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
5911 N Keating Avenue Chicago, IL Meticulously maintained & recently renovated 4 bedroom + family room/3 bath with rarely av...	4 beds \| 3 baths \| N/A	$749,500	Airbnb cash on cash: 0.98% Traditional cash on cash: 0.93% Airbnb Rental Income: $2925 Traditional Rental Income: $2216 Airbnb ROI: 0.98% Traditional ROI: 0.93%
2854 S Central Park Ave Chicago, IL 2854 S Central Park Ave, Chicago, IL 60623 \| Single Family Residential	5 beds \| 2 baths \| 896 sq.ft.	$348,500	Airbnb cash on cash: 6.31% Traditional cash on cash: 3.07% Airbnb Rental Income: $3680 Traditional Rental Income: $1819 Airbnb ROI: 6.31% Traditional ROI: 3.07%
3035 N Luna Ave Chicago, IL Classic Chicago bungalow with 3 full bedroom's on the first floor. Many beautiful intact ...	6 beds \| 2 baths \| 1,600 sq.ft.	$499,500	Airbnb cash on cash: 5.87% Traditional cash on cash: 4.17% Airbnb Rental Income: $4741 Traditional Rental Income: $2970 Airbnb ROI: 5.87% Traditional ROI: 4.17%
480 N Mcclurg Ct #413 Chicago, IL 480 N Mcclurg Ct #413, Chicago, IL 60611 \| Condo/Coop	2 beds \| 2 baths \| 1,208 sq.ft.	$399,000	Airbnb cash on cash: 0.34% Traditional cash on cash: -0.03% Airbnb Rental Income: $3258 Traditional Rental Income: $2388 Airbnb ROI: 0.34% Traditional ROI: -0.03%
4837 S Long Ave Chicago, IL 4837 S Long Ave, Chicago, IL 60638 \| Single Family Residential	7 beds \| 2 baths \| 1,700 sq.ft.	$418,900	Airbnb cash on cash: 2.81% Traditional cash on cash: 2.2% Airbnb Rental Income: $3190 Traditional Rental Income: $2232 Airbnb ROI: 2.81% Traditional ROI: 2.2%
20 N State St #1013 Chicago, IL Rare opportunity to own a truly unique industrial penthouse loft in one of the Loop's most...	1 beds \| 1 baths \| N/A	$275,000	Airbnb cash on cash: 0.13% Traditional cash on cash: -0.8% Airbnb Rental Income: $1982 Traditional Rental Income: $1222 Airbnb ROI: 0.13% Traditional ROI: -0.8%
1339 W Ancona St Chicago, IL Exceptional newer-construction fee-simple single-family home on a quiet one-way street in ...	4 beds \| 3 baths \| 2,800 sq.ft.	$1,099,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.6% Airbnb Rental Income: $3909 Traditional Rental Income: $3060 Airbnb ROI: 0.61% Traditional ROI: 0.6%
4757 S Langley Ave Chicago, IL 4757 S Langley Ave, Chicago, IL 60615 \| Single Family Residential	4 beds \| 2 baths \| 2,520 sq.ft.	$585,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.89% Airbnb Rental Income: $3481 Traditional Rental Income: $2357 Airbnb ROI: 1.54% Traditional ROI: 0.89%
1663 W Pratt Blvd #2 Chicago, IL Welcome home to this beautifully maintained 2 bedroom plus den condominium nestled in the ...	2 beds \| 1 baths \| 900 sq.ft.	$225,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 3.46% Airbnb Rental Income: $2210 Traditional Rental Income: $1650 Airbnb ROI: 3.47% Traditional ROI: 3.46%
2533 W Warren Blvd Chicago, IL 2533 W Warren Blvd, Chicago, IL 60612 \| Other	N/A beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: 1.55% Traditional cash on cash: -0.55% Airbnb Rental Income: $2492 Traditional Rental Income: $1101 Airbnb ROI: 1.55% Traditional ROI: -0.55%
1525 S lawndale Avenue Chicago, IL	3 beds \| 2 baths \| 1,381 sq.ft.	$249,000	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.06% Airbnb Rental Income: $2280 Traditional Rental Income: $1634 Airbnb ROI: 4.39% Traditional ROI: 4.06%
6092 N Sauganash Ave Chicago, IL 6092 N Sauganash Ave, Chicago, IL 60646 \| Single Family Residential	5 beds \| 3 baths \| 4,342 sq.ft.	$1,175,000	Airbnb cash on cash: 1.03% Traditional cash on cash: -0.3% Airbnb Rental Income: $5995 Traditional Rental Income: $3352 Airbnb ROI: 1.03% Traditional ROI: -0.3%
758 N Larrabee Street #514 Chicago, IL Experience true loft living in this stunning and sun-drenched 2-bedroom, 2-bath residence ...	2 beds \| 2 baths \| 1,200 sq.ft.	$375,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 0.28% Airbnb Rental Income: $3007 Traditional Rental Income: $2041 Airbnb ROI: 1.07% Traditional ROI: 0.28%
7749 S Muskegon Ave Chicago, IL FREE - FREE 32" TV - MOVE RIGHT IN -ONE MONTH FREE RENT!!!- DECEMBER ON US!! TO THIS SPACI...	10 beds \| 3 baths \| 1,000 sq.ft.	$279,900	Airbnb cash on cash: 5.35% Traditional cash on cash: 2.18% Airbnb Rental Income: $3055 Traditional Rental Income: $1523 Airbnb ROI: 5.35% Traditional ROI: 2.18%
