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
6431 N Paulina St Chicago, IL 6431 N Paulina St, Chicago, IL 60626 \| Single Family Residential	5 beds \| 3 baths \| 4,641 sq.ft.	$925,000	Airbnb cash on cash: 0.27% Traditional cash on cash: -0.16% Airbnb Rental Income: $3985 Traditional Rental Income: $2756 Airbnb ROI: 0.27% Traditional ROI: -0.16%
1354 W Estes Ave #1N Chicago, IL 1354 W Estes Ave #1N, Chicago, IL 60626 \| Condo/Coop	1 beds \| 1 baths \| 750 sq.ft.	$174,500	Airbnb cash on cash: 2.73% Traditional cash on cash: 1.63% Airbnb Rental Income: $1872 Traditional Rental Income: $1188 Airbnb ROI: 2.73% Traditional ROI: 1.63%
4950 N Marine Dr #1009 Chicago, IL 4950 N Marine Dr #1009, Chicago, IL 60640 \| Condo/Coop	1 beds \| 1 baths \| 700 sq.ft.	$179,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 0.89% Airbnb Rental Income: $1997 Traditional Rental Income: $1474 Airbnb ROI: 0.9% Traditional ROI: 0.89%
7627 S Ridgeland Ave Chicago, IL 7627 S Ridgeland Ave, Chicago, IL 60649 \| Single Family Residential	6 beds \| 2 baths \| 1,500 sq.ft.	$339,999	Airbnb cash on cash: 3.16% Traditional cash on cash: 0.97% Airbnb Rental Income: $2793 Traditional Rental Income: $1440 Airbnb ROI: 3.16% Traditional ROI: 0.97%
3150 N Sheffield Ave #612 Chicago, IL 3150 N Sheffield Ave #612, Chicago, IL 60657 \| Condo/Coop	N/A beds \| 1 baths \| 550 sq.ft.	$195,000	Airbnb cash on cash: 7.36% Traditional cash on cash: -0.14% Airbnb Rental Income: $3037 Traditional Rental Income: $954 Airbnb ROI: 7.36% Traditional ROI: -0.14%
1958 W Norwood St #4B Chicago, IL 1958 W Norwood St #4B, Chicago, IL 60660 \| Condo/Coop	2 beds \| 1 baths \| 950 sq.ft.	$163,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 3.26% Airbnb Rental Income: $2113 Traditional Rental Income: $1524 Airbnb ROI: 3.57% Traditional ROI: 3.26%
1630 W Columbia Ave #GN Chicago, IL 1630 W Columbia Ave #GN, Chicago, IL 60626 \| Condo/Coop	2 beds \| 1 baths \| N/A	$235,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 0.29% Airbnb Rental Income: $2105 Traditional Rental Income: $1200 Airbnb ROI: 1.93% Traditional ROI: 0.29%
531 W 61st Pl Chicago, IL 531 W 61st Pl, Chicago, IL 60621 \| Multi Family	5 beds \| 2 baths \| N/A	$199,000	Airbnb cash on cash: 7.64% Traditional cash on cash: 7.27% Airbnb Rental Income: $2802 Traditional Rental Income: $2076 Airbnb ROI: 7.64% Traditional ROI: 7.27%
2245 W Farwell Ave #3B Chicago, IL 2245 W Farwell Ave #3B, Chicago, IL 60645 \| Condo/Coop	1 beds \| 1 baths \| 700 sq.ft.	$145,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.46% Airbnb Rental Income: $1779 Traditional Rental Income: $1236 Airbnb ROI: 2.87% Traditional ROI: 2.46%
5612 S Troy St Chicago, IL 5612 S Troy St, Chicago, IL 60629 \| Single Family Residential	2 beds \| 1 baths \| 936 sq.ft.	$209,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.8% Airbnb Rental Income: $1887 Traditional Rental Income: $1288 Airbnb ROI: 3.29% Traditional ROI: 2.8%
1621 W Rascher Ave #G Chicago, IL 1621 W Rascher Ave #G, Chicago, IL 60640 \| Condo/Coop	3 beds \| 2 baths \| N/A	$389,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 0.88% Airbnb Rental Income: $3268 Traditional Rental Income: $1804 Airbnb ROI: 2.88% Traditional ROI: 0.88%
5048 N Wolcott St #2N Chicago, IL 5048 N Wolcott St #2N, Chicago, IL 60640 \| Condo/Coop	2 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 0.13% Traditional cash on cash: -0.61% Airbnb Rental Income: $2588 Traditional Rental Income: $1625 Airbnb ROI: 0.13% Traditional ROI: -0.61%
8019 S Marshfield Ave Chicago, IL 8019 S Marshfield Ave, Chicago, IL 60620 \| Multi Family	4 beds \| 2 baths \| N/A	$300,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 3.24% Airbnb Rental Income: $2796 Traditional Rental Income: $1925 Airbnb ROI: 4.01% Traditional ROI: 3.24%
4856 N Paulina St #3W Chicago, IL	1 beds \| 1 baths \| N/A	$175,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 0.72% Airbnb Rental Income: $2039 Traditional Rental Income: $1036 Airbnb ROI: 3.56% Traditional ROI: 0.72%
