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 550 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
4004 N Clarendon Avenue #1 Chicago, IL Welcome to this stunning home featuring beautiful vintage details and millwork with modern...	4 beds \| 2 baths \| 2,750 sq.ft.	$639,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $3310 Airbnb ROI: N/A Traditional ROI: 3.09%
4836 S Dorchester Avenue Chicago, IL Stunning 3-Flat Georgian Style Multi-Family Building in the Hyde Park/Kenwood Community, w...	7 beds \| 5 baths \| N/A	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.55% Airbnb Rental Income: $null Traditional Rental Income: $2659 Airbnb ROI: N/A Traditional ROI: 0.55%
1671 W Farwell Avenue #2N Chicago, IL You will fall in love with this bright and spacious 3-bed, 2-bath duplex offering two ful...	3 beds \| 2 baths \| 1,465 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $2383 Airbnb ROI: N/A Traditional ROI: 4.67%
2922 N Sheffield Avenue #3 Chicago, IL This sophisticated 4-bedroom, 2.5-bath residence, ideally situated in the heart of Lakevie...	4 beds \| 3 baths \| 2,800 sq.ft.	$1,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.15% Airbnb Rental Income: $null Traditional Rental Income: $3557 Airbnb ROI: N/A Traditional ROI: 0.15%
1555 N Talman Avenue #3F Chicago, IL Step into sunlight and style in this stunning corner duplex penthouse. Soaring windows flo...	3 beds \| 3 baths \| N/A	$590,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $3028 Airbnb ROI: N/A Traditional ROI: 2.88%
1210 N ASTOR Street #1A Chicago, IL Vintage character and charm enhanced with complementary high end finishes, this impeccably...	4 beds \| 4 baths \| 3,213 sq.ft.	$1,190,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.45% Airbnb Rental Income: $null Traditional Rental Income: $3956 Airbnb ROI: N/A Traditional ROI: 0.45%
7223 N Oakley Avenue #1E Chicago, IL Spacious and inviting 2 bed, 2 bath duplex-down condo in the heart of West Ridge! This hom...	2 beds \| 2 baths \| 1,600 sq.ft.	$295,800	Airbnb cash on cash: N/A Traditional cash on cash: 5.67% Airbnb Rental Income: $null Traditional Rental Income: $2479 Airbnb ROI: N/A Traditional ROI: 5.67%
4244 S Prairie Avenue Chicago, IL	2 beds \| 3 baths \| N/A	$899,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.06% Airbnb Rental Income: $null Traditional Rental Income: $2501 Airbnb ROI: N/A Traditional ROI: 1.06%
5221 S Carpenter Street Chicago, IL Beautifully maintained frame 2-flat on a quiet, school-zone block with a spacious backyard...	4 beds \| 2 baths \| 1,768 sq.ft.	$330,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.06% Airbnb Rental Income: $null Traditional Rental Income: $2441 Airbnb ROI: N/A Traditional ROI: 6.06%
817 W 54th Street Chicago, IL Solid Brick Two-Unit Income Property in New City! This well-maintained building features t...	6 beds \| 2 baths \| N/A	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.55% Airbnb Rental Income: $null Traditional Rental Income: $2346 Airbnb ROI: N/A Traditional ROI: 6.55%
6017 W Montrose Avenue Chicago, IL This is an exceptional opportunity to own a well-maintained brick two-unit building with a...	6 beds \| 2 baths \| N/A	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.86% Airbnb Rental Income: $null Traditional Rental Income: $2676 Airbnb ROI: N/A Traditional ROI: 1.86%
4702 W Ohio Street Chicago, IL Welcome to this wonderful 2 flat in the developing neighborhood of Austin. This fenced in ...	4 beds \| 2 baths \| N/A	$449,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $2545 Airbnb ROI: N/A Traditional ROI: 3.75%
1350 N Claremont Avenue #1 Chicago, IL Exceptional Wicker Park Newer Construction offers Mammoth Expansive three-bedroom, three f...	3 beds \| 3 baths \| N/A	$839,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.44% Airbnb Rental Income: $null Traditional Rental Income: $3167 Airbnb ROI: N/A Traditional ROI: 1.44%
4614 N Springfield Avenue Chicago, IL Beautiful Chicago Multi-unit with 120,000 worth of updates completed by owner when he was ...	6 beds \| 3 baths \| N/A	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $2687 Airbnb ROI: N/A Traditional ROI: 2.47%
3700 N Lake Shore Drive #307 Chicago, IL Spectacular Lakeview 2 bed, 2.5 bath duplex located directly on Lake Shore Drive, offering...	2 beds \| 3 baths \| 1,600 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.46% Airbnb Rental Income: $null Traditional Rental Income: $2740 Airbnb ROI: N/A Traditional ROI: 2.46%
