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
5320 N Sheridan Road #1011 Chicago, IL Welcome to "The Metropolitan Condominium complex". This corner unit with an open floorplan...	1 beds \| 1 baths \| 840 sq.ft.	$199,900	Airbnb cash on cash: 2.37% Traditional cash on cash: 2.35% Airbnb Rental Income: $2071 Traditional Rental Income: $1534 Airbnb ROI: 2.37% Traditional ROI: 2.35%
5415 N Sheridan Road #4815 Chicago, IL EDGEWATER BEACH. READY FOR A QUICK CLOSING! . LUXURY HIGH RISE BUILDING. HIGHFLOOR. RARELY...	1 beds \| 1 baths \| 680 sq.ft.	$169,900	Airbnb cash on cash: 1.08% Traditional cash on cash: 0.98% Airbnb Rental Income: $2071 Traditional Rental Income: $1521 Airbnb ROI: 1.08% Traditional ROI: 0.98%
8143 S Colfax Avenue Chicago, IL Price Improvement! As-is Pre-Foreclosure/Short Sale Opportunity - 8143 S Colfax Ave, Chica...	8 beds \| N/A baths \| N/A	$379,000	Airbnb cash on cash: 9.25% Traditional cash on cash: 3.25% Airbnb Rental Income: $5042 Traditional Rental Income: $1878 Airbnb ROI: 9.25% Traditional ROI: 3.25%
1442 W Irving Park Road Chicago, IL Renovated 2-Flat in Prime Lakeview - High-Performing Airbnb Investment 1442 W Irving Pa...	9 beds \| N/A baths \| N/A	$1,500,000	Airbnb cash on cash: 0.02% Traditional cash on cash: -0.11% Airbnb Rental Income: $3415 Traditional Rental Income: $2476 Airbnb ROI: 0.02% Traditional ROI: -0.11%
9326 S Manistee Avenue Chicago, IL Solid Brick Bungalow Rehab. 3bed, 1 bath home has Granite Countertop Kitchen, Ceramic Floo...	3 beds \| 1 baths \| N/A	$229,000	Airbnb cash on cash: 5.53% Traditional cash on cash: 4.09% Airbnb Rental Income: $2199 Traditional Rental Income: $1332 Airbnb ROI: 5.53% Traditional ROI: 4.09%
5320 N Sheridan Road #2304 Chicago, IL Welcome to The Metropolitan Condominiums, one of Edgewater Beach's most coveted addresses ...	1 beds \| 1 baths \| 800 sq.ft.	$199,000	Airbnb cash on cash: 0.9% Traditional cash on cash: -0.27% Airbnb Rental Income: $2071 Traditional Rental Income: $1316 Airbnb ROI: 0.9% Traditional ROI: -0.27%
9116 S South Chicago Avenue Chicago, IL Come see this nice, 4 unit building located in a nice area. Each unit has 2 bedrooms and 2...	8 beds \| N/A baths \| N/A	$420,000	Airbnb cash on cash: 8.26% Traditional cash on cash: 2.13% Airbnb Rental Income: $5042 Traditional Rental Income: $1600 Airbnb ROI: 8.26% Traditional ROI: 2.13%
2914 W Polk Street Chicago, IL Step right up into this fully renovated multi-unit gem in the heart of the near-West side!...	5 beds \| N/A baths \| N/A	$499,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.08% Airbnb Rental Income: $2677 Traditional Rental Income: $1888 Airbnb ROI: 2.41% Traditional ROI: 2.08%
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: 3.85% Traditional cash on cash: 3.44% Airbnb Rental Income: $2454 Traditional Rental Income: $1728 Airbnb ROI: 3.85% 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: 0.28% Traditional cash on cash: -0.22% Airbnb Rental Income: $1760 Traditional Rental Income: $1174 Airbnb ROI: 0.28% Traditional ROI: -0.22%
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: 3.12% Traditional cash on cash: 2.23% Airbnb Rental Income: $2936 Traditional Rental Income: $1900 Airbnb ROI: 3.12% Traditional ROI: 2.23%
1918 S Kedzie Avenue Chicago, IL Turnkey three-unit Graystone in North Lawndale offering solid cash flow and modern updates...	6 beds \| N/A baths \| N/A	$485,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 2.22% Airbnb Rental Income: $2899 Traditional Rental Income: $1723 Airbnb ROI: 3.33% Traditional ROI: 2.22%
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: 7.97% Traditional cash on cash: 5.38% Airbnb Rental Income: $1816 Traditional Rental Income: $1001 Airbnb ROI: 7.97% Traditional ROI: 5.38%
1549 S Saint Louis Avenue Chicago, IL Step into a rare investment opportunity in the heart of North Lawndale with this beautiful...	12 beds \| N/A baths \| N/A	$460,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 1.91% Airbnb Rental Income: $2677 Traditional Rental Income: $1547 Airbnb ROI: 3.06% Traditional ROI: 1.91%
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: 6.07% Traditional cash on cash: 4.08% Airbnb Rental Income: $3494 Traditional Rental Income: $2014 Airbnb ROI: 6.07% 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: 2.12% Traditional cash on cash: 0.87% Airbnb Rental Income: $2430 Traditional Rental Income: $1184 Airbnb ROI: 2.12% Traditional ROI: 0.87%
