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    Chicago, IL Short Term Rental Properties for Sale

    14 results
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    Two-Unit Brick Building in Chicago
    $339,000
    0.09 Acres

    Two-Unit Brick Building in Chicago

    5632 S Wabash Ave, Chicago, IL 60637

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

    • Income Potential: Lower unit previously generated $24,000 annually as a short‑term rental.
    • Large Units: Expansive layouts with three spacious bedrooms and one full bathroom in each unit.
    • Move‑In Ready: Re‑stained hardwood floors, kitchens and bathrooms in superb condition.
    • In‑Unit Laundry: Both residences feature in‑unit laundry.
    • Development Area: Poised for appreciation due to nearby multi‑billion‑dollar investments, including the Obama Presidential Library.
    Updated: Mar 4
    View details
    Renovated Multi-Family Building
    $925,000
    0.08 Acres

    Renovated Multi-Family Building

    5426 N Western Ave, Chicago, IL 60625

    Impeccably maintained building near Lincoln Square, Ravenswood + Andersonville.

    • Fully renovated in 2023 with modern systems and low maintenance.
    • Two upgraded units: 4BR/2BA duplex and a 3BR/1BA unit with stylish kitchens.
    • Projected Cap Rate of 6.8% with strong rental income; Unit #1 rented for $4,500 and Unit #2 at $2,750 per month.
    • Prime location near shopping, dining, parks, and transit.
    • Desirable amenities included: EV charger, keyless entry, in‑unit washer/dryers, and radon mitigation.
    Updated: Mar 4
    View details
    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 Ave, Chicago, IL 60619
    View details
    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
    View details
    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
    View details
    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
    View details
    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
    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
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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
    View details
    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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    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
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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
    View details
    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
    View details
    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
    View details
    Based on your search, we've compiled 18 Potential Opportunities for your consideration. Besides 14 Active listings in Chicago, IL, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Explore Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Union Pier Cottages Collection
    $3,995,000
    0.46 Acres

    Union Pier Cottages Collection

    Exclusive lake town retreat near beaches and downtown Union Pier.

    10222 Town Line Rd, Union Pier, MI 49129
    View details
    Fire Fly Co-op Unit
    $340,000

    Fire Fly Co-op Unit

    Co-op unit with deeded beach rights and rental income.

    15657 Lakeshore Rd, Union Pier, MI 49129
    View details
    Prime Commercial Parcel in Bridgman
    $119,000
    1.11 Acres

    Prime Commercial Parcel in Bridgman

    One-acre commercial parcel with high visibility and development potential.

    10067 Red Arrow Hwy, Bridgman, MI 49106
    View details
    Prime Commercial Land in Bridgman
    $119,000
    1.11 Acres

    Prime Commercial Land in Bridgman

    One-acre commercial parcel with high visibility and access.

    10067 Red Arrow Hwy, Bridgman, MI 49106
    View details

    Chicago, IL Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 14 short term rental properties for sale in Chicago, IL, showcased through 14 active listings on our real estate platform. These investment opportunities span a total of 17,860 square feet of properties for sale, with an estimated market value of $3,877,344.

    Sale prices for short term rental properties in Chicago, IL start at $339,000, averaging $646,224, 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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    Most Searched ZIP Codes in Chicago, IL

    • 60612
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    • 60619
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    • 60622
    • 60637
    • 60644
    • 60647
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