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
4038 W Addison St Chicago, IL	5 beds \| 3 baths \| 3,651 sq.ft.	$900,000	Airbnb cash on cash: 2.13% Traditional cash on cash: -0.08% Airbnb Rental Income: $5759 Traditional Rental Income: $2758 Airbnb ROI: 2.13% Traditional ROI: -0.08%
2201 W Wabansia Ave #12 Chicago, IL 2201 W Wabansia Ave #12, Chicago, IL 60647 \| Condo/Coop	2 beds \| 2 baths \| 1,200 sq.ft.	$435,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 0.79% Airbnb Rental Income: $3646 Traditional Rental Income: $2175 Airbnb ROI: 2.44% Traditional ROI: 0.79%
2826 S KARLOV Avenue Chicago, IL Charming 4 bedroom, 2 bathroom single family home in the heart of Little Village. This wel...	3 beds \| 2 baths \| N/A	$250,000	Airbnb cash on cash: 9.27% Traditional cash on cash: 6.84% Airbnb Rental Income: $3573 Traditional Rental Income: $2214 Airbnb ROI: 9.27% Traditional ROI: 6.84%
4518 S Drexel Boulevard Chicago, IL Named BEST RENOVATION IN CHICAGO by Curbed Magazine! The magnificent Krause Mansion was de...	5 beds \| 5 baths \| 7,000 sq.ft.	$1,750,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 1.01% Airbnb Rental Income: $7363 Traditional Rental Income: $4975 Airbnb ROI: 1.61% Traditional ROI: 1.01%
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%
5623 S Newcastle Avenue Chicago, IL Nestled in a prime location, this 2-unit property offers a unique opportunity for investor...	6 beds \| N/A baths \| N/A	$529,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 2.72% Airbnb Rental Income: $3284 Traditional Rental Income: $2527 Airbnb ROI: 2.76% Traditional ROI: 2.72%
3242 W 115th Street Chicago, IL Welcome to your perfect starter home, ideally situated on a uniquely large 30' x 169' lot ...	2 beds \| 2 baths \| 1,104 sq.ft.	$235,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 3.74% Airbnb Rental Income: $2397 Traditional Rental Income: $1599 Airbnb ROI: 4.68% Traditional ROI: 3.74%
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.	$799,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 0.33% Airbnb Rental Income: $3941 Traditional Rental Income: $2848 Airbnb ROI: 0.66% Traditional ROI: 0.33%
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%
50 E 16th Street #305 Chicago, IL Discover this gorgeous 2-bedroom, 1-bathroom corner unit that boasts an abundance of natur...	2 beds \| 1 baths \| 1,478 sq.ft.	$365,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 2.85% Airbnb Rental Income: $3776 Traditional Rental Income: $2718 Airbnb ROI: 3.55% Traditional ROI: 2.85%
474 N Lake Shore Dr #5011 Chicago, IL 474 N Lake Shore Dr #5011, Chicago, IL 60611 \| Condo/Coop	N/A beds \| 1 baths \| 650 sq.ft.	$240,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 0.11% Airbnb Rental Income: $2544 Traditional Rental Income: $1598 Airbnb ROI: 1.58% Traditional ROI: 0.11%
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%
2236 W Palmer Street Chicago, IL Welcome to this stunningly renovated home, perfectly situated in a premiere location of Bu...	4 beds \| 4 baths \| 3,600 sq.ft.	$1,275,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 1.26% Airbnb Rental Income: $6266 Traditional Rental Income: $4008 Airbnb ROI: 2.13% Traditional ROI: 1.26%
1816 W Belmont Avenue #2 Chicago, IL Welcome to this stunning and meticulously maintained 2-bedroom, 2-bathroom residence in th...	2 beds \| 2 baths \| 1,300 sq.ft.	$499,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 1.36% Airbnb Rental Income: $3122 Traditional Rental Income: $2108 Airbnb ROI: 2.01% Traditional ROI: 1.36%
10544 S Edbrooke Avenue Chicago, IL Beautiful Newer Built Home New Hardwood Floors, Modern Kitchen Cabinets, Counter Tops, Sin...	3 beds \| 2 baths \| 1,800 sq.ft.	$224,500	Airbnb cash on cash: 8.71% Traditional cash on cash: 6.78% Airbnb Rental Income: $2991 Traditional Rental Income: $1893 Airbnb ROI: 8.71% Traditional ROI: 6.78%
1600 S Prairie Avenue #903 Chicago, IL Meticulously upgraded 2 bed 2 bath, at the luxurious Prairie Pointe building in an unbeata...	2 beds \| 2 baths \| 1,443 sq.ft.	$489,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 0.14% Airbnb Rental Income: $3776 Traditional Rental Income: $2477 Airbnb ROI: 1.19% Traditional ROI: 0.14%
6 N Michigan Avenue #601 Chicago, IL Revised pricing now includes parking! Ever wonder what it's like to see The Bean and Lake ...	2 beds \| 2 baths \| 1,350 sq.ft.	$594,900	Airbnb cash on cash: 3.49% Traditional cash on cash: -0.49% Airbnb Rental Income: $5753 Traditional Rental Income: $2398 Airbnb ROI: 3.49% Traditional ROI: -0.49%
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%
130 N Garland Court #3202 Chicago, IL West-Facing Luxury Condo with Unobstructed City Views! Meticulously maintained 3-Bedroom 2...	3 beds \| 2 baths \| 1,653 sq.ft.	$730,000	Airbnb cash on cash: 3.35% Traditional cash on cash: -0.42% Airbnb Rental Income: $6877 Traditional Rental Income: $2973 Airbnb ROI: 3.35% Traditional ROI: -0.42%
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	$485,000	Airbnb cash on cash: 4.31% Traditional cash on cash: -0.3% Airbnb Rental Income: $5753 Traditional Rental Income: $2517 Airbnb ROI: 4.31% Traditional ROI: -0.3%
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: 8.94% Traditional cash on cash: 1.81% Airbnb Rental Income: $3812 Traditional Rental Income: $1656 Airbnb ROI: 8.94% Traditional ROI: 1.81%
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%
444 W Fullerton Parkway #804 Chicago, IL Bask in natural light and enjoy incredible panoramic skyline views from this recently upda...	2 beds \| 2 baths \| N/A	$399,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 0.94% Airbnb Rental Income: $4067 Traditional Rental Income: $2771 Airbnb ROI: 2.09% Traditional ROI: 0.94%
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%
1632 S Indiana Avenue #606 Chicago, IL Experience the best of South Loop living in this impeccably maintained brick and timber lo...	1 beds \| 1 baths \| N/A	$245,000	Airbnb cash on cash: 6.64% Traditional cash on cash: 4.11% Airbnb Rental Income: $3314 Traditional Rental Income: $1989 Airbnb ROI: 6.64% Traditional ROI: 4.11%
910 N Lake Shore Drive #820 Chicago, IL Light filled, modern 3 bedroom at 910 N Lakeshore Drive in the heart of the Streeterville ...	3 beds \| 2 baths \| N/A	$399,000	Airbnb cash on cash: 8.9% Traditional cash on cash: 0.64% Airbnb Rental Income: $7491 Traditional Rental Income: $2963 Airbnb ROI: 8.9% Traditional ROI: 0.64%
4343 N Clarendon Avenue #1102 Chicago, IL CALLING ALL INVESTORS-- Southeast corner unit on a high floor offering breathtaking views ...	2 beds \| 2 baths \| 1,150 sq.ft.	$279,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 1.49% Airbnb Rental Income: $3122 Traditional Rental Income: $2345 Airbnb ROI: 1.75% Traditional ROI: 1.49%
208 W Washington Street #1910 Chicago, IL Experience urban luxury in this stunning and spacious 2 bed, 2 bath Northeast, corner unit...	2 beds \| 2 baths \| 1,270 sq.ft.	$349,999	Airbnb cash on cash: 4.04% Traditional cash on cash: 1.14% Airbnb Rental Income: $4585 Traditional Rental Income: $2679 Airbnb ROI: 4.04% Traditional ROI: 1.14%
65 E Monroe Street #4604 Chicago, IL Beautiful corner two bedroom, two-and-a-half-bathroom condo at Park Monroe with 10' floor ...	2 beds \| 3 baths \| 1,726 sq.ft.	$885,000	Airbnb cash on cash: 0.74% Traditional cash on cash: -0.92% Airbnb Rental Income: $5753 Traditional Rental Income: $3237 Airbnb ROI: 0.74% Traditional ROI: -0.92%

