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    Cook County, IL Short Term Rental Properties for Sale

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    Chicago, IL Springfield, IL Rockford, IL
    15 results
    Contemporary Chicago Multifamily Property
    $799,000
    3,150 SF

    Contemporary Chicago Multifamily Property

    2832 W WILCOX Street, Chicago, IL 60612

    Move-in ready, flexible two-flat in West Loop.

    • Flexible 2‑flat design allows for single‑family living, generational living, Airbnb, guest suite, or traditional rental income.
    • Upper 2‑level unit features 3 bedrooms, 2.5 baths, open‑concept living space, professional‑grade kitchen, and primary suite with dual walk‑in closets and luxurious bath.
    • English garden‑level unit offers 2 bedrooms, 2 baths, full kitchen, and private side entry.
    • Contemporary design with brick and limestone facade, black windows, and high‑end finishes throughout (quartz countertops, stainless steel appliances, hardwood floors).
    • Includes a large rear deck, backyard, and two‑car garage.
    Updated: May 27
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    Oak Park Multifamily Investment Opportunity
    $1,200,000
    0.14 Acres

    Oak Park Multifamily Investment Opportunity

    214 Chicago Avenue, Oak Park, IL 60302

    Three income-producing structures in the heart of Oak Park.

    • Three income‑producing structures: 3‑unit building, coach house, and 3‑car garage.
    • Extensively renovated in 2020 with new windows and separate HVAC systems. Roof in excellent condition.
    • Coach house offers versatility as a premium long‑term rental, owner‑occupied residence, or short‑term rental.
    • Solid brick construction provides durability.
    • Tenants pay their own gas and electric utilities, maximizing owner cash flow.
    Updated: May 29
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    Six-Unit Multifamily Investment Opportunity
    $595,000
    0.07 Acres

    Six-Unit Multifamily Investment Opportunity

    Well-maintained Chicago multifamily property with income potential.

    8624 S Maryland Avenue, Chicago, IL 60619
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    Modern-Industrial Chicago Two-Unit Property
    $650,000

    Modern-Industrial Chicago Two-Unit Property

    Unique two-unit property with modern-industrial design and income potential.

    1011 N MOZART Street, Chicago, IL 60622
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    Multi-Unit Property with Income Potential
    $250,000
    0.06 Acres

    Multi-Unit Property with Income Potential

    Versatile multi-unit property with income potential in Chicago, IL.

    5756 S Princeton Avenue, Chicago, IL 60621
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    Renovated Multifamily Property in Berwyn
    $508,000

    Renovated Multifamily Property in Berwyn

    Fully renovated duplex with income potential in Berwyn, Illinois.

    2108 Highland Avenue, Berwyn, IL 60402
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    Chicago Multifamily Investment Opportunity
    $945,000

    Chicago Multifamily Investment Opportunity

    Updated multifamily property in booming East Humboldt Park.

    843 N Francisco Avenue, Chicago, IL 60622
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    Two-Unit Brick Building in Chicago
    $299,999
    0.09 Acres

    Two-Unit Brick Building in Chicago

    Well-maintained two-unit building with income potential and recent upgrades.

    5632 S Wabash Avenue, Chicago, IL 60637
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    Multi-Unit Building Near Logan Square
    $785,000

    Multi-Unit Building Near Logan Square

    Meticulously maintained multi-unit building near public transportation and local dining.

    3036 N Kedzie Avenue, Chicago, IL 60618
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    River North Mixed-Use Investment Opportunity
    $2,150,000

    River North Mixed-Use Investment Opportunity

    Income-producing property with five units, billboard income, and shared patio.

    642 North Dearborn Street, Chicago, IL 60654
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    River North Mixed-Use Investment Property
    $2,150,000

    River North Mixed-Use Investment Property

    Income-producing property with five units, billboard income, and shared patio.

    642 North Dearborn Street, Chicago, IL 60654
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    Gold Coast Investment Portfolio
    $2,785,000
    1,560 SF

    Gold Coast Investment Portfolio

    Commercial and residential condos in a prime location.

    1140 N Lasalle Dr, Chicago, IL
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    Chicago Two-Unit Flat Opportunity
    $344,900

    Chicago Two-Unit Flat Opportunity

    Renovated two-unit flat in Grand Crossing, ideal for house-hacking.

    7140 S Eberhart Avenue, Chicago, IL 60619
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    Well-Maintained Two-Unit Brick Building
    $339,000

    Well-Maintained Two-Unit Brick Building

    Two-unit building with income potential and recent improvements.

    5632 S Wabash Avenue, Chicago, IL 60637
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    Beverly Mixed-Use Investment Opportunity
    $945,000
    6,250 SF

    Beverly Mixed-Use Investment Opportunity

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

    2022 W 95th Street, Chicago, IL 60643
    View details
    Based on your search, we've compiled 15 Potential Opportunities for your consideration. Besides 15 Active listings in Cook County, IL, we suggest exploring several alternatives:

    Cook County, IL Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 15 short term rental properties for sale in Cook County, IL, showcased through 15 active listings on our real estate platform. These investment opportunities span a total of 10,960 square feet of properties for sale, with an estimated market value of $4,529,000.

    Sale prices for short term rental properties in Cook County, IL start at $799,000, averaging $1,509,666, and reaching up to $2,785,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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