6415 S Evans Avenue Chicago, IL Turnkey investment or live-in opportunity in Chicago's West Woodlawn neighborhood. This fu...	7 beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 1.3% Airbnb Rental Income: $2576 Traditional Rental Income: $1633 Airbnb ROI: 1.83% Traditional ROI: 1.3%
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: 1.53% Traditional cash on cash: 0.91% Airbnb Rental Income: $2588 Traditional Rental Income: $1595 Airbnb ROI: 1.53% Traditional ROI: 0.91%
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	$225,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 1.9% Airbnb Rental Income: $1932 Traditional Rental Income: $1406 Airbnb ROI: 1.97% Traditional ROI: 1.9%
8613 S Colfax Avenue Chicago, IL *PROFESSIONAL PICTURES, VIDEO, VIRTUAL TOUR, FLOOR PLANS ARE COMING SOON*Welcome to yo...	3 beds \| 2 baths \| 1,808 sq.ft.	$297,900	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.9% Airbnb Rental Income: $2199 Traditional Rental Income: $1503 Airbnb ROI: 4.4% Traditional ROI: 3.9%
4624 N Commons Drive #111 Chicago, IL WELCOME TO THIS BEAUTIFULLY LARGE UPDATED 1 BEDROOM AND 1 BATHROOM CONDO WITH 1 CAR GARAGE...	1 beds \| 1 baths \| N/A	$167,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 2.42% Airbnb Rental Income: $2082 Traditional Rental Income: $1178 Airbnb ROI: 4.73% Traditional ROI: 2.42%
4103 N Narragansett Avenue Chicago, IL Looking for a Land! This Developer's dream lot alert! Rare .42-acre double-wide lot-60'x2...	3 beds \| 3 baths \| 17,940 sq.ft.	$850,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.01% Airbnb Rental Income: $2106 Traditional Rental Income: $1501 Airbnb ROI: 0.09% Traditional ROI: 0.01%
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: 0.35% Traditional cash on cash: -0.03% Airbnb Rental Income: $2334 Traditional Rental Income: $1641 Airbnb ROI: 0.35% Traditional ROI: -0.03%
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 \| 2 baths \| N/A	$424,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 2.67% Airbnb Rental Income: $2454 Traditional Rental Income: $1829 Airbnb ROI: 2.74% Traditional ROI: 2.67%
1339 N Dearborn Street #2B Chicago, IL JUST RENOVATED - 1B1B condo in the heart of Gold Coast, blocks away from Lincoln Park, Div...	1 beds \| 1 baths \| 750 sq.ft.	$239,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.91% Airbnb Rental Income: $2041 Traditional Rental Income: $1404 Airbnb ROI: 1.38% Traditional ROI: 0.91%
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: 3.01% Traditional cash on cash: 0.5% Airbnb Rental Income: $2021 Traditional Rental Income: $1078 Airbnb ROI: 3.01% Traditional ROI: 0.5%
3638 N Pine Grove Avenue #G2 Chicago, IL Discover the perfect blend of comfort and convenience in this east-facing 1-bedroom, 1-bat...	1 beds \| 1 baths \| 650 sq.ft.	$179,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 2.95% Airbnb Rental Income: $1792 Traditional Rental Income: $1290 Airbnb ROI: 3.03% Traditional ROI: 2.95%
5942 S Calumet Avenue Chicago, IL Great Investment Opportunity For Owner Occupant with the potential to live rent free Or In...	12 beds \| 3 baths \| N/A	$585,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 2.07% Airbnb Rental Income: $2936 Traditional Rental Income: $2144 Airbnb ROI: 2.28% Traditional ROI: 2.07%
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: 1.39% Traditional cash on cash: 0.55% Airbnb Rental Income: $2146 Traditional Rental Income: $1393 Airbnb ROI: 1.39% Traditional ROI: 0.55%
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: 5.45% Traditional cash on cash: 4.81% Airbnb Rental Income: $3494 Traditional Rental Income: $2512 Airbnb ROI: 5.45% Traditional ROI: 4.81%
40 E 9th Street #609 Chicago, IL Experience comfort and convenience in this spacious 3-bedroom, 2-bath condo located in Chi...	3 beds \| 2 baths \| 1,350 sq.ft.	$395,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.07% Airbnb Rental Income: $2941 Traditional Rental Income: $2242 Airbnb ROI: 0.12% Traditional ROI: 0.07%
10 E Ontario Street #2304 Chicago, IL This lovely rehabbed one bedroom at Ontario Place has a beautiful open white kitchen with ...	1 beds \| 1 baths \| 795 sq.ft.	$245,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 0.65% Airbnb Rental Income: $2146 Traditional Rental Income: $1464 Airbnb ROI: 1.24% Traditional ROI: 0.65%
5611 N Glenwood Avenue #G Chicago, IL Hot Andersonville! Newly renovated 1-bedroom unit-an ideal starter home in one of Chicago...	1 beds \| 1 baths \| N/A	$200,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 1.48% Airbnb Rental Income: $1981 Traditional Rental Income: $998 Airbnb ROI: 3.93% Traditional ROI: 1.48%

