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    Chicago, IL Short Term Rental Properties for Sale

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    Springfield, IL Hoffman Estates, IL Belleville, IL
    15 results
    Contemporary Multifamily Property in Chicago
    $850,000

    Contemporary Multifamily Property in Chicago

    2832 W WILCOX Street, Chicago, IL 60612

    Move-in ready duplex in West Loop, ideal for investors.

    • Flexible 2‑flat design allows for varied living arrangements or rental income.
    • Move‑in ready, new construction with contemporary design and high‑end finishes.
    • Spacious duplex‑up owner's unit featuring 3 beds, 2.5 baths, 2100 sq ft, open concept layout, fireplace, professional grade kitchen, and luxurious primary suite.
    • English garden level rental unit (2 bed, 2 bath, 1050 sq ft) with private side entry and full kitchen.
    • Dual primary suites, HVAC systems, laundry centers, and kitchens offer maximum flexibility.
    Updated: Mar 24
    View details
    Two-Unit Brick Building in Chicago
    $324,500
    0.09 Acres

    Two-Unit Brick Building in Chicago

    5632 S Wabash Avenue, Chicago, IL 60637

    Well-maintained two-unit building with income potential in Chicago.

    • Potential for $15,000 in grants and a home warranty.
    • Two‑unit brick building with spacious layouts and soaring ceilings.
    • Each unit has three bedrooms and one full bathroom.
    • In‑unit laundry in both residences.
    • Lower unit has a proven short‑term rental income history of $24,000 annually (utilized only half of the year).
    Updated: Apr 8
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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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    Chicago Multifamily Investment Opportunity
    $525,000

    Chicago Multifamily Investment Opportunity

    Well-maintained 2-unit building with income potential near DePaul University.

    1903 W Fullerton Avenue, Chicago, IL 60614
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    Chicago Two-Unit Flat Opportunity
    $344,900

    Chicago Two-Unit Flat Opportunity

    Solid brick 2-unit flat in Grand Crossing neighborhood.

    7140 S Eberhart Avenue, Chicago, IL 60619
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    Budlong Woods Multi-Unit Property
    $999,900
    0.09 Acres

    Budlong Woods Multi-Unit Property

    Impeccably maintained multi-unit property in Budlong Woods.

    5429 N Campbell Avenue, Chicago, IL 60625
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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 Avenue, Chicago, IL 60622
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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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    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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    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
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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
    View details
    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
    View details
    Based on your search, we've compiled 19 Potential Opportunities for your consideration. Besides 15 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.

    Harbert Multi-Unit Investment Opportunity
    $2,950,000
    8,000 SF

    Harbert Multi-Unit Investment Opportunity

    Updated multi-unit property in desirable Harbor Country location.

    13662 Red Arrow Highway, Harbert, MI 49115
    View details
    Two Homes, One Property
    $404,900
    0.67 Acres

    Two Homes, One Property

    Two separate homes on a .67 acre lot.

    11471 W Leland Avenue, Beach Park, IL 60099
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    Harbert Multi-Unit Income Property
    $2,950,000
    0.35 Acres

    Harbert Multi-Unit Income Property

    Updated multi-unit property in desirable Harbor Country location.

    13662 Red Arrow Highway, Harbert, MI 49115
    View details
    Two Homes on Large Lot
    $414,900

    Two Homes on Large Lot

    Two homes on one property with income potential.

    11471 W Leland Avenue, Beach Park, IL 60099
    View details

    Chicago, IL Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 15 short term rental properties for sale in Chicago, IL, showcased through 15 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 $3,794,400.

    Sale prices for short term rental properties in Chicago, IL start at $324,500, averaging $758,880, and reaching up to $999,900 — 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

    • 60619
    • 60618
    • 60622
    • 60637
    • 60654
    • 60612
    • 60614
    • 60615
    • 60625
    • 60647

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