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    Chicago, IL Short Term Rental Properties for Sale

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    Carbondale, IL Cicero, IL Oak Park, IL Berwyn, IL River Forest, IL Forest Park, IL Evanston, IL Lincolnwood, IL
    20 properties
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    2-Unit Brick Duplex
    Updated: Sep 28
    2-Unit Brick Duplex

    3847 N Spaulding Avenue, Chicago, IL 60618

    $1,050,000
    0.08 AC lot
    Two‑unit brick duplex built in 1915 on a 0.08‑acre lot
    First unit is a duplex with approximately 1,800 sq ft, 3 bedrooms, and 2 baths
    Copper plumbing (2021‑2025), roof resealed in 2023, and electrical updates in 2022 and 2023
    2021 sump pumps, drain tile, and tankless water heaters; HVAC dated 2021 and 2022
    Heated and air‑conditioned 2.5‑car garage
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    Furnished Mixed-Use Property
    Updated: Jul 13
    Furnished Mixed-Use Property

    815 N MILWAUKEE Avenue, Chicago, IL 60622

    $1,400,000
    0.06 AC lot
    3,208 interior/liveable square feet across the main level and loft
    2,522 SF full unfinished basement
    Fully furnished standalone mixed‑use property
    Private unfinished rooftop with brand‑new roof
    Brand‑new dual zoned HVAC system
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    Multifamily Building with On-Site Parking
    Multifamily Building with On-Site Parking

    8624 S Maryland Avenue, Chicago, IL 60619

    $595,000
    0.07 AC lot

    Separate kitchens, living rooms, and dining areas provide independent layouts across the residential units.

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    See hot listings in Chicago

    Scored against comparables nationwide. These are worth a look.

    Scored against comparables nationwide. These are worth a look.

    Cap Rate available after sign in
    Est. NOI available after sign in
    Local Demand available after sign in
    Six-Unit Apartment Building
    Six-Unit Apartment Building

    8624 S Maryland Ave, Chicago, IL 60619

    $595,000
    3,952 sqft

    Independent residential layouts include private kitchens, living rooms, and dining areas for flexible rental operations.

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    Brick Triplex With Owner’s Duplex
    Brick Triplex With Owner’s Duplex

    1347 W Granville Avenue, Chicago, IL 60660

    $1,485,000

    Three-unit brick property with private laundry, HVAC, parking, and a backyard near transit and neighborhood amenities.

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    Renovated Brick Triplex
    Renovated Brick Triplex

    6835 S Clyde Avenue, Chicago, IL 60649

    $749,900
    0.08 AC lot

    Fully renovated multifamily property with three spacious residences, a basement, detached garage, and outdoor space.

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    Updated Georgian Triplex
    Updated Georgian Triplex

    4836 S Dorchester Avenue, Chicago, IL 60615

    $925,000

    Brick three-unit property with a front porch, fenced grounds, public utilities, and a mix of original and updated interior finishes.

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    Furnished Mixed-Use Building with Loft
    Furnished Mixed-Use Building with Loft

    815 N Milwaukee Ave, Chicago, IL 60622

    $1,400,000
    2,500 sqft

    Standalone commercial building with loft space, full basement, furnished interiors, private rooftop, and dual-zone HVAC.

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    Rehabilitated Triplex with Lower Unit
    Rehabilitated Triplex with Lower Unit

    6627 S Maryland Avenue, Chicago, IL 60637

    $849,000
    3,300 sqft

    Legal three-flat featuring a duplex residence, separate lower-level apartment, and comprehensive permitted renovation.

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    Renovated Two-Unit Residential Building
    Renovated Two-Unit Residential Building

    3847 N Spaulding Avenue, Chicago, IL 60618

    $1,050,000

    Both residences include in-unit laundry, with a heated and air-conditioned garage serving the property.

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    Legal 3-Unit Multifamily Building
    Legal 3-Unit Multifamily Building

    2901 N SACRAMENTO Avenue, Chicago, IL 60618

    $1,300,000

    Fully renovated income property with separate utility accounts, updated kitchens, in-unit laundry, and a shared garage.

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    Duplex with Rooftop Deck
    Duplex with Rooftop Deck

    1327 W WALTON Street, Chicago, IL 60642

    $1,399,000

    Two-unit residence featuring an updated apartment, extensive outdoor space, and flexible occupancy configuration.

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    Brick 2-Flat with Rear Parking
    Brick 2-Flat with Rear Parking

    3556 W Dickens Ave, Chicago, IL 60647

    $549,000

    Two residences offer updated kitchens, a private deck, and rear parking within walking distance of The 606 Trail.

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    Three-Unit Mixed-Use Property
    Three-Unit Mixed-Use Property

    548 E 61st St, Chicago, IL 60637

    $850,000

    Includes furnished short-term lodging, a four-bedroom shared residence, and a first-floor commercial suite.

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    Two-Bedroom Short-Term Rental Property
    Two-Bedroom Short-Term Rental Property

    2042 N Winchester Avenue Unit: 2E, Chicago, IL 60614

    $475,000

    The HOA permits short-term and nightly vacation rentals in this two-level residence with private outdoor space.

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    All-Brick 3-Unit Triplex
    All-Brick 3-Unit Triplex

    6112 S Vernon Avenue, Chicago, IL 60637

    $740,000

    Rehabilitated multifamily property with hardwood flooring, fireplaces, updated systems, and a two-car garage.

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    Greystone Two-Unit Building
    Greystone Two-Unit Building

    7144 S INGLESIDE Avenue, Chicago, IL 60621

    $411,000

    Remodeled interiors and a two-car garage support current short-term rental use.

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    Renovated 3-Flat with Garage
    Renovated 3-Flat with Garage

    6835 S Clyde Ave, Chicago, IL 60649

    $749,900

    Fully renovated all-brick triplex with three 3-bed/2-bath units, a full basement, and a 2-car garage.

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    Historic Brownstone Triplex
    Historic Brownstone Triplex

    57 E Cedar Street, Chicago, IL 60611

    $1,699,990

    Three residential units include a two-bedroom residence and two one-bedroom apartments, with a transferable Airbnb license.

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    Renovated Legal Two-Flat with Garden Unit
    Renovated Legal Two-Flat with Garden Unit

    1940 N Monticello Avenue, Chicago, IL 60647

    Contact for pricing

    Legal two-flat with a finished garden unit, multiple updated systems, and three kitchens, plus a 2-car garage and carport.

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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 20 Active Listings in Chicago, IL

    Chicago, IL Short Term Rental Properties Market Trends and Statistics

    Explore 20 short term rental properties for sale in Chicago, IL, showcased through 20 active listings on our real estate platform. These investment opportunities span a total of 9,752 square feet of properties for sale, with an estimated market value of $18,272,790.

    Sale prices for short term rental properties in Chicago, IL start at $411,000, averaging $961,725, and reaching up to $1,699,990 — 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

    Commercial property segments ranked by active listings on the market

    Duplexes 676
    Apartment buildings 