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 Avenue Chicago, IL Welcome to Hegewisch - a warm, close-knit Chicago neighborhood known for its small-town fe...	3 beds \| 2 baths \| 1,100 sq.ft.	$189,900	Airbnb cash on cash: 5.96% Traditional cash on cash: 8.18% Airbnb Rental Income: $1996 Traditional Rental Income: $1876 Airbnb ROI: 5.96% Traditional ROI: 8.18%
8333 S Baltimore Ave Chicago, IL 8333 S Baltimore Ave, Chicago, IL 60617 \| Single Family Residential	4 beds \| 3 baths \| 2,186 sq.ft.	$245,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 8.9% Airbnb Rental Income: $2232 Traditional Rental Income: $2901 Airbnb ROI: 3.58% Traditional ROI: 8.9%
11830 S Eggleston Ave Chicago, IL This is a 2-unit property that is a must-see. Each unit has 2 beds, 1 bath. There is poten...	4 beds \| 2 baths \| N/A	$298,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.18% Airbnb Rental Income: $null Traditional Rental Income: $2333 Airbnb ROI: N/A Traditional ROI: 6.18%
3906 W Montrose Ave Chicago, IL 3906 W Montrose Ave, Chicago, IL 60618 \| Single Family Residential	5 beds \| 2 baths \| 1,120 sq.ft.	$509,999	Airbnb cash on cash: 4.54% Traditional cash on cash: 1.25% Airbnb Rental Income: $4796 Traditional Rental Income: $2240 Airbnb ROI: 4.54% Traditional ROI: 1.25%
8831 S Eggleston Ave Chicago, IL This Auburn Gresham (West Chatham) Handyman Special was Rehabbed in 2013 and has been well...	3 beds \| 1 baths \| 1,375 sq.ft.	$227,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 6.1% Airbnb Rental Income: $1282 Traditional Rental Income: $1756 Airbnb ROI: 2.02% Traditional ROI: 6.1%
1620 W 77th St Chicago, IL 1620 W 77th St, Chicago, IL 60620 \| Single Family Residential	4 beds \| 3 baths \| 2,500 sq.ft.	$380,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 5.18% Airbnb Rental Income: $2150 Traditional Rental Income: $3097 Airbnb ROI: 0.99% Traditional ROI: 5.18%
8015 S Justine St Chicago, IL 8015 S Justine St, Chicago, IL 60620 \| Single Family Residential	3 beds \| 3 baths \| 1,178 sq.ft.	$335,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.88% Airbnb Rental Income: $1617 Traditional Rental Income: $2337 Airbnb ROI: 0.14% Traditional ROI: 3.88%
8031 S Woodlawn Ave Chicago, IL 8031 S Woodlawn Ave, Chicago, IL 60619 \| Single Family Residential	4 beds \| 2 baths \| 864 sq.ft.	$249,900	Airbnb cash on cash: 3.05% Traditional cash on cash: 3.4% Airbnb Rental Income: $2118 Traditional Rental Income: $1659 Airbnb ROI: 3.05% Traditional ROI: 3.4%
5415 N Sheridan Rd #4407 Chicago, IL Rarely available , 44th floor. Luxury high rise building. Spectacular lake and north view...	N/A beds \| 1 baths \| 580 sq.ft.	$164,900	Airbnb cash on cash: -1.58% Traditional cash on cash: 1.64% Airbnb Rental Income: $1198 Traditional Rental Income: $1317 Airbnb ROI: -1.58% Traditional ROI: 1.64%
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.	$179,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 2.5% Airbnb Rental Income: $1955 Traditional Rental Income: $1566 Airbnb ROI: 1.77% Traditional ROI: 2.5%
6631 N Caldwell Avenue Chicago, IL CHARM ABOUNDS IN THIS LOVINGLY MAINTAINED BRICK CAPE COD IN THE HIGHLY SOUGHT AFTER EDGEBR...	3 beds \| 3 baths \| 1,545 sq.ft.	$599,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.53% Airbnb Rental Income: $2464 Traditional Rental Income: $2211 Airbnb ROI: -0.09% Traditional ROI: 0.53%
5400 S HARPER Avenue #402 Chicago, IL Experience the best of Hyde Park living in this beautifully maintained 2-bedroom, 1-bath c...	2 beds \| 1 baths \| 900 sq.ft.	$245,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 1.2% Airbnb Rental Income: $1406 Traditional Rental Income: $1394 Airbnb ROI: -0.57% Traditional ROI: 1.2%
5300 South Shore Drive #63 Chicago, IL High floor, great views, very quiet! Thick concrete floors and ceilings. 10 windows in the...	2 beds \| 2 baths \| 1,500 sq.ft.	$149,900	Airbnb cash on cash: -2.72% Traditional cash on cash: -3.03% Airbnb Rental Income: $2145 Traditional Rental Income: $1554 Airbnb ROI: -2.72% Traditional ROI: -3.03%
340 E Randolph St #205 Chicago, IL 340 E Randolph St #205, Chicago, IL 60601 \| Condo/Coop	1 beds \| 1 baths \| 1,224 sq.ft.	$895,000	Airbnb cash on cash: -3.23% Traditional cash on cash: -2.07% Airbnb Rental Income: $1626 Traditional Rental Income: $2134 Airbnb ROI: -3.23% Traditional ROI: -2.07%
