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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3906 W Montrose Ave Chicago, IL 3906 W Montrose Ave, Chicago, IL 60618 \| Single Family Residential	5 beds \| 2 baths \| 1,120 sq.ft.	$509,999	Airbnb cash on cash: 4.54% Traditional cash on cash: 1.25% Airbnb Rental Income: $4796 Traditional Rental Income: $2240 Airbnb ROI: 4.54% Traditional ROI: 1.25%
5602 N Fairview Ave Chicago, IL 5602 N Fairview Ave, Chicago, IL 60631 \| Other	2 beds \| N/A baths \| 0 sq.ft.	$469,000	Airbnb cash on cash: 1.43% Traditional cash on cash: -1.02% Airbnb Rental Income: $2801 Traditional Rental Income: $1070 Airbnb ROI: 1.43% Traditional ROI: -1.02%
6562 N Damen Avenue Chicago, IL Welcome to this two-story, 3-bedroom 2-bath home with a finished basement and 2-car garage...	3 beds \| 2 baths \| 1,769 sq.ft.	$470,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 2.1% Airbnb Rental Income: $2899 Traditional Rental Income: $2182 Airbnb ROI: 2.2% Traditional ROI: 2.1%
4420 S Berkeley Ave Chicago, IL 4420 S Berkeley Ave, Chicago, IL 60653 \| Single Family Residential	4 beds \| 3 baths \| 3,300 sq.ft.	$659,500	Airbnb cash on cash: 1.11% Traditional cash on cash: 0.69% Airbnb Rental Income: $3559 Traditional Rental Income: $2520 Airbnb ROI: 1.11% Traditional ROI: 0.69%
801 S Plymouth Court #906 Chicago, IL Bright and airy one-bedroom in the heart of Printers Row, featuring an open-concept layout...	1 beds \| 1 baths \| N/A	$175,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 0.86% Airbnb Rental Income: $2199 Traditional Rental Income: $1525 Airbnb ROI: 1.57% Traditional ROI: 0.86%
3849 N Nora Ave Chicago, IL	5 beds \| 3 baths \| 1,638 sq.ft.	$465,000	Airbnb cash on cash: 5.78% Traditional cash on cash: 2.88% Airbnb Rental Income: $5055 Traditional Rental Income: $2762 Airbnb ROI: 5.78% Traditional ROI: 2.88%
367 W Locust Street #305 Chicago, IL Experience elevated city living in this exceptional 3-bedroom, 3-full-bath contemporary re...	3 beds \| 3 baths \| 1,852 sq.ft.	$825,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 0.69% Airbnb Rental Income: $4766 Traditional Rental Income: $3392 Airbnb ROI: 1.2% Traditional ROI: 0.69%
20 N State Street #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	$259,000	Airbnb cash on cash: 1.87% Traditional cash on cash: -0.85% Airbnb Rental Income: $2489 Traditional Rental Income: $1222 Airbnb ROI: 1.87% Traditional ROI: -0.85%
310 S Michigan Ave #1700 Chicago, IL 310 S Michigan Ave #1700, Chicago, IL 60604 \| Condo/Coop	3 beds \| 3 baths \| 1,904 sq.ft.	$799,000	Airbnb cash on cash: 0.66% Traditional cash on cash: -2.56% Airbnb Rental Income: $6720 Traditional Rental Income: $3011 Airbnb ROI: 0.66% Traditional ROI: -2.56%
4733 N Kenmore Avenue #4 Chicago, IL Charming Garden Unit in the Heart of Uptown - Your Own Private Entrance! Welcome home to t...	2 beds \| 1 baths \| 1,100 sq.ft.	$264,900	Airbnb cash on cash: 4.23% Traditional cash on cash: 3.22% Airbnb Rental Income: $2555 Traditional Rental Income: $1688 Airbnb ROI: 4.23% Traditional ROI: 3.22%
7017 S Hermitage Avenue Chicago, IL Beautifully updated Chicago bungalow offering 7 bedrooms and 3 bathrooms on a double lot. ...	5 beds \| 3 baths \| 1,148 sq.ft.	$348,000	Airbnb cash on cash: 5.8% Traditional cash on cash: 4.39% Airbnb Rental Income: $3134 Traditional Rental Income: $1962 Airbnb ROI: 5.8% Traditional ROI: 4.39%
4628 S Langley Avenue Chicago, IL Stunning and modern 5-bedroom, 3.5-bath home with over 3,200 sq ft of finished living spac...	5 beds \| 4 baths \| 2,386 sq.ft.	$689,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.6% Airbnb Rental Income: $2646 Traditional Rental Income: $1908 Airbnb ROI: 0.77% Traditional ROI: 0.6%
