Airbnb Properties for Sale in Chicago, IL

Looking for a vacation rental investment in Chicago, IL with high ROI ?

Explore a range of newly added short-term rental homes in Chicago, IL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chicago, IL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
339 W 23rd Place Chicago, IL great building in the heart of chinatown ,new brick front wall and windows . this building...	9 beds \| N/A baths \| N/A	$915,000	Airbnb cash on cash: 0.18% Traditional cash on cash: -0.32% Airbnb Rental Income: $2608 Traditional Rental Income: $1557 Airbnb ROI: 0.18% Traditional ROI: -0.32%
6321 N Hermitage Avenue Chicago, IL Newly Rehabbed Vintage all Blonde Brick Octagon 2 unit. This is in Edgewater ,one of Chica...	6 beds \| N/A baths \| N/A	$900,000	Airbnb cash on cash: 1.43% Traditional cash on cash: -0.25% Airbnb Rental Income: $4069 Traditional Rental Income: $1794 Airbnb ROI: 1.43% Traditional ROI: -0.25%
8004 S May Street Chicago, IL Fantastic opportunity to own a spacious, well-maintained brick 2-flat on a quiet, tree-lin...	6 beds \| N/A baths \| N/A	$335,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.44% Airbnb Rental Income: $2566 Traditional Rental Income: $1728 Airbnb ROI: 4.14% Traditional ROI: 3.44%
7537 S Clyde Ave Chicago, IL 7537 S Clyde Ave, Chicago, IL 60649 \| Single Family Residential	5 beds \| 4 baths \| 2,857 sq.ft.	$425,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 0.12% Airbnb Rental Income: $2464 Traditional Rental Income: $1434 Airbnb ROI: 1.2% Traditional ROI: 0.12%
801 S Plymouth Court #809 Chicago, IL Bright 1 BED 1 BATH condo in the best south loop location. Beautiful floors, ample walk in...	1 beds \| 1 baths \| N/A	$220,000	Airbnb cash on cash: 0.22% Traditional cash on cash: -0.22% Airbnb Rental Income: $1747 Traditional Rental Income: $1174 Airbnb ROI: 0.22% Traditional ROI: -0.22%
6849 S Green Street Chicago, IL Spacious Updated 2-Unit Building in Englewood Discover an income-producing opportunity wi...	5 beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: 6.82% Traditional cash on cash: 5.43% Airbnb Rental Income: $2892 Traditional Rental Income: $1860 Airbnb ROI: 6.82% Traditional ROI: 5.43%
5729 S MICHIGAN Avenue Chicago, IL Maintained large exterior brick 3 flat in Washington Park Area, on a uniform block with or...	8 beds \| N/A baths \| N/A	$430,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 2.23% Airbnb Rental Income: $2629 Traditional Rental Income: $1900 Airbnb ROI: 2.48% Traditional ROI: 2.23%
803 E 41st Street #3A Chicago, IL Step into 803 E 41st St Unit 3A, a thoughtfully updated duplex condo that combines stylish...	2 beds \| 2 baths \| 1,707 sq.ft.	$295,000	Airbnb cash on cash: 6.81% Traditional cash on cash: 3.9% Airbnb Rental Income: $3501 Traditional Rental Income: $1919 Airbnb ROI: 6.81% Traditional ROI: 3.9%
1338 W Estes Avenue #3N Chicago, IL Step into this sun-filled top-floor unit in a beautiful courtyard building on a lovely tre...	1 beds \| 1 baths \| N/A	$174,900	Airbnb cash on cash: 1.94% Traditional cash on cash: 1.64% Airbnb Rental Income: $1700 Traditional Rental Income: $1177 Airbnb ROI: 1.94% Traditional ROI: 1.64%
6141 N Campbell Avenue Chicago, IL Brown Brick 2-flat with un finished basement 3bed rooms each floor. first floor has 1....	6 beds \| N/A baths \| N/A	$614,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 0.07% Airbnb Rental Income: $2934 Traditional Rental Income: $1742 Airbnb ROI: 0.97% Traditional ROI: 0.07%
8245 S Burley Avenue Chicago, IL Amazing opportunity to start or increase your Portfolio. Large Multi-Unit with Positive c...	8 beds \| N/A baths \| N/A	$380,000	Airbnb cash on cash: 5.76% Traditional cash on cash: 4.08% Airbnb Rental Income: $3362 Traditional Rental Income: $2014 Airbnb ROI: 5.76% Traditional ROI: 4.08%