Vacation Rentals in Chicago

There are 111 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 $213. The cash on cash return on vacation rentals in Chicago is N/A%. The average monthly short term rental income in Chicago is $1,792.

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

There are 111 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 30%.

In 2025, the highest Airbnb occupancy rate in Chicago are in East Chatham (23%), South Shore (22%) 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

5320 N Sheridan Road #1011

Chicago, IL

1 beds | 1 baths | 840 sq.ft.

$199,900

Airbnb cash on cash: 2.37%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $2071

Traditional Rental Income: $1534

Airbnb ROI: 2.37%

Traditional ROI: 2.35%

5415 N Sheridan Road #4815

Chicago, IL

1 beds | 1 baths | 680 sq.ft.

$169,900

Airbnb cash on cash: 1.08%

Traditional cash on cash: 0.98%

Airbnb Rental Income: $2071

Traditional Rental Income: $1521

Airbnb ROI: 1.08%

Traditional ROI: 0.98%

8143 S Colfax Avenue

Chicago, IL

8 beds | N/A baths | N/A

$379,000

Airbnb cash on cash: 9.25%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $5042

Traditional Rental Income: $1878

Airbnb ROI: 9.25%

Traditional ROI: 3.25%

1442 W Irving Park Road

Chicago, IL

9 beds | N/A baths | N/A

$1,500,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: -0.11%

Airbnb Rental Income: $3415

Traditional Rental Income: $2476

Airbnb ROI: 0.02%

Traditional ROI: -0.11%

9326 S Manistee Avenue

Chicago, IL

3 beds | 1 baths | N/A

$229,000

Airbnb cash on cash: 5.53%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $2199

Traditional Rental Income: $1332

Airbnb ROI: 5.53%

Traditional ROI: 4.09%

5320 N Sheridan Road #2304

Chicago, IL

1 beds | 1 baths | 800 sq.ft.

$199,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: -0.27%

Airbnb Rental Income: $2071

Traditional Rental Income: $1316

Airbnb ROI: 0.9%

Traditional ROI: -0.27%

9116 S South Chicago Avenue

Chicago, IL

8 beds | N/A baths | N/A

$420,000

Airbnb cash on cash: 8.26%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $5042

Traditional Rental Income: $1600

Airbnb ROI: 8.26%

Traditional ROI: 2.13%

2914 W Polk Street

Chicago, IL

5 beds | N/A baths | N/A

$499,900

Airbnb cash on cash: 2.41%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $2677

Traditional Rental Income: $1888

Airbnb ROI: 2.41%