Cook County, IL Short term rental properties for sale

Updated: Sep 28

2-Unit Brick Duplex

3847 N Spaulding Avenue, Chicago, IL 60618

$1,050,000

0.08 AC lot

Two‑unit brick duplex built in 1915 on a 0.08‑acre lot
First unit is a duplex with approximately 1,800 sq ft, 3 bedrooms, and 2 baths
Copper plumbing (2021‑2025), roof resealed in 2023, and electrical updates in 2022 and 2023
2021 sump pumps, drain tile, and tankless water heaters; HVAC dated 2021 and 2022
Heated and air‑conditioned 2.5‑car garage

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Updated: Jul 13

Furnished Mixed-Use Property

815 N MILWAUKEE Avenue, Chicago, IL 60622

$1,400,000

0.06 AC lot

3,208 interior/liveable square feet across the main level and loft
2,522 SF full unfinished basement
Fully furnished standalone mixed‑use property
Private unfinished rooftop with brand‑new roof
Brand‑new dual zoned HVAC system

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Multifamily Building with On-Site Parking

8624 S Maryland Avenue, Chicago, IL 60619

$595,000

0.07 AC lot

Separate kitchens, living rooms, and dining areas provide independent layouts across the residential units.

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Six-Unit Apartment Building

8624 S Maryland Ave, Chicago, IL 60619

$595,000

3,952 sqft

Independent residential layouts include private kitchens, living rooms, and dining areas for flexible rental operations.

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Brick Triplex with Coach House

214 Chicago Avenue, Oak Park, IL 60302

$1,150,000

0.14 AC lot

Oak Park property combines three apartments, a renovated coach house, basement laundry, and a detached garage.

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Brick Triplex With Owner’s Duplex

1347 W Granville Avenue, Chicago, IL 60660

$1,485,000

Three-unit brick property with private laundry, HVAC, parking, and a backyard near transit and neighborhood amenities.

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Renovated Brick Triplex

6835 S Clyde Avenue, Chicago, IL 60649

$749,900

0.08 AC lot

Fully renovated multifamily property with three spacious residences, a basement, detached garage, and outdoor space.

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Furnished Mixed-Use Building with Loft

815 N Milwaukee Ave, Chicago, IL 60622

$1,400,000

2,500 sqft

Standalone commercial building with loft space, full basement, furnished interiors, private rooftop, and dual-zone HVAC.

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Updated Georgian Triplex

4836 S Dorchester Avenue, Chicago, IL 60615

$925,000

Brick three-unit property with a front porch, fenced grounds, public utilities, and a mix of original and updated interior finishes.

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Rehabilitated Triplex with Lower Unit

6627 S Maryland Avenue, Chicago, IL 60637

$849,000

3,300 sqft

Legal three-flat featuring a duplex residence, separate lower-level apartment, and comprehensive permitted renovation.

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Renovated Two-Unit Residential Building

3847 N Spaulding Avenue, Chicago, IL 60618

$1,050,000

Both residences include in-unit laundry, with a heated and air-conditioned garage serving the property.

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Legal 3-Unit Multifamily Building

2901 N SACRAMENTO Avenue, Chicago, IL 60618

$1,300,000

Fully renovated income property with separate utility accounts, updated kitchens, in-unit laundry, and a shared garage.

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Duplex with Rooftop Deck

1327 W WALTON Street, Chicago, IL 60642

$1,399,000

Two-unit residence featuring an updated apartment, extensive outdoor space, and flexible occupancy configuration.

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Brick 2-Flat with Rear Parking

3556 W Dickens Ave, Chicago, IL 60647

$549,000

Two residences offer updated kitchens, a private deck, and rear parking within walking distance of The 606 Trail.

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Three-Unit Mixed-Use Property

548 E 61st St, Chicago, IL 60637

$850,000

Includes furnished short-term lodging, a four-bedroom shared residence, and a first-floor commercial suite.

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Two-Bedroom Short-Term Rental Property

2042 N Winchester Avenue Unit: 2E, Chicago, IL 60614

$475,000

The HOA permits short-term and nightly vacation rentals in this two-level residence with private outdoor space.

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All-Brick 3-Unit Triplex

6112 S Vernon Avenue, Chicago, IL 60637

$740,000

Rehabilitated multifamily property with hardwood flooring, fireplaces, updated systems, and a two-car garage.

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Greystone Two-Unit Building

7144 S INGLESIDE Avenue, Chicago, IL 60621

$411,000

Remodeled interiors and a two-car garage support current short-term rental use.

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Renovated 3-Flat with Garage

6835 S Clyde Ave, 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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Historic Brownstone Triplex

57 E Cedar Street, Chicago, IL 60611

$1,699,990

Three residential units include a two-bedroom residence and two one-bedroom apartments, with a transferable Airbnb license.

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Renovated Legal Two-Flat with Garden Unit

1940 N Monticello Avenue, Chicago, IL 60647

Contact for pricing

Legal two-flat with a finished garden unit, multiple updated systems, and three kitchens, plus a 2-car garage and carport.

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Cook County, IL Short Term Rental Properties Market Trends and Statistics

Explore 21 short term rental properties for sale in Cook County, IL, showcased through 21 active listings on our real estate platform. These investment opportunities span a total of 9,752 square feet of properties for sale, with an estimated market value of $19,422,790.

Sale prices for short term rental properties in Cook County, IL start at $411,000, averaging $971,139, and reaching up to $1,699,990 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Featured Cook County Real Estate Agencies

Realmo connects you with licensed Cook County CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

Dream Town Realty

1950 North Sedgwick Chicago, IL 60614

Phone: 13122658000

www.dreamtown.com

Chicago Real Estate Resources

932 W. Grace Street Chicago, IL 60613

Phone: 17733279300

www.crer.com

American International Realty Corp.

6138 N.Lincoln Ave. Chicago, IL 60659

Phone: 17735099493