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
3950 N LAKE SHORE Drive #801 Chicago, IL LARGE 2 BDRM 1 BATH - SOUTH AND EAST VIEW - REHABBED UNIT WITH NEWER KITCHEN AND BATH. STA...	2 beds \| 1 baths \| N/A	$268,700	Airbnb cash on cash: 0.07% Traditional cash on cash: -0.29% Airbnb Rental Income: $2029 Traditional Rental Income: $1410 Airbnb ROI: 0.07% Traditional ROI: -0.29%
32 S Menard Avenue Chicago, IL This well-maintained vintage 4-flat (6 full units, 2 non-conforming), built in 1918, has b...	21 beds \| 10 baths \| N/A	$1,100,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 0.68% Airbnb Rental Income: $3599 Traditional Rental Income: $2469 Airbnb ROI: 1.01% Traditional ROI: 0.68%
6030 N Sheridan Rd #301 Chicago, IL ELEGANT EDGEWATER! WONDERFUL TREE TOP, FRONT STREET FACING, VERY WELL MAINTAINED & SPACIOU...	1 beds \| 1 baths \| N/A	$168,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 0.08% Airbnb Rental Income: $1624 Traditional Rental Income: $1026 Airbnb ROI: 0.95% Traditional ROI: 0.08%
320 N Menard Avenue Chicago, IL	5 beds \| 3 baths \| 2,650 sq.ft.	$449,999	Airbnb cash on cash: 5.21% Traditional cash on cash: 3.72% Airbnb Rental Income: $3599 Traditional Rental Income: $2184 Airbnb ROI: 5.21% Traditional ROI: 3.72%
4224 N Kimball Ave Chicago, IL 4224 N Kimball Ave, Chicago, IL 60618 \| Multi Family	5 beds \| 3 baths \| N/A	$620,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 1.18% Airbnb Rental Income: $4292 Traditional Rental Income: $2661 Airbnb ROI: 2.44% Traditional ROI: 1.18%
1908 S Sawyer Ave Chicago, IL Check out this 4 bedroom 2 full bath rowhouse in the North Lawndale neighborhood. Freshly...	6 beds \| 3 baths \| 1,800 sq.ft.	$339,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 3.12% Airbnb Rental Income: $3106 Traditional Rental Income: $1652 Airbnb ROI: 5.47% Traditional ROI: 3.12%
4825 S Central Ave Chicago, IL 4825 S Central Ave, Chicago, IL 60638 \| Other	N/A beds \| N/A baths \| N/A	$249,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 1.48% Airbnb Rental Income: $1738 Traditional Rental Income: $1202 Airbnb ROI: 1.72% Traditional ROI: 1.48%
5523 W Huron Street Chicago, IL WELCOME TO YOUR NEW HOME! BEAUTIFULLY UPDATED TWO FLAT WITH BASEMENT THAT CAN BE CONVERTED...	5 beds \| 2 baths \| N/A	$400,000	Airbnb cash on cash: 5% Traditional cash on cash: 2.62% Airbnb Rental Income: $3599 Traditional Rental Income: $1916 Airbnb ROI: 5% Traditional ROI: 2.62%
2730 W 16th St Chicago, IL Looking for your first investment property THIS IS IT!! Great tenants and well maintained ...	7 beds \| 3 baths \| N/A	$549,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 1.98% Airbnb Rental Income: $3106 Traditional Rental Income: $1815 Airbnb ROI: 3.12% Traditional ROI: 1.98%
9608 S Wallace St Chicago, IL 9608 S Wallace St, Chicago, IL 60628 \| Single Family Residential	2 beds \| 1 baths \| 960 sq.ft.	$130,000	Airbnb cash on cash: 6.49% Traditional cash on cash: 5.88% Airbnb Rental Income: $1793 Traditional Rental Income: $1229 Airbnb ROI: 6.49% Traditional ROI: 5.88%
2038 E 73rd St Chicago, IL 2038 E 73rd St, Chicago, IL 60649 \| Single Family Residential	5 beds \| 2 baths \| 2,185 sq.ft.	$289,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 3.56% Airbnb Rental Income: $3122 Traditional Rental Income: $1944 Airbnb ROI: 5.28% Traditional ROI: 3.56%
4327 W Monroe Street Chicago, IL Investment opportunity at 4327 W Monroe St in Chicago! This two-flat is fully occupied, ma...	5 beds \| 2 baths \| N/A	$310,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 3.33% Airbnb Rental Income: $2589 Traditional Rental Income: $1611 Airbnb ROI: 4.56% Traditional ROI: 3.33%
4912 W Wrightwood Ave Chicago, IL 4912 W Wrightwood Ave, Chicago, IL 60639 \| Single Family Residential	5 beds \| 4 baths \| 2,480 sq.ft.	$619,999	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.16% Airbnb Rental Income: $3130 Traditional Rental Income: $2070 Airbnb ROI: 0.77% Traditional ROI: 0.16%
2833 W Polk Street Chicago, IL	9 beds \| 3 baths \| N/A	$779,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.5% Airbnb Rental Income: $3106 Traditional Rental Income: $1760 Airbnb ROI: 1.38% Traditional ROI: 0.5%
5642-44 S Ashland Ave Chicago, IL 5642-44 S Ashland Ave, Chicago, IL 60636 \| Other	N/A beds \| N/A baths \| N/A	$90,000	Airbnb cash on cash: 9.73% Traditional cash on cash: 8.85% Airbnb Rental Income: $1701 Traditional Rental Income: $1151 Airbnb ROI: 9.73% Traditional ROI: 8.85%