210 S Desplaines St #2203 Chicago, IL Spacious Penthouse level Jr 1Br In West Loop, Cherry floors and cabinets, granite countert...	1 beds \| 1 baths \| 605 sq.ft.	$265,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 2.21% Airbnb Rental Income: $2288 Traditional Rental Income: $2036 Airbnb ROI: 0.94% Traditional ROI: 2.21%
5602 N Fairview Ave Chicago, IL 5602 N Fairview Ave, Chicago, IL 60631 \| Other	2 beds \| N/A baths \| 0 sq.ft.	$469,000	Airbnb cash on cash: 1.43% Traditional cash on cash: -1.02% Airbnb Rental Income: $2801 Traditional Rental Income: $1070 Airbnb ROI: 1.43% Traditional ROI: -1.02%
2646 E 77th Street Chicago, IL Welcome home to this beautifully appointed (3) Bedroom (3.5) Bath residence where generous...	3 beds \| 4 baths \| 1,789 sq.ft.	$275,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 2.99% Airbnb Rental Income: $1824 Traditional Rental Income: $1345 Airbnb ROI: 2.94% Traditional ROI: 2.99%
7363 South Shore Drive #508 Chicago, IL Investor special! This 1-bedroom, 1-bath condo offers an excellent opportunity for buyers ...	1 beds \| 1 baths \| 800 sq.ft.	$50,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 9.81% Airbnb Rental Income: $1446 Traditional Rental Income: $1302 Airbnb ROI: 4.19% Traditional ROI: 9.81%
1425 E 68th St #1 Chicago, IL 1425 E 68th St #1, Chicago, IL 60637 \| Condo/Coop	3 beds \| 2 baths \| 1,937 sq.ft.	$184,900	Airbnb cash on cash: 1.52% Traditional cash on cash: 6.13% Airbnb Rental Income: $1903 Traditional Rental Income: $2207 Airbnb ROI: 1.52% Traditional ROI: 6.13%
841 W Belle Plaine Avenue #3 Chicago, IL Wow! Must see this unique, spacious top-floor 2-bedroom, 1.5-bath vintage condo in desirab...	2 beds \| 2 baths \| 1,482 sq.ft.	$389,500	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.77% Airbnb Rental Income: $2257 Traditional Rental Income: $2149 Airbnb ROI: -0.48% Traditional ROI: 0.77%
9020 S Carpenter Street Chicago, IL Welcome to this nicely updated home offering the perfect combination of comfort, style, an...	3 beds \| 2 baths \| 1,400 sq.ft.	$205,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 6.94% Airbnb Rental Income: $1771 Traditional Rental Income: $1757 Airbnb ROI: 4.52% Traditional ROI: 6.94%
6955 S Honore St Chicago, IL SOLID 2 FLAT WITH FIRST FLOOR DUPLEX. TENANT INCOME IN BOTH UNITS. BUILDING IN GREAT SHAP...	6 beds \| 2 baths \| 2,124 sq.ft.	$354,700	Airbnb cash on cash: 1.95% Traditional cash on cash: 5.86% Airbnb Rental Income: $1525 Traditional Rental Income: $2384 Airbnb ROI: 1.95% Traditional ROI: 5.86%
4528 W Washington Blvd Chicago, IL 4528 W Washington Blvd, Chicago, IL 60624 \| Single Family Residential	3 beds \| 2 baths \| 1,955 sq.ft.	$469,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 2.03% Airbnb Rental Income: $1571 Traditional Rental Income: $2409 Airbnb ROI: -0.91% Traditional ROI: 2.03%
2035 W Division Street #3 Chicago, IL Welcome to this spacious 2-bedroom, 2-bathroom home in the heart of Wicker Park, offering ...	2 beds \| 2 baths \| 1,500 sq.ft.	$549,999	Airbnb cash on cash: -0.54% Traditional cash on cash: 1.89% Airbnb Rental Income: $2147 Traditional Rental Income: $2851 Airbnb ROI: -0.54% Traditional ROI: 1.89%
6562 N Damen Avenue Chicago, IL Welcome to this two-story, 3-bedroom 2-bath home with a finished basement and 2-car garage...	3 beds \| 2 baths \| 1,769 sq.ft.	$460,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 2.16% Airbnb Rental Income: $2899 Traditional Rental Income: $2182 Airbnb ROI: 2.27% Traditional ROI: 2.16%
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: 0.14% Traditional cash on cash: 0.63% Airbnb Rental Income: $2908 Traditional Rental Income: $2659 Airbnb ROI: 0.14% Traditional ROI: 0.63%
4901 S Kimbark Ave Chicago, IL 4901 S Kimbark Ave, Chicago, IL 60615 \| Single Family Residential	8 beds \| 5 baths \| 6,500 sq.ft.	$2,295,000	Airbnb cash on cash: -2.26% Traditional cash on cash: -0.99% Airbnb Rental Income: $2908 Traditional Rental Income: $4925 Airbnb ROI: -2.26% Traditional ROI: -0.99%
1220 N Damen Ave Chicago, IL 1220 N Damen Ave, Chicago, IL 60622 \| Single Family Residential	4 beds \| 4 baths \| 5,000 sq.ft.	$2,199,800	Airbnb cash on cash: -1.75% Traditional cash on cash: -1.48% Airbnb Rental Income: $4033 Traditional Rental Income: $3739 Airbnb ROI: -1.75% Traditional ROI: -1.48%
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.	$369,900	Airbnb cash on cash: 1.82% Traditional cash on cash: 3.09% Airbnb Rental Income: $2455 Traditional Rental Income: $2300 Airbnb ROI: 1.82% Traditional ROI: 3.09%