7725 S Wood St Chicago, IL 7725 S Wood St, Chicago, IL 60620 \| Single Family Residential	5 beds \| 2 baths \| 1,168 sq.ft.	$329,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 1.99% Airbnb Rental Income: $2331 Traditional Rental Income: $1710 Airbnb ROI: 2.13% Traditional ROI: 1.99%
6310 N Troy St Chicago, IL 6310 N Troy St, Chicago, IL 60659 \| Other	N/A beds \| N/A baths \| N/A	$229,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 0.36% Airbnb Rental Income: $1713 Traditional Rental Income: $872 Airbnb ROI: 2.06% Traditional ROI: 0.36%
3222 W Berteau Ave #2 Chicago, IL 3222 W Berteau Ave #2, Chicago, IL 60618 \| Condo/Coop	2 beds \| 1 baths \| N/A	$240,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 0.74% Airbnb Rental Income: $1935 Traditional Rental Income: $1290 Airbnb ROI: 1.33% Traditional ROI: 0.74%
1703 W Wallen Ave #3C Chicago, IL 1703 W Wallen Ave #3C, Chicago, IL 60626 \| Condo/Coop	2 beds \| 1 baths \| 625 sq.ft.	$165,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 2.23% Airbnb Rental Income: $2105 Traditional Rental Income: $1329 Airbnb ROI: 3.73% Traditional ROI: 2.23%
4745 N Ravenswood Ave #113 Chicago, IL 4745 N Ravenswood Ave #113, Chicago, IL 60640 \| Condo/Coop	1 beds \| 1 baths \| 870 sq.ft.	$289,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.25% Airbnb Rental Income: $2039 Traditional Rental Income: $1412 Airbnb ROI: 0.61% Traditional ROI: 0.25%
1255 N Sandburg Ter #503 Chicago, IL 1255 N Sandburg Ter #503, Chicago, IL 60610 \| Condo/Coop	2 beds \| 1 baths \| N/A	$389,000	Airbnb cash on cash: 0.19% Traditional cash on cash: -1.43% Airbnb Rental Income: $2569 Traditional Rental Income: $1364 Airbnb ROI: 0.19% Traditional ROI: -1.43%
4016 N Albany Ave #3 Chicago, IL	2 beds \| 1 baths \| N/A	$260,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 0.56% Airbnb Rental Income: $1935 Traditional Rental Income: $1309 Airbnb ROI: 1.03% Traditional ROI: 0.56%
1811 W Superior St Chicago, IL 1811 W Superior St, Chicago, IL 60622 \| Single Family Residential	5 beds \| 2 baths \| 1,880 sq.ft.	$675,000	Airbnb cash on cash: 1% Traditional cash on cash: 0.44% Airbnb Rental Income: $3553 Traditional Rental Income: $2421 Airbnb ROI: 1% Traditional ROI: 0.44%
4250 N Marine Dr #2803 Chicago, IL 4250 N Marine Dr #2803, Chicago, IL 60613 \| Condo/Coop	1 beds \| 1 baths \| 525 sq.ft.	$165,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 1.21% Airbnb Rental Income: $2005 Traditional Rental Income: $1284 Airbnb ROI: 2.46% Traditional ROI: 1.21%
2045 N Larrabee St #7106 Chicago, IL 2045 N Larrabee St #7106, Chicago, IL 60614 \| Condo/Coop	2 beds \| 1 baths \| N/A	$399,000	Airbnb cash on cash: 0.12% Traditional cash on cash: -1.2% Airbnb Rental Income: $2390 Traditional Rental Income: $1309 Airbnb ROI: 0.12% Traditional ROI: -1.2%
600 S Dearborn St #1007 Chicago, IL 600 S Dearborn St #1007, Chicago, IL 60605 \| Condo/Coop	2 beds \| 1 baths \| N/A	$299,000	Airbnb cash on cash: 0.37% Traditional cash on cash: -0.81% Airbnb Rental Income: $2214 Traditional Rental Income: $1326 Airbnb ROI: 0.37% Traditional ROI: -0.81%
5616 N Kenmore Ave #5A Chicago, IL 5616 N Kenmore Ave #5A, Chicago, IL 60660 \| Condo/Coop	1 beds \| 1 baths \| N/A	$225,000	Airbnb cash on cash: 1.43% Traditional cash on cash: -0.42% Airbnb Rental Income: $1955 Traditional Rental Income: $1046 Airbnb ROI: 1.43% Traditional ROI: -0.42%
5742 W Byron St Chicago, IL 5742 W Byron St, Chicago, IL 60634 \| Single Family Residential	5 beds \| 2 baths \| 1,219 sq.ft.	$410,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 1.98% Airbnb Rental Income: $3105 Traditional Rental Income: $2102 Airbnb ROI: 2.75% Traditional ROI: 1.98%
1456 N Artesian Ave #3R Chicago, IL 1456 N Artesian Ave #3R, Chicago, IL 60622 \| Condo/Coop	2 beds \| 1 baths \| N/A	$325,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 0.08% Airbnb Rental Income: $2092 Traditional Rental Income: $1306 Airbnb ROI: 0.89% Traditional ROI: 0.08%
2141 W Summerdale Ave Chicago, IL 2141 W Summerdale Ave, Chicago, IL 60625 \| Single Family Residential	3 beds \| 1 baths \| 731 sq.ft.	$400,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 0.27% Airbnb Rental Income: $2187 Traditional Rental Income: $1413 Airbnb ROI: 0.86% Traditional ROI: 0.27%