657 N PINE Avenue Chicago, IL Beautiful New Construction in Austin! This stunning 5-bedroom, 3.5-bathroom home offers m...	5 beds \| 4 baths \| 3,336 sq.ft.	$559,999	Airbnb cash on cash: 1.11% Traditional cash on cash: 0.87% Airbnb Rental Income: $1800 Traditional Rental Income: $1184 Airbnb ROI: 1.11% Traditional ROI: 0.87%
6833 S Green St Chicago, IL 6833 S Green St, Chicago, IL 60621 \| Multi Family	6 beds \| 2 baths \| N/A	$260,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.19% Airbnb Rental Income: $2892 Traditional Rental Income: $1915 Airbnb ROI: 5.44% Traditional ROI: 4.19%
7440 S Oglesby Avenue Chicago, IL Modern Luxury Meets South Shore Charm - Welcome to 7440 S Oglesby Ave Step into elevate...	5 beds \| 4 baths \| 3,000 sq.ft.	$635,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 0.91% Airbnb Rental Income: $2464 Traditional Rental Income: $1595 Airbnb ROI: 1.36% Traditional ROI: 0.91%
4743 S Keeler Avenue Chicago, IL Welcome to your fully rehabbed home at 4743 S Keeler Ave in vibrant Chicago, IL. This char...	3 beds \| 2 baths \| 1,820 sq.ft.	$418,888	Airbnb cash on cash: 2.47% Traditional cash on cash: 2.32% Airbnb Rental Income: $2346 Traditional Rental Income: $1706 Airbnb ROI: 2.47% Traditional ROI: 2.32%
1415 N Massasoit Avenue Chicago, IL Fantastic Investment or Owner-Occupant Opportunity in Austin! Don't miss this well-mainta...	4 beds \| N/A baths \| N/A	$449,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.58% Airbnb Rental Income: $2220 Traditional Rental Income: $1584 Airbnb ROI: 1.76% Traditional ROI: 1.58%
7019 N Ridge Boulevard #3B Chicago, IL In a beautiful landscape court yard building one bedroom one bath condo, located in Rogers...	1 beds \| 1 baths \| N/A	$144,900	Airbnb cash on cash: 3.47% Traditional cash on cash: 3.31% Airbnb Rental Income: $1700 Traditional Rental Income: $1206 Airbnb ROI: 3.47% Traditional ROI: 3.31%
1740 W Foster Avenue #3R Chicago, IL West Andersonville condo with parking. This apartment is located at the rear of the buildi...	1 beds \| 2 baths \| N/A	$230,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 1.84% Airbnb Rental Income: $2304 Traditional Rental Income: $1406 Airbnb ROI: 3.33% Traditional ROI: 1.84%
4036 W 57th Street Chicago, IL Stunning renovation in Prime Chicago location! Welcome to this beautifully updated brick G...	3 beds \| 1 baths \| 1,200 sq.ft.	$349,900	Airbnb cash on cash: 3.09% Traditional cash on cash: 2.11% Airbnb Rental Income: $2346 Traditional Rental Income: $1444 Airbnb ROI: 3.09% Traditional ROI: 2.11%
8634 S Carpenter Street Chicago, IL This a beautiful 5 bedroom 1 bath brick bungalow with lots of natural sunlight throughout ...	5 beds \| 1 baths \| 1,400 sq.ft.	$229,900	Airbnb cash on cash: 6.9% Traditional cash on cash: 6.59% Airbnb Rental Income: $2566 Traditional Rental Income: $1883 Airbnb ROI: 6.9% Traditional ROI: 6.59%
5030 S Archer Avenue Chicago, IL Amazing location and incredible visibility right on ARCHER Ave in this excellent business ...	3 beds \| N/A baths \| N/A	$629,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 0.24% Airbnb Rental Income: $2346 Traditional Rental Income: $1230 Airbnb ROI: 1.15% Traditional ROI: 0.24%
4102 S Cottage Grove Avenue #3S Chicago, IL Welcome home to this stunning and spacious duplex condo in historic Bronzeville! Offering ...	3 beds \| 3 baths \| 2,700 sq.ft.	$335,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 5.62% Airbnb Rental Income: $3501 Traditional Rental Income: $2646 Airbnb ROI: 5.89% Traditional ROI: 5.62%
6716 S May St Chicago, IL 6716 S May St, Chicago, IL 60621 \| Multi Family	11 beds \| 3 baths \| N/A	$350,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.27% Airbnb Rental Income: $2892 Traditional Rental Income: $1905 Airbnb ROI: 3.23% Traditional ROI: 2.27%
7835 S Carpenter Street Chicago, IL WOW,PREPARE TO BE IMPRESSED WITH THIS STUNNING 2 UNITS HOME . FIRST FLLOR UNIT HAS 4 BEDRO...	7 beds \| N/A baths \| N/A	$424,900	Airbnb cash on cash: 2.97% Traditional cash on cash: 2.67% Airbnb Rental Income: $2566 Traditional Rental Income: $1829 Airbnb ROI: 2.97% Traditional ROI: 2.67%

