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
7240 S Oakley Avenue Chicago, IL BRING YOUR CLIENTS! THIS BEAUTHY LOOKS LITTLE BUT IS ENORMOUS! WITH PLANE OF ROOMS IDEAL F...	4 beds \| 2 baths \| 1,016 sq.ft.	$318,990	Airbnb cash on cash: 3.51% Traditional cash on cash: 5.23% Airbnb Rental Income: $2153 Traditional Rental Income: $2121 Airbnb ROI: 3.51% Traditional ROI: 5.23%
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.	$329,500	Airbnb cash on cash: 2.45% Traditional cash on cash: 3.16% Airbnb Rental Income: $1921 Traditional Rental Income: $1632 Airbnb ROI: 2.45% Traditional ROI: 3.16%
4141 N KEDZIE Avenue #307 Chicago, IL Come see this stunning 2 bed / 2 bath condo loaded with upgrades! Step inside to a bright,...	2 beds \| 2 baths \| 1,691 sq.ft.	$424,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.02% Airbnb Rental Income: $2292 Traditional Rental Income: $2573 Airbnb ROI: -0.12% Traditional ROI: 2.02%
5151 W Winona Street Chicago, IL Welcome to this exquisite agent-owned residence located in the heart of Jefferson Park. Th...	5 beds \| 3 baths \| N/A	$775,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 2.63% Airbnb Rental Income: $2734 Traditional Rental Income: $3337 Airbnb ROI: 0.91% Traditional ROI: 2.63%
1919 N Kenmore Avenue #1 Chicago, IL Tucked into the heart of Lincoln Park on a picturesque, tree-lined street, this masterfull...	3 beds \| 3 baths \| N/A	$890,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 1.06% Airbnb Rental Income: $4317 Traditional Rental Income: $2867 Airbnb ROI: 1.71% Traditional ROI: 1.06%
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.	$425,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 1.76% Airbnb Rental Income: $2152 Traditional Rental Income: $2949 Airbnb ROI: -1.62% Traditional ROI: 1.76%
4144 N Sheridan Road #408 Chicago, IL Nestled within the storied elegance of The Park Sheridan, a former grand hotel located in ...	2 beds \| 2 baths \| 1,100 sq.ft.	$390,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 1.86% Airbnb Rental Income: $2379 Traditional Rental Income: $2465 Airbnb ROI: 0.02% Traditional ROI: 1.86%
7216 S CENTRAL PARK Avenue Chicago, IL Well-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi...	3 beds \| 2 baths \| N/A	$315,300	Airbnb cash on cash: 1.33% Traditional cash on cash: 5.75% Airbnb Rental Income: $1498 Traditional Rental Income: $2371 Airbnb ROI: 1.33% Traditional ROI: 5.75%
2423 W Erie Street Chicago, IL Welcome to your dream home in the highly desirable Smith Park neighborhood, crafted by acc...	4 beds \| 4 baths \| N/A	$999,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 1.8% Airbnb Rental Income: $2285 Traditional Rental Income: $4258 Airbnb ROI: -0.93% Traditional ROI: 1.8%
5151 W Fletcher Street Chicago, IL Huge Price Reduction Move right into this stunning, fully updated 6-bedroom, 3-bathro...	4 beds \| 3 baths \| 3,450 sq.ft.	$620,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 3.76% Airbnb Rental Income: $2223 Traditional Rental Income: $3449 Airbnb ROI: 0.68% Traditional ROI: 3.76%
6558 N Washtenaw Avenue #2 Chicago, IL Spacious 3 bedroom, 2 bathroom condo with modern updates, washer/dryer in-unit and a priva...	3 beds \| 2 baths \| 1,500 sq.ft.	$297,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 3.86% Airbnb Rental Income: $2160 Traditional Rental Income: $2173 Airbnb ROI: 1.85% Traditional ROI: 3.86%
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: 0.1% Traditional cash on cash: 0.55% Airbnb Rental Income: $2925 Traditional Rental Income: $2659 Airbnb ROI: 0.1% Traditional ROI: 0.55%
2128 N WINCHESTER Avenue Chicago, IL Welcome to this beautifully rehabbed 4-bedroom, 3.5-bathroom home in the heart of Bucktown...	3 beds \| 4 baths \| 4,200 sq.ft.	$1,350,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 0.19% Airbnb Rental Income: $2470 Traditional Rental Income: $3589 Airbnb ROI: -1.18% Traditional ROI: 0.19%
3036 N Luna Avenue Chicago, IL Spacious & Stylish 5-Bedroom Home with Modern Upgrades! Welcome to your new home-offering...	3 beds \| 3 baths \| 2,532 sq.ft.	$535,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.51% Airbnb Rental Income: $1719 Traditional Rental Income: $3396 Airbnb ROI: 0.2% Traditional ROI: 4.51%
8151 S Bennett Avenue Chicago, IL This expansive brick 2-flat offers versatile living across three fully finished levels. En...	9 beds \| 3 baths \| N/A	$250,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 9.21% Airbnb Rental Income: $2511 Traditional Rental Income: $2779 Airbnb ROI: 5.5% Traditional ROI: 9.21%
