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
4517 N Whipple Street Chicago, IL Stunning 5 bedroom 3.5 bath luxury farmhouse nestled in between the Ravenswood Manor and E...	4 beds \| 4 baths \| N/A	$999,000	Airbnb cash on cash: 1.25% Traditional cash on cash: -0.24% Airbnb Rental Income: $4331 Traditional Rental Income: $2037 Airbnb ROI: 1.25% Traditional ROI: -0.24%
4836 S Dorchester Avenue Chicago, IL Stunning 3-Flat Georgian Style Multi-Family Building in Hyde Park, where historical elegan...	6 beds \| N/A baths \| N/A	$1,150,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 0.32% Airbnb Rental Income: $7292 Traditional Rental Income: $2659 Airbnb ROI: 3.33% Traditional ROI: 0.32%
1711 W Division Street #204 Chicago, IL Impressive, light-filled condo in a boutique elevator building set in the heart of Wicker ...	2 beds \| 2 baths \| 1,750 sq.ft.	$749,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.41% Airbnb Rental Income: $3941 Traditional Rental Income: $2848 Airbnb ROI: 0.77% Traditional ROI: 0.41%
1619 N BELL Avenue Chicago, IL Welcome to your new home that embodies the epitome of luxury, located in the vibrant heart...	5 beds \| 4 baths \| 4,350 sq.ft.	$1,899,000	Airbnb cash on cash: 1.05% Traditional cash on cash: -0.21% Airbnb Rental Income: $7817 Traditional Rental Income: $4093 Airbnb ROI: 1.05% Traditional ROI: -0.21%
1815 N Harding Avenue Chicago, IL BRICK BUNGALOW LOCATED IN QUIET TREE LINED STREET. 3 LEVEL OF LIVING SPACE. ZIP CODE 60647...	4 beds \| 3 baths \| N/A	$519,000	Airbnb cash on cash: 8.95% Traditional cash on cash: 4.9% Airbnb Rental Income: $6798 Traditional Rental Income: $3509 Airbnb ROI: 8.95% Traditional ROI: 4.9%
2541 S Normal Avenue Chicago, IL 3-story single family home with attached 2-car garage, located 5 blocks from Chinatown, mi...	4 beds \| 3 baths \| 1,980 sq.ft.	$508,000	Airbnb cash on cash: 8.11% Traditional cash on cash: 3.4% Airbnb Rental Income: $6366 Traditional Rental Income: $2882 Airbnb ROI: 8.11% Traditional ROI: 3.4%
420 E WATERSIDE Drive #1312 Chicago, IL REGATTA ON LAKE SHORE EAST! Views, views & more views of the river, our beautiful Lake Mic...	2 beds \| 2 baths \| 1,586 sq.ft.	$699,900	Airbnb cash on cash: 1.71% Traditional cash on cash: -1.37% Airbnb Rental Income: $5862 Traditional Rental Income: $2683 Airbnb ROI: 1.71% Traditional ROI: -1.37%
65 E Monroe Street #4312 Chicago, IL This beautiful 2bed/2bath +den is truly move-in ready! Wonderful open concept floorplan fe...	2 beds \| 2 baths \| N/A	$475,000	Airbnb cash on cash: 4.42% Traditional cash on cash: -0.28% Airbnb Rental Income: $5753 Traditional Rental Income: $2517 Airbnb ROI: 4.42% Traditional ROI: -0.28%
633 S Plymouth Court #1107 Chicago, IL Night View of State Street (pic); Details for comfort and convenience have been considered...	1 beds \| 1 baths \| 850 sq.ft.	$196,850	Airbnb cash on cash: 8.89% Traditional cash on cash: 1.76% Airbnb Rental Income: $3812 Traditional Rental Income: $1656 Airbnb ROI: 8.89% Traditional ROI: 1.76%
6118 N SHERIDAN Road #304 Chicago, IL Charming 2-Bedroom, 1-Bath Unit! This delightful unit features beautiful wood floors tha...	2 beds \| 1 baths \| 1,000 sq.ft.	$199,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 2.9% Airbnb Rental Income: $2729 Traditional Rental Income: $1887 Airbnb ROI: 3.95% Traditional ROI: 2.9%
3548 W Belle Plaine Avenue #1 Chicago, IL Welcome to the Irving Park neighborhood! This 1 bed, 1 bath unit can be found on a quiet t...	1 beds \| 1 baths \| N/A	$164,500	Airbnb cash on cash: 4.58% Traditional cash on cash: 2.55% Airbnb Rental Income: $2075 Traditional Rental Income: $1221 Airbnb ROI: 4.58% Traditional ROI: 2.55%
918 N NOBLE Street Chicago, IL WALK TO MULTIPLE PARKS INCL PREMIER ECKHART PARK, CHICAGO/DIVISION STRIPS & ALL WEST TOWN ...	5 beds \| 5 baths \| N/A	$1,299,500	Airbnb cash on cash: 4.76% Traditional cash on cash: 1.96% Airbnb Rental Income: $10422 Traditional Rental Income: $5108 Airbnb ROI: 4.76% Traditional ROI: 1.96%
1350 W Rosedale Avenue #2 Chicago, IL This oversized 3 bed 2 bath home seamlessly combines thoughtful updates with timeless vint...	3 beds \| 2 baths \| 1,500 sq.ft.	$525,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 2.23% Airbnb Rental Income: $3974 Traditional Rental Income: $2596 Airbnb ROI: 3.31% Traditional ROI: 2.23%
