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 677 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: N/A Traditional cash on cash: 0.63% Airbnb Rental Income: $null Traditional Rental Income: $2659 Airbnb ROI: N/A 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: 0.79% Traditional cash on cash: 3.6% Airbnb Rental Income: $2250 Traditional Rental Income: $2870 Airbnb ROI: 0.79% Traditional ROI: 3.6%
8330 S Buffalo Ave Chicago, IL	9 beds \| 4 baths \| N/A	$399,999	Airbnb cash on cash: 1.32% Traditional cash on cash: 6.72% Airbnb Rental Income: $1680 Traditional Rental Income: $3237 Airbnb ROI: 1.32% 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: -0.52% Traditional cash on cash: -0.94% Airbnb Rental Income: $4155 Traditional Rental Income: $1874 Airbnb ROI: -0.52% 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: -1.68% Traditional cash on cash: 6.29% Airbnb Rental Income: $1255 Traditional Rental Income: $6787 Airbnb ROI: -1.68% Traditional ROI: 6.29%
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: 0.43% Traditional cash on cash: 6.23% Airbnb Rental Income: $1261 Traditional Rental Income: $3085 Airbnb ROI: 0.43% Traditional ROI: 6.23%
11317 S Edbrooke Ave Chicago, IL	5 beds \| 2 baths \| N/A	$189,900	Airbnb cash on cash: 2.17% Traditional cash on cash: 10.11% Airbnb Rental Income: $1360 Traditional Rental Income: $2377 Airbnb ROI: 2.17% Traditional ROI: 10.11%
7224 S Saint Lawrence Ave Chicago, IL Exceptional investment opportunity at this yellow brick 2 unit located in the heart of the...	6 beds \| 2 baths \| N/A	$330,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 3.44% Airbnb Rental Income: $1136 Traditional Rental Income: $1786 Airbnb ROI: 0.12% Traditional ROI: 3.44%
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: 0.3% Traditional cash on cash: 5.22% Airbnb Rental Income: $2473 Traditional Rental Income: $6337 Airbnb ROI: 0.3% Traditional ROI: 5.22%
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: 0.25% Traditional cash on cash: 3.95% Airbnb Rental Income: $1376 Traditional Rental Income: $2344 Airbnb ROI: 0.25% Traditional ROI: 3.95%
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: 1.07% Traditional cash on cash: 8.57% Airbnb Rental Income: $1044 Traditional Rental Income: $2035 Airbnb ROI: 1.07% 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	$925,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 2.98% Airbnb Rental Income: $2685 Traditional Rental Income: $4007 Airbnb ROI: 0.71% Traditional ROI: 2.98%
1732 W Wallen Ave Chicago, IL	6 beds \| 3 baths \| N/A	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.94% Airbnb Rental Income: $null Traditional Rental Income: $3396 Airbnb ROI: N/A Traditional ROI: 2.94%
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: -0.15% Traditional cash on cash: 3.96% Airbnb Rental Income: $1172 Traditional Rental Income: $2328 Airbnb ROI: -0.15% 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: 6.42% Traditional cash on cash: 6.39% Airbnb Rental Income: $3401 Traditional Rental Income: $2637 Airbnb ROI: 6.42% Traditional ROI: 6.39%
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	$785,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 2.49% Airbnb Rental Income: $1233 Traditional Rental Income: $3302 Airbnb ROI: -0.87% Traditional ROI: 2.49%
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	$234,900	Airbnb cash on cash: 2.28% Traditional cash on cash: 7.43% Airbnb Rental Income: $1316 Traditional Rental Income: $2053 Airbnb ROI: 2.28% Traditional ROI: 7.43%
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: -0.54% Traditional cash on cash: 3.69% Airbnb Rental Income: $1730 Traditional Rental Income: $6562 Airbnb ROI: -0.54% 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	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.09% Airbnb Rental Income: $null Traditional Rental Income: $2596 Airbnb ROI: N/A Traditional ROI: 6.09%
2541 W Argyle St Chicago, IL THIS MAGNIFICENT BRICK MULTI-UNIT SITS ON AN OVERSIZED (30X160) CHICAGO LOT NESTLED ON A Q...	6 beds \| 3 baths \| N/A	$950,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.77% Airbnb Rental Income: $2228 Traditional Rental Income: $3240 Airbnb ROI: -0.01% Traditional ROI: 1.77%
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: 0.21% Traditional cash on cash: 3.36% Airbnb Rental Income: $1172 Traditional Rental Income: $1878 Airbnb ROI: 0.21% Traditional ROI: 3.36%
8232 S Marshfield Ave Chicago, IL Looking for income property? Look no further. Don't miss out on this gem and it's oversize...	6 beds \| 2 baths \| N/A	$300,000	Airbnb cash on cash: 7.7% Traditional cash on cash: 6.12% Airbnb Rental Income: $3640 Traditional Rental Income: $2399 Airbnb ROI: 7.7% Traditional ROI: 6.12%
1604 S Ridgeway Ave Chicago, IL WELCOME TO YOUR NEW HOME! UPDATED THREE FLAT WITH EACH SPACIOUS UNIT OFFERING 3 BEDROOMS, ...	9 beds \| 6 baths \| N/A	$475,000	Airbnb cash on cash: 1% Traditional cash on cash: 1.74% Airbnb Rental Income: $2026 Traditional Rental Income: $1829 Airbnb ROI: 1% Traditional ROI: 1.74%
