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.

Multi Family for Sale in Chicago, IL

Search for Multi Family for Sale in Chicago, Illinois. Browse all of Mashvisor’s Multi Family listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 1,076 Multi Family listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4836 S Dorchester Ave Chicago, IL Looking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Sing...	7 beds \| 3 baths \| N/A	$925,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 0.63% Airbnb Rental Income: $2540 Traditional Rental Income: $2659 Airbnb ROI: -0.22% Traditional ROI: 0.63%
3301 N Ozanam Ave Chicago, IL Excellent investment opportunity in a desirable Northwest Chicago neighborhood. This fully...	5 beds \| 3 baths \| N/A	$450,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 3.6% Airbnb Rental Income: $2474 Traditional Rental Income: $2870 Airbnb ROI: 1.23% Traditional ROI: 3.6%
8330 S Buffalo Ave Chicago, IL	9 beds \| 4 baths \| N/A	$399,999	Airbnb cash on cash: 0.52% Traditional cash on cash: 6.72% Airbnb Rental Income: $1322 Traditional Rental Income: $3237 Airbnb ROI: 0.52% Traditional ROI: 6.72%
33 E Division St Chicago, IL 33 E Division was originally constructed in 1881. This historic Potter Palmer Greystone si...	7 beds \| 7 baths \| N/A	$3,600,000	Airbnb cash on cash: -0.26% Traditional cash on cash: -0.94% Airbnb Rental Income: $5225 Traditional Rental Income: $1874 Airbnb ROI: -0.26% Traditional ROI: -0.94%
4736 S Prairie Ave Chicago, IL Bronzeville Exceptionally Striking, Classic Iconic Chicago, 3 unit 3 Story 1890's Greyston...	9 beds \| 6 baths \| N/A	$799,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 6.29% Airbnb Rental Income: $3680 Traditional Rental Income: $6787 Airbnb ROI: 1.04% Traditional ROI: 6.29%
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%
4149 N Wolcott Ave Chicago, IL Attractive 3 unit investment property in sought after North Center neighborhood. The uniqu...	4 beds \| 3 baths \| N/A	$995,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 1.14% Airbnb Rental Income: $2766 Traditional Rental Income: $2840 Airbnb ROI: 0.35% Traditional ROI: 1.14%
625 N Monticello Ave Chicago, IL Beautiful move-in ready brick 2-flat is a must see!! The 1ST Fl is duplexed into the lower...	9 beds \| 4 baths \| 1,795 sq.ft.	$409,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 6.23% Airbnb Rental Income: $3038 Traditional Rental Income: $3085 Airbnb ROI: 4.3% Traditional ROI: 6.23%
11317 S Edbrooke Ave Chicago, IL	5 beds \| 2 baths \| N/A	$179,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 10.71% Airbnb Rental Income: $1408 Traditional Rental Income: $2377 Airbnb ROI: 2.58% Traditional ROI: 10.71%
5760 S Wells St Chicago, IL	7 beds \| 3 baths \| 2,236 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.46% Airbnb Rental Income: $null Traditional Rental Income: $2374 Airbnb ROI: N/A Traditional ROI: 10.46%
6711 S Paxton Ave Chicago, IL Jumbo three flat, just steps off Jackson Park golf course, harbor and lakefront. Over 6000...	12 beds \| 6 baths \| N/A	$975,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 5.22% Airbnb Rental Income: $2503 Traditional Rental Income: $6337 Airbnb ROI: 0.32% Traditional ROI: 5.22%
7065 N Wolcott Ave Chicago, IL Amazing Greystone 2 flat with a finished lower level for additional living space in East R...	7 beds \| 5 baths \| N/A	$749,995	Airbnb cash on cash: 0.37% Traditional cash on cash: 5.4% Airbnb Rental Income: $2103 Traditional Rental Income: $5083 Airbnb ROI: 0.37% Traditional ROI: 5.4%
2037 N Tripp Ave Chicago, IL Turnkey investment opportunity in the Hermosa Neighborhood! This fully rented, income-prod...	4 beds \| 3 baths \| N/A	$449,900	Airbnb cash on cash: -1.12% Traditional cash on cash: 5.26% Airbnb Rental Income: $863 Traditional Rental Income: $3218 Airbnb ROI: -1.12% Traditional ROI: 5.26%