2001 S Calumet Ave #412 Chicago, IL 2001 S Calumet Ave #412, Chicago, IL 60616 \| Condo/Coop	1 beds \| 1 baths \| 900 sq.ft.	$250,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 2.1% Airbnb Rental Income: $3314 Traditional Rental Income: $1767 Airbnb ROI: 5.52% Traditional ROI: 2.1%
121 W DELAWARE Place Chicago, IL Welcome to this exquisite rowhome located on a quiet one-way street just steps from Washin...	5 beds \| 5 baths \| 4,000 sq.ft.	$1,740,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 0.41% Airbnb Rental Income: $12964 Traditional Rental Income: $5139 Airbnb ROI: 3.8% Traditional ROI: 0.41%
1158 W Armitage Avenue #202 Chicago, IL Rarely available in Lincoln Park, step into this one-of-a-kind loft with soaring 11' concr...	2 beds \| 2 baths \| 1,800 sq.ft.	$749,000	Airbnb cash on cash: 0.49% Traditional cash on cash: -0.8% Airbnb Rental Income: $4157 Traditional Rental Income: $2377 Airbnb ROI: 0.49% Traditional ROI: -0.8%
150 W Superior Street #603 Chicago, IL Welcome to your spacious 2-bedroom, 1-bath condo with stunning eastern city skyline views!...	2 beds \| 1 baths \| 1,100 sq.ft.	$389,900	Airbnb cash on cash: 5.76% Traditional cash on cash: -0.52% Airbnb Rental Income: $5288 Traditional Rental Income: $1920 Airbnb ROI: 5.76% Traditional ROI: -0.52%
7148 S Cornell Avenue Chicago, IL *SELLER SAYS SELL!!! TWO COMPLETELY SEPARATE UNITS* Welcome to one of the most UNIQUE ...	6 beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: 9.48% Traditional cash on cash: 4.48% Airbnb Rental Income: $5409 Traditional Rental Income: $2450 Airbnb ROI: 9.48% Traditional ROI: 4.48%
7558 W Palatine Avenue Chicago, IL Luxury custom brick ranch on oversized lot in Norwood Park, featuring open floor plan on m...	3 beds \| 2 baths \| 2,400 sq.ft.	$475,955	Airbnb cash on cash: 4.03% Traditional cash on cash: 3.57% Airbnb Rental Income: $3703 Traditional Rental Income: $2689 Airbnb ROI: 4.03% Traditional ROI: 3.57%
111 S Peoria Street #209 Chicago, IL Move right into this first time resale at Illume, the West Loop's premier building ideally...	3 beds \| 3 baths \| 1,891 sq.ft.	$1,125,000	Airbnb cash on cash: 0.31% Traditional cash on cash: -1.23% Airbnb Rental Income: $6019 Traditional Rental Income: $3212 Airbnb ROI: 0.31% Traditional ROI: -1.23%
1356 N State Parkway Chicago, IL Rarely available desirable Gold Coast Location, Graystone charm, minimalistic style and vi...	4 beds \| 4 baths \| 5,080 sq.ft.	$2,475,000	Airbnb cash on cash: 0.45% Traditional cash on cash: -0.83% Airbnb Rental Income: $8459 Traditional Rental Income: $3929 Airbnb ROI: 0.45% Traditional ROI: -0.83%
4855 N Avers Avenue #1 Chicago, IL Charming and Sunny 2-Bedroom in Albany Park Discover this beautiful and sunny 2-bedroom, ...	2 beds \| 1 baths \| 990 sq.ft.	$199,900	Airbnb cash on cash: 7.36% Traditional cash on cash: 5.67% Airbnb Rental Income: $2781 Traditional Rental Income: $1807 Airbnb ROI: 7.36% Traditional ROI: 5.67%
6418 S Greenwood Avenue Chicago, IL Discover the charm of Woodlawn in this impeccably renovated Classic Greystone, where timel...	4 beds \| 4 baths \| N/A	$649,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 1.53% Airbnb Rental Income: $4913 Traditional Rental Income: $2214 Airbnb ROI: 4.32% Traditional ROI: 1.53%
4241 N Austin Avenue Chicago, IL Under appraised VALUE!!! Come see this completely renovated - LIKE NEW CONSTRUCTION - but ...	5 beds \| 3 baths \| 2,376 sq.ft.	$645,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 3.7% Airbnb Rental Income: $5149 Traditional Rental Income: $3588 Airbnb ROI: 4.56% Traditional ROI: 3.7%
360 W ILLINOIS Street #1D Chicago, IL Super chic concrete loft in one of River North's most sought after buildings, the Sexton, ...	2 beds \| 2 baths \| 1,575 sq.ft.	$585,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 0.81% Airbnb Rental Income: $4846 Traditional Rental Income: $2901 Airbnb ROI: 2.55% Traditional ROI: 0.81%
1160 S MICHIGAN Avenue #1607 Chicago, IL Introducing The Columbian, a magnificent new construction on Michigan Avenue in the heart ...	3 beds \| 3 baths \| 1,909 sq.ft.	$800,000	Airbnb cash on cash: 1.33% Traditional cash on cash: -0.24% Airbnb Rental Income: $5470 Traditional Rental Income: $3204 Airbnb ROI: 1.33% Traditional ROI: -0.24%
175 E Delaware Place #4811 Chicago, IL RARE 2 bedroom, 2 bathroom condo located on the 48th floor with unobstructed, stunning vie...	2 beds \| 2 baths \| 1,250 sq.ft.	$499,900	Airbnb cash on cash: 3.51% Traditional cash on cash: -0.39% Airbnb Rental Income: $5288 Traditional Rental Income: $2395 Airbnb ROI: 3.51% Traditional ROI: -0.39%