780 S Federal St #906 Chicago, IL 780 S Federal St #906, Chicago, IL 60605 \| Condo/Coop	1 beds \| 1 baths \| N/A	$200,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 0.68% Airbnb Rental Income: $2199 Traditional Rental Income: $1505 Airbnb ROI: 1.41% Traditional ROI: 0.68%
5551 S Kimbark Avenue #18 Chicago, IL Top-floor one-bedroom, one-bath condo with views of a landscaped courtyard featuring matur...	1 beds \| 1 baths \| 980 sq.ft.	$174,900	Airbnb cash on cash: 1.09% Traditional cash on cash: 1.03% Airbnb Rental Income: $1791 Traditional Rental Income: $1294 Airbnb ROI: 1.09% Traditional ROI: 1.03%
3232 N Oleander Avenue Chicago, IL Don't let the exterior fool you. This home offers far more living space than you might exp...	3 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 3.08% Airbnb Rental Income: $3095 Traditional Rental Income: $2327 Airbnb ROI: 3.22% Traditional ROI: 3.08%
20 E Goethe Street #206 Chicago, IL Vintage Gold Coast charm meets city convenience in this inviting 1 bedroom, 1 bath condo. ...	1 beds \| 1 baths \| N/A	$175,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 2.18% Airbnb Rental Income: $2039 Traditional Rental Income: $1401 Airbnb ROI: 2.83% Traditional ROI: 2.18%
40 E 9th Street #1809 Chicago, IL Welcome to an exceptional high-floor residence where sophisticated style, elevated views, ...	2 beds \| 2 baths \| 1,350 sq.ft.	$320,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 0.7% Airbnb Rental Income: $3456 Traditional Rental Income: $2353 Airbnb ROI: 1.82% Traditional ROI: 0.7%
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: 1.57% Traditional cash on cash: -0.55% Airbnb Rental Income: $2500 Traditional Rental Income: $1101 Airbnb ROI: 1.57% Traditional ROI: -0.55%
2966 W Nelson St Chicago, IL 2966 W Nelson St, Chicago, IL 60618 \| Single Family Residential	4 beds \| 3 baths \| 1,741 sq.ft.	$699,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 0.22% Airbnb Rental Income: $3122 Traditional Rental Income: $2359 Airbnb ROI: 0.3% Traditional ROI: 0.22%
950 N Michigan Ave #2305 Chicago, IL Welcome to one of Chicago's premier addresses - One Mag Mile - where full service and soph...	3 beds \| 2 baths \| 1,860 sq.ft.	$939,000	Airbnb cash on cash: 0.76% Traditional cash on cash: -0.92% Airbnb Rental Income: $6014 Traditional Rental Income: $3353 Airbnb ROI: 0.76% Traditional ROI: -0.92%
260 E Chestnut St #1511 Chicago, IL 260 E Chestnut St #1511, Chicago, IL 60611 \| Condo/Coop	1 beds \| 1 baths \| 575 sq.ft.	$249,900	Airbnb cash on cash: 0.8% Traditional cash on cash: -0.04% Airbnb Rental Income: $2220 Traditional Rental Income: $1461 Airbnb ROI: 0.8% Traditional ROI: -0.04%
1359 E 57th Street #1 Chicago, IL Historic 3-bedroom, 2-bath residence in the iconic Kenwood Green community! This beautiful...	3 beds \| 2 baths \| N/A	$385,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 0.66% Airbnb Rental Income: $2538 Traditional Rental Income: $1631 Airbnb ROI: 1.47% Traditional ROI: 0.66%
4914 W Congress Parkway Chicago, IL Incredible opportunity to finish out a classic Austin bungalow! Newly rehabbed, drop dead ...	4 beds \| 2 baths \| 968 sq.ft.	$279,900	Airbnb cash on cash: 5.65% Traditional cash on cash: 5.09% Airbnb Rental Income: $2814 Traditional Rental Income: $2010 Airbnb ROI: 5.65% Traditional ROI: 5.09%
175 E Delaware Place #6611 Chicago, IL Some addresses simply carry weight. The Residences at 175 E Delaware Place is one of them,...	3 beds \| 2 baths \| 1,707 sq.ft.	$774,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 0.98% Airbnb Rental Income: $5688 Traditional Rental Income: $4393 Airbnb ROI: 1.2% Traditional ROI: 0.98%