7613 S Hermitage Ave Chicago, IL This beautiful Chicago brick bungalow home was renovated in 2023. This home has been touch...	7 beds \| 3 baths \| 2,234 sq.ft.	$269,999	Airbnb cash on cash: 8.8% Traditional cash on cash: 6.82% Airbnb Rental Income: $3406 Traditional Rental Income: $2145 Airbnb ROI: 8.8% Traditional ROI: 6.82%
5337 W Barry Ave Chicago, IL Beautiful Cragin neighborhood home with 4 Bedrooms and 4 Full Baths. An enormous Eat-in Ki...	5 beds \| 4 baths \| 0 sq.ft.	$615,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 4.46% Airbnb Rental Income: $4741 Traditional Rental Income: $3605 Airbnb ROI: 4.73% Traditional ROI: 4.46%
600 S Dearborn St #808-810 Chicago, IL	2 beds \| 2 baths \| 1,800 sq.ft.	$485,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.38% Airbnb Rental Income: $3107 Traditional Rental Income: $2222 Airbnb ROI: 0.77% Traditional ROI: 0.38%
1924 W Farragut Avenue Chicago, IL A rare offering in Ravenswood/Bowmanville, this five-bedroom single-family home has been t...	5 beds \| 6 baths \| 3,942 sq.ft.	$1,725,000	Airbnb cash on cash: 0.17% Traditional cash on cash: -0.17% Airbnb Rental Income: $3816 Traditional Rental Income: $2441 Airbnb ROI: 0.17% Traditional ROI: -0.17%
6 E Monroe St #1403 Chicago, IL Location! Location! Location! This 14th floor condo is perfectly situated just 1 block fro...	1 beds \| 1 baths \| 700 sq.ft.	$223,000	Airbnb cash on cash: 0.5% Traditional cash on cash: -0.31% Airbnb Rental Income: $1982 Traditional Rental Income: $1292 Airbnb ROI: 0.5% Traditional ROI: -0.31%
221 E Walton Pl #14B Chicago, IL Rare opportunity in a boutique Gold Coast building! This spacious 3-bedroom condo offers b...	3 beds \| 2 baths \| 1,450 sq.ft.	$550,000	Airbnb cash on cash: 0.13% Traditional cash on cash: -2.69% Airbnb Rental Income: $4122 Traditional Rental Income: $1798 Airbnb ROI: 0.13% Traditional ROI: -2.69%
30 E Huron St #2007 Chicago, IL View our virtual 3D tour! Bright and sunny northwest corner 2-bedroom condo in an unbeatab...	2 beds \| 1 baths \| 900 sq.ft.	$370,000	Airbnb cash on cash: 0.94% Traditional cash on cash: -0.78% Airbnb Rental Income: $2869 Traditional Rental Income: $1603 Airbnb ROI: 0.94% Traditional ROI: -0.78%
5632 W Pensacola Ave Chicago, IL PROPERTY IN NEED OF REPAIRS. GREAT FOR A REHAB PROJECT OR HANDYMAN.	5 beds \| 3 baths \| 1,425 sq.ft.	$725,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 1.92% Airbnb Rental Income: $5661 Traditional Rental Income: $2546 Airbnb ROI: 4.85% Traditional ROI: 1.92%
211 E Ohio St #2118 Chicago, IL Enjoy abundant natural light in this highly sought-after south-facing 2-bedroom, 2-bathroo...	2 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 1.21% Traditional cash on cash: -1.64% Airbnb Rental Income: $3258 Traditional Rental Income: $1655 Airbnb ROI: 1.21% Traditional ROI: -1.64%
7256 W Thorndale Ave Chicago, IL Light and bright 3 bedroom, 1.5 bath home situated on an oversized 41 x 145 lot in desirab...	3 beds \| 1 baths \| 1,400 sq.ft.	$449,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 1.4% Airbnb Rental Income: $2465 Traditional Rental Income: $1565 Airbnb ROI: 2.11% Traditional ROI: 1.4%
7431 N Hoyne Ave #G Chicago, IL Located in West Rogers Park, this 2 bedroom garden condo features a separate living and di...	2 beds \| 1 baths \| 800 sq.ft.	$144,900	Airbnb cash on cash: 7.69% Traditional cash on cash: 5.74% Airbnb Rental Income: $2210 Traditional Rental Income: $1382 Airbnb ROI: 7.69% Traditional ROI: 5.74%
2527 W Harrison St #2 Chicago, IL Modern, light-filled condo in the UIC medical district boasts beautiful cherry hardwood fl...	2 beds \| 2 baths \| N/A	$295,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 3.9% Airbnb Rental Income: $2559 Traditional Rental Income: $1927 Airbnb ROI: 3.96% Traditional ROI: 3.9%
1412 W Fuller Street Chicago, IL Located on a quiet, tree-lined street in a desirable pocket of Bridgeport, this single-fam...	4 beds \| 4 baths \| N/A	$599,900	Airbnb cash on cash: 0.85% Traditional cash on cash: 0.35% Airbnb Rental Income: $2741 Traditional Rental Income: $1816 Airbnb ROI: 0.85% Traditional ROI: 0.35%