5029 W Altgeld St Chicago, IL INCREDIBLE OPPORTUNITY TO OWN THIS REMODELED ALL BRICK 2-FLAT IN RAPIDLY APPRECIATING BELM...	6 beds \| 3 baths \| N/A	$669,500	Airbnb cash on cash: 1.69% Traditional cash on cash: 1.55% Airbnb Rental Income: $3130 Traditional Rental Income: $2333 Airbnb ROI: 1.69% Traditional ROI: 1.55%
11345 S Ada Street Chicago, IL Discover your new home at 11345 S Ada St, Chicago! This charming 2-bedroom townhouse offer...	2 beds \| 1 baths \| 500 sq.ft.	$139,000	Airbnb cash on cash: 7.8% Traditional cash on cash: 5.26% Airbnb Rental Income: $1938 Traditional Rental Income: $1087 Airbnb ROI: 7.8% Traditional ROI: 5.26%
3800 W 55th St Chicago, IL 3800 W 55th St, Chicago, IL 60632 \| Other	N/A beds \| N/A baths \| N/A	$360,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 0.04% Airbnb Rental Income: $1738 Traditional Rental Income: $1202 Airbnb ROI: 0.21% Traditional ROI: 0.04%
4916 W Hutchinson St Chicago, IL Multiple offers received. Highest and best due by Saturday, May 16, at 5 pm. This beau...	8 beds \| 3 baths \| N/A	$680,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 2.02% Airbnb Rental Income: $4280 Traditional Rental Income: $3050 Airbnb ROI: 2.54% Traditional ROI: 2.02%
1132 N Waller Ave Chicago, IL Attention Investors/Rehabbers.Great Opportunity.in thriving Austin Neighborhood. Interior ...	5 beds \| 3 baths \| 1,800 sq.ft.	$449,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 1.71% Airbnb Rental Income: $3099 Traditional Rental Income: $1539 Airbnb ROI: 3.74% Traditional ROI: 1.71%
4557 S Francisco Ave Chicago, IL 4557 S Francisco Ave, Chicago, IL 60632 \| Other	N/A beds \| N/A baths \| N/A	$114,900	Airbnb cash on cash: 7.03% Traditional cash on cash: 5.9% Airbnb Rental Income: $1701 Traditional Rental Income: $1103 Airbnb ROI: 7.03% Traditional ROI: 5.9%
2437 N Central Ave Chicago, IL Incredible opportunity to own this well-maintained 2-flat on an oversized lot, offering ex...	8 beds \| 4 baths \| N/A	$599,900	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.87% Airbnb Rental Income: $3852 Traditional Rental Income: $2673 Airbnb ROI: 3.49% Traditional ROI: 2.87%
5068 W Congress Pkwy Chicago, IL 5068 W Congress Pkwy, Chicago, IL 60644 \| Single Family Residential	5 beds \| 2 baths \| 2,500 sq.ft.	$379,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 1.14% Airbnb Rental Income: $3599 Traditional Rental Income: $1652 Airbnb ROI: 4.4% Traditional ROI: 1.14%
4119 W Adams St Chicago, IL Property is being sold in an as-is condition, and the condition is unknown and may include...	8 beds \| 2 baths \| N/A	$250,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 3.22% Airbnb Rental Income: $2589 Traditional Rental Income: $1618 Airbnb ROI: 4.71% Traditional ROI: 3.22%
6740 S Laflin St Chicago, IL 6740 S Laflin St, Chicago, IL 60636 \| Single Family Residential	7 beds \| 2 baths \| 1,284 sq.ft.	$340,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 0.74% Airbnb Rental Income: $1903 Traditional Rental Income: $1364 Airbnb ROI: 0.84% Traditional ROI: 0.74%
5033 W Washington Blvd Chicago, IL Welcome to this fully renovated LEGAL 3-unit building on the Washington Blvd treeline. Thi...	10 beds \| 3 baths \| N/A	$600,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 2.44% Airbnb Rental Income: $3599 Traditional Rental Income: $2420 Airbnb ROI: 3.14% Traditional ROI: 2.44%
4904 W Byron Street Chicago, IL This Two Flat style detached family home offers 6 bedrooms and 3 bathrooms with approximat...	6 beds \| 3 baths \| N/A	$367,350	Airbnb cash on cash: 6.61% Traditional cash on cash: 5.56% Airbnb Rental Income: $4280 Traditional Rental Income: $3016 Airbnb ROI: 6.61% Traditional ROI: 5.56%
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: $1342 Traditional Rental Income: $879 Airbnb ROI: 0.87% Traditional ROI: 0.63%
5020 W Fletcher St Chicago, IL Incredibly rare opportunity to add instant sweat equity to this classic brick bungalow in ...	4 beds \| 3 baths \| 2,469 sq.ft.	$579,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 1.27% Airbnb Rental Income: $2294 Traditional Rental Income: $1635 Airbnb ROI: 1.43% Traditional ROI: 1.27%
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: 4.41% Traditional cash on cash: 0.46% Airbnb Rental Income: $2335 Traditional Rental Income: $897 Airbnb ROI: 4.41% Traditional ROI: 0.46%
8 W Monroe St #1800 Chicago, IL Sunny 2 bedrooms with 1 1/2 bathrooms condo unit located in Downtown Theatre District. Hig...	2 beds \| 1 baths \| 980 sq.ft.	$259,000	Airbnb cash on cash: 0.09% Traditional cash on cash: -1.08% Airbnb Rental Income: $2488 Traditional Rental Income: $1598 Airbnb ROI: 0.09% Traditional ROI: -1.08%

