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.

Investment Property for Sale in Chicago, IL

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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: 0.24% Traditional cash on cash: 7.5% Airbnb Rental Income: $834 Traditional Rental Income: $1876 Airbnb ROI: 0.24% Traditional ROI: 7.5%
7801 S Ada Street Chicago, IL Welcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham...	3 beds \| 3 baths \| 1,200 sq.ft.	$240,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 8.19% Airbnb Rental Income: $793 Traditional Rental Income: $2306 Airbnb ROI: 0.1% Traditional ROI: 8.19%
5918 S Albany Avenue Chicago, IL GREAT OPPORTUNITY TO OWN IN THIS FAST APPRECIATING AREA !!! REAR OF THE LOT !!BRICK SINGLE...	2 beds \| 2 baths \| 832 sq.ft.	$175,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 9.26% Airbnb Rental Income: $1113 Traditional Rental Income: $2024 Airbnb ROI: 1.54% Traditional ROI: 9.26%
5701 N Sheridan Road #3E Chicago, IL Bright, beautifully maintained 1-bedroom with sweeping lake and skyline views in the highl...	1 beds \| 1 baths \| 850 sq.ft.	$199,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 2.3% Airbnb Rental Income: $1581 Traditional Rental Income: $1566 Airbnb ROI: -0.01% Traditional ROI: 2.3%
5130 S Menard Ave Chicago, IL 5130 S Menard Ave, Chicago, IL 60638 \| Single Family Residential	3 beds \| 1 baths \| 945 sq.ft.	$280,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 2.29% Airbnb Rental Income: $1225 Traditional Rental Income: $1551 Airbnb ROI: -0.44% Traditional ROI: 2.29%
5705 S Nottingham Ave Chicago, IL 5705 S Nottingham Ave, Chicago, IL 60638 \| Single Family Residential	2 beds \| 2 baths \| 929 sq.ft.	$429,000	Airbnb cash on cash: -2.28% Traditional cash on cash: 0.95% Airbnb Rental Income: $807 Traditional Rental Income: $1782 Airbnb ROI: -2.28% Traditional ROI: 0.95%
5728 S Stony Island Ave #2 Chicago, IL 5728 S Stony Island Ave #2, Chicago, IL 60637 \| Condo/Coop	1 beds \| 1 baths \| 900 sq.ft.	$95,000	Airbnb cash on cash: -10.89% Traditional cash on cash: 2% Airbnb Rental Income: $376 Traditional Rental Income: $1318 Airbnb ROI: -10.89% Traditional ROI: 2%
945 E Hyde Park Blvd #2 Chicago, IL Welcome to The Courtyard On The Boulevard. This vintage Hyde Park condominium boasts the l...	2 beds \| 1 baths \| 1,100 sq.ft.	$180,000	Airbnb cash on cash: -5.79% Traditional cash on cash: 1.72% Airbnb Rental Income: $606 Traditional Rental Income: $1603 Airbnb ROI: -5.79% Traditional ROI: 1.72%
5801 S Blackstone Ave Chicago, IL 5801 S Blackstone Ave, Chicago, IL 60637 \| Single Family Residential	5 beds \| 4 baths \| 3,919 sq.ft.	$1,745,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.28% Airbnb Rental Income: $null Traditional Rental Income: $3303 Airbnb ROI: N/A Traditional ROI: -1.28%
1709 NORTH PARK Avenue #1 Chicago, IL This charming vintage-chic condo blends classic character with thoughtful updates in a pri...	2 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 0.88% Airbnb Rental Income: $1561 Traditional Rental Income: $2399 Airbnb ROI: -1.52% Traditional ROI: 0.88%
1905 N Bissell Street #2 Chicago, IL Impeccably designed resale from critically acclaimed PLD Development. This highly upgraded...	3 beds \| 2 baths \| N/A	$950,000	Airbnb cash on cash: -1.93% Traditional cash on cash: 1.7% Airbnb Rental Income: $1458 Traditional Rental Income: $4238 Airbnb ROI: -1.93% Traditional ROI: 1.7%
801 S Plymouth Court #1111 Chicago, IL Rarely available Penthouse unit overlooking Sears Tower (Willis) and downtown Chicago. 2 l...	2 beds \| 2 baths \| 1,300 sq.ft.	$265,000	Airbnb cash on cash: -4.73% Traditional cash on cash: 3.58% Airbnb Rental Income: $886 Traditional Rental Income: $2626 Airbnb ROI: -4.73% Traditional ROI: 3.58%
1645 W Ogden Avenue #530 Chicago, IL Rarely available 3 bed, 2 bath loft in the West Loop with soaring 14' ceilings and oversiz...	3 beds \| 2 baths \| 1,415 sq.ft.	$485,000	Airbnb cash on cash: -3.55% Traditional cash on cash: -0.1% Airbnb Rental Income: $1068 Traditional Rental Income: $2264 Airbnb ROI: -3.55% Traditional ROI: -0.1%
5602 N Fairview Ave Chicago, IL 5602 N Fairview Ave, Chicago, IL 60631 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$474,900	Airbnb cash on cash: -1.94% Traditional cash on cash: -1.05% Airbnb Rental Income: $1036 Traditional Rental Income: $1070 Airbnb ROI: -1.94% Traditional ROI: -1.05%
5555 N Cumberland Avenue #413 Chicago, IL This elegant high-rise residence offers a refined living experience in a prime location. S...	2 beds \| 2 baths \| 1,700 sq.ft.	$425,000	Airbnb cash on cash: -1.77% Traditional cash on cash: 2.84% Airbnb Rental Income: $1150 Traditional Rental Income: $2606 Airbnb ROI: -1.77% Traditional ROI: 2.84%
