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    Chicago, IL Short Term Rental Properties for Sale

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    Cicero, IL Oak Park, IL Stickney, IL
    13 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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    Six-Unit Multifamily Investment Opportunity
    $595,000
    0.07 Acres

    Six-Unit Multifamily Investment Opportunity

    8624 S Maryland Avenue, 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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    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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    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 17 Potential Opportunities for your consideration. Besides 13 Active listings in Chicago, IL, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Opportunities in Nearby Cities

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

    New Buffalo Multi-Unit Investment
    $249,000
    0.23 Acres

    New Buffalo Multi-Unit Investment

    Multi-unit property near downtown New Buffalo's beach and amenities.

    5 N Eagle Street, New Buffalo, MI 49117
    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
    View details
    Multi-Unit Building Near Beach
    $249,000
    0.23 Acres

    Multi-Unit Building Near Beach

    Three-unit building near beach, shops, and restaurants.

    5 N Eagle St, New Buffalo, MI 49117
    View details
    Two Homes on Large Lot
    $414,900
    0.67 Acres

    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 13 short term rental properties for sale in Chicago, IL, showcased through 13 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 Chicago, 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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    Top Commercial Asset Segments

    Apartment buildings 491
    Duplexes 364
    Triplexes 162
    Quadplexes 67
    Short term rental properties 14

    Property Size Breakdown

    The majority of commercial real estate listings in Chicago fall within the 10,000+ square foot range.

    Demographics Overview

    Population 2.91M
    Population Growth (5Y) +0.6%
    Median Household Income $76,477
    College Educated 44.3%

    High-Yield Neighborhoods for Investment

    Identify Chicago submarkets with the highest inventory density on the market and evaluate the median listing prices of real estate assets

    Neighborhood Average Price
    60621 $250K
    60637 $319.5K
    60619 $428.3K
    60618 $785K
    60622 $797.5K

    Taxes & Financing

    Average Loan-to-Value 65.0%

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    Most Searched ZIP Codes in Chicago, IL

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    • 60654
    • 60612
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    • 60643

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