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 Ave Chicago, IL This well-maintained vintage 4-flat (6 full units, 2 non-conforming), built in 1918, has b...	21 beds \| 8 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 Ave 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%
5919 N Bernard St Chicago, IL Beautifully updated and expansive 5-bedroom w/ and option to make a 6th bedroom, 3-bath re...	5 beds \| 3 baths \| 2,515 sq.ft.	$645,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.73% Airbnb Rental Income: $5206 Traditional Rental Income: $3180 Airbnb ROI: 4.34% Traditional ROI: 2.73%
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%
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 St 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 St 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%
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 St 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%
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%
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%
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%
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%
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%
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%
844 N Laramie Ave Chicago, IL VERY LARGE HOUSE IN GOOD CONDITION , WITH 3.5 BATHS , HUGE MASTER BEDROOMS WITH SKYLIGHTS ...	5 beds \| 4 baths \| 1,500 sq.ft.	$384,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 5.74% Airbnb Rental Income: $3599 Traditional Rental Income: $2701 Airbnb ROI: 6.05% Traditional ROI: 5.74%
2911 W 25th St Chicago, IL Property was originally 4 Flat but has been gutted to the studs. Next door Lot at 2909 W. ...	N/A beds \| N/A baths \| N/A	$289,000	Airbnb cash on cash: 0.63% Traditional cash on cash: -0.1% Airbnb Rental Income: $1317 Traditional Rental Income: $712 Airbnb ROI: 0.63% Traditional ROI: -0.1%
224 N Lockwood Ave Chicago, IL Excellent opportunity for owner occupied or investment! This well-maintained 2-flat buildi...	6 beds \| 2 baths \| N/A	$390,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.28% Airbnb Rental Income: $3599 Traditional Rental Income: $2417 Airbnb ROI: 5.36% Traditional ROI: 4.28%
8051 S Escanaba Ave Chicago, IL 8051 S Escanaba Ave, Chicago, IL 60617 \| Single Family Residential	5 beds \| 2 baths \| 1,040 sq.ft.	$284,900	Airbnb cash on cash: 5.4% Traditional cash on cash: 2.03% Airbnb Rental Income: $3122 Traditional Rental Income: $1506 Airbnb ROI: 5.4% Traditional ROI: 2.03%
1131 S Sacramento Boulevard Chicago, IL Investor Alert: Secure a high-potential asset on the historic South Sacramento Blvd. This ...	42 beds \| 21 baths \| N/A	$1,299,999	Airbnb cash on cash: 0.02% Traditional cash on cash: -1.12% Airbnb Rental Income: $3106 Traditional Rental Income: $1022 Airbnb ROI: 0.02% Traditional ROI: -1.12%
8819 S Carpenter St Chicago, IL Great opportunity in Auburn Gresham. This 2-bedroom, 1.5-bath home offers strong potential...	5 beds \| 2 baths \| 1,952 sq.ft.	$359,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 2.04% Airbnb Rental Income: $1959 Traditional Rental Income: $1259 Airbnb ROI: 2.58% Traditional ROI: 2.04%
7951 S Muskegon Avenue Chicago, IL 17-unit building ideal for value-add investors looking to build sweat equity. Can be combi...	17 beds \| 17 baths \| N/A	$739,900	Airbnb cash on cash: 0.02% Traditional cash on cash: -0.54% Airbnb Rental Income: $3122 Traditional Rental Income: $2027 Airbnb ROI: 0.02% Traditional ROI: -0.54%
7959 S Muskegon Avenue Chicago, IL 16 unit building ideal for value-add investors looking to build sweat equity. Can be combi...	16 beds \| 16 baths \| N/A	$759,900	Airbnb cash on cash: 0.26% Traditional cash on cash: -0.25% Airbnb Rental Income: $3122 Traditional Rental Income: $2051 Airbnb ROI: 0.26% Traditional ROI: -0.25%
855 N Lockwood Avenue Chicago, IL Good Building with good income, always been easy to rent, located in very quiet block, all...	12 beds \| 10 baths \| N/A	$948,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 0.02% Airbnb Rental Income: $3599 Traditional Rental Income: $2218 Airbnb ROI: 0.69% Traditional ROI: 0.02%
6823-25 S RIDGELAND Avenue Chicago, IL A recently improved 6-unit multifamily asset offering a blend of modern updates and remain...	11 beds \| 9 baths \| N/A	$650,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.12% Airbnb Rental Income: $3122 Traditional Rental Income: $1948 Airbnb ROI: 1.89% Traditional ROI: 1.12%

Vacation Rentals in Chicago

There are 88 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $409,500 and the average price per square foot is $232. The cash on cash return on vacation rentals in Chicago is -1.00%. The average monthly short term rental income in Chicago is $1,421.

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

There are 88 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 Ave

Chicago, IL

21 beds | 8 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 Ave

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%

5919 N Bernard St

Chicago, IL

5 beds | 3 baths | 2,515 sq.ft.

$645,000

Airbnb cash on cash: 4.34%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $5206

Traditional Rental Income: $3180

Airbnb ROI: 4.34%

Traditional ROI: 2.73%

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%

Traditional ROI: 2.62%

2038 E 73rd St

Chicago, IL

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 St

Chicago, IL

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%