5759 S Campbell Ave Chicago, IL BRICK TWO FLAT IN GAGE PARK ON A CORNER LOT. EACH UNIT HAS 3 BEDS 1 BATH, SPACIOUS LIVING ...	9 beds \| 3 baths \| N/A	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.81% Airbnb Rental Income: $null Traditional Rental Income: $3133 Airbnb ROI: N/A Traditional ROI: 6.81%
2455 N Sawyer Ave Chicago, IL All-brick three-flat on a wide corner lot in the heart of Logan Square - well-maintained, ...	7 beds \| 4 baths \| N/A	$1,249,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 1.56% Airbnb Rental Income: $1730 Traditional Rental Income: $4384 Airbnb ROI: -1.14% Traditional ROI: 1.56%
3600 S Marshfield Ave Chicago, IL Excellent 3-Unit Investment Opportunity in Prime Chicago Location!Well-maintained multi-un...	9 beds \| 6 baths \| N/A	$628,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 8.56% Airbnb Rental Income: $1519 Traditional Rental Income: $6389 Airbnb ROI: -0.5% Traditional ROI: 8.56%
2812 S Trumbull Ave Chicago, IL	4 beds \| 2 baths \| N/A	$439,900	Airbnb cash on cash: 4.61% Traditional cash on cash: 2.76% Airbnb Rental Income: $3401 Traditional Rental Income: $1886 Airbnb ROI: 4.61% Traditional ROI: 2.76%
6016 S Carpenter St Chicago, IL Alert! The reserve price is being revealed on this property so you will know the bid to b...	5 beds \| 2 baths \| 2,078 sq.ft.	$367,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $2139 Airbnb ROI: N/A Traditional ROI: 2.68%
848 N Latrobe Ave Chicago, IL Welcome to this beautifully reimagined two-unit property in the heart of the Austin neighb...	5 beds \| 2 baths \| N/A	$499,990	Airbnb cash on cash: -0.29% Traditional cash on cash: 4.5% Airbnb Rental Income: $1292 Traditional Rental Income: $3124 Airbnb ROI: -0.29% Traditional ROI: 4.5%
2425 N Geneva Ter Chicago, IL 2425 North Geneva Terrace is a 4 unit greystone apartment building. The property features ...	14 beds \| 7 baths \| 5,936 sq.ft.	$3,000,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.41% Airbnb Rental Income: $3346 Traditional Rental Income: $5983 Airbnb ROI: -0.81% Traditional ROI: 0.41%
9108 S Loomis St Chicago, IL Well maintained owner occupied 2 unit building. Both units are 2 bedrooms and 1 bathroom. ...	4 beds \| 2 baths \| 2,466 sq.ft.	$335,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 4.72% Airbnb Rental Income: $1010 Traditional Rental Income: $2235 Airbnb ROI: -0.31% Traditional ROI: 4.72%
6624 S Rhodes Ave Chicago, IL Great investment opportunity available here with this 2 unit historic Grey Stone building ...	6 beds \| 2 baths \| 2,336 sq.ft.	$365,000	Airbnb cash on cash: 6.99% Traditional cash on cash: 3.88% Airbnb Rental Income: $3996 Traditional Rental Income: $2076 Airbnb ROI: 6.99% Traditional ROI: 3.88%
6406 S Maplewood Ave Chicago, IL FULL GUT RENOVATION ON THIS 2 FLAT MULTI-FAMILY UNIT CONSISTING OF 3 BEDROOMS; MASTER BEDR...	14 beds \| 2 baths \| 2,150 sq.ft.	$450,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 3.17% Airbnb Rental Income: $1632 Traditional Rental Income: $2078 Airbnb ROI: 1.02% Traditional ROI: 3.17%
3003 S Kenneth Ave Chicago, IL Two unit brick building on a spacious corner double lot! 2 car garage with driveway. Each ...	5 beds \| 3 baths \| N/A	$299,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 5.75% Airbnb Rental Income: $1876 Traditional Rental Income: $2556 Airbnb ROI: 1.56% Traditional ROI: 5.75%
5930 S King Dr Chicago, IL Prime Washington Park development opportunity offering scale, flexibility, and park-front ...	12 beds \| 8 baths \| N/A	$550,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 7.24% Airbnb Rental Income: $1316 Traditional Rental Income: $5414 Airbnb ROI: -1.52% Traditional ROI: 7.24%
4040 S Wabash Ave Chicago, IL	10 beds \| 5 baths \| N/A	$779,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 3.84% Airbnb Rental Income: $1338 Traditional Rental Income: $4167 Airbnb ROI: -0.63% Traditional ROI: 3.84%
727 N Springfield Ave Chicago, IL Two Brick Flat in Humboldt Park 1/2 block from Chicago Ave. 3 electric meters, Circuit bre...	5 beds \| 2 baths \| N/A	$265,000	Airbnb cash on cash: 5.67% Traditional cash on cash: 8.61% Airbnb Rental Income: $2467 Traditional Rental Income: $2602 Airbnb ROI: 5.67% Traditional ROI: 8.61%
11146 S Vernon Ave Chicago, IL * MULTIPLE OFFERS, Offers due Friday at noon* Bring your Investor clients to this Turnkey...	9 beds \| 3 baths \| N/A	$489,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 4.08% Airbnb Rental Income: $740 Traditional Rental Income: $2853 Airbnb ROI: -1.22% Traditional ROI: 4.08%
8125 S Evans Ave Chicago, IL Welcome to a versatile and income-generating multi-family mult-unit situated in a cozy, we...	6 beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 6.92% Airbnb Rental Income: $1376 Traditional Rental Income: $2833 Airbnb ROI: 0.79% Traditional ROI: 6.92%
5515 S Princeton Ave Chicago, IL MULTI-FAMILY 2 FLAT W/ FULL FINISHED BASEMENT!! CORNER LOT W/ DIRECT ACCESS TO EXPRESSWAY!...	6 beds \| 2 baths \| 2,094 sq.ft.	$165,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 10.94% Airbnb Rental Income: $1316 Traditional Rental Income: $2218 Airbnb ROI: 2.61% Traditional ROI: 10.94%