2317 S Winchester Avenue Chicago, IL INVESTOR SPECIAL! GREAT OPPORTUNITY WITH ENDLESS POTENTIAL! Calling all investors, reh...	4 beds \| 2 baths \| 2,400 sq.ft.	$299,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 5.62% Airbnb Rental Income: $3566 Traditional Rental Income: $2416 Airbnb ROI: 6.92% Traditional ROI: 5.62%
7337 S South Shore Dr #326 Chicago, IL 7337 S South Shore Dr #326, Chicago, IL 60649 \| Condo/Coop	1 beds \| 1 baths \| 800 sq.ft.	$69,999	Airbnb cash on cash: 0.6% Traditional cash on cash: -0.02% Airbnb Rental Income: $1446 Traditional Rental Income: $973 Airbnb ROI: 0.6% Traditional ROI: -0.02%
125 S Jefferson Street #2407 Chicago, IL Experience city living in this elevated 24th-Floor Corner Residence at Park Alexandria in ...	2 beds \| 2 baths \| 1,370 sq.ft.	$449,000	Airbnb cash on cash: 0.33% Traditional cash on cash: -1.17% Airbnb Rental Income: $3294 Traditional Rental Income: $1924 Airbnb ROI: 0.33% Traditional ROI: -1.17%
4914 W Van Buren Street Chicago, IL	5 beds \| 3 baths \| N/A	$434,900	Airbnb cash on cash: 9.83% Traditional cash on cash: 3.55% Airbnb Rental Income: $6189 Traditional Rental Income: $2410 Airbnb ROI: 9.83% Traditional ROI: 3.55%
420 W Ontario St #410 Chicago, IL Rarely available Penthouse Timber Lofts in Heart of River North! Move-in Condition. Two B...	2 beds \| 2 baths \| 1,100 sq.ft.	$485,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 0.69% Airbnb Rental Income: $3728 Traditional Rental Income: $2117 Airbnb ROI: 2.45% Traditional ROI: 0.69%
1540 N Lasalle Dr #201 Chicago, IL View our virtual 3D tour! Don't miss this large Old Town/Gold Coast corner unit with plent...	1 beds \| 1 baths \| 800 sq.ft.	$319,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 0.66% Airbnb Rental Income: $1983 Traditional Rental Income: $1448 Airbnb ROI: 0.71% Traditional ROI: 0.66%
1239 N State Parkway #2 Chicago, IL A very unique opportunity to own a full-floor residence in an intimate 3-unit boutique bui...	3 beds \| 3 baths \| 2,470 sq.ft.	$1,145,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 0.85% Airbnb Rental Income: $6014 Traditional Rental Income: $3861 Airbnb ROI: 1.76% Traditional ROI: 0.85%
201 E Chestnut St #14A Chicago, IL BEAUTIFUL CORNER UNIT WITH GREAT NATURAL LIGHT AND A LARGE PRIVATE BALCONY. HAND SCRAPPED ...	2 beds \| 2 baths \| 1,600 sq.ft.	$445,000	Airbnb cash on cash: 0.95% Traditional cash on cash: -0.78% Airbnb Rental Income: $3773 Traditional Rental Income: $2233 Airbnb ROI: 0.95% Traditional ROI: -0.78%
600 N Fairbanks Ct #3105 Chicago, IL Impeccable high floor corner unit at the iconic award winning Helmut Jahn designed 600 Fai...	2 beds \| 2 baths \| 1,290 sq.ft.	$675,000	Airbnb cash on cash: 0.13% Traditional cash on cash: -1.17% Airbnb Rental Income: $3742 Traditional Rental Income: $2107 Airbnb ROI: 0.13% Traditional ROI: -1.17%
934 E 55th St Chicago, IL Need I say more, Location, Location, Location...... Lovely townhome located across the st...	3 beds \| 2 baths \| 1,543 sq.ft.	$598,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 1.05% Airbnb Rental Income: $2538 Traditional Rental Income: $1851 Airbnb ROI: 1.18% Traditional ROI: 1.05%
6331 N Fairfield Ave #303 Chicago, IL Sunny Top Floor Oversized 3 Bedroom, 1.5 Bath, Corner Unit Offers Separate Dining Area and...	3 beds \| 1 baths \| 1,200 sq.ft.	$286,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 2.68% Airbnb Rental Income: $2899 Traditional Rental Income: $1658 Airbnb ROI: 4.8% Traditional ROI: 2.68%
600 N Kingsbury St #1012 Chicago, IL Incredible views and light from this south facing beautiful split 2 bed 2 bath at Park Pla...	2 beds \| 2 baths \| 1,040 sq.ft.	$460,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 0.54% Airbnb Rental Income: $3728 Traditional Rental Income: $2102 Airbnb ROI: 2.44% Traditional ROI: 0.54%

