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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20 N State Street #807 Chicago, IL Modern loft-style 1 bed + office/1 bath condo in the heart of the Loop! Live in the center...	1 beds \| 1 baths \| N/A	$249,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 0.35% Airbnb Rental Income: $2127 Traditional Rental Income: $1575 Airbnb ROI: 0.38% Traditional ROI: 0.35%
900 W AINSLIE Street #A Chicago, IL LARGE, WELL KEPT, CLEAN, DUPLEX DOWN located in WALKABLE and CONVENIENT UPTOWN! SUNNY & SP...	2 beds \| 2 baths \| N/A	$329,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 4.39% Airbnb Rental Income: $2968 Traditional Rental Income: $2245 Airbnb ROI: 4.52% Traditional ROI: 4.39%
5330 S Wabash Avenue Chicago, IL ((MUST SEE LEGAL (((3))) UNIT MULTI-FAMILY WITH A CAP RATE OF 8.4)) Come take a look at th...	12 beds \| N/A baths \| N/A	$799,999	Airbnb cash on cash: 1.21% Traditional cash on cash: 1.16% Airbnb Rental Income: $3011 Traditional Rental Income: $2283 Airbnb ROI: 1.21% Traditional ROI: 1.16%
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: 0.19% Traditional cash on cash: -0.11% Airbnb Rental Income: $3713 Traditional Rental Income: $2476 Airbnb ROI: 0.19% Traditional ROI: -0.11%
6214 S Morgan Street Chicago, IL Discover this stunningly rehabbed 2-unit gem, designed to deliver comfort, style, and inco...	7 beds \| N/A baths \| N/A	$339,900	Airbnb cash on cash: 5.22% Traditional cash on cash: 5.02% Airbnb Rental Income: $2802 Traditional Rental Income: $2083 Airbnb ROI: 5.22% Traditional ROI: 5.02%
461 W 28th Place Chicago, IL Remarkable 3 legal unit building (with coach house), fully renovated with open floor plans...	9 beds \| N/A baths \| N/A	$680,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 0.91% Airbnb Rental Income: $2813 Traditional Rental Income: $2068 Airbnb ROI: 1.05% Traditional ROI: 0.91%
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: 0.38% Traditional cash on cash: -0.32% Airbnb Rental Income: $2813 Traditional Rental Income: $1557 Airbnb ROI: 0.38% Traditional ROI: -0.32%
2214 N Mango Avenue Chicago, IL Beautifully updated 2-unit home in Belmont Cragin! The main unit features 4 bedrooms and 2...	5 beds \| N/A baths \| N/A	$450,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 4.2% Airbnb Rental Income: $3542 Traditional Rental Income: $2655 Airbnb ROI: 4.45% Traditional ROI: 4.2%
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: 1.35% Traditional cash on cash: -0.25% Airbnb Rental Income: $3985 Traditional Rental Income: $1794 Airbnb ROI: 1.35% Traditional ROI: -0.25%
3852 W Gladys Avenue Chicago, IL Jumbo legal 3-unit, brick with an extra garden unit in Garfield Park! Each unit covers 150...	12 beds \| N/A baths \| N/A	$524,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 2.13% Airbnb Rental Income: $2506 Traditional Rental Income: $1882 Airbnb ROI: 2.16% Traditional ROI: 2.13%
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: 3.2% Traditional cash on cash: 2.13% Airbnb Rental Income: $2653 Traditional Rental Income: $1600 Airbnb ROI: 3.2% Traditional ROI: 2.13%
3809 N Kenmore Avenue Chicago, IL Prime Investment Opportunity! Nestled in the heart of Lakeview/Wrigleyville, this high-inc...	7 beds \| N/A baths \| N/A	$1,475,000	Airbnb cash on cash: 0.05% Traditional cash on cash: -0.84% Airbnb Rental Income: $3967 Traditional Rental Income: $1890 Airbnb ROI: 0.05% Traditional ROI: -0.84%
6610 S Saint Lawrence Avenue Chicago, IL Step into immediate equity with this exceptional brand new renovated massive two-unit buil...	5 beds \| N/A baths \| N/A	$599,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 0.89% Airbnb Rental Income: $2788 Traditional Rental Income: $1564 Airbnb ROI: 1.91% Traditional ROI: 0.89%
7742 S Hermitage Avenue Chicago, IL Welcome to this beautifully renovated five-bedroom, three-bathroom bungalow nestled on a q...	5 beds \| 3 baths \| 2,100 sq.ft.	$289,999	Airbnb cash on cash: 4.21% Traditional cash on cash: 3.73% Airbnb Rental Income: $2331 Traditional Rental Income: $1622 Airbnb ROI: 4.21% Traditional ROI: 3.73%
1658 W Farwell Ave #GC Chicago, IL 1658 W Farwell Ave #GC, Chicago, IL 60626 \| Condo/Coop	2 beds \| 1 baths \| 750 sq.ft.	$165,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.48% Airbnb Rental Income: $2105 Traditional Rental Income: $1421 Airbnb ROI: 4.4% Traditional ROI: 3.48%
6605 S Maryland Ave Chicago, IL 6605 S Maryland Ave, Chicago, IL 60637 \| Multi Family	9 beds \| 3 baths \| N/A	$495,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 0.69% Airbnb Rental Income: $2788 Traditional Rental Income: $1918 Airbnb ROI: 1.16% Traditional ROI: 0.69%
2445 E 74th Place Chicago, IL Calling all Contractors & Investors! Great 4 unit building with each unit currently havin...	16 beds \| N/A baths \| N/A	$364,999	Airbnb cash on cash: 4.69% Traditional cash on cash: 4.34% Airbnb Rental Income: $3174 Traditional Rental Income: $2336 Airbnb ROI: 4.69% Traditional ROI: 4.34%
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: 7.37% Traditional cash on cash: 5.98% Airbnb Rental Income: $3020 Traditional Rental Income: $2013 Airbnb ROI: 7.37% Traditional ROI: 5.98%
6508 N Richmond Street #1D Chicago, IL All new one bedroom unit , high end finishes newer appliances , great starter home , great...	1 beds \| 1 baths \| 550 sq.ft.	$134,900	Airbnb cash on cash: 4.97% Traditional cash on cash: 4.22% Airbnb Rental Income: $1779 Traditional Rental Income: $1197 Airbnb ROI: 4.97% Traditional ROI: 4.22%
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: 3.27% Traditional cash on cash: 2.23% Airbnb Rental Income: $3011 Traditional Rental Income: $1900 Airbnb ROI: 3.27% Traditional ROI: 2.23%
1918 S Kedzie Avenue Chicago, IL Location, Location, Location. Fantastic opportunity to purchase this beautiful 3 unit Gray...	6 beds \| N/A baths \| N/A	$498,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 2.15% Airbnb Rental Income: $3194 Traditional Rental Income: $1723 Airbnb ROI: 3.76% Traditional ROI: 2.15%
7650 S Bishop Street Chicago, IL Don't miss this brick 2-unit in Auburn Gresham. Each unit features a large living room, di...	6 beds \| N/A baths \| N/A	$299,900	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.85% Airbnb Rental Income: $2796 Traditional Rental Income: $2020 Airbnb ROI: 5.28% Traditional ROI: 4.85%
7959 S Essex Avenue Chicago, IL Great Investment opportunity! Beautifully rehabbed 3 unit building. You can live in one un...	9 beds \| N/A baths \| N/A	$519,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 1.91% Airbnb Rental Income: $2670 Traditional Rental Income: $1760 Airbnb ROI: 2.48% Traditional ROI: 1.91%