200 E Delaware Place #8-9C Chicago, IL To quote Oprah, "You get a CAR..." (with home sale)! Give yourself the ultimate holiday up...	4 beds \| 4 baths \| N/A	$1,299,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.53% Airbnb Rental Income: $null Traditional Rental Income: $4025 Airbnb ROI: N/A Traditional ROI: 0.53%
2569 S emerald Avenue Chicago, IL location ,location ,location !! 3 Flat Brick house ,each unit have 3 bed 2 bath , central ...	9 beds \| 6 baths \| N/A	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.41% Airbnb Rental Income: $null Traditional Rental Income: $2061 Airbnb ROI: N/A Traditional ROI: 0.41%
4838 W Fulton Street Chicago, IL Up and coming Austin area cash cow! Sold As-Is. Remodeled 1st floor in 2025. New roof in 2...	5 beds \| 2 baths \| N/A	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $2326 Airbnb ROI: N/A Traditional ROI: 4.98%
6437 S Marshfield Ave Chicago, IL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	7 beds \| 3 baths \| 1,076 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.97% Airbnb Rental Income: $null Traditional Rental Income: $1226 Airbnb ROI: N/A Traditional ROI: 1.97%
6932 S Green Street Chicago, IL Welcome to this beautifully updated multi-unit property in the heart of Englewood. Fully r...	7 beds \| 2 baths \| N/A	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.92% Airbnb Rental Income: $null Traditional Rental Income: $2493 Airbnb ROI: N/A Traditional ROI: 4.92%
5417 W Van Buren Street Chicago, IL Great opportunity to own a rental property! All brick two unit with finished basement and...	6 beds \| 2 baths \| N/A	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.55% Airbnb Rental Income: $null Traditional Rental Income: $3549 Airbnb ROI: N/A Traditional ROI: 9.55%
1204 N Spaulding Avenue #1N Chicago, IL Experience modern Chicago living in this stunning, sun-drenched duplex-down condo just ste...	4 beds \| 3 baths \| 2,317 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $3333 Airbnb ROI: N/A Traditional ROI: 2.97%
7965 S Phillips Avenue Chicago, IL Explore a distinctive investment opportunity nestled in the heart of Chicago's vibrant and...	9 beds \| 7 baths \| N/A	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.2% Airbnb Rental Income: $null Traditional Rental Income: $2332 Airbnb ROI: N/A Traditional ROI: 3.2%
4551 S MICHIGAN Avenue #B Chicago, IL Spacious 3BR, 2.5BA Duplex, Open floor plan , Hardwood floors, Newer carpet upper level an...	3 beds \| 3 baths \| 1,545 sq.ft.	$259,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $2043 Airbnb ROI: N/A Traditional ROI: 5.94%
3247 W Berteau Ave Chicago, IL 3247 W Berteau Ave, Chicago, IL 60618 \| Multi Family	4 beds \| 3 baths \| N/A	$630,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $2718 Airbnb ROI: N/A Traditional ROI: 2.17%
3912 W Congress Parkway Chicago, IL Legal 2 Unit with finished duplex-down basement in HOT Garfield Park! ** This spacious 202...	7 beds \| 5 baths \| N/A	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $2671 Airbnb ROI: N/A Traditional ROI: 3.39%
2925 S SHIELDS Avenue Chicago, IL 2 flats in prime Bridgeport location. 4 bedrooms & 1 full bath on first floor ,4 bedrooms ...	8 beds \| 3 baths \| N/A	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.46% Airbnb Rental Income: $null Traditional Rental Income: $2228 Airbnb ROI: N/A Traditional ROI: 1.46%
8822 S Exchange Avenue Chicago, IL Calling all Landlords!!! Looking for an income property? Here's a 3-unit building! FULLY O...	11 beds \| 5 baths \| N/A	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.31% Airbnb Rental Income: $null Traditional Rental Income: $2179 Airbnb ROI: N/A Traditional ROI: 9.31%
10230 S Yates Boulevard Chicago, IL Calling all Landlords!!! Looking for an income property? Here's a 3-unit building! TENANT ...	8 beds \| 3 baths \| N/A	$191,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.68% Airbnb Rental Income: $null Traditional Rental Income: $2238 Airbnb ROI: N/A Traditional ROI: 9.68%
529 N Wood St Chicago, IL	3 beds \| 2 baths \| 680 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.94% Airbnb Rental Income: $null Traditional Rental Income: $1746 Airbnb ROI: N/A Traditional ROI: 0.94%
1823 W Cullerton St Chicago, IL	6 beds \| 4 baths \| 666 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.51% Airbnb Rental Income: $null Traditional Rental Income: $1734 Airbnb ROI: N/A Traditional ROI: 2.51%
2651 W Augusta Boulevard #3 Chicago, IL JUST COMPLETED! FOR LIMITED TIME, DEVELOPER/PREFERRED LENDER ARE OFFERING A 1% BUY DOWN ON...	2 beds \| 2 baths \| 1,600 sq.ft.	$749,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.06% Airbnb Rental Income: $null Traditional Rental Income: $2496 Airbnb ROI: N/A Traditional ROI: 2.06%