Vacation Rentals in Chicago

There are 104 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $369,900 and the average price per square foot is $212. The cash on cash return on vacation rentals in Chicago is N/A%. The average monthly short term rental income in Chicago is $1,835.

Chicago, IL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 104 Airbnb properties available for sale in Chicago.

In 2025, the best neighborhood to buy short term rental property is East Chatham.

In October 2025, the average Airbnb occupancy rate in Chicago is 31%.

In 2025, the highest Airbnb occupancy rate in Chicago are in East Chatham (25%), South Shore (27%) and South Shore (29%).

Airbnb data on vacation rentals in Chicago, IL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chicago, IL market insights, guest information and booking details, seasonality trends and historical Chicago, IL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Chicago, IL

339 W 23rd Place

Chicago, IL

9 beds | N/A baths | N/A

$915,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: -0.32%

Airbnb Rental Income: $2608

Traditional Rental Income: $1557

Airbnb ROI: 0.18%

Traditional ROI: -0.32%

6321 N Hermitage Avenue

Chicago, IL

6 beds | N/A baths | N/A

$900,000

Airbnb cash on cash: 1.43%

Traditional cash on cash: -0.25%

Airbnb Rental Income: $4069

Traditional Rental Income: $1794

Airbnb ROI: 1.43%

Traditional ROI: -0.25%

8004 S May Street

Chicago, IL

6 beds | N/A baths | N/A

$335,000

Airbnb cash on cash: 4.14%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $2566

Traditional Rental Income: $1728

Airbnb ROI: 4.14%

Traditional ROI: 3.44%

7537 S Clyde Ave

Chicago, IL

5 beds | 4 baths | 2,857 sq.ft.

$425,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $2464

Traditional Rental Income: $1434

Airbnb ROI: 1.2%

Traditional ROI: 0.12%

801 S Plymouth Court #809

Chicago, IL

1 beds | 1 baths | N/A

$220,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: -0.22%

Airbnb Rental Income: $1747

Traditional Rental Income: $1174

Airbnb ROI: 0.22%

Traditional ROI: -0.22%

6849 S Green Street

Chicago, IL

5 beds | N/A baths | N/A

$275,000

Airbnb cash on cash: 6.82%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $2892

Traditional Rental Income: $1860

Airbnb ROI: 6.82%

Traditional ROI: 5.43%

5729 S MICHIGAN Avenue

Chicago, IL

8 beds | N/A baths | N/A

$430,000

Airbnb cash on cash: 2.48%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $2629

Traditional Rental Income: $1900

Airbnb ROI: 2.48%

Traditional ROI: 2.23%

803 E 41st Street #3A

Chicago, IL

2 beds | 2 baths | 1,707 sq.ft.

$295,000

Airbnb cash on cash: 6.81%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $3501

Traditional Rental Income: $1919

Airbnb ROI: 6.81%