Vacation Rentals in Chicago

There are 1,906 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $359,000 and the average price per square foot is $201. The cash on cash return on vacation rentals in Chicago is 4.00%. The average monthly short term rental income in Chicago is $3,700.

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

There are 1,906 Airbnb properties available for sale in Chicago.

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

In November 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

4038 W Addison St

Chicago, IL

5 beds | 3 baths | 3,651 sq.ft.

$900,000

Airbnb cash on cash: 2.13%

Traditional cash on cash: -0.08%

Airbnb Rental Income: $5759

Traditional Rental Income: $2758

Airbnb ROI: 2.13%

Traditional ROI: -0.08%

2201 W Wabansia Ave #12

Chicago, IL

2 beds | 2 baths | 1,200 sq.ft.

$435,000

Airbnb cash on cash: 2.44%

Traditional cash on cash: 0.79%

Airbnb Rental Income: $3646

Traditional Rental Income: $2175

Airbnb ROI: 2.44%

Traditional ROI: 0.79%

2826 S KARLOV Avenue

Chicago, IL

3 beds | 2 baths | N/A

$250,000

Airbnb cash on cash: 9.27%

Traditional cash on cash: 6.84%

Airbnb Rental Income: $3573

Traditional Rental Income: $2214

Airbnb ROI: 9.27%

Traditional ROI: 6.84%

4518 S Drexel Boulevard

Chicago, IL

5 beds | 5 baths | 7,000 sq.ft.

$1,750,000

Airbnb cash on cash: 1.61%

Traditional cash on cash: 1.01%

Airbnb Rental Income: $7363

Traditional Rental Income: $4975

Airbnb ROI: 1.61%

Traditional ROI: 1.01%

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%

5623 S Newcastle Avenue

Chicago, IL

6 beds | N/A baths | N/A

$529,000

Airbnb cash on cash: 2.76%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $3284

Traditional Rental Income: $2527

Airbnb ROI: 2.76%

Traditional ROI: 2.72%

3242 W 115th Street

Chicago, IL

2 beds | 2 baths | 1,104 sq.ft.

$235,000

Airbnb cash on cash: 4.68%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $2397

Traditional Rental Income: $1599

Airbnb ROI: 4.68%

Traditional ROI: 3.74%

1711 W Division Street #204

Chicago, IL

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

$799,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $3941

Traditional Rental Income: $2848

Airbnb ROI: 0.66%