5422 N Natoma Ave Chicago, IL 5422 N Natoma Ave, Chicago, IL 60656 \| Single Family Residential	3 beds \| 2 baths \| 2,337 sq.ft.	$619,000	Airbnb cash on cash: -1.4% Traditional cash on cash: 0.89% Airbnb Rental Income: $1620 Traditional Rental Income: $2487 Airbnb ROI: -1.4% Traditional ROI: 0.89%
5038 N Rutherford Ave Chicago, IL 5038 N Rutherford Ave, Chicago, IL 60656 \| Single Family Residential	4 beds \| 3 baths \| 1,854 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.28% Airbnb Rental Income: $null Traditional Rental Income: $2395 Airbnb ROI: N/A Traditional ROI: 0.28%
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: 1.17% Traditional cash on cash: 6.44% Airbnb Rental Income: $1019 Traditional Rental Income: $1757 Airbnb ROI: 1.17% Traditional ROI: 6.44%
2854 S Central Park Ave Chicago, IL 2854 S Central Park Ave, Chicago, IL 60623 \| Single Family Residential	5 beds \| 2 baths \| 896 sq.ft.	$348,500	Airbnb cash on cash: 5.69% Traditional cash on cash: 3.07% Airbnb Rental Income: $3437 Traditional Rental Income: $1819 Airbnb ROI: 5.69% Traditional ROI: 3.07%
4836 S Dorchester Avenue Chicago, IL Looking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Sing...	6 beds \| 5 baths \| N/A	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.63% Airbnb Rental Income: $null Traditional Rental Income: $2659 Airbnb ROI: N/A Traditional ROI: 0.63%
1905 W Fullerton Ave Chicago, IL	N/A beds \| N/A baths \| 777 sq.ft.	$399,900	Airbnb cash on cash: -1.39% Traditional cash on cash: -0.38% Airbnb Rental Income: $1171 Traditional Rental Income: $1166 Airbnb ROI: -1.39% Traditional ROI: -0.38%
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: -2.82% Traditional cash on cash: -1.55% Airbnb Rental Income: $1476 Traditional Rental Income: $3739 Airbnb ROI: -2.82% Traditional ROI: -1.55%
6816 W 65th Street #5 Chicago, IL Beautifully up-kept townhouse in the Chicago land area. Home offers natural light througho...	3 beds \| 3 baths \| 1,850 sq.ft.	$379,900	Airbnb cash on cash: -0.23% Traditional cash on cash: 2.99% Airbnb Rental Income: $1611 Traditional Rental Income: $2300 Airbnb ROI: -0.23% Traditional ROI: 2.99%
3553 W Sunnyside Ave #1 Chicago, IL 3553 W Sunnyside Ave #1, Chicago, IL 60625 \| Condo/Coop	1 beds \| 1 baths \| 725 sq.ft.	$164,900	Airbnb cash on cash: -2.77% Traditional cash on cash: 1.74% Airbnb Rental Income: $1001 Traditional Rental Income: $1355 Airbnb ROI: -2.77% Traditional ROI: 1.74%
2645 W Haddon Ave #2 Chicago, IL 2645 W Haddon Ave #2, Chicago, IL 60622 \| Condo/Coop	2 beds \| 2 baths \| 1,200 sq.ft.	$419,000	Airbnb cash on cash: -2.27% Traditional cash on cash: 1.48% Airbnb Rental Income: $1066 Traditional Rental Income: $2169 Airbnb ROI: -2.27% Traditional ROI: 1.48%
832 N Washtenaw Avenue #3 Chicago, IL Perched up above the neighborhood with privacy and natural light in every direction, welco...	2 beds \| 2 baths \| N/A	$560,000	Airbnb cash on cash: -1.63% Traditional cash on cash: 2.03% Airbnb Rental Income: $1066 Traditional Rental Income: $2615 Airbnb ROI: -1.63% Traditional ROI: 2.03%
2334 W Ohio Street Chicago, IL Spectacular home on a 30' wide lot with amazing finishes throughout. Exclusive all-masonry...	5 beds \| 4 baths \| 4,584 sq.ft.	$1,950,000	Airbnb cash on cash: -2.37% Traditional cash on cash: -0.55% Airbnb Rental Income: $413 Traditional Rental Income: $3443 Airbnb ROI: -2.37% Traditional ROI: -0.55%
3214 S Canal St Chicago, IL 3214 S Canal St, Chicago, IL 60616 \| Single Family Residential	5 beds \| 5 baths \| 8,800 sq.ft.	$1,808,000	Airbnb cash on cash: -2.64% Traditional cash on cash: -0.37% Airbnb Rental Income: $1580 Traditional Rental Income: $4939 Airbnb ROI: -2.64% Traditional ROI: -0.37%
2045 W Concord Place #604 Chicago, IL Experience the best of Bucktown living in this thoughtfully designed 2-bedroom, 2-bath pen...	2 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: -2.55% Traditional cash on cash: -0.19% Airbnb Rental Income: $1071 Traditional Rental Income: $1973 Airbnb ROI: -2.55% Traditional ROI: -0.19%
1732 N Winchester Ave Chicago, IL Modern 4 level home with 5BR + office featuring 4 bedrooms upstairs in A+ location in the ...	6 beds \| 4 baths \| N/A	$1,925,000	Airbnb cash on cash: -2.47% Traditional cash on cash: 0.25% Airbnb Rental Income: $398 Traditional Rental Income: $4997 Airbnb ROI: -2.47% Traditional ROI: 0.25%
680 S Federal St #904 Chicago, IL 680 S Federal St #904, Chicago, IL 60605 \| Condo/Coop	N/A beds \| 1 baths \| 505 sq.ft.	$135,000	Airbnb cash on cash: -4.81% Traditional cash on cash: 1.62% Airbnb Rental Income: $685 Traditional Rental Income: $1216 Airbnb ROI: -4.81% Traditional ROI: 1.62%

