Real Estate Investment Properties for Sale in Chicago, IL

Looking for investment property in Chicago, IL with high ROI ?

Explore a variety of short-term homes & houses in Chicago, IL. Invest wisely with VRBO & Chicago, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Chicago, IL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2610 W 80th St Chicago, IL 2610 W 80th St, Chicago, IL 60652 \| Single Family Residential	2 beds \| 1 baths \| 855 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.99% Airbnb Rental Income: $null Traditional Rental Income: $1328 Airbnb ROI: N/A Traditional ROI: 1.99%
7801 S Ada Street Chicago, IL Welcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham...	3 beds \| 3 baths \| 1,200 sq.ft.	$399,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $2306 Airbnb ROI: N/A Traditional ROI: 4.56%
1722 N Keeler Avenue Chicago, IL Hot Hermosa location! Updated single family home on a great block. House went through ext...	3 beds \| 1 baths \| 842 sq.ft.	$299,950	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $1632 Airbnb ROI: N/A Traditional ROI: 3.56%
60 E Monroe St #2001 Chicago, IL 60 E Monroe St #2001, Chicago, IL 60603 \| Condo/Coop	3 beds \| 2 baths \| 1,750 sq.ft.	$1,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.56% Airbnb Rental Income: $null Traditional Rental Income: $2745 Airbnb ROI: N/A Traditional ROI: -2.56%
1160 S Michigan Ave #2502 Chicago, IL 1160 S Michigan Ave #2502, Chicago, IL 60605 \| Condo/Coop	2 beds \| 2 baths \| 1,231 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.59% Airbnb Rental Income: $null Traditional Rental Income: $2449 Airbnb ROI: N/A Traditional ROI: 0.59%
1528 W Monroe St #200 Chicago, IL 1528 W Monroe St #200, Chicago, IL 60607 \| Condo/Coop	3 beds \| 2 baths \| 1,550 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.11% Airbnb Rental Income: $null Traditional Rental Income: $2512 Airbnb ROI: N/A Traditional ROI: 0.11%
7228 N Rogers Avenue Chicago, IL This is a 3 Bedroom, 1.5 Bath, 2 story, frame farm house with 1 Deeded Parking Space. It i...	2 beds \| 3 baths \| 1,600 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $2651 Airbnb ROI: N/A Traditional ROI: 4.28%
4343 N Clarendon Avenue #707 Chicago, IL Investors! Welcome to Buena Park. This incredible unit is a large one bedroom one bath wit...	1 beds \| 1 baths \| 790 sq.ft.	$139,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $1894 Airbnb ROI: N/A Traditional ROI: 4.01%
9100 S Wallace Street Chicago, IL Welcome to 9100 S Wallace - a beautifully renovated 3-bedroom, 3-bathroom home offering mo...	2 beds \| 3 baths \| 1,312 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 4.86%
6929 S Loomis Boulevard Chicago, IL This house has everything your client requested. 5 bedrooms, 3 full bathrooms, Full finis...	4 beds \| 3 baths \| 1,000 sq.ft.	$255,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.02% Airbnb Rental Income: $null Traditional Rental Income: $2322 Airbnb ROI: N/A Traditional ROI: 8.02%
7216 S CENTRAL PARK Avenue Chicago, IL Well-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi...	3 beds \| 2 baths \| 1,080 sq.ft.	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.33% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 6.33%
7205 S HAMLIN Avenue Chicago, IL Maintenance free 4 bedroom ranch with finished basement. 3 bedrooms on the main and one in...	3 beds \| 2 baths \| 1,080 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.15% Airbnb Rental Income: $null Traditional Rental Income: $1877 Airbnb ROI: N/A Traditional ROI: 4.15%
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.	$387,546	Airbnb cash on cash: N/A Traditional cash on cash: 1.5% Airbnb Rental Income: $null Traditional Rental Income: $1819 Airbnb ROI: N/A Traditional ROI: 1.5%
4836 S Dorchester Avenue Chicago, IL Stunning 3-Flat Georgian Style Multi-Family Building in the Hyde Park/Kenwood Community, w...	6 beds \| N/A baths \| N/A	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.55% Airbnb Rental Income: $null Traditional Rental Income: $2659 Airbnb ROI: N/A Traditional ROI: 0.55%
8151 S Bennett Avenue Chicago, IL This expansive brick 2-flat offers versatile living across three fully finished levels. En...	9 beds \| N/A baths \| N/A	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.21% Airbnb Rental Income: $null Traditional Rental Income: $2779 Airbnb ROI: N/A Traditional ROI: 9.21%
5455 N Sheridan Rd #1904 Chicago, IL 5455 N Sheridan Rd #1904, Chicago, IL 60640 \| Condo/Coop	2 beds \| 1 baths \| 850 sq.ft.	$299,990	Airbnb cash on cash: N/A Traditional cash on cash: -1.66% Airbnb Rental Income: $null Traditional Rental Income: $1529 Airbnb ROI: N/A Traditional ROI: -1.66%