Your search for investment property begins and ends here

Multi Family for Sale in Chicago, IL

4004 N Clarendon Avenue #1

Chicago, IL

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

$639,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.09%

Airbnb Rental Income: $null

Traditional Rental Income: $3310

Airbnb ROI: N/A

Traditional ROI: 3.09%

4836 S Dorchester Avenue

Chicago, IL

7 beds | 5 baths | N/A

$975,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.55%

Airbnb Rental Income: $null

Traditional Rental Income: $2659

Airbnb ROI: N/A

Traditional ROI: 0.55%

1671 W Farwell Avenue #2N

Chicago, IL

3 beds | 2 baths | 1,465 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.67%

Airbnb Rental Income: $null

Traditional Rental Income: $2383

Airbnb ROI: N/A

Traditional ROI: 4.67%

2922 N Sheffield Avenue #3

Chicago, IL

4 beds | 3 baths | 2,800 sq.ft.

$1,495,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.15%

Airbnb Rental Income: $null

Traditional Rental Income: $3557

Airbnb ROI: N/A

Traditional ROI: 0.15%

1555 N Talman Avenue #3F

Chicago, IL

3 beds | 3 baths | N/A

$590,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.88%

Airbnb Rental Income: $null

Traditional Rental Income: $3028

Airbnb ROI: N/A

Traditional ROI: 2.88%

1210 N ASTOR Street #1A

Chicago, IL

4 beds | 4 baths | 3,213 sq.ft.

$1,190,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.45%

Airbnb Rental Income: $null

Traditional Rental Income: $3956

Airbnb ROI: N/A

Traditional ROI: 0.45%

7223 N Oakley Avenue #1E

Chicago, IL

2 beds | 2 baths | 1,600 sq.ft.

$295,800

Airbnb cash on cash: N/A

Traditional cash on cash: 5.67%

Airbnb Rental Income: $null

Traditional Rental Income: $2479

Airbnb ROI: N/A

Traditional ROI: 5.67%

4244 S Prairie Avenue

Chicago, IL

2 beds | 3 baths | N/A

$899,999

Airbnb cash on cash: N/A

Traditional cash on cash: 1.06%

Airbnb Rental Income: $null

Traditional Rental Income: $2501

Airbnb ROI: N/A