Vacation Rentals in Chicago

There are 94 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $379,900 and the average price per square foot is $212. The cash on cash return on vacation rentals in Chicago is -1.00%. The average monthly short term rental income in Chicago is $1,374.

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

There are 94 Airbnb properties available for sale in Chicago.

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

In May 2026, the average Airbnb occupancy rate in Chicago is 25%.

In 2026, the highest Airbnb occupancy rate in Chicago are in Hanson Park (24%), South Shore (21%) and South Shore (30%).

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

3950 N LAKE SHORE Drive #801

Chicago, IL

2 beds | 1 baths | N/A

$268,700

Airbnb cash on cash: 0.07%

Traditional cash on cash: -0.29%

Airbnb Rental Income: $2029

Traditional Rental Income: $1410

Airbnb ROI: 0.07%

Traditional ROI: -0.29%

32 S Menard Avenue

Chicago, IL

21 beds | 10 baths | N/A

$1,100,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 0.68%

Airbnb Rental Income: $3599

Traditional Rental Income: $2469

Airbnb ROI: 1.01%

Traditional ROI: 0.68%

6030 N Sheridan Rd #301

Chicago, IL

1 beds | 1 baths | N/A

$168,000

Airbnb cash on cash: 0.95%

Traditional cash on cash: 0.08%

Airbnb Rental Income: $1624

Traditional Rental Income: $1026

Airbnb ROI: 0.95%

Traditional ROI: 0.08%

320 N Menard Avenue

Chicago, IL

5 beds | 3 baths | 2,650 sq.ft.

$449,999

Airbnb cash on cash: 5.21%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $3599

Traditional Rental Income: $2184

Airbnb ROI: 5.21%

Traditional ROI: 3.72%

4224 N Kimball Ave

Chicago, IL

5 beds | 3 baths | N/A

$620,000

Airbnb cash on cash: 2.44%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $4292

Traditional Rental Income: $2661

Airbnb ROI: 2.44%

Traditional ROI: 1.18%

1908 S Sawyer Ave

Chicago, IL

6 beds | 3 baths | 1,800 sq.ft.

$339,000

Airbnb cash on cash: 5.47%

Traditional cash on cash: 3.12%

Airbnb Rental Income: $3106

Traditional Rental Income: $1652

Airbnb ROI: 5.47%

Traditional ROI: 3.12%

4825 S Central Ave

Chicago, IL

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

$249,000

Airbnb cash on cash: 1.72%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $1738

Traditional Rental Income: $1202

Airbnb ROI: 1.72%

Traditional ROI: 1.48%

5523 W Huron Street

Chicago, IL

5 beds | 2 baths | N/A

$400,000

Airbnb cash on cash: 5%

Traditional cash on cash: 2.62%

Airbnb Rental Income: $3599

Traditional Rental Income: $1916

Airbnb ROI: 5%