Vacation Rentals in Chicago

There are 193 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $374,500 and the average price per square foot is $216. The cash on cash return on vacation rentals in Chicago is N/A%. The average monthly short term rental income in Chicago is $2,060.

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

There are 193 Airbnb properties available for sale in Chicago.

In 2025, the best neighborhood to buy short term rental property is Eden Green.

In September 2025, the average Airbnb occupancy rate in Chicago is 33%.

In 2025, the highest Airbnb occupancy rate in Chicago are in Eden Green (28%), Englewood (31%) and Englewood (27%).

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

20 N State Street #807

Chicago, IL

1 beds | 1 baths | N/A

$249,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 0.35%

Airbnb Rental Income: $2127

Traditional Rental Income: $1575

Airbnb ROI: 0.38%

Traditional ROI: 0.35%

900 W AINSLIE Street #A

Chicago, IL

2 beds | 2 baths | N/A

$329,000

Airbnb cash on cash: 4.52%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $2968

Traditional Rental Income: $2245

Airbnb ROI: 4.52%

Traditional ROI: 4.39%

5330 S Wabash Avenue

Chicago, IL

12 beds | N/A baths | N/A

$799,999

Airbnb cash on cash: 1.21%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $3011

Traditional Rental Income: $2283

Airbnb ROI: 1.21%

Traditional ROI: 1.16%

1442 W Irving Park Road

Chicago, IL

9 beds | N/A baths | N/A

$1,500,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: -0.11%

Airbnb Rental Income: $3713

Traditional Rental Income: $2476

Airbnb ROI: 0.19%

Traditional ROI: -0.11%

6214 S Morgan Street

Chicago, IL

7 beds | N/A baths | N/A

$339,900

Airbnb cash on cash: 5.22%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $2802

Traditional Rental Income: $2083

Airbnb ROI: 5.22%

Traditional ROI: 5.02%

461 W 28th Place

Chicago, IL

9 beds | N/A baths | N/A

$680,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 0.91%

Airbnb Rental Income: $2813

Traditional Rental Income: $2068

Airbnb ROI: 1.05%

Traditional ROI: 0.91%

339 W 23rd Place

Chicago, IL

9 beds | N/A baths | N/A

$915,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: -0.32%

Airbnb Rental Income: $2813

Traditional Rental Income: $1557

Airbnb ROI: 0.38%

Traditional ROI: -0.32%

2214 N Mango Avenue

Chicago, IL

5 beds | N/A baths | N/A

$450,000

Airbnb cash on cash: 4.45%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $3542

Traditional Rental Income: $2655

Airbnb ROI: 4.45%