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: N/A

Traditional cash on cash: 0.63%

Airbnb Rental Income: $null

Traditional Rental Income: $2659

Airbnb ROI: N/A

Traditional ROI: 0.63%

3301 N Ozanam Ave

Chicago, IL

5 beds | 3 baths | N/A

$450,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $2250

Traditional Rental Income: $2870

Airbnb ROI: 0.79%

Traditional ROI: 3.6%

8330 S Buffalo Ave

Chicago, IL

9 beds | 4 baths | N/A

$399,999

Airbnb cash on cash: 1.32%

Traditional cash on cash: 6.72%

Airbnb Rental Income: $1680

Traditional Rental Income: $3237

Airbnb ROI: 1.32%

Traditional ROI: 6.72%

33 E Division St

Chicago, IL

7 beds | 7 baths | N/A

$3,600,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: -0.94%

Airbnb Rental Income: $4155

Traditional Rental Income: $1874

Airbnb ROI: -0.52%

Traditional ROI: -0.94%

4736 S Prairie Ave

Chicago, IL

9 beds | 6 baths | N/A

$799,000

Airbnb cash on cash: -1.68%

Traditional cash on cash: 6.29%

Airbnb Rental Income: $1255

Traditional Rental Income: $6787

Airbnb ROI: -1.68%

Traditional ROI: 6.29%

625 N Monticello Ave

Chicago, IL

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

$409,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $1261

Traditional Rental Income: $3085

Airbnb ROI: 0.43%

Traditional ROI: 6.23%

11317 S Edbrooke Ave

Chicago, IL

5 beds | 2 baths | N/A

$189,900

Airbnb cash on cash: 2.17%

Traditional cash on cash: 10.11%

Airbnb Rental Income: $1360

Traditional Rental Income: $2377

Airbnb ROI: 2.17%

Traditional ROI: 10.11%

7224 S Saint Lawrence Ave

Chicago, IL

6 beds | 2 baths | N/A

$330,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $1136

Traditional Rental Income: $1786

Airbnb ROI: 0.12%