Chicago, IL Short term rental properties for sale

Updated: Feb 27

Six-Unit Multifamily Investment Opportunity

8624 S Maryland Avenue, Chicago, IL 60619

$595,000

0.07 AC lot

6‑unit multi‑family property built in 1959 with brick construction and a composition roof
Total of 10 bedrooms and 6 bathrooms, with each unit featuring its own kitchen, living room, and dining area
Two units currently leased for immediate rental income
Three units operating as active Airbnb rentals; one unit already secured for 160 rental days
Six dedicated parking spaces for residents and guests

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Updated: Jun 10

Two-Unit Townhome-Style Multifamily

2170 N Lincoln Avenue, Chicago, IL 60614

$1,249,000

Rarely available Lincoln Park townhome‑style 2‑unit property steps from Oz Park
Owner’s duplex unit features 3 bedrooms, all on one level, plus 2 full baths
Open kitchen with quartz counters, custom backsplash, stainless steel appliances, and 42‑inch cabinets; leads to dining area and private deck
Updated baths with natural stone and tile; hardwood floors throughout; living room fireplace
In‑unit washer and dryer plus central forced‑air heat and natural gas heating; public sewer

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Two-Unit Multifamily Property

3749 S Union Avenue, Chicago, IL 60609

$555,555

0.07 AC lot

Two-unit building with updated roof and major mechanicals, supported by separate utilities for each residence.

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Beverly Mixed-Use Investment Opportunity

2022 W 95th Street, Chicago, IL 60643

$945,000

6,250 sqft

Renovated Chicago mixed-use building with restaurant, office, and residential units.

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Commercial Live-Work Loft Property

815 N MILWAUKEE Avenue, Chicago, IL 60622

$1,450,000

0.06 AC lot

Fully furnished standalone loft with commercial zoning, dual-zoned HVAC, unfinished basement, and unfinished rooftop.

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Renovated 3-Flat with Short-Term Unit

6835 S Clyde Avenue, Chicago, IL 60649

$749,900

0.08 AC lot

Turnkey all-brick triplex with three 3BR/2BA units, a full basement, and one unit currently operating as a short-term rental.

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Two-Unit Brick Multifamily Building

5632 S Wabash Avenue, Chicago, IL 60637

$299,999

0.09 AC lot

Well-maintained two-unit brick building with in-unit laundry and spacious three-bedroom layouts.

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Renovated Two-Unit Multifamily

1520 N Campbell Avenue, Chicago, IL 60622

$875,000

Renovated two-unit building with separate HVAC and utilities, plus a new oversized two-car garage and deck.

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Legal Three-Unit Building with Multiple HVAC

2516 W Lyndale Street, Chicago, IL 60647

$1,075,000

Three-unit multifamily with separate HVAC systems, rear decks, shared laundry, and gated parking for two cars.

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Renovated Two-Unit Income Duplex

1520 N Campbell Avenue, Chicago, IL 60622

$849,000

Recently renovated two-unit duplex with separate utilities and an oversized two-car garage and backyard.

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Well-Maintained Two-Unit Brick Building

5632 S Wabash Avenue, Chicago, IL 60637

$299,999

Two-unit building with income potential and recent improvements.

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Two-Flat Multifamily Property

4440 W 55th Street, Chicago, IL 60632

$649,900

1986-built two-flat with three-bedroom layouts, soundproof windows, and a two-car garage, sold as-is.

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Georgian Style Multi-Family Building

4836 S Dorchester Avenue, Chicago, IL 60615

$925,000

Stunning 3-flat in Hyde Park/Kenwood, updated with modern amenities.

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Renovated 3-Flat with Garage

6835 S Clyde Avenue, Chicago, IL 60649

$749,900

Fully renovated all-brick triplex with three 3-bed/2-bath units, a full basement, and a 2-car garage.

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All-Electric 3-Unit Multifamily Property

1817 N Lawndale Avenue, Chicago, IL 60647

$875,000

Three boutique apartments in an all-electric building, furnished and equipped for short-term or long-term rental use.

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Fully Renovated Two-Unit Duplex

5310 S Wood Street, Chicago, IL 60609

$442,500

Turnkey, fully renovated two-unit duplex with finished basement and attic spaces for flexible live-and-rent options.

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Boutique Three-Unit Smart Apartments

1817 N Lawndale Avenue, Chicago, IL 60647

$875,000

Three renovated apartments in an all-electric, smart-controlled building, offered furnished and ready for short- or long-term use.

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Multi-Unit Residential Income Property

3036 N Kedzie Avenue, Chicago, IL 60618

$785,000

Three-unit building with updated roof, electric panels, windows, and mechanicals, including a private rear patio.

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Chicago, IL Short Term Rental Properties Market Trends and Statistics

Explore 18 short term rental properties for sale in Chicago, IL, showcased through 18 active listings on our real estate platform. These investment opportunities span a total of 6,250 square feet of properties for sale, with an estimated market value of $945,000.

Sale prices for short term rental properties in Chicago, IL start at $945,000, averaging $945,000, and reaching up to $945,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Neighborhood	Average Price
60621	$250K
60637	$319.5K
60609	$442.5K
60619	$470K
60632	$649.9K

Neighborhood

Average Price

60621

$250K

60637

$319.5K

60609

$442.5K

60619

$470K

60632

$649.9K