5814 S Massasoit Ave Chicago, IL 5814 S Massasoit Ave, Chicago, IL 60638 \| Single Family Residential	3 beds \| 1 baths \| 1,017 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.35% Airbnb Rental Income: $null Traditional Rental Income: $1643 Airbnb ROI: N/A Traditional ROI: 1.35%
3214 S Canal St Chicago, IL 3214 S Canal St, Chicago, IL 60616 \| Single Family Residential	5 beds \| 5 baths \| 8,800 sq.ft.	$1,849,999	Airbnb cash on cash: N/A Traditional cash on cash: -0.44% Airbnb Rental Income: $null Traditional Rental Income: $4939 Airbnb ROI: N/A Traditional ROI: -0.44%
175 E Delaware Place #7204 Chicago, IL Welcome to your home in the sky, offering breathtaking North-facing views from the 72nd fl...	2 beds \| 2 baths \| 1,470 sq.ft.	$720,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.79% Airbnb Rental Income: $null Traditional Rental Income: $2363 Airbnb ROI: N/A Traditional ROI: -1.79%
401 E Ontario Street #1805 Chicago, IL Lovely junior one bedroom in desirable Streeterville neighborhood located steps from the l...	1 beds \| 1 baths \| 700 sq.ft.	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.41% Airbnb Rental Income: $null Traditional Rental Income: $1767 Airbnb ROI: N/A Traditional ROI: 1.41%
3558 W Belle Plaine Avenue #3 Chicago, IL Bright and full of personality, this two-bedroom Irving Park condo offers stylish comfort ...	2 beds \| 1 baths \| 1,000 sq.ft.	$255,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $1787 Airbnb ROI: N/A Traditional ROI: 2.72%
4824 S Kildare Avenue Chicago, IL The opportunity to own one of the most traditional home in the history of architecture in ...	3 beds \| 2 baths \| N/A	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.11% Airbnb Rental Income: $null Traditional Rental Income: $2383 Airbnb ROI: N/A Traditional ROI: 5.11%
3821 N Ottawa Avenue Chicago, IL Incredible value and opportunity to purchase this cozy 3Br/1.5Ba home in the Belmont Heigh...	3 beds \| 2 baths \| N/A	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.1% Airbnb Rental Income: $null Traditional Rental Income: $2491 Airbnb ROI: N/A Traditional ROI: 6.1%
9101 S Racine Ave Chicago, IL 9101 S Racine Ave, Chicago, IL 60620 \| Single Family Residential	4 beds \| 3 baths \| 2,800 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.05% Airbnb Rental Income: $null Traditional Rental Income: $3104 Airbnb ROI: N/A Traditional ROI: 6.05%
544 E 46th Pl Chicago, IL 544 E 46th Pl, Chicago, IL 60653 \| Single Family Residential	5 beds \| 3 baths \| 3,000 sq.ft.	$760,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $3288 Airbnb ROI: N/A Traditional ROI: 1.25%
4531 S Lawler Avenue Chicago, IL Pristine 3bed/2bath raised ranch ready for move-in. Spacious layout with finished baseme...	3 beds \| 2 baths \| 1,008 sq.ft.	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.36% Airbnb Rental Income: $null Traditional Rental Income: $1920 Airbnb ROI: N/A Traditional ROI: 4.36%
3916 W Grand Avenue Chicago, IL Move in ready! This cozy single-family home has a lot to offer with three full bathrooms, ...	3 beds \| 3 baths \| 900 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.6% Airbnb Rental Income: $null Traditional Rental Income: $2318 Airbnb ROI: N/A Traditional ROI: 5.6%
2650 N Lakeview Ave #3101 Chicago, IL 2650 N Lakeview Ave #3101, Chicago, IL 60614 \| Condo/Coop	2 beds \| 2 baths \| 1,250 sq.ft.	$519,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.36% Airbnb Rental Income: $null Traditional Rental Income: $2213 Airbnb ROI: N/A Traditional ROI: -1.36%
1720 N Mohawk St Chicago, IL 1720 N Mohawk St, Chicago, IL 60614 \| Single Family Residential	6 beds \| 5 baths \| 5,900 sq.ft.	$4,095,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.95% Airbnb Rental Income: $null Traditional Rental Income: $5071 Airbnb ROI: N/A Traditional ROI: -1.95%
1205 W 97th Pl Chicago, IL 1205 W 97th Pl, Chicago, IL 60643 \| Single Family Residential	5 beds \| 2 baths \| 3,308 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2242 Airbnb ROI: N/A Traditional ROI: 4.37%
545 N Dearborn St #3601 Chicago, IL 545 N Dearborn St #3601, Chicago, IL 60654 \| Condo/Coop	3 beds \| 2 baths \| 2,500 sq.ft.	$1,149,000	Airbnb cash on cash: N/A Traditional cash on cash: -3.59% Airbnb Rental Income: $null Traditional Rental Income: $2863 Airbnb ROI: N/A Traditional ROI: -3.59%
1112 N Dearborn St #1 Chicago, IL 1112 N Dearborn St #1, Chicago, IL 60610 \| Condo/Coop	2 beds \| 2 baths \| 2,255 sq.ft.	$1,395,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.19% Airbnb Rental Income: $null Traditional Rental Income: $2743 Airbnb ROI: N/A Traditional ROI: -2.19%
401 E Ontario Street #809 Chicago, IL LOCATION, LOCATION, LOCATION! This OVERSIZED CORNER unit with gorgeous city and lake views...	2 beds \| 2 baths \| 1,200 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.49% Airbnb Rental Income: $null Traditional Rental Income: $2619 Airbnb ROI: N/A Traditional ROI: 0.49%

