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    Cook County, IL Short Term Rental Properties for Sale

    17 results
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    Renovated Multi-Family Property, Chicago
    $925,000
    0.08 Acres

    Renovated Multi-Family Property, Chicago

    5426 N Western Ave, Chicago, IL 60625

    Impeccably maintained, fully renovated multi-family property in Chicago.

    • Fully renovated in 2023 with new plumbing, electrical, tankless water heaters, central heating/cooling, kitchens, baths, windows, doors, and lighting.
    • Two upgraded units: a 4BR/2BA duplex (potential owner's unit) and a 3BR/1BA unit, both with modern amenities and finishes.
    • Projected 6.8% Cap Rate and strong rental income potential.
    • Prime location near shopping, dining, parks, and transit in Lincoln Square, Ravenswood, and Andersonville.
    • Features an EV charger in the garage and a radon mitigation system installed in 2025.
    Updated: Mar 4
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    Six-Unit Multifamily Investment Opportunity
    $595,000
    0.07 Acres

    Six-Unit Multifamily Investment Opportunity

    8624 S Maryland Ave, Chicago, IL 60619

    Well-maintained Chicago multifamily property with income potential.

    • Immediate income from two long‑term leases and three active Airbnb units.
    • High rental potential with 6 independent units, each with a kitchen, living room, and dining area.
    • Opportunity to increase value by renovating the unfinished unit.
    • Equipped with a 24‑hour security surveillance system.
    • Six dedicated parking spaces for residents and guests.
    Updated: Feb 27
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    Renovated Two-Flat in Austin
    $475,000

    Renovated Two-Flat in Austin

    Fully renovated 7 bed/3 bath two-flat in Chicago's Austin neighborhood.

    5038 W Fulton St, Chicago, IL 60644
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    Multi-Unit Building with Rental Potential
    $900,000

    Multi-Unit Building with Rental Potential

    Well-maintained Chicago building with multiple units and revenue streams.

    3036 N Kedzie Ave, Chicago, IL 60618
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    Two-Unit Brick Building in Chicago
    $339,000
    0.09 Acres

    Two-Unit Brick Building in Chicago

    Well-maintained two-unit building with short-term rental potential.

    5632 S Wabash Ave, Chicago, IL 60637
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    Classic Chicago Brown Brick Building
    $994,900
    0.08 Acres

    Classic Chicago Brown Brick Building

    Completely transformed 2-unit with finished basement in Irving Park.

    3847 N Spaulding Ave, Chicago, IL 60618
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    Victorian Three-Flat in Oak Park
    $723,000

    Victorian Three-Flat in Oak Park

    Charming Victorian three-flat in Oak Park's historic district.

    227 N Marion St, Oak Park, IL 60302
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    Chicago Two-Unit Flat Opportunity
    $344,900

    Chicago Two-Unit Flat Opportunity

    Solid brick 2-unit flat in Grand Crossing, Chicago.

    7140 S Eberhart Ave, Chicago, IL 60619
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    Historic Limestone Multi-Unit in Chicago
    $499,222
    0.06 Acres

    Historic Limestone Multi-Unit in Chicago

    Rehabbed multi-unit near Downtown Chicago with income potential.

    209 S Albany Ave, Chicago, IL 60612
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    Wicker Park Income Property
    $950,000
    0.05 Acres

    Wicker Park Income Property

    Turnkey income-producing property in Wicker Park with Airbnb potential.

    1730 W Beach Ave, Chicago, IL 60622
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    Logan Square Multi-Unit Investment
    $1,200,000

    Logan Square Multi-Unit Investment

    Three-unit building in Logan Square with income potential.

    2516 W Lyndale St, Chicago, IL 60647
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    Remodeled Triplex: Turnkey Investment
    $299,000

    Remodeled Triplex: Turnkey Investment

    Remodeled triplex in prime location, ideal for investors or owner-occupants.

    98 W 154 St, Harvey, IL 60426
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    Historic Chicago Multi-Unit Investment Opportunity
    $499,222
    0.06 Acres

    Historic Chicago Multi-Unit Investment Opportunity

    Classic limestone 2-unit near downtown Chicago, fully rehabbed in 2020.

    209 S Albany Ave, Chicago, IL 60612
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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 La Salle Dr, Chicago, IL 60610
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    Designer Home Near Lakeview
    Contact for pricing
    525 SF

    Designer Home Near Lakeview

    Custom-designed apartment with modern upgrades, near the lake and amenities.

    539 W Stratford Pl, Chicago, IL 60657
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    Chicago Ridge Condo with Garage
    Contact for pricing

    Chicago Ridge Condo with Garage

    Like-new one-bedroom condo with in-unit laundry and private garage.

    10620 S Central Ave, Chicago Ridge, IL 60415
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    Stylish Condo with City Views
    $395,000

    Stylish Condo with City Views

    Southeast corner condo with sweeping city views in River North.

    30 E Huron St, Chicago, IL 60611
    View details
    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 17 Active Listings in Cook County, IL

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

    Explore 17 short term rental properties for sale in Cook County, IL, showcased through 17 active listings on our real estate platform. These investment opportunities span a total of 21,344 square feet of properties for sale, with an estimated market value of $4,802,344.

    Sale prices for short term rental properties in Cook County, IL start at $339,000, averaging $686,049, and reaching up to $994,900 — 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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