Real Estate investment in Chicago, IL

There are 5,759 properties for sale in the city of Chicago . The median list price in Chicago is $375,000 and the average price per square foot is $209. In May 2026, the average monthly cash on cash return in Chicago is 2.00%. The average monthly rental income in Chicago is $2,173.

Chicago, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 5,759 investment properties available for sale in Chicago.

In 2026, the best neighborhood to buy investment property is Hanson Park.

The ROI for Long-Term is higher than the Short-Term in Chicago with average rental income of $2,173.

Your search for investment property begins and ends here

Investment Property 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: 0.24%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $834

Traditional Rental Income: $1876

Airbnb ROI: 0.24%

Traditional ROI: 7.5%

7801 S Ada Street

Chicago, IL

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

$240,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 8.19%

Airbnb Rental Income: $793

Traditional Rental Income: $2306

Airbnb ROI: 0.1%

Traditional ROI: 8.19%

5918 S Albany Avenue

Chicago, IL

2 beds | 2 baths | 832 sq.ft.

$175,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 9.26%

Airbnb Rental Income: $1113

Traditional Rental Income: $2024

Airbnb ROI: 1.54%

Traditional ROI: 9.26%

5701 N Sheridan Road #3E

Chicago, IL

1 beds | 1 baths | 850 sq.ft.

$199,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $1581

Traditional Rental Income: $1566

Airbnb ROI: -0.01%

Traditional ROI: 2.3%

5130 S Menard Ave

Chicago, IL

3 beds | 1 baths | 945 sq.ft.

$280,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $1225

Traditional Rental Income: $1551

Airbnb ROI: -0.44%

Traditional ROI: 2.29%

5705 S Nottingham Ave

Chicago, IL

2 beds | 2 baths | 929 sq.ft.

$429,000

Airbnb cash on cash: -2.28%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $807

Traditional Rental Income: $1782

Airbnb ROI: -2.28%

Traditional ROI: 0.95%

5728 S Stony Island Ave #2

Chicago, IL

1 beds | 1 baths | 900 sq.ft.

$95,000

Airbnb cash on cash: -10.89%

Traditional cash on cash: 2%

Airbnb Rental Income: $376

Traditional Rental Income: $1318

Airbnb ROI: -10.89%

Traditional ROI: 2%

945 E Hyde Park Blvd #2

Chicago, IL

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

$180,000

Airbnb cash on cash: -5.79%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $606

Traditional Rental Income: $1603

Airbnb ROI: -5.79%