.	$320,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 5.99% Airbnb Rental Income: $1959 Traditional Rental Income: $2428 Airbnb ROI: 2.72% Traditional ROI: 5.99%
2107 W Bradley Pl Chicago, IL 2107 W Bradley Pl, Chicago, IL 60618 \| Single Family Residential	6 beds \| 4 baths \| 6,300 sq.ft.	$3,175,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.88% Airbnb Rental Income: $null Traditional Rental Income: $4172 Airbnb ROI: N/A Traditional ROI: -1.88%
3830 N Lowell Ave Chicago, IL 3830 N Lowell Ave, Chicago, IL 60641 \| Single Family Residential	6 beds \| 5 baths \| 5,300 sq.ft.	$1,899,000	Airbnb cash on cash: -1.4% Traditional cash on cash: -0.35% Airbnb Rental Income: $4280 Traditional Rental Income: $5227 Airbnb ROI: -1.4% Traditional ROI: -0.35%
6236 W Cuyler Ave Chicago, IL Only a re-location makes this home available!! Totally remodeled in 2018 - 3 bedrooms, 3 ...	4 beds \| 3 baths \| 2,400 sq.ft.	$545,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $3362 Airbnb ROI: N/A Traditional ROI: 4.73%
1742 N Bissell St Chicago, IL Situated on one of the most prestigious streets in Lincoln Park, this brick three-story si...	4 beds \| 3 baths \| N/A	$1,350,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 3.17% Airbnb Rental Income: $2678 Traditional Rental Income: $7155 Airbnb ROI: -0.91% Traditional ROI: 3.17%
2122 N Magnolia Ave Chicago, IL 2122 N Magnolia Ave, Chicago, IL 60614 \| Single Family Residential	6 beds \| 5 baths \| 5,500 sq.ft.	$3,500,000	Airbnb cash on cash: -2.58% Traditional cash on cash: -2.51% Airbnb Rental Income: $2987 Traditional Rental Income: $2539 Airbnb ROI: -2.58% Traditional ROI: -2.51%
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.	$130,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 11.3% Airbnb Rental Income: $1500 Traditional Rental Income: $1731 Airbnb ROI: 5.94% Traditional ROI: 11.3%
7935 S Kingston Ave Chicago, IL 7935 S Kingston Ave, Chicago, IL 60617 \| Single Family Residential	5 beds \| 2 baths \| 1,100 sq.ft.	$145,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 9.42% Airbnb Rental Income: $1714 Traditional Rental Income: $1847 Airbnb ROI: 5.04% Traditional ROI: 9.42%
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: 2.28% Traditional cash on cash: 3.82% Airbnb Rental Income: $1903 Traditional Rental Income: $1962 Airbnb ROI: 2.28% Traditional ROI: 3.82%
6619 S Ellis Ave Chicago, IL 6619 S Ellis Ave, Chicago, IL 60637 \| Single Family Residential	4 beds \| 2 baths \| 2,929 sq.ft.	$249,900	Airbnb cash on cash: -2.23% Traditional cash on cash: 5.92% Airbnb Rental Income: $622 Traditional Rental Income: $2255 Airbnb ROI: -2.23% Traditional ROI: 5.92%
4757 S Langley Ave Chicago, IL 4757 S Langley Ave, Chicago, IL 60615 \| Single Family Residential	4 beds \| 2 baths \| 2,520 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.89% Airbnb Rental Income: $null Traditional Rental Income: $2357 Airbnb ROI: N/A Traditional ROI: 0.89%
2447 N Greenview Ave Chicago, IL 2447 N Greenview Ave, Chicago, IL 60614 \| Single Family Residential	6 beds \| 4 baths \| 4,000 sq.ft.	$2,399,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.43% Airbnb Rental Income: $null Traditional Rental Income: $4167 Airbnb ROI: N/A Traditional ROI: -1.43%
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: -1.18% Traditional cash on cash: -0.82% Airbnb Rental Income: $2746 Traditional Rental Income: $2676 Airbnb ROI: -1.18% Traditional ROI: -0.82%
1532 W Wolfram St Chicago, IL Welcome to this beautifully maintained 5 Bedroom + 3.1 Bathroom Single Family Home with an...	5 beds \| 3 baths \| 4,500 sq.ft.	$1,900,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.16% Airbnb Rental Income: $null Traditional Rental Income: $4397 Airbnb ROI: N/A Traditional ROI: -0.16%
2744 W Catalpa Ave Chicago, IL Beautiful Updated 3-Bedroom Georgian Home in Budlong Woods - Corner Lot! Welcome to this s...	3 beds \| 3 baths \| 2,163 sq.ft.	$625,000	Airbnb cash on cash: -1.1% Traditional cash on cash: 2.39% Airbnb Rental Income: $1331 Traditional Rental Income: $2958 Airbnb ROI: -1.1% Traditional ROI: 2.39%
1418 N Waller Ave Chicago, IL 1418 N Waller Ave, Chicago, IL 60651 \| Single Family Residential	2 beds \| 2 baths \| 794 sq.ft.	$325,000	Airbnb cash on cash: -1.69% Traditional cash on cash: 2.18% Airbnb Rental Income: $909 Traditional Rental Income: $1749 Airbnb ROI: -1.69% Traditional ROI: 2.18%
1333 W 71st St Chicago, IL Great Rental Income Property Opportunity or Let a Tenant Pay Your Mortgage! Very Nice Bung...	5 beds \| 2 baths \| 1,600 sq.ft.	$182,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.35% Airbnb Rental Income: $null Traditional Rental Income: $1998 Airbnb ROI: N/A Traditional ROI: 9.35%
9020 S King Dr Chicago, IL This beautifully remolded brick Georgian features 3 bedrooms and 2 full bathrooms, along w...	3 beds \| 2 baths \| 1,216 sq.ft.	$246,900	Airbnb cash on cash: 0.96% Traditional cash on cash: 4.42% Airbnb Rental Income: $1211 Traditional Rental Income: $1629 Airbnb ROI: 0.96% Traditional ROI: 4.42%
9432 S Vernon Ave Chicago, IL Attention all investors and savvy home owners!! This spacious and bright brick bungalow i...	4 beds \| 3 baths \| 2,800 sq.ft.	$299,500	Airbnb cash on cash: 0.96% Traditional cash on cash: 5.25% Airbnb Rental Income: $1248 Traditional Rental Income: $2062 Airbnb ROI: 0.96% Traditional ROI: 5.25%
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.	$269,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 7.43% Airbnb Rental Income: $1149 Traditional Rental Income: $2376 Airbnb ROI: 1.11% Traditional ROI: 7.43%
53 E 101st St Chicago, IL SHORT SALE	5 beds \| 2 baths \| 1,080 sq.ft.	$129,900	Airbnb cash on cash: 4.64% Traditional cash on cash: 11.24% Airbnb Rental Income: $1333 Traditional Rental Income: $1747 Airbnb ROI: 4.64% Traditional ROI: 11.24%
4740 S Ingleside Ave Chicago, IL Get ready to fall in love with this luxurious penthouse condo in the opulent Kenwood Landm...	3 beds \| 2 baths \| 1,800 sq.ft.	$325,000	Airbnb cash on cash: -3.3% Traditional cash on cash: 3.49% Airbnb Rental Income: $883 Traditional Rental Income: $2621 Airbnb ROI: -3.3% Traditional ROI: 3.49%
5450 N Natoma Ave Chicago, IL You will fall in love with this new construction classic Chicago 2 story home! Great open ...	5 beds \| 3 baths \| 3,500 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $2992 Airbnb ROI: N/A Traditional ROI: 2.17%
1900 N Kenneth Avenue Chicago, IL Welcome home to this beautifully maintained all-brick ranch. This 3-BED, 2-BATH gem has be...	2 beds \| 2 baths \| 899 sq.ft.	$385,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.24% Airbnb Rental Income: $929 Traditional Rental Income: $1939 Airbnb ROI: -0.51% Traditional ROI: 3.24%
9925 S Maplewood Ave Chicago, IL Welcome to this charming all-brick Georgian on a wonderful block in West Beverly! This wel...	3 beds \| 1 baths \| 1,625 sq.ft.	$408,900	Airbnb cash on cash: -1.39% Traditional cash on cash: 3.05% Airbnb Rental Income: $723 Traditional Rental Income: $2113 Airbnb ROI: -1.39% Traditional ROI: 3.05%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chicago, IL

