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
3042 W Irving Park Rd Chicago, IL	N/A beds \| N/A baths \| N/A	$279,900	Airbnb cash on cash: 0.17% Traditional cash on cash: -0.07% Airbnb Rental Income: $1418 Traditional Rental Income: $929 Airbnb ROI: 0.17% Traditional ROI: -0.07%
5009-15 S Homan Ave Chicago, IL 5009-15 S Homan Ave, Chicago, IL 60632 \| Other	N/A beds \| N/A baths \| N/A	$280,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 0.42% Airbnb Rental Income: $2848 Traditional Rental Income: $1059 Airbnb ROI: 4.69% Traditional ROI: 0.42%
4229 S Archer Ave Chicago, IL	N/A beds \| N/A baths \| N/A	$449,000	Airbnb cash on cash: 7.84% Traditional cash on cash: -0.58% Airbnb Rental Income: $5930 Traditional Rental Income: $1213 Airbnb ROI: 7.84% Traditional ROI: -0.58%
4675 S Archer Ave Chicago, IL 4675 S Archer Ave, Chicago, IL 60632 \| Other	N/A beds \| N/A baths \| N/A	$1,299,000	Airbnb cash on cash: 0.6% Traditional cash on cash: -2.33% Airbnb Rental Income: $5930 Traditional Rental Income: $1215 Airbnb ROI: 0.6% Traditional ROI: -2.33%
3675 N Elston Ave Chicago, IL 3675 N Elston Ave, Chicago, IL 60618 \| Other	N/A beds \| N/A baths \| N/A	$249,900	Airbnb cash on cash: 0.58% Traditional cash on cash: 0.43% Airbnb Rental Income: $1418 Traditional Rental Income: $959 Airbnb ROI: 0.58% Traditional ROI: 0.43%
4634 N Avers Ave Chicago, IL 4634 N Avers Ave, Chicago, IL 60625 \| Other	N/A beds \| N/A baths \| N/A	$215,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 0.63% Airbnb Rental Income: $1341 Traditional Rental Income: $879 Airbnb ROI: 0.87% Traditional ROI: 0.63%
2224 W Taylor St Chicago, IL 2224 W Taylor St, Chicago, IL 60612 \| Other	N/A beds \| N/A baths \| N/A	$230,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 0.46% Airbnb Rental Income: $1345 Traditional Rental Income: $897 Airbnb ROI: 0.62% Traditional ROI: 0.46%
2419 N Central Ave Chicago, IL 2419 N Central Ave, Chicago, IL 60639 \| Other	N/A beds \| N/A baths \| N/A	$295,000	Airbnb cash on cash: 6.5% Traditional cash on cash: -0.17% Airbnb Rental Income: $3585 Traditional Rental Income: $945 Airbnb ROI: 6.5% Traditional ROI: -0.17%
1756 W 48th St Chicago, IL 1756 W 48th St, Chicago, IL 60609 \| Other	N/A beds \| N/A baths \| N/A	$115,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 2.78% Airbnb Rental Income: $1386 Traditional Rental Income: $758 Airbnb ROI: 4.65% Traditional ROI: 2.78%
5243 W Fullerton Ave Chicago, IL 5243 W Fullerton Ave, Chicago, IL 60639 \| Other	N/A beds \| N/A baths \| N/A	$575,000	Airbnb cash on cash: 1.79% Traditional cash on cash: -1.54% Airbnb Rental Income: $3585 Traditional Rental Income: $1013 Airbnb ROI: 1.79% Traditional ROI: -1.54%
5226 S Loomis St Chicago, IL 5226 S Loomis St, Chicago, IL 60609 \| Other	N/A beds \| N/A baths \| N/A	$145,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 1.72% Airbnb Rental Income: $1386 Traditional Rental Income: $778 Airbnb ROI: 3.07% Traditional ROI: 1.72%
5756 S Princeton Ave Chicago, IL Attention Investors! Discover an incredible opportunity for investors and owner-occupants ...	8 beds \| 3 baths \| N/A	$254,000	Airbnb cash on cash: 7.44% Traditional cash on cash: 7.36% Airbnb Rental Income: $2833 Traditional Rental Income: $2152 Airbnb ROI: 7.44% Traditional ROI: 7.36%
4926 S Western Ave Chicago, IL	N/A beds \| N/A baths \| N/A	$295,000	Airbnb cash on cash: 4.29% Traditional cash on cash: -0.65% Airbnb Rental Income: $2848 Traditional Rental Income: $811 Airbnb ROI: 4.29% Traditional ROI: -0.65%
5155 S Archer Ave Chicago, IL 5155 S Archer Ave, Chicago, IL 60632 \| Other	N/A beds \| N/A baths \| N/A	$900,990	Airbnb cash on cash: 2.3% Traditional cash on cash: -2.45% Airbnb Rental Income: $5930 Traditional Rental Income: $769 Airbnb ROI: 2.3% Traditional ROI: -2.45%
5639 S Princeton Avenue Chicago, IL All brick 6 flat in the booming Englewood community! All units are 3 bedroom, 1 bath apart...	18 beds \| N/A baths \| N/A	$450,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 3.43% Airbnb Rental Income: $2833 Traditional Rental Income: $2063 Airbnb ROI: 3.69% Traditional ROI: 3.43%
310 E Pershing Rd Chicago, IL 310 E Pershing Rd, Chicago, IL 60653 \| Other	N/A beds \| N/A baths \| N/A	$145,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.57% Airbnb Rental Income: $975 Traditional Rental Income: $618 Airbnb ROI: 0.61% Traditional ROI: 0.57%
3329 N Drake Ave Chicago, IL 3329 N Drake Ave, Chicago, IL 60618 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: 0.02% Traditional cash on cash: -0.49% Airbnb Rental Income: $1441 Traditional Rental Income: $867 Airbnb ROI: 0.02% Traditional ROI: -0.49%
3149 W Wellington Ave #1 Chicago, IL 3149 W Wellington Ave #1, Chicago, IL 60618 \| Condo/Coop	N/A beds \| 1 baths \| 500 sq.ft.	$154,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.33% Airbnb Rental Income: $1476 Traditional Rental Income: $886 Airbnb ROI: 1.38% Traditional ROI: 0.33%

