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 841 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: -1.07% Traditional cash on cash: 0.63% Airbnb Rental Income: $1661 Traditional Rental Income: $2659 Airbnb ROI: -1.07% Traditional ROI: 0.63%
8330 S Buffalo Ave Chicago, IL	9 beds \| 4 baths \| N/A	$399,999	Airbnb cash on cash: 0.12% Traditional cash on cash: 6.72% Airbnb Rental Income: $1139 Traditional Rental Income: $3237 Airbnb ROI: 0.12% 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: -0.29% Traditional cash on cash: -0.94% Airbnb Rental Income: $5094 Traditional Rental Income: $1874 Airbnb ROI: -0.29% 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: -2.06% Traditional cash on cash: 6.29% Airbnb Rental Income: $917 Traditional Rental Income: $6787 Airbnb ROI: -2.06% 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: 5.35% Traditional cash on cash: 2.18% Airbnb Rental Income: $3055 Traditional Rental Income: $1523 Airbnb ROI: 5.35% Traditional ROI: 2.18%
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: 3.72% Traditional cash on cash: 6.23% Airbnb Rental Income: $2772 Traditional Rental Income: $3085 Airbnb ROI: 3.72% Traditional ROI: 6.23%
11317 S Edbrooke Ave Chicago, IL	5 beds \| 2 baths \| N/A	$179,900	Airbnb cash on cash: 2.78% Traditional cash on cash: 10.71% Airbnb Rental Income: $1451 Traditional Rental Income: $2377 Airbnb ROI: 2.78% Traditional ROI: 10.71%
5760 S Wells St Chicago, IL	7 beds \| 3 baths \| 2,236 sq.ft.	$175,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 10.46% Airbnb Rental Income: $1411 Traditional Rental Income: $2374 Airbnb ROI: 2.14% 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: 0.17% Traditional cash on cash: 5.22% Airbnb Rental Income: $2340 Traditional Rental Income: $6337 Airbnb ROI: 0.17% Traditional ROI: 5.22%
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: 0.68% Traditional cash on cash: 5.26% Airbnb Rental Income: $1772 Traditional Rental Income: $3218 Airbnb ROI: 0.68% 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: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $2344 Airbnb ROI: N/A 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: -0.44% Traditional cash on cash: 0.63% Airbnb Rental Income: $2247 Traditional Rental Income: $2347 Airbnb ROI: -0.44% Traditional ROI: 0.63%
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	$499,999	Airbnb cash on cash: 0.74% Traditional cash on cash: 5.87% Airbnb Rental Income: $2006 Traditional Rental Income: $3881 Airbnb ROI: 0.74% Traditional ROI: 5.87%
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: 0.81% Traditional cash on cash: 8.57% Airbnb Rental Income: $986 Traditional Rental Income: $2035 Airbnb ROI: 0.81% 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: -0.42% Traditional cash on cash: 2.98% Airbnb Rental Income: $1522 Traditional Rental Income: $4007 Airbnb ROI: -0.42% Traditional ROI: 2.98%
3707 W Mclean Ave Chicago, IL Legal 4 flat on a DOUBLE LOT in Desirable Logan Square! Absolute moneymaker perfect for se...	9 beds \| 4 baths \| N/A	$799,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.4% Airbnb Rental Income: $1968 Traditional Rental Income: $4147 Airbnb ROI: -0.22% Traditional ROI: 3.4%
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	$2,250,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 1.91% Airbnb Rental Income: $262 Traditional Rental Income: $6356 Airbnb ROI: -1.12% Traditional ROI: 1.91%
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	$774,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.5% Airbnb Rental Income: $1619 Traditional Rental Income: $2485 Airbnb ROI: -0.34% Traditional ROI: 1.5%
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: 0.04% Traditional cash on cash: 3.96% Airbnb Rental Income: $1257 Traditional Rental Income: $2328 Airbnb ROI: 0.04% Traditional ROI: 3.96%
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	$239,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 8.54% Airbnb Rental Income: $1451 Traditional Rental Income: $2417 Airbnb ROI: 2.36% Traditional ROI: 8.54%
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: 0.46% Traditional cash on cash: 7.43% Airbnb Rental Income: $1257 Traditional Rental Income: $3023 Airbnb ROI: 0.46% 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	$785,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 2.49% Airbnb Rental Income: $1389 Traditional Rental Income: $3302 Airbnb ROI: -0.7% Traditional ROI: 2.49%
5400 W Augusta Blvd Chicago, IL Excellent investment opportunity in Chicago with great cash-flow potential! This 2-unit re...	8 beds \| 4 baths \| N/A	$425,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 7.83% Airbnb Rental Income: $1306 Traditional Rental Income: $4033 Airbnb ROI: -0.04% Traditional ROI: 7.83%
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	$214,900	Airbnb cash on cash: 2.96% Traditional cash on cash: 8.2% Airbnb Rental Income: $1411 Traditional Rental Income: $2053 Airbnb ROI: 2.96% Traditional ROI: 8.2%
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: -0.39% Traditional cash on cash: 3.69% Airbnb Rental Income: $1968 Traditional Rental Income: $6562 Airbnb ROI: -0.39% 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: 6.21% Traditional cash on cash: 6.09% Airbnb Rental Income: $3387 Traditional Rental Income: $2596 Airbnb ROI: 6.21% Traditional ROI: 6.09%
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: 0.42% Traditional cash on cash: 3.36% Airbnb Rental Income: $1257 Traditional Rental Income: $1878 Airbnb ROI: 0.42% Traditional ROI: 3.36%
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: -0.91% Traditional cash on cash: 6.22% Airbnb Rental Income: $1389 Traditional Rental Income: $3837 Airbnb ROI: -0.91% Traditional ROI: 6.22%
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: -0.34% Traditional cash on cash: 2.01% Airbnb Rental Income: $1389 Traditional Rental Income: $2206 Airbnb ROI: -0.34% Traditional ROI: 2.01%
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: 1.48% Traditional cash on cash: 1.74% Airbnb Rental Income: $2280 Traditional Rental Income: $1829 Airbnb ROI: 1.48% Traditional ROI: 1.74%
151 N Long Ave Chicago, IL Fantastic opportunity to own a fully gut-renovated, all-brick 2-flat in Chicago! Perfect f...	6 beds \| 2 baths \| N/A	$500,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 4.06% Airbnb Rental Income: $3898 Traditional Rental Income: $2849 Airbnb ROI: 4.51% Traditional ROI: 4.06%
6938 S Peoria St Chicago, IL WOW! THIS IS A GREAT OPPORTUNITY FOR THE SMART BUYER TO PUT THEIR TAX MONEY TO GOOD USE. ...	6 beds \| 2 baths \| 3,210 sq.ft.	$335,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 4.98% Airbnb Rental Income: $3387 Traditional Rental Income: $2405 Airbnb ROI: 5.71% Traditional ROI: 4.98%
2812 S Trumbull Ave Chicago, IL	4 beds \| 2 baths \| N/A	$429,900	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.85% Airbnb Rental Income: $2687 Traditional Rental Income: $1886 Airbnb ROI: 3.26% Traditional ROI: 2.85%
2655 N Marmora Ave Chicago, IL SOLD-AS-IS I am very spacious inside I can accommodate plenty of your guests and more....	7 beds \| 3 baths \| 1,920 sq.ft.	$440,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 4.92% Airbnb Rental Income: $2006 Traditional Rental Income: $2943 Airbnb ROI: 1.37% Traditional ROI: 4.92%
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.	$355,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 2.89% Airbnb Rental Income: $3387 Traditional Rental Income: $2139 Airbnb ROI: 4.38% Traditional ROI: 2.89%
8045 S Carpenter St Chicago, IL Investor opportunity! This property is being offered at Public Auction on 07-09-2019. Visi...	8 beds \| 4 baths \| 4,977 sq.ft.	$249,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 11.53% Airbnb Rental Income: $1412 Traditional Rental Income: $3479 Airbnb ROI: 0.94% Traditional ROI: 11.53%
4935 W Henderson St Chicago, IL Solid, well maintained brick 2-flat in hot Portage Park! Original hardwood floors on 1st &...	5 beds \| 3 baths \| 2,208 sq.ft.	$537,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 4% Airbnb Rental Income: $3228 Traditional Rental Income: $3182 Airbnb ROI: 2.64% Traditional ROI: 4%
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: 1.33% Traditional cash on cash: 3.88% Airbnb Rental Income: $1666 Traditional Rental Income: $2076 Airbnb ROI: 1.33% 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: 0.76% Traditional cash on cash: 3.17% Airbnb Rental Income: $1504 Traditional Rental Income: $2078 Airbnb ROI: 0.76% Traditional ROI: 3.17%