2432 W Ohio Street Chicago, IL Stunning Multi-Level Home in Prime West Town Location Nestled in the heart of West Town, ...	4 beds \| 3 baths \| 2,574 sq.ft.	$799,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 1.32% Airbnb Rental Income: $2285 Traditional Rental Income: $3071 Airbnb ROI: -0.5% Traditional ROI: 1.32%
1530 S State Street #620 Chicago, IL Beautiful 1BR/1BA, true concrete loft in the historic Beatrice Cold Storage building with ...	1 beds \| 1 baths \| N/A	$299,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.53% Airbnb Rental Income: $2042 Traditional Rental Income: $2050 Airbnb ROI: -0.38% Traditional ROI: 1.53%
1211 S Prairie Avenue #3502 Chicago, IL Welcome to luxury living at One Museum Park East! Experience breathtaking panoramic views...	2 beds \| 3 baths \| 2,197 sq.ft.	$1,350,000	Airbnb cash on cash: -2.73% Traditional cash on cash: -1.49% Airbnb Rental Income: $2152 Traditional Rental Income: $3158 Airbnb ROI: -2.73% Traditional ROI: -1.49%
212 E Cullerton St #702 Chicago, IL	2 beds \| 2 baths \| 1,200 sq.ft.	$388,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.04% Airbnb Rental Income: $2288 Traditional Rental Income: $1950 Airbnb ROI: -0.59% Traditional ROI: 0.04%
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: -2.19% Traditional cash on cash: -1.79% Airbnb Rental Income: $2736 Traditional Rental Income: $2363 Airbnb ROI: -2.19% 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.	$265,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 1.37% Airbnb Rental Income: $2399 Traditional Rental Income: $1767 Airbnb ROI: 1.54% Traditional ROI: 1.37%
345 N Canal Street #1003 Chicago, IL Fully rehabbed luxury condo in the iconic Fulton House, located in Chicago's sought-after ...	2 beds \| 1 baths \| N/A	$419,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 0% Airbnb Rental Income: $2736 Traditional Rental Income: $1731 Airbnb ROI: 0.92% Traditional ROI: 0%
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.	$329,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 4.04% Airbnb Rental Income: $1652 Traditional Rental Income: $1920 Airbnb ROI: 1.67% Traditional ROI: 4.04%
55 W Goethe Street #1222 Chicago, IL OPEN HOSUE CANCELLED. Nestled in one of Chicago's most sought-after gated communities-Beek...	3 beds \| 4 baths \| 2,968 sq.ft.	$1,225,000	Airbnb cash on cash: -2.17% Traditional cash on cash: -0.77% Airbnb Rental Income: $2991 Traditional Rental Income: $3901 Airbnb ROI: -2.17% Traditional ROI: -0.77%
545 N Dearborn Street #1202 Chicago, IL Renovated 850 sq. ft. 1BR at Grand Plaza in River North. Features hardwood floors, chef's ...	1 beds \| 1 baths \| 850 sq.ft.	$300,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.3% Airbnb Rental Income: $2298 Traditional Rental Income: $2007 Airbnb ROI: 0.31% Traditional ROI: 1.3%
21 E Huron Street #706 Chicago, IL When Parisian charm meets New York Edge in the heart of Chicago - Unlike Anything You've S...	2 beds \| 2 baths \| 1,771 sq.ft.	$1,650,000	Airbnb cash on cash: -1.77% Traditional cash on cash: -1.38% Airbnb Rental Income: $2736 Traditional Rental Income: $2683 Airbnb ROI: -1.77% Traditional ROI: -1.38%
630 N State Street #1406 Chicago, IL Back on the market due to buyer unable to sell their property. Experience refined urban li...	2 beds \| 2 baths \| 1,241 sq.ft.	$485,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.41% Airbnb Rental Income: $2736 Traditional Rental Income: $2698 Airbnb ROI: -0.93% Traditional ROI: 0.41%
2 E Erie Street #1605 Chicago, IL An exceptional opportunity in the heart of River North-just steps from Michigan Avenue. Ev...	3 beds \| 3 baths \| 2,082 sq.ft.	$885,000	Airbnb cash on cash: -1.99% Traditional cash on cash: -0.72% Airbnb Rental Income: $2938 Traditional Rental Income: $3302 Airbnb ROI: -1.99% Traditional ROI: -0.72%
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.	$425,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.4% Airbnb Rental Income: $3098 Traditional Rental Income: $2619 Airbnb ROI: -0.16% Traditional ROI: 0.4%
2244 W IRVING PARK Road Chicago, IL PRIME CANDIDATE FOR OWNER OCCUPANT, FHA 203K BUYER! Single family home located in high tr...	3 beds \| 2 baths \| N/A	$624,900	Airbnb cash on cash: 0.16% Traditional cash on cash: 1.56% Airbnb Rental Income: $2477 Traditional Rental Income: $2696 Airbnb ROI: 0.16% Traditional ROI: 1.56%