Vacation Rentals in Chicago

There are 1,198 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $409,805 and the average price per square foot is $233. The cash on cash return on vacation rentals in Chicago is 1.00%. The average monthly short term rental income in Chicago is $2,181.

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

There are 1,198 Airbnb properties available for sale in Chicago.

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

In November 2026, the average Airbnb occupancy rate in Chicago is 36%.

In 2026, the highest Airbnb occupancy rate in Chicago are in Hanson Park (35%), South Shore (33%) and South Shore (40%).

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

3906 W Montrose Ave

Chicago, IL

5 beds | 2 baths | 1,120 sq.ft.

$509,999

Airbnb cash on cash: 4.54%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $4796

Traditional Rental Income: $2240

Airbnb ROI: 4.54%

Traditional ROI: 1.25%

5602 N Fairview Ave

Chicago, IL

2 beds | N/A baths | 0 sq.ft.

$469,000

Airbnb cash on cash: 1.43%

Traditional cash on cash: -1.02%

Airbnb Rental Income: $2801

Traditional Rental Income: $1070

Airbnb ROI: 1.43%

Traditional ROI: -1.02%

6562 N Damen Avenue

Chicago, IL

3 beds | 2 baths | 1,769 sq.ft.

$470,000

Airbnb cash on cash: 2.2%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $2899

Traditional Rental Income: $2182

Airbnb ROI: 2.2%

Traditional ROI: 2.1%

4420 S Berkeley Ave

Chicago, IL

4 beds | 3 baths | 3,300 sq.ft.

$659,500

Airbnb cash on cash: 1.11%

Traditional cash on cash: 0.69%

Airbnb Rental Income: $3559

Traditional Rental Income: $2520

Airbnb ROI: 1.11%

Traditional ROI: 0.69%

801 S Plymouth Court #906

Chicago, IL

1 beds | 1 baths | N/A

$175,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 0.86%

Airbnb Rental Income: $2199

Traditional Rental Income: $1525

Airbnb ROI: 1.57%

Traditional ROI: 0.86%

3849 N Nora Ave

Chicago, IL

5 beds | 3 baths | 1,638 sq.ft.

$465,000

Airbnb cash on cash: 5.78%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $5055

Traditional Rental Income: $2762

Airbnb ROI: 5.78%

Traditional ROI: 2.88%

367 W Locust Street #305

Chicago, IL

3 beds | 3 baths | 1,852 sq.ft.

$825,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 0.69%

Airbnb Rental Income: $4766

Traditional Rental Income: $3392

Airbnb ROI: 1.2%

Traditional ROI: 0.69%

20 N State Street #1013

Chicago, IL

1 beds | 1 baths | N/A

$259,000

Airbnb cash on cash: 1.87%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $2489

Traditional Rental Income: $1222

Airbnb ROI: 1.87%