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: 0.17% Traditional cash on cash: -0.32% Airbnb Rental Income: $2590 Traditional Rental Income: $1557 Airbnb ROI: 0.17% Traditional ROI: -0.32%
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: 4.41% Traditional cash on cash: 3.44% Airbnb Rental Income: $2667 Traditional Rental Income: $1728 Airbnb ROI: 4.41% Traditional ROI: 3.44%
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: 1.2% Traditional cash on cash: -0.22% Airbnb Rental Income: $1990 Traditional Rental Income: $1174 Airbnb ROI: 1.2% Traditional ROI: -0.22%
7316 S Dante Avenue Chicago, IL Excellent opportunity in heart of historic South Shore neighborhood. Solid brick 2-flat wi...	9 beds \| N/A baths \| N/A	$240,000	Airbnb cash on cash: 6.31% Traditional cash on cash: 5.98% Airbnb Rental Income: $2732 Traditional Rental Income: $2013 Airbnb ROI: 6.31% Traditional ROI: 5.98%
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: 7.22% Traditional cash on cash: 5.43% Airbnb Rental Income: $3015 Traditional Rental Income: $1860 Airbnb ROI: 7.22% 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%
8153 S Calumet Avenue Chicago, IL Cozy 2-bedroom home in one level, large living room, kitchen and bathroom, small laundry a...	2 beds \| 1 baths \| 500 sq.ft.	$130,000	Airbnb cash on cash: 6.74% Traditional cash on cash: 5.38% Airbnb Rental Income: $1632 Traditional Rental Income: $1001 Airbnb ROI: 6.74% Traditional ROI: 5.38%
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: 0.99% Traditional cash on cash: 0.87% Airbnb Rental Income: $1721 Traditional Rental Income: $1184 Airbnb ROI: 0.99% Traditional ROI: 0.87%
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: 1.14% Traditional cash on cash: 0.91% Airbnb Rental Income: $2309 Traditional Rental Income: $1595 Airbnb ROI: 1.14% Traditional ROI: 0.91%
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: 1.69% Traditional cash on cash: 1.58% Airbnb Rental Income: $2183 Traditional Rental Income: $1584 Airbnb ROI: 1.69% 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: 3.54% Traditional cash on cash: 3.31% Airbnb Rental Income: $1713 Traditional Rental Income: $1206 Airbnb ROI: 3.54% Traditional ROI: 3.31%
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: 2.37% Traditional cash on cash: 2.11% Airbnb Rental Income: $2063 Traditional Rental Income: $1444 Airbnb ROI: 2.37% Traditional ROI: 2.11%
8634 S Carpenter Street Chicago, IL This beautiful 5 bedroom 1 bath brick bungalow with lots of natural sunlight throughout is...	5 beds \| 1 baths \| 1,400 sq.ft.	$229,900	Airbnb cash on cash: 7.28% Traditional cash on cash: 6.59% Airbnb Rental Income: $2667 Traditional Rental Income: $1883 Airbnb ROI: 7.28% Traditional ROI: 6.59%
6039 S CARPENTER Street Chicago, IL First floor kitchen and trim have been newly updated since original rehab. Lovely 2 unit ...	9 beds \| N/A baths \| N/A	$274,900	Airbnb cash on cash: 7.33% Traditional cash on cash: 6.25% Airbnb Rental Income: $3015 Traditional Rental Income: $2043 Airbnb ROI: 7.33% Traditional ROI: 6.25%
2947 S Farrell St Chicago, IL 2947 S Farrell St, Chicago, IL 60608 \| Single Family Residential	4 beds \| 2 baths \| 1,508 sq.ft.	$399,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 0.32% Airbnb Rental Income: $2355 Traditional Rental Income: $1427 Airbnb ROI: 1.25% Traditional ROI: 0.32%
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: 0.75% Traditional cash on cash: 0.24% Airbnb Rental Income: $2063 Traditional Rental Income: $1230 Airbnb ROI: 0.75% Traditional ROI: 0.24%
345 N Canal Street #1301 Chicago, IL Riverfront living * Historic loft conversion * West and south-facing balcony with skyline ...	2 beds \| 1 baths \| 1,150 sq.ft.	$325,000	Airbnb cash on cash: 0.75% Traditional cash on cash: -0.03% Airbnb Rental Income: $2481 Traditional Rental Income: $1641 Airbnb ROI: 0.75% Traditional ROI: -0.03%
1960 W Hood Avenue #2C Chicago, IL Spacious and well-maintained 2-bedroom, 1-bathroom unit in a boutique elevator building in...	2 beds \| 1 baths \| 950 sq.ft.	$93,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 2.71% Airbnb Rental Income: $2083 Traditional Rental Income: $1448 Airbnb ROI: 3.8% Traditional ROI: 2.71%
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: 3.18% Traditional cash on cash: 2.67% Airbnb Rental Income: $2667 Traditional Rental Income: $1829 Airbnb ROI: 3.18% Traditional ROI: 2.67%
6300 N Sheridan Road #406 Chicago, IL Back on the market and ready for a quick close - this stylish, fully updated condo won't l...	1 beds \| 1 baths \| 700 sq.ft.	$174,900	Airbnb cash on cash: 2.81% Traditional cash on cash: 0.5% Airbnb Rental Income: $1981 Traditional Rental Income: $1078 Airbnb ROI: 2.81% Traditional ROI: 0.5%
7035 N Sheridan Road #G Chicago, IL East Rogers Park's coveted corner of Sheridan and Greenleaf is where this nice cozy one be...	1 beds \| 1 baths \| 600 sq.ft.	$140,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 4.57% Airbnb Rental Income: $1713 Traditional Rental Income: $1114 Airbnb ROI: 5.5% Traditional ROI: 4.57%
7523 S Kimbark Avenue Chicago, IL Discover a fantastic investment opportunity in the vibrant Grand Crossing neighborhood, ju...	7 beds \| N/A baths \| N/A	$219,000	Airbnb cash on cash: 8.31% Traditional cash on cash: 7.68% Airbnb Rental Income: $2732 Traditional Rental Income: $1959 Airbnb ROI: 8.31% Traditional ROI: 7.68%
10 E Ontario Street #1806 Chicago, IL Bright & Stylish 18th-Floor Condo with Stunning City Views - 10 E Ontario, River North. St...	1 beds \| 1 baths \| 700 sq.ft.	$260,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 0.55% Airbnb Rental Income: $1900 Traditional Rental Income: $1393 Airbnb ROI: 0.55% Traditional ROI: 0.55%
5946 S THROOP Street Chicago, IL MULTIPLE OFFERS !!!!!CALLING FOR FINAL BEST 4/29/25 5PM !!!!!! Great investment!!!! V...	8 beds \| N/A baths \| N/A	$265,000	Airbnb cash on cash: 7.79% Traditional cash on cash: 7.27% Airbnb Rental Income: $3015 Traditional Rental Income: $2192 Airbnb ROI: 7.79% Traditional ROI: 7.27%
7934 S Escanaba Avenue Chicago, IL Solid brick 2 flat with a coach house. Rehab was started, all the heavy lifting is done. ...	7 beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 4.81% Airbnb Rental Income: $3362 Traditional Rental Income: $2512 Airbnb ROI: 5.12% Traditional ROI: 4.81%

