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
4517 N Whipple Street Chicago, IL Stunning 5 bedroom 3.5 bath luxury farmhouse nestled in between the Ravenswood Manor and E...	4 beds \| 4 baths \| N/A	$999,000	Airbnb cash on cash: 1.25% Traditional cash on cash: -0.24% Airbnb Rental Income: $4331 Traditional Rental Income: $2037 Airbnb ROI: 1.25% Traditional ROI: -0.24%
5737 N Oriole Avenue Chicago, IL Perfect LOCATION! This lovely updated brick home is ideally situated close to exceptional ...	2 beds \| 2 baths \| 1,875 sq.ft.	$440,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.95% Airbnb Rental Income: $1741 Traditional Rental Income: $2596 Airbnb ROI: 0.71% Traditional ROI: 3.95%
6207 S Justine Street Chicago, IL Don't miss this solid yellow brick bungalow with a brick garage! This spacious and well-ap...	3 beds \| 3 baths \| 1,870 sq.ft.	$340,000	Airbnb cash on cash: 5.22% Traditional cash on cash: 7.59% Airbnb Rental Income: $2797 Traditional Rental Income: $2899 Airbnb ROI: 5.22% Traditional ROI: 7.59%
4836 S Dorchester Avenue Chicago, IL Stunning 3-Flat Georgian Style Multi-Family Building in Hyde Park, where historical elegan...	6 beds \| N/A baths \| N/A	$1,150,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 0.32% Airbnb Rental Income: $7292 Traditional Rental Income: $2659 Airbnb ROI: 3.33% Traditional ROI: 0.32%
1122 W Catalpa Avenue #501 Chicago, IL Beautifully appointed move-in ready corner unit concrete loft drenched in natural light st...	2 beds \| 2 baths \| N/A	$299,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 1.51% Airbnb Rental Income: $2832 Traditional Rental Income: $2382 Airbnb ROI: 0.76% Traditional ROI: 1.51%
5623 S Newcastle Avenue Chicago, IL Nestled in a prime location, this 2-unit property offers a unique opportunity for investor...	6 beds \| N/A baths \| N/A	$529,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 2.72% Airbnb Rental Income: $3284 Traditional Rental Income: $2527 Airbnb ROI: 2.76% Traditional ROI: 2.72%
4848 N Central Ave #301 Chicago, IL 4848 N Central Ave #301, Chicago, IL 60630 \| Condo/Coop	3 beds \| 2 baths \| 1,500 sq.ft.	$395,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 0.83% Airbnb Rental Income: $2437 Traditional Rental Income: $2063 Airbnb ROI: 0.23% Traditional ROI: 0.83%
1711 W Division Street #204 Chicago, IL Impressive, light-filled condo in a boutique elevator building set in the heart of Wicker ...	2 beds \| 2 baths \| 1,750 sq.ft.	$749,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.41% Airbnb Rental Income: $3941 Traditional Rental Income: $2848 Airbnb ROI: 0.77% Traditional ROI: 0.41%
1619 N BELL Avenue Chicago, IL Welcome to your new home that embodies the epitome of luxury, located in the vibrant heart...	5 beds \| 4 baths \| 4,350 sq.ft.	$1,899,000	Airbnb cash on cash: 1.05% Traditional cash on cash: -0.21% Airbnb Rental Income: $7817 Traditional Rental Income: $4093 Airbnb ROI: 1.05% Traditional ROI: -0.21%
840 N Lake Shore Drive #1502 Chicago, IL This stunning two-bedroom, two-and-a-half-bath condo in one of Chicago's premier buildings...	2 beds \| 3 baths \| 2,158 sq.ft.	$1,395,000	Airbnb cash on cash: -1.91% Traditional cash on cash: -2.14% Airbnb Rental Income: $5454 Traditional Rental Income: $4062 Airbnb ROI: -1.91% Traditional ROI: -2.14%
1815 N Harding Avenue Chicago, IL BRICK BUNGALOW LOCATED IN QUIET TREE LINED STREET. 3 LEVEL OF LIVING SPACE. ZIP CODE 60647...	4 beds \| 3 baths \| N/A	$519,000	Airbnb cash on cash: 8.95% Traditional cash on cash: 4.9% Airbnb Rental Income: $6798 Traditional Rental Income: $3509 Airbnb ROI: 8.95% Traditional ROI: 4.9%
8246 S Calumet Avenue Chicago, IL Welcome home to this charming two-story brick home in Chicago. This meticulously maintaine...	3 beds \| 2 baths \| 2,091 sq.ft.	$309,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 7.36% Airbnb Rental Income: $2385 Traditional Rental Income: $2818 Airbnb ROI: 3.85% Traditional ROI: 7.36%
41 S Albany Avenue Chicago, IL Explore the inviting embrace of 41 S Albany as your new home! This stunning property is ta...	2 beds \| 3 baths \| 1,558 sq.ft.	$229,900	Airbnb cash on cash: 6.48% Traditional cash on cash: 9.4% Airbnb Rental Income: $2466 Traditional Rental Income: $2500 Airbnb ROI: 6.48% Traditional ROI: 9.4%
2129 N Kedvale Avenue Chicago, IL Welcome home to 2129 Kedvale, a gut-remodeled three-story home in the desirable Hermosa/ W...	4 beds \| 3 baths \| 3,400 sq.ft.	$625,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 1.77% Airbnb Rental Income: $6798 Traditional Rental Income: $2452 Airbnb ROI: 6.96% Traditional ROI: 1.77%
5826 W Gunnison Street Chicago, IL Beautifully rehabbed and freshly painted 4 bed/2 bath brick bungalow located on a quiet tr...	4 beds \| 2 baths \| N/A	$525,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 3.13% Airbnb Rental Income: $1911 Traditional Rental Income: $2785 Airbnb ROI: 0.31% Traditional ROI: 3.13%