Vacation Rentals in Chicago

There are 30 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $378,000 and the average price per square foot is $218. The cash on cash return on vacation rentals in Chicago is N/A%. The average monthly short term rental income in Chicago is $2,005.

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

There are 30 Airbnb properties available for sale in Chicago.

In 2025, the best neighborhood to buy short term rental property is Eden Green.

In September 2025, the average Airbnb occupancy rate in Chicago is 33%.

In 2025, the highest Airbnb occupancy rate in Chicago are in Eden Green (28%), Englewood (31%) and Englewood (27%).

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

6431 N Paulina St

Chicago, IL

5 beds | 3 baths | 4,641 sq.ft.

$925,000

Airbnb cash on cash: 0.27%

Traditional cash on cash: -0.16%

Airbnb Rental Income: $3985

Traditional Rental Income: $2756

Airbnb ROI: 0.27%

Traditional ROI: -0.16%

1354 W Estes Ave #1N

Chicago, IL

1 beds | 1 baths | 750 sq.ft.

$174,500

Airbnb cash on cash: 2.73%

Traditional cash on cash: 1.63%

Airbnb Rental Income: $1872

Traditional Rental Income: $1188

Airbnb ROI: 2.73%

Traditional ROI: 1.63%

4950 N Marine Dr #1009

Chicago, IL

1 beds | 1 baths | 700 sq.ft.

$179,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: 0.89%

Airbnb Rental Income: $1997

Traditional Rental Income: $1474

Airbnb ROI: 0.9%

Traditional ROI: 0.89%

7627 S Ridgeland Ave

Chicago, IL

6 beds | 2 baths | 1,500 sq.ft.

$339,999

Airbnb cash on cash: 3.16%

Traditional cash on cash: 0.97%

Airbnb Rental Income: $2793

Traditional Rental Income: $1440

Airbnb ROI: 3.16%

Traditional ROI: 0.97%

3150 N Sheffield Ave #612

Chicago, IL

N/A beds | 1 baths | 550 sq.ft.

$195,000

Airbnb cash on cash: 7.36%

Traditional cash on cash: -0.14%

Airbnb Rental Income: $3037

Traditional Rental Income: $954

Airbnb ROI: 7.36%

Traditional ROI: -0.14%

1958 W Norwood St #4B

Chicago, IL

2 beds | 1 baths | 950 sq.ft.

$163,000

Airbnb cash on cash: 3.57%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $2113

Traditional Rental Income: $1524

Airbnb ROI: 3.57%

Traditional ROI: 3.26%

1630 W Columbia Ave #GN

Chicago, IL

2 beds | 1 baths | N/A

$235,000

Airbnb cash on cash: 1.93%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $2105

Traditional Rental Income: $1200

Airbnb ROI: 1.93%

Traditional ROI: 0.29%

531 W 61st Pl

Chicago, IL

5 beds | 2 baths | N/A

$199,000

Airbnb cash on cash: 7.64%

Traditional cash on cash: 7.27%

Airbnb Rental Income: $2802

Traditional Rental Income: $2076

Airbnb ROI: 7.64%