Vacation Rentals in Chicago

There are 20 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $360,000 and the average price per square foot is $204. The cash on cash return on vacation rentals in Chicago is -2.00%. The average monthly short term rental income in Chicago is $1,053.

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

There are 20 Airbnb properties available for sale in Chicago.

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

In April 2026, the average Airbnb occupancy rate in Chicago is 19%.

In 2026, the highest Airbnb occupancy rate in Chicago are in Hanson Park (21%), South Shore (27%) and South Shore (23%).

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

3042 W Irving Park Rd

Chicago, IL

N/A beds | N/A baths | N/A

$279,900

Airbnb cash on cash: 0.17%

Traditional cash on cash: -0.07%

Airbnb Rental Income: $1418

Traditional Rental Income: $929

Airbnb ROI: 0.17%

Traditional ROI: -0.07%

5009-15 S Homan Ave

Chicago, IL

N/A beds | N/A baths | N/A

$280,000

Airbnb cash on cash: 4.69%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $2848

Traditional Rental Income: $1059

Airbnb ROI: 4.69%

Traditional ROI: 0.42%

4229 S Archer Ave

Chicago, IL

N/A beds | N/A baths | N/A

$449,000

Airbnb cash on cash: 7.84%

Traditional cash on cash: -0.58%

Airbnb Rental Income: $5930

Traditional Rental Income: $1213

Airbnb ROI: 7.84%

Traditional ROI: -0.58%

4675 S Archer Ave

Chicago, IL

N/A beds | N/A baths | N/A

$1,299,000

Airbnb cash on cash: 0.6%

Traditional cash on cash: -2.33%

Airbnb Rental Income: $5930

Traditional Rental Income: $1215

Airbnb ROI: 0.6%

Traditional ROI: -2.33%

3675 N Elston Ave

Chicago, IL

N/A beds | N/A baths | N/A

$249,900

Airbnb cash on cash: 0.58%

Traditional cash on cash: 0.43%

Airbnb Rental Income: $1418

Traditional Rental Income: $959

Airbnb ROI: 0.58%

Traditional ROI: 0.43%

4634 N Avers Ave

Chicago, IL

N/A beds | N/A baths | N/A

$215,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $1341

Traditional Rental Income: $879

Airbnb ROI: 0.87%

Traditional ROI: 0.63%

2224 W Taylor St

Chicago, IL

N/A beds | N/A baths | N/A

$230,000

Airbnb cash on cash: 0.62%

Traditional cash on cash: 0.46%

Airbnb Rental Income: $1345

Traditional Rental Income: $897

Airbnb ROI: 0.62%

Traditional ROI: 0.46%

2419 N Central Ave

Chicago, IL

N/A beds | N/A baths | N/A

$295,000

Airbnb cash on cash: 6.5%

Traditional cash on cash: -0.17%

Airbnb Rental Income: $3585

Traditional Rental Income: $945

Airbnb ROI: 6.5%