4840 S Dorchester Avenue #1 Chicago, IL The Dorchester Collection is a newly-constructed elegant gated townhome development locate...	3 beds \| 3 baths \| N/A	$925,000	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.38% Airbnb Rental Income: $3221 Traditional Rental Income: $2846 Airbnb ROI: -0.79% Traditional ROI: -0.38%
4840 S Dorchester Avenue #4 Chicago, IL 6 out of 13 units sold! The Dorchester Collection is a newly-constructed elegant gated tow...	4 beds \| 4 baths \| N/A	$850,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 1.18% Airbnb Rental Income: $4725 Traditional Rental Income: $3886 Airbnb ROI: 1.01% Traditional ROI: 1.18%
11251 S Parnell Ave Chicago, IL 11251 S Parnell Ave, Chicago, IL 60628 \| Single Family Residential	4 beds \| 2 baths \| 2,500 sq.ft.	$314,900	Airbnb cash on cash: 3.83% Traditional cash on cash: 4.69% Airbnb Rental Income: $2852 Traditional Rental Income: $2442 Airbnb ROI: 3.83% Traditional ROI: 4.69%
655 W 111th Street Chicago, IL Step into this charming and beautifully renovated Cape Cod-style home, perfectly situated ...	4 beds \| 2 baths \| 1,400 sq.ft.	$279,900	Airbnb cash on cash: 6.89% Traditional cash on cash: 7.67% Airbnb Rental Income: $2998 Traditional Rental Income: $2515 Airbnb ROI: 6.89% Traditional ROI: 7.67%
7915 S Paxton Avenue Chicago, IL "Welcome to your dream home! This spacious and amazing house is perfect for your family's ...	4 beds \| 3 baths \| 3,100 sq.ft.	$289,999	Airbnb cash on cash: 8.96% Traditional cash on cash: 9.81% Airbnb Rental Income: $3870 Traditional Rental Income: $3268 Airbnb ROI: 8.96% Traditional ROI: 9.81%
8135 S Muskegon Avenue Chicago, IL Welcome home to this beautiful recently rehabbed home. This home offers modern finishes wi...	2 beds \| 2 baths \| 1,600 sq.ft.	$185,000	Airbnb cash on cash: 7.45% Traditional cash on cash: 9.59% Airbnb Rental Income: $2230 Traditional Rental Income: $2046 Airbnb ROI: 7.45% Traditional ROI: 9.59%
919 N Hermitage Avenue #2 Chicago, IL Live in a thoughtfully renovated second floor 2-bedroom, 2-bath, 1-garage space condo loca...	2 beds \| 2 baths \| 1,250 sq.ft.	$535,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 1.79% Airbnb Rental Income: $3941 Traditional Rental Income: $2367 Airbnb ROI: 3.25% Traditional ROI: 1.79%
2755 W Melrose St #2 Chicago, IL 2755 W Melrose St #2, Chicago, IL 60618 \| Condo/Coop	1 beds \| 1 baths \| N/A	$219,900	Airbnb cash on cash: 2.86% Traditional cash on cash: 0.59% Airbnb Rental Income: $2243 Traditional Rental Income: $1207 Airbnb ROI: 2.86% Traditional ROI: 0.59%
2541 S Normal Avenue Chicago, IL 3-story single family home with attached 2-car garage, located 5 blocks from Chinatown, mi...	4 beds \| 3 baths \| 1,980 sq.ft.	$508,000	Airbnb cash on cash: 8.11% Traditional cash on cash: 3.4% Airbnb Rental Income: $6366 Traditional Rental Income: $2882 Airbnb ROI: 8.11% Traditional ROI: 3.4%
420 E WATERSIDE Drive #1312 Chicago, IL REGATTA ON LAKE SHORE EAST! Views, views & more views of the river, our beautiful Lake Mic...	2 beds \| 2 baths \| 1,586 sq.ft.	$699,900	Airbnb cash on cash: 1.71% Traditional cash on cash: -1.37% Airbnb Rental Income: $5862 Traditional Rental Income: $2683 Airbnb ROI: 1.71% Traditional ROI: -1.37%
65 E Monroe Street #4312 Chicago, IL This beautiful 2bed/2bath +den is truly move-in ready! Wonderful open concept floorplan fe...	2 beds \| 2 baths \| N/A	$475,000	Airbnb cash on cash: 4.42% Traditional cash on cash: -0.28% Airbnb Rental Income: $5753 Traditional Rental Income: $2517 Airbnb ROI: 4.42% Traditional ROI: -0.28%
801 S Plymouth Ct #315 Chicago, IL 801 S Plymouth Ct #315, Chicago, IL 60605 \| Condo/Coop	2 beds \| 2 baths \| 1,014 sq.ft.	$288,900	Airbnb cash on cash: 9.83% Traditional cash on cash: 1.69% Airbnb Rental Income: $5557 Traditional Rental Income: $2225 Airbnb ROI: 9.83% Traditional ROI: 1.69%
633 S Plymouth Court #1107 Chicago, IL Night View of State Street (pic); Details for comfort and convenience have been considered...	1 beds \| 1 baths \| 850 sq.ft.	$196,850	Airbnb cash on cash: 8.89% Traditional cash on cash: 1.76% Airbnb Rental Income: $3812 Traditional Rental Income: $1656 Airbnb ROI: 8.89% Traditional ROI: 1.76%
6118 N SHERIDAN Road #304 Chicago, IL Charming 2-Bedroom, 1-Bath Unit! This delightful unit features beautiful wood floors tha...	2 beds \| 1 baths \| 1,000 sq.ft.	$199,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 2.9% Airbnb Rental Income: $2729 Traditional Rental Income: $1887 Airbnb ROI: 3.95% Traditional ROI: 2.9%
3548 W Belle Plaine Avenue #1 Chicago, IL Welcome to the Irving Park neighborhood! This 1 bed, 1 bat unit can be found on a quiet tr...	1 beds \| 1 baths \| N/A	$164,500	Airbnb cash on cash: 4.58% Traditional cash on cash: 2.55% Airbnb Rental Income: $2075 Traditional Rental Income: $1221 Airbnb ROI: 4.58% Traditional ROI: 2.55%

