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
5911 N Keating Avenue Chicago, IL Meticulously maintained & recently renovated 4 bedroom + family room/3 bath with rarely av...	4 beds \| 3 baths \| N/A	$749,500	Airbnb cash on cash: 0.94% Traditional cash on cash: 0.93% Airbnb Rental Income: $2892 Traditional Rental Income: $2216 Airbnb ROI: 0.94% Traditional ROI: 0.93%
2854 S Central Park Ave Chicago, IL 2854 S Central Park Ave, Chicago, IL 60623 \| Single Family Residential	5 beds \| 2 baths \| 896 sq.ft.	$348,500	Airbnb cash on cash: 7.12% Traditional cash on cash: 3.07% Airbnb Rental Income: $3998 Traditional Rental Income: $1819 Airbnb ROI: 7.12% Traditional ROI: 3.07%
3035 N Luna Ave Chicago, IL Classic Chicago bungalow with 3 full bedroom's on the first floor. Many beautiful intact ...	6 beds \| 2 baths \| 1,600 sq.ft.	$499,500	Airbnb cash on cash: 5.78% Traditional cash on cash: 4.17% Airbnb Rental Income: $4692 Traditional Rental Income: $2970 Airbnb ROI: 5.78% Traditional ROI: 4.17%
6118 N Sheridan Rd #310 Chicago, IL 6118 N Sheridan Rd #310, Chicago, IL 60660 \| Condo/Coop	1 beds \| 1 baths \| 561 sq.ft.	$149,000	Airbnb cash on cash: 1.66% Traditional cash on cash: -0.04% Airbnb Rental Income: $1948 Traditional Rental Income: $1191 Airbnb ROI: 1.66% Traditional ROI: -0.04%
4837 S Long Ave Chicago, IL 4837 S Long Ave, Chicago, IL 60638 \| Single Family Residential	7 beds \| 2 baths \| 1,700 sq.ft.	$418,900	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.2% Airbnb Rental Income: $3217 Traditional Rental Income: $2232 Airbnb ROI: 2.87% Traditional ROI: 2.2%
442 W Dickens Ave #3 Chicago, IL 442 W Dickens Ave #3, Chicago, IL 60614 \| Condo/Coop	2 beds \| 1 baths \| 1,233 sq.ft.	$550,000	Airbnb cash on cash: 0.36% Traditional cash on cash: -1.3% Airbnb Rental Income: $3285 Traditional Rental Income: $1694 Airbnb ROI: 0.36% Traditional ROI: -1.3%
1228 W 96th St Chicago, IL Charming 5-bedroom, 2-bath brick bungalow offering plenty of space for a growing or multi-...	5 beds \| 2 baths \| 1,632 sq.ft.	$320,000	Airbnb cash on cash: 7.02% Traditional cash on cash: 5.99% Airbnb Rental Income: $3511 Traditional Rental Income: $2428 Airbnb ROI: 7.02% Traditional ROI: 5.99%
7017 S Hermitage Ave Chicago, IL Come and view your new home today in the heart of West Englewood! This fully insulated rem...	7 beds \| 3 baths \| 1,148 sq.ft.	$349,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 4.38% Airbnb Rental Income: $3100 Traditional Rental Income: $1962 Airbnb ROI: 5.7% Traditional ROI: 4.38%
628 N Rockwell St Chicago, IL Located ON Smith Park in Ukrainian Village with forever views east to Chicago's skyline, t...	4 beds \| 3 baths \| 3,800 sq.ft.	$1,299,900	Airbnb cash on cash: 0.14% Traditional cash on cash: -0.03% Airbnb Rental Income: $4157 Traditional Rental Income: $3074 Airbnb ROI: 0.14% Traditional ROI: -0.03%
222 E Pearson St #1104 Chicago, IL 222 E Pearson St #1104, Chicago, IL 60611 \| Condo/Coop	2 beds \| 1 baths \| 1,000 sq.ft.	$334,900	Airbnb cash on cash: 0.52% Traditional cash on cash: -1.06% Airbnb Rental Income: $3123 Traditional Rental Income: $1915 Airbnb ROI: 0.52% Traditional ROI: -1.06%
20 E Goethe St #206 Chicago, IL Ever dreamed of living in the Heart of the Gold Coast in a classic, vintage building? Her...	1 beds \| 1 baths \| 650 sq.ft.	$195,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 2.13% Airbnb Rental Income: $1917 Traditional Rental Income: $1401 Airbnb ROI: 2.17% Traditional ROI: 2.13%
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: 1.94% Traditional cash on cash: -0.55% Airbnb Rental Income: $2668 Traditional Rental Income: $1101 Airbnb ROI: 1.94% Traditional ROI: -0.55%
839 W 54th St Chicago, IL PROPERTY IS IN GOOD SHAPE. REMODELED A FEW YEARS BACK. READY TO MOVE IN. SECTION 8 READY O...	3 beds \| 1 baths \| 1,200 sq.ft.	$219,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 4.89% Airbnb Rental Income: $2032 Traditional Rental Income: $1433 Airbnb ROI: 5.24% Traditional ROI: 4.89%
6092 N Sauganash Ave Chicago, IL 6092 N Sauganash Ave, Chicago, IL 60646 \| Single Family Residential	5 beds \| 3 baths \| 4,342 sq.ft.	$1,175,000	Airbnb cash on cash: 0.55% Traditional cash on cash: -0.3% Airbnb Rental Income: $5359 Traditional Rental Income: $3352 Airbnb ROI: 0.55% Traditional ROI: -0.3%
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.	$70,000	Airbnb cash on cash: 3.2% Traditional cash on cash: -0.02% Airbnb Rental Income: $1663 Traditional Rental Income: $973 Airbnb ROI: 3.2% Traditional ROI: -0.02%
758 N Larrabee Street #514 Chicago, IL Experience true loft living in this stunning and sun-drenched 2-bedroom, 2-bath residence ...	2 beds \| 2 baths \| 1,200 sq.ft.	$375,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 0.28% Airbnb Rental Income: $2842 Traditional Rental Income: $2041 Airbnb ROI: 0.67% Traditional ROI: 0.28%