13223 S Buffalo Ave

Chicago, IL

3 beds | 2 baths | 1,100 sq.ft.

$199,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $830

Traditional Rental Income: $1876

Airbnb ROI: 0.23%

Traditional ROI: 7.5%

7801 S Ada St

Chicago, IL

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

$240,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 8.19%

Airbnb Rental Income: $704

Traditional Rental Income: $2306

Airbnb ROI: -0.23%

Traditional ROI: 8.19%

5705 S Nottingham Ave

Chicago, IL

2 beds | 2 baths | 929 sq.ft.

$399,900

Airbnb cash on cash: -2.18%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $819

Traditional Rental Income: $1782

Airbnb ROI: -2.18%

Traditional ROI: 1.26%

10139 S May St

Chicago, IL

4 beds | 2 baths | 1,013 sq.ft.

$258,900

Airbnb cash on cash: -1.26%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $917

Traditional Rental Income: $1847

Airbnb ROI: -1.26%

Traditional ROI: 3.94%

9020 S Carpenter St

Chicago, IL

3 beds | 2 baths | 1,400 sq.ft.

$219,900

Airbnb cash on cash: 1.69%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $1148

Traditional Rental Income: $1757

Airbnb ROI: 1.69%

Traditional ROI: 6.44%

1220 N Damen Ave

Chicago, IL

4 beds | 4 baths | 5,000 sq.ft.

$2,300,000

Airbnb cash on cash: -2.75%

Traditional cash on cash: -1.55%

Airbnb Rental Income: $1652

Traditional Rental Income: $3739

Airbnb ROI: -2.75%

Traditional ROI: -1.55%

3310 N Harding Ave

Chicago, IL

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

$1,249,999

Airbnb cash on cash: N/A

Traditional cash on cash: 1.01%

Airbnb Rental Income: $null

Traditional Rental Income: $4227

Airbnb ROI: N/A

Traditional ROI: 1.01%

4834 N Mulligan Ave

Chicago, IL

3 beds | 2 baths | 1,800 sq.ft.

$526,900

Airbnb cash on cash: -1.37%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $1450

Traditional Rental Income: $2435

Airbnb ROI: -1.37%