Vacation Rentals in Chicago

There are 1,534 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $340,000 and the average price per square foot is $192. The cash on cash return on vacation rentals in Chicago is 5.00%. The average monthly short term rental income in Chicago is $3,646.

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

There are 1,534 Airbnb properties available for sale in Chicago.

In 2024, the best neighborhood to buy short term rental property is Englewood.

In December 2024, the average Airbnb occupancy rate in Chicago is 71%.

In 2024, the highest Airbnb occupancy rate in Chicago are in Englewood (59%), Fuller Park (57%) and Fuller Park (66%).

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

4517 N Whipple Street

Chicago, IL

4 beds | 4 baths | N/A

$999,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $4331

Traditional Rental Income: $2037

Airbnb ROI: 1.25%

Traditional ROI: -0.24%

4836 S Dorchester Avenue

Chicago, IL

6 beds | N/A baths | N/A

$1,150,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 0.32%

Airbnb Rental Income: $7292

Traditional Rental Income: $2659

Airbnb ROI: 3.33%

Traditional ROI: 0.32%

1711 W Division Street #204

Chicago, IL

2 beds | 2 baths | 1,750 sq.ft.

$749,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $3941

Traditional Rental Income: $2848

Airbnb ROI: 0.77%

Traditional ROI: 0.41%

1619 N BELL Avenue

Chicago, IL

5 beds | 4 baths | 4,350 sq.ft.

$1,899,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: -0.21%

Airbnb Rental Income: $7817

Traditional Rental Income: $4093

Airbnb ROI: 1.05%

Traditional ROI: -0.21%

1815 N Harding Avenue

Chicago, IL

4 beds | 3 baths | N/A

$519,000

Airbnb cash on cash: 8.95%

Traditional cash on cash: 4.9%

Airbnb Rental Income: $6798

Traditional Rental Income: $3509

Airbnb ROI: 8.95%

Traditional ROI: 4.9%

2541 S Normal Avenue

Chicago, IL

4 beds | 3 baths | 1,980 sq.ft.

$508,000

Airbnb cash on cash: 8.11%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $6366

Traditional Rental Income: $2882

Airbnb ROI: 8.11%

Traditional ROI: 3.4%

420 E WATERSIDE Drive #1312

Chicago, IL

2 beds | 2 baths | 1,586 sq.ft.

$699,900

Airbnb cash on cash: 1.71%

Traditional cash on cash: -1.37%

Airbnb Rental Income: $5862

Traditional Rental Income: $2683

Airbnb ROI: 1.71%

Traditional ROI: -1.37%

65 E Monroe Street #4312

Chicago, IL

2 beds | 2 baths | N/A

$475,000

Airbnb cash on cash: 4.42%

Traditional cash on cash: -0.28%

Airbnb Rental Income: $5753

Traditional Rental Income: $2517

Airbnb ROI: 4.42%