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    Cook County, IL Short Term Rental Properties for Sale

    11 results
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    Chicago Brown Brick 2-Unit
    $994,900
    0.08 Acres

    Chicago Brown Brick 2-Unit

    3847 N Spaulding Ave, Chicago, IL 60618

    Completely transformed 2-unit property in Irving Park neighborhood.

    • Completely renovated 2‑unit property with a 3rd unit in the finished basement
    • Luxurious duplex‑down unit features a rare 4‑bedroom, 2‑bath layout, including a spacious primary suite and walk‑in closet
    • Finished and climate‑controlled 2.5‑car garage suitable for parking, storage, or workshop
    • Prime location in the highly coveted Irving Park neighborhood, directly across from a charter school and near expressway/Blue Line
    • Second‑floor unit with open‑concept design, quartz finishes, hardwood floors, and in‑unit laundry (also in the duplex unit)
    Updated: Jan 6
    View details
    Chicago Duplex with Airbnb Potential
    $950,000
    0.05 Acres

    Chicago Duplex with Airbnb Potential

    1730 W Beach Ave, Chicago, IL 60622

    Duplex near transportation and amenities, potential for short-term rentals.

    • Two units offer rental income or multi‑generational living.
    • Proven Airbnb income history, financials available.
    • Updated kitchens with granite counters and stainless steel appliances in both units.
    • In‑unit laundry in both units.
    • Three private outdoor spaces: two decks and one patio.
    Updated: Jan 3
    View details
    Renovated Multifamily Property in Berwyn
    $520,000

    Renovated Multifamily Property in Berwyn

    Fully renovated duplex with income potential in Berwyn, Illinois.

    2108 Highland Ave, Berwyn, IL 60402
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    Turnkey Two-Flat Investment Property
    $699,999
    0.07 Acres

    Turnkey Two-Flat Investment Property

    Modernized two-flat in Chicago, ideal for investors or owner-occupants.

    321 S Richmond St, Chicago, IL 60612
    View details
    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
    View details
    Marshall Boulevard Four-Flat Investment
    $750,000

    Marshall Boulevard Four-Flat Investment

    Four-flat building with coach house near transportation, shopping, and dining.

    2249 S Marshall Blvd, Chicago, IL 60623
    View details
    Chicago Ridge Condo with Garage
    $169,900

    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
    View details
    Rehabilitated Chicago Multifamily Investment Property
    $250,000

    Rehabilitated Chicago Multifamily Investment Property

    Newly renovated two-unit building with high-income potential in Chicago.

    5805 S La Salle St, Chicago, IL 60621
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    Designer Home Near Lakeview
    $180,000
    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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    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
    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
    View details
    Based on your search, we've compiled 11 Potential Opportunities for your consideration. Besides 11 Active listings in Cook County, IL, we suggest exploring several alternatives:

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

    Explore 11 short term rental properties for sale in Cook County, IL, showcased through 11 active listings on our real estate platform. These investment opportunities span a total of 11,326 square feet of properties for sale, with an estimated market value of $3,144,121.

    Prices for short term rental properties in Cook County, IL start at $499,222, averaging $786,030, and reaching up to $994,900 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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    Browse Short term rental properties for Sale Near Cook, IL

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