Vacation Rentals in Chicago

There are 815 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $419,749 and the average price per square foot is $240. The cash on cash return on vacation rentals in Chicago is N/A%. The average monthly short term rental income in Chicago is $2,039.

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

There are 815 Airbnb properties available for sale in Chicago.

In 2026, the best neighborhood to buy short term rental property is Hanson Park.

In July 2026, the average Airbnb occupancy rate in Chicago is 28%.

In 2026, the highest Airbnb occupancy rate in Chicago are in Hanson Park (30%), South Shore (26%) and South Shore (33%).

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

5911 N Keating Avenue

Chicago, IL

4 beds | 3 baths | N/A

$749,500

Airbnb cash on cash: 0.98%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $2925

Traditional Rental Income: $2216

Airbnb ROI: 0.98%

Traditional ROI: 0.93%

2854 S Central Park Ave

Chicago, IL

5 beds | 2 baths | 896 sq.ft.

$348,500

Airbnb cash on cash: 6.31%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $3680

Traditional Rental Income: $1819

Airbnb ROI: 6.31%

Traditional ROI: 3.07%

3035 N Luna Ave

Chicago, IL

6 beds | 2 baths | 1,600 sq.ft.

$499,500

Airbnb cash on cash: 5.87%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $4741

Traditional Rental Income: $2970

Airbnb ROI: 5.87%

Traditional ROI: 4.17%

480 N Mcclurg Ct #413

Chicago, IL

2 beds | 2 baths | 1,208 sq.ft.

$399,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: -0.03%

Airbnb Rental Income: $3258

Traditional Rental Income: $2388

Airbnb ROI: 0.34%

Traditional ROI: -0.03%

4837 S Long Ave

Chicago, IL

7 beds | 2 baths | 1,700 sq.ft.

$418,900

Airbnb cash on cash: 2.81%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $3190

Traditional Rental Income: $2232

Airbnb ROI: 2.81%

Traditional ROI: 2.2%

20 N State St #1013

Chicago, IL

1 beds | 1 baths | N/A

$275,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: -0.8%

Airbnb Rental Income: $1982

Traditional Rental Income: $1222

Airbnb ROI: 0.13%

Traditional ROI: -0.8%

1339 W Ancona St

Chicago, IL

4 beds | 3 baths | 2,800 sq.ft.

$1,099,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $3909

Traditional Rental Income: $3060

Airbnb ROI: 0.61%

Traditional ROI: 0.6%

4757 S Langley Ave

Chicago, IL

4 beds | 2 baths | 2,520 sq.ft.

$585,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 0.89%

Airbnb Rental Income: $3481

Traditional Rental Income: $2357

Airbnb ROI: 1.54%