Real Estate investment in Chicago, IL

There are 2,890 properties for sale in the city of Chicago . The median list price in Chicago is $340,000 and the average price per square foot is $193. In December 2024, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,412.

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

There are 2,890 investment properties available for sale in Chicago.

In 2024, the best neighborhood to buy investment property is Englewood.

The ROI for Short-Term is higher than the Long-Term in Chicago with average rental income of $3,646.

Your search for investment property begins and ends here

Investment Property for Sale in Chicago, IL

4517 N Whipple Street

Chicago, IL

4 beds | 4 baths | N/A

$999,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $4331

Traditional Rental Income: $2037

Airbnb ROI: 1.25%

Traditional ROI: -0.24%

5737 N Oriole Avenue

Chicago, IL

2 beds | 2 baths | 1,875 sq.ft.

$440,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1741

Traditional Rental Income: $2596

Airbnb ROI: 0.71%

Traditional ROI: 3.95%

6207 S Justine Street

Chicago, IL

3 beds | 3 baths | 1,870 sq.ft.

$340,000

Airbnb cash on cash: 5.22%

Traditional cash on cash: 7.59%

Airbnb Rental Income: $2797

Traditional Rental Income: $2899

Airbnb ROI: 5.22%

Traditional ROI: 7.59%

4836 S Dorchester Avenue

Chicago, IL

6 beds | N/A baths | N/A

$1,150,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 0.32%

Airbnb Rental Income: $7292

Traditional Rental Income: $2659

Airbnb ROI: 3.33%

Traditional ROI: 0.32%

1122 W Catalpa Avenue #501

Chicago, IL

2 beds | 2 baths | N/A

$299,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2832

Traditional Rental Income: $2382

Airbnb ROI: 0.76%

Traditional ROI: 1.51%

5623 S Newcastle Avenue

Chicago, IL

6 beds | N/A baths | N/A

$529,000

Airbnb cash on cash: 2.76%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $3284

Traditional Rental Income: $2527

Airbnb ROI: 2.76%

Traditional ROI: 2.72%

4848 N Central Ave #301

Chicago, IL

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

$395,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $2437

Traditional Rental Income: $2063

Airbnb ROI: 0.23%

Traditional ROI: 0.83%

1711 W Division Street #204

Chicago, IL

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

$749,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $3941

Traditional Rental Income: $2848

Airbnb ROI: 0.77%