4953 N Meade Ave Chicago, IL 4953 N Meade Ave, Chicago, IL 60630 \| Single Family Residential	3 beds \| 2 baths \| 1,940 sq.ft.	$485,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 1.03% Airbnb Rental Income: $2693 Traditional Rental Income: $2032 Airbnb ROI: 1.08% Traditional ROI: 1.03%
4855 N Washtenaw Ave #2 Chicago, IL Expect to be impressed! Beautifully rehabbed vintage condo in intimate Chicago classic 3-f...	3 beds \| 1 baths \| 1,600 sq.ft.	$525,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 0.49% Airbnb Rental Income: $2455 Traditional Rental Income: $1697 Airbnb ROI: 0.82% Traditional ROI: 0.49%
1225 N Orleans St #602 Chicago, IL Best of Old Town on quiet cul du sac in a beautiful park like setting. Updated 2 bed/2 bat...	2 beds \| 2 baths \| 1,200 sq.ft.	$460,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 1.74% Airbnb Rental Income: $2998 Traditional Rental Income: $2183 Airbnb ROI: 2.03% Traditional ROI: 1.74%
7749 S Muskegon Ave Chicago, IL FREE - FREE 32" TV - MOVE RIGHT IN -ONE MONTH FREE RENT!!!- DECEMBER ON US!! TO THIS SPACI...	10 beds \| 3 baths \| 1,000 sq.ft.	$279,900	Airbnb cash on cash: 4.64% Traditional cash on cash: 2.18% Airbnb Rental Income: $2832 Traditional Rental Income: $1523 Airbnb ROI: 4.64% Traditional ROI: 2.18%
7613 S Hermitage Ave Chicago, IL This beautiful Chicago brick bungalow home was renovated in 2023. This home has been touch...	7 beds \| 3 baths \| 2,234 sq.ft.	$269,999	Airbnb cash on cash: 9.11% Traditional cash on cash: 6.82% Airbnb Rental Income: $3501 Traditional Rental Income: $2145 Airbnb ROI: 9.11% Traditional ROI: 6.82%
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.	$495,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 0.8% Airbnb Rental Income: $2899 Traditional Rental Income: $2117 Airbnb ROI: 1.03% Traditional ROI: 0.8%
7837 S Laflin St Chicago, IL BRICK BUNGALOW ON OVERSIZED LOT WITH GARAGE. SOLD IN AS IS CONDITION. NEW WINDOWS AND WO...	6 beds \| 2 baths \| 1,476 sq.ft.	$315,000	Airbnb cash on cash: 7.32% Traditional cash on cash: 5.14% Airbnb Rental Income: $3583 Traditional Rental Income: $2153 Airbnb ROI: 7.32% Traditional ROI: 5.14%
5337 W Barry Ave Chicago, IL Beautiful Cragin neighborhood home with 4 Bedrooms and 4 Full Baths. An enormous Eat-in Ki...	5 beds \| 4 baths \| 0 sq.ft.	$615,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 4.46% Airbnb Rental Income: $4692 Traditional Rental Income: $3605 Airbnb ROI: 4.66% Traditional ROI: 4.46%
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: 4.71% Traditional cash on cash: 2.68% Airbnb Rental Income: $2871 Traditional Rental Income: $1658 Airbnb ROI: 4.71% Traditional ROI: 2.68%
5357 N Paulina St #1 Chicago, IL Andersonville High End Gem! 2 Bedroom plus a den/3rd bedroom. Beautiful gourmet kitchen wi...	3 beds \| 2 baths \| 0 sq.ft.	$599,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 0.43% Airbnb Rental Income: $2915 Traditional Rental Income: $1808 Airbnb ROI: 1.21% Traditional ROI: 0.43%
1310 N Ritchie Ct #7D Chicago, IL Unit facing the lake. Spacious master bedroom, organized walk-in closet, 2nd bedroom has ...	3 beds \| 2 baths \| 1,550 sq.ft.	$549,000	Airbnb cash on cash: 0.87% Traditional cash on cash: -1.96% Airbnb Rental Income: $4624 Traditional Rental Income: $2214 Airbnb ROI: 0.87% Traditional ROI: -1.96%
221 E Walton Pl #14B Chicago, IL Rare opportunity in a boutique Gold Coast building! This spacious 3-bedroom condo offers b...	3 beds \| 2 baths \| 1,450 sq.ft.	$550,000	Airbnb cash on cash: 0.61% Traditional cash on cash: -2.69% Airbnb Rental Income: $4418 Traditional Rental Income: $1798 Airbnb ROI: 0.61% Traditional ROI: -2.69%
30 E Huron St #2007 Chicago, IL View our virtual 3D tour! Bright and sunny northwest corner 2-bedroom condo in an unbeatab...	2 beds \| 1 baths \| 900 sq.ft.	$365,000	Airbnb cash on cash: 1.58% Traditional cash on cash: -0.78% Airbnb Rental Income: $3123 Traditional Rental Income: $1603 Airbnb ROI: 1.58% Traditional ROI: -0.78%
2605 S Indiana Ave #1208 Chicago, IL Beautiful 1 bedroom condo with balcony at the Stratford Condominiums. Enjoy the floor-to-c...	1 beds \| 1 baths \| 727 sq.ft.	$134,500	Airbnb cash on cash: 0.32% Traditional cash on cash: 0.07% Airbnb Rental Income: $1587 Traditional Rental Income: $1102 Airbnb ROI: 0.32% Traditional ROI: 0.07%
5953 S Elizabeth St Chicago, IL REGULAR SALE. BRICK SINGLE FAMILY HOME REMODELED AND READY TO MOVE IN. MAIN LEVEL FEATURES...	5 beds \| 3 baths \| 900 sq.ft.	$219,900	Airbnb cash on cash: 7.57% Traditional cash on cash: 7.56% Airbnb Rental Income: $2730 Traditional Rental Income: $2083 Airbnb ROI: 7.57% Traditional ROI: 7.56%