Real Estate investment in Chicago, IL

There are 5,287 properties for sale in the city of Chicago . The median list price in Chicago is $334,900 and the average price per square foot is $189. In December 2025, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,143.

Chicago, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 5,287 investment properties available for sale in Chicago.

In 2025, the best neighborhood to buy investment property is South Shore.

The ROI for Short-Term is higher than the Long-Term in Chicago with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Chicago, IL

2610 W 80th St

Chicago, IL

2 beds | 1 baths | 855 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.99%

Airbnb Rental Income: $null

Traditional Rental Income: $1328

Airbnb ROI: N/A

Traditional ROI: 1.99%

7801 S Ada Street

Chicago, IL

3 beds | 3 baths | 1,200 sq.ft.

$399,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2306

Airbnb ROI: N/A

Traditional ROI: 4.56%

1722 N Keeler Avenue

Chicago, IL

3 beds | 1 baths | 842 sq.ft.

$299,950

Airbnb cash on cash: N/A

Traditional cash on cash: 3.56%

Airbnb Rental Income: $null

Traditional Rental Income: $1632

Airbnb ROI: N/A

Traditional ROI: 3.56%

60 E Monroe St #2001

Chicago, IL

3 beds | 2 baths | 1,750 sq.ft.

$1,000,000

Airbnb cash on cash: N/A

Traditional cash on cash: -2.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2745

Airbnb ROI: N/A

Traditional ROI: -2.56%

1160 S Michigan Ave #2502

Chicago, IL

2 beds | 2 baths | 1,231 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.59%

Airbnb Rental Income: $null

Traditional Rental Income: $2449

Airbnb ROI: N/A

Traditional ROI: 0.59%

1528 W Monroe St #200

Chicago, IL

3 beds | 2 baths | 1,550 sq.ft.

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.11%

Airbnb Rental Income: $null

Traditional Rental Income: $2512

Airbnb ROI: N/A

Traditional ROI: 0.11%

7228 N Rogers Avenue

Chicago, IL

2 beds | 3 baths | 1,600 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.28%

Airbnb Rental Income: $null

Traditional Rental Income: $2651

Airbnb ROI: N/A

Traditional ROI: 4.28%

4343 N Clarendon Avenue #707

Chicago, IL

1 beds | 1 baths | 790 sq.ft.

$139,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.01%

Airbnb Rental Income: $null

Traditional Rental Income: $1894

Airbnb ROI: N/A