Real Estate investment in Chicago, IL

There are 5,883 properties for sale in the city of Chicago . The median list price in Chicago is $409,805 and the average price per square foot is $232. In November 2026, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,005.

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

There are 5,883 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 $2,005.

Your search for investment property begins and ends here

Investment Property for Sale in Chicago, IL

13223 S Buffalo Avenue

Chicago, IL

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

$189,900

Airbnb cash on cash: 5.96%

Traditional cash on cash: 8.18%

Airbnb Rental Income: $1996

Traditional Rental Income: $1876

Airbnb ROI: 5.96%

Traditional ROI: 8.18%

8333 S Baltimore Ave

Chicago, IL

4 beds | 3 baths | 2,186 sq.ft.

$245,000

Airbnb cash on cash: 3.58%

Traditional cash on cash: 8.9%

Airbnb Rental Income: $2232

Traditional Rental Income: $2901

Airbnb ROI: 3.58%

Traditional ROI: 8.9%

11830 S Eggleston Ave

Chicago, IL

4 beds | 2 baths | N/A

$298,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.18%

Airbnb Rental Income: $null

Traditional Rental Income: $2333

Airbnb ROI: N/A

Traditional ROI: 6.18%

3906 W Montrose Ave

Chicago, IL

5 beds | 2 baths | 1,120 sq.ft.

$509,999

Airbnb cash on cash: 4.54%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $4796

Traditional Rental Income: $2240

Airbnb ROI: 4.54%

Traditional ROI: 1.25%

8831 S Eggleston Ave

Chicago, IL

3 beds | 1 baths | 1,375 sq.ft.

$227,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 6.1%

Airbnb Rental Income: $1282

Traditional Rental Income: $1756

Airbnb ROI: 2.02%

Traditional ROI: 6.1%

1620 W 77th St

Chicago, IL

4 beds | 3 baths | 2,500 sq.ft.

$380,000

Airbnb cash on cash: 0.99%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $2150

Traditional Rental Income: $3097

Airbnb ROI: 0.99%

Traditional ROI: 5.18%

8015 S Justine St

Chicago, IL

3 beds | 3 baths | 1,178 sq.ft.

$335,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $1617

Traditional Rental Income: $2337

Airbnb ROI: 0.14%

Traditional ROI: 3.88%

8031 S Woodlawn Ave

Chicago, IL

4 beds | 2 baths | 864 sq.ft.

$249,900

Airbnb cash on cash: 3.05%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $2118

Traditional Rental Income: $1659

Airbnb ROI: 3.05%