Vacation Rentals in Chicago

There are 1,255 vacation rental properties available for sale in the city of Chicago . The median list price of Airbnb properties available for sale in Chicago is $419,749 and the average price per square foot is $247. The cash on cash return on vacation rentals in Chicago is N/A%. The average monthly short term rental income in Chicago is $1,972.

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

There are 1,255 Airbnb properties available for sale in Chicago.

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

In September 2026, the average Airbnb occupancy rate in Chicago is 30%.

In 2026, the highest Airbnb occupancy rate in Chicago are in Hanson Park (31%), South Shore (30%) and South Shore (36%).

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

5911 N Keating Avenue

Chicago, IL

4 beds | 3 baths | N/A

$749,500

Airbnb cash on cash: 0.94%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $2892

Traditional Rental Income: $2216

Airbnb ROI: 0.94%

Traditional ROI: 0.93%

2854 S Central Park Ave

Chicago, IL

5 beds | 2 baths | 896 sq.ft.

$348,500

Airbnb cash on cash: 7.12%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $3998

Traditional Rental Income: $1819

Airbnb ROI: 7.12%

Traditional ROI: 3.07%

3035 N Luna Ave

Chicago, IL

6 beds | 2 baths | 1,600 sq.ft.

$499,500

Airbnb cash on cash: 5.78%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $4692

Traditional Rental Income: $2970

Airbnb ROI: 5.78%

Traditional ROI: 4.17%

6118 N Sheridan Rd #310

Chicago, IL

1 beds | 1 baths | 561 sq.ft.

$149,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: -0.04%

Airbnb Rental Income: $1948

Traditional Rental Income: $1191

Airbnb ROI: 1.66%

Traditional ROI: -0.04%

4837 S Long Ave

Chicago, IL

7 beds | 2 baths | 1,700 sq.ft.

$418,900

Airbnb cash on cash: 2.87%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $3217

Traditional Rental Income: $2232

Airbnb ROI: 2.87%

Traditional ROI: 2.2%

442 W Dickens Ave #3

Chicago, IL

2 beds | 1 baths | 1,233 sq.ft.

$550,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: -1.3%

Airbnb Rental Income: $3285

Traditional Rental Income: $1694

Airbnb ROI: 0.36%

Traditional ROI: -1.3%

1228 W 96th St

Chicago, IL

5 beds | 2 baths | 1,632 sq.ft.

$320,000

Airbnb cash on cash: 7.02%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $3511

Traditional Rental Income: $2428

Airbnb ROI: 7.02%

Traditional ROI: 5.99%

7017 S Hermitage Ave

Chicago, IL

7 beds | 3 baths | 1,148 sq.ft.

$349,000

Airbnb cash on cash: 5.7%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $3100

Traditional Rental Income: $1962

Airbnb ROI: 5.7%