Vacation Rentals in Chicago

There are 98 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $369,000 and the average price per square foot is $213. The cash on cash return on vacation rentals in Chicago is N/A%. The average monthly short term rental income in Chicago is $1,841.

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

There are 98 Airbnb properties available for sale in Chicago.

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

In November 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: 0.17%

Traditional cash on cash: -0.32%

Airbnb Rental Income: $2590

Traditional Rental Income: $1557

Airbnb ROI: 0.17%

Traditional ROI: -0.32%

8004 S May Street

Chicago, IL

6 beds | N/A baths | N/A

$335,000

Airbnb cash on cash: 4.41%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $2667

Traditional Rental Income: $1728

Airbnb ROI: 4.41%

Traditional ROI: 3.44%

801 S Plymouth Court #809

Chicago, IL

1 beds | 1 baths | N/A

$220,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: -0.22%

Airbnb Rental Income: $1990

Traditional Rental Income: $1174

Airbnb ROI: 1.2%

Traditional ROI: -0.22%

7316 S Dante Avenue

Chicago, IL

9 beds | N/A baths | N/A

$240,000

Airbnb cash on cash: 6.31%

Traditional cash on cash: 5.98%

Airbnb Rental Income: $2732

Traditional Rental Income: $2013

Airbnb ROI: 6.31%

Traditional ROI: 5.98%

6849 S Green Street

Chicago, IL

5 beds | N/A baths | N/A

$275,000

Airbnb cash on cash: 7.22%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $3015

Traditional Rental Income: $1860

Airbnb ROI: 7.22%

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%

8153 S Calumet Avenue

Chicago, IL

2 beds | 1 baths | 500 sq.ft.

$130,000

Airbnb cash on cash: 6.74%

Traditional cash on cash: 5.38%

Airbnb Rental Income: $1632

Traditional Rental Income: $1001

Airbnb ROI: 6.74%

Traditional ROI: 5.38%

8245 S Burley Avenue

Chicago, IL

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%