Real Estate investment in Chicago, IL

There are 3,873 properties for sale in the city of Chicago . The median list price in Chicago is $369,900 and the average price per square foot is $215. In September 2025, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,369.

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

There are 3,873 investment properties available for sale in Chicago.

In 2025, the best neighborhood to buy investment property is Little Village.

The ROI for Long-Term is higher than the Short-Term in Chicago with average rental income of $2,369.

Your search for investment property begins and ends here

Investment Property for Sale in Chicago, IL

7240 S Oakley Avenue

Chicago, IL

4 beds | 2 baths | 1,016 sq.ft.

$318,990

Airbnb cash on cash: 3.51%

Traditional cash on cash: 5.23%

Airbnb Rental Income: $2153

Traditional Rental Income: $2121

Airbnb ROI: 3.51%

Traditional ROI: 5.23%

1722 N Keeler Avenue

Chicago, IL

3 beds | 1 baths | 842 sq.ft.

$329,500

Airbnb cash on cash: 2.45%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $1921

Traditional Rental Income: $1632

Airbnb ROI: 2.45%

Traditional ROI: 3.16%

4141 N KEDZIE Avenue #307

Chicago, IL

2 beds | 2 baths | 1,691 sq.ft.

$424,900

Airbnb cash on cash: -0.12%

Traditional cash on cash: 2.02%

Airbnb Rental Income: $2292

Traditional Rental Income: $2573

Airbnb ROI: -0.12%

Traditional ROI: 2.02%

5151 W Winona Street

Chicago, IL

5 beds | 3 baths | N/A

$775,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2734

Traditional Rental Income: $3337

Airbnb ROI: 0.91%

Traditional ROI: 2.63%

1919 N Kenmore Avenue #1

Chicago, IL

3 beds | 3 baths | N/A

$890,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $4317

Traditional Rental Income: $2867

Airbnb ROI: 1.71%

Traditional ROI: 1.06%

1160 S Michigan Ave #2502

Chicago, IL

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

$425,000

Airbnb cash on cash: -1.62%

Traditional cash on cash: 1.76%

Airbnb Rental Income: $2152

Traditional Rental Income: $2949

Airbnb ROI: -1.62%

Traditional ROI: 1.76%

4144 N Sheridan Road #408

Chicago, IL

2 beds | 2 baths | 1,100 sq.ft.

$390,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $2379

Traditional Rental Income: $2465

Airbnb ROI: 0.02%

Traditional ROI: 1.86%

7216 S CENTRAL PARK Avenue

Chicago, IL

3 beds | 2 baths | N/A

$315,300

Airbnb cash on cash: 1.33%

Traditional cash on cash: 5.75%

Airbnb Rental Income: $1498

Traditional Rental Income: $2371

Airbnb ROI: 1.33%