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: -1.07%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $1661

Traditional Rental Income: $2659

Airbnb ROI: -1.07%

Traditional ROI: 0.63%

8330 S Buffalo Ave

Chicago, IL

9 beds | 4 baths | N/A

$399,999

Airbnb cash on cash: 0.12%

Traditional cash on cash: 6.72%

Airbnb Rental Income: $1139

Traditional Rental Income: $3237

Airbnb ROI: 0.12%

Traditional ROI: 6.72%

33 E Division St

Chicago, IL

7 beds | 7 baths | N/A

$3,600,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: -0.94%

Airbnb Rental Income: $5094

Traditional Rental Income: $1874

Airbnb ROI: -0.29%

Traditional ROI: -0.94%

4736 S Prairie Ave

Chicago, IL

9 beds | 6 baths | N/A

$799,000

Airbnb cash on cash: -2.06%

Traditional cash on cash: 6.29%

Airbnb Rental Income: $917

Traditional Rental Income: $6787

Airbnb ROI: -2.06%

Traditional ROI: 6.29%

7749 S Muskegon Ave

Chicago, IL

10 beds | 3 baths | 1,000 sq.ft.

$279,900

Airbnb cash on cash: 5.35%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $3055

Traditional Rental Income: $1523

Airbnb ROI: 5.35%

Traditional ROI: 2.18%

625 N Monticello Ave

Chicago, IL

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

$409,000

Airbnb cash on cash: 3.72%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $2772

Traditional Rental Income: $3085

Airbnb ROI: 3.72%

Traditional ROI: 6.23%

11317 S Edbrooke Ave

Chicago, IL

5 beds | 2 baths | N/A

$179,900

Airbnb cash on cash: 2.78%

Traditional cash on cash: 10.71%

Airbnb Rental Income: $1451

Traditional Rental Income: $2377

Airbnb ROI: 2.78%

Traditional ROI: 10.71%

5760 S Wells St

Chicago, IL

7 beds | 3 baths | 2,236 sq.ft.

$175,000

Airbnb cash on cash: 2.14%

Traditional cash on cash: 10.46%

Airbnb Rental Income: $1411

Traditional Rental Income: $2374

Airbnb ROI: 2.14%