7917 S Maryland Ave Chicago, IL This Beautiful building was completely rehabbed in 2020. Gleaming hardwood floors througho...	6 beds \| 3 baths \| N/A	$399,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.95% Airbnb Rental Income: $1328 Traditional Rental Income: $2344 Airbnb ROI: 0.14% Traditional ROI: 3.95%
1907 W Irving Park Rd Chicago, IL HUD-Owned Opportunity in North Center! Classic brick two-flat offering outstanding potenti...	4 beds \| 2 baths \| N/A	$660,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.63% Airbnb Rental Income: $1956 Traditional Rental Income: $2347 Airbnb ROI: -0.84% Traditional ROI: 0.63%
7955 S Manistee Ave Chicago, IL	9 beds \| 3 baths \| N/A	$450,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 3.83% Airbnb Rental Income: $1264 Traditional Rental Income: $2570 Airbnb ROI: -0.21% Traditional ROI: 3.83%
2341 N Merrimac Ave Chicago, IL Brick 2 flat close to Riis Park and to the brick yard, 2nd floor with 2 bedrooms, separate...	5 beds \| 4 baths \| N/A	$489,000	Airbnb cash on cash: 2% Traditional cash on cash: 6.02% Airbnb Rental Income: $2681 Traditional Rental Income: $3881 Airbnb ROI: 2% Traditional ROI: 6.02%
3103 N Kedzie Ave Chicago, IL LOCATION - LOCATION - LOCATION - POTENTIAL - POTENTIAL - POTENTIAL in high-demand Logan Sq...	6 beds \| 3 baths \| N/A	$775,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.84% Airbnb Rental Income: $1974 Traditional Rental Income: $2991 Airbnb ROI: -0.28% Traditional ROI: 1.84%
2843 W Fletcher St Chicago, IL Recently rehabbed fully rented two-flat in the heart of Avondale near Logan Square. Update...	5 beds \| 2 baths \| 2,960 sq.ft.	$799,900	Airbnb cash on cash: -0.62% Traditional cash on cash: 1.02% Airbnb Rental Income: $1974 Traditional Rental Income: $2676 Airbnb ROI: -0.62% Traditional ROI: 1.02%
7348 S Vernon Ave Chicago, IL Come and view this large 4 unit building in sought after Park Manor! The building offers ...	6 beds \| 4 baths \| 3,976 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.67% Airbnb Rental Income: $null Traditional Rental Income: $3698 Airbnb ROI: N/A Traditional ROI: 6.67%
7142 S Lowe Ave Chicago, IL Affordable brick 2 flat featuring a 2 bedroom and 3 bedroom unit. Individual heat, and co...	5 beds \| 2 baths \| 2,442 sq.ft.	$189,999	Airbnb cash on cash: 2.66% Traditional cash on cash: 8.57% Airbnb Rental Income: $1388 Traditional Rental Income: $2035 Airbnb ROI: 2.66% Traditional ROI: 8.57%
2939 N Hamlin Ave Chicago, IL Looking for Multi Unit building in Avondale? Here's a Great Property for Investors/Rehabbe...	8 beds \| 4 baths \| N/A	$899,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.1% Airbnb Rental Income: $1480 Traditional Rental Income: $4007 Airbnb ROI: -0.44% Traditional ROI: 3.1%
6414 N Francisco Ave Chicago, IL Brand-new construction four-unit building in the heart of Rogers Park - thoughtfully desig...	12 beds \| 8 baths \| N/A	$2,150,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 2.05% Airbnb Rental Income: $176 Traditional Rental Income: $6356 Airbnb ROI: -1.16% Traditional ROI: 2.05%
5910 N Campbell Ave Chicago, IL WOW- This Arcadia Terrace 2-Flat is a real stunner. Each real 3-bedroom, 1-bath apartment,...	6 beds \| 2 baths \| N/A	$770,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.51% Airbnb Rental Income: $1745 Traditional Rental Income: $2485 Airbnb ROI: -0.19% Traditional ROI: 1.51%
8239 S Colfax Ave Chicago, IL Fantastic investment opportunity in the heart of South Chicago! This solid brick 4-unit bu...	12 beds \| 5 baths \| N/A	$399,900	Airbnb cash on cash: 0.05% Traditional cash on cash: 3.96% Airbnb Rental Income: $1264 Traditional Rental Income: $2328 Airbnb ROI: 0.05% Traditional ROI: 3.96%
2647 S Trumbull Ave Chicago, IL Solid brick 2-flat in the heart of South Lawndale/Little Village offering great potential ...	4 beds \| 2 baths \| N/A	$284,900	Airbnb cash on cash: 0.94% Traditional cash on cash: 6.39% Airbnb Rental Income: $1635 Traditional Rental Income: $2637 Airbnb ROI: 0.94% Traditional ROI: 6.39%
11221 S King Dr Chicago, IL Spacious 2,840 sq. ft. brick two-flat situated directly across from a park. Both units fea...	5 beds \| 2 baths \| N/A	$235,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 8.7% Airbnb Rental Income: $1408 Traditional Rental Income: $2417 Airbnb ROI: 2.25% Traditional ROI: 8.7%
5459 N Lovejoy Ave Chicago, IL Jefferson Park beauty with a large corner double lot. Unique legal two unit building: the ...	5 beds \| 3 baths \| 3,600 sq.ft.	$779,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $3432 Airbnb ROI: N/A Traditional ROI: 2.59%
8632 S Escanaba Ave Chicago, IL Well-kept 3-unit home in Chicago's Hyde Park. This giant 3-flat is priced to sell featuri...	6 beds \| 3 baths \| N/A	$329,999	Airbnb cash on cash: 0.47% Traditional cash on cash: 7.43% Airbnb Rental Income: $1264 Traditional Rental Income: $3023 Airbnb ROI: 0.47% Traditional ROI: 7.43%
3154 S May St Chicago, IL Newly Remodeled 4 unit solid brick building in the heart of Bridgeport. The building featu...	8 beds \| 4 baths \| N/A	$755,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 2.63% Airbnb Rental Income: $1675 Traditional Rental Income: $3302 Airbnb ROI: -0.35% Traditional ROI: 2.63%
132 W 113th St Chicago, IL A great 2 story 2 flat all brick building in the West Roseland area. Great investment opp...	6 beds \| 2 baths \| N/A	$202,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 8.73% Airbnb Rental Income: $1339 Traditional Rental Income: $2053 Airbnb ROI: 2.88% Traditional ROI: 8.73%
2442 N Lawndale Ave Chicago, IL Excelent investment!!!! let the tenants pay your mortgage, 3 Legal Units building plus fin...	9 beds \| 6 baths \| N/A	$1,349,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 3.69% Airbnb Rental Income: $1908 Traditional Rental Income: $6562 Airbnb ROI: -0.43% Traditional ROI: 3.69%
6140 S Aberdeen St Chicago, IL Investor opportunity in a classic Chicago greystone 2-flat with two occupied, updated 3-be...	6 beds \| 2 baths \| N/A	$285,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 7.07% Airbnb Rental Income: $2730 Traditional Rental Income: $2596 Airbnb ROI: 5.17% Traditional ROI: 7.07%
8143 S Colfax Ave Chicago, IL Price Improvement! As-is - 8143 S Colfax Ave, Chicago, IL 60617 4 Units \| 2 Beds / 1 Bath ...	8 beds \| 4 baths \| N/A	$369,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.36% Airbnb Rental Income: $1264 Traditional Rental Income: $1878 Airbnb ROI: 0.43% Traditional ROI: 3.36%
7037 S Washtenaw Ave Chicago, IL TURNKEY INVESTMENT. Nothing to do but collect rent. Can be packaged with 7027 S. Washte...	6 beds \| 2 baths \| 2,624 sq.ft.	$300,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 6.09% Airbnb Rental Income: $1360 Traditional Rental Income: $2452 Airbnb ROI: 0.75% Traditional ROI: 6.09%
3442 S Lowe Ave Chicago, IL Hot Bridgeport renovation opportunity priced for serious buyers, builders, and investors. ...	6 beds \| 4 baths \| N/A	$429,900	Airbnb cash on cash: -0.32% Traditional cash on cash: 6.22% Airbnb Rental Income: $1675 Traditional Rental Income: $3837 Airbnb ROI: -0.32% Traditional ROI: 6.22%
7638 S Carpenter St Chicago, IL Welcome to Auburn Gresham's newest gem in multi-family living! This meticulously crafted p...	6 beds \| 2 baths \| N/A	$399,900	Airbnb cash on cash: 0.57% Traditional cash on cash: 4.61% Airbnb Rental Income: $1388 Traditional Rental Income: $2485 Airbnb ROI: 0.57% Traditional ROI: 4.61%
3623 S Emerald Ave Chicago, IL LOCATION!! LOCATION!! Remodeled 2 unit solid brick building in the heart of Bridgeport. Th...	5 beds \| 3 baths \| 1,672 sq.ft.	$565,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 2.01% Airbnb Rental Income: $1675 Traditional Rental Income: $2206 Airbnb ROI: 0.12% Traditional ROI: 2.01%

Your search for investment property begins and ends here

Multi Family for Sale in Chicago, IL

4836 S Dorchester Ave

Chicago, IL

7 beds | 3 baths | N/A

$925,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $2540

Traditional Rental Income: $2659

Airbnb ROI: -0.22%

Traditional ROI: 0.63%

3301 N Ozanam Ave

Chicago, IL

5 beds | 3 baths | N/A

$450,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $2474

Traditional Rental Income: $2870

Airbnb ROI: 1.23%

Traditional ROI: 3.6%

8330 S Buffalo Ave

Chicago, IL

9 beds | 4 baths | N/A

$399,999

Airbnb cash on cash: 0.52%

Traditional cash on cash: 6.72%

Airbnb Rental Income: $1322

Traditional Rental Income: $3237

Airbnb ROI: 0.52%

Traditional ROI: 6.72%

33 E Division St

Chicago, IL

7 beds | 7 baths | N/A

$3,600,000

Airbnb cash on cash: -0.26%

Traditional cash on cash: -0.94%

Airbnb Rental Income: $5225

Traditional Rental Income: $1874

Airbnb ROI: -0.26%

Traditional ROI: -0.94%

4736 S Prairie Ave

Chicago, IL

9 beds | 6 baths | N/A

$799,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 6.29%

Airbnb Rental Income: $3680

Traditional Rental Income: $6787

Airbnb ROI: 1.04%

Traditional ROI: 6.29%

7749 S Muskegon Ave

Chicago, IL

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%

4149 N Wolcott Ave

Chicago, IL

4 beds | 3 baths | N/A

$995,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $2766

Traditional Rental Income: $2840

Airbnb ROI: 0.35%

Traditional ROI: 1.14%

625 N Monticello Ave

Chicago, IL

9 beds | 4 baths | 1,795 sq.ft.

$409,000

Airbnb cash on cash: 4.3%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $3038

Traditional Rental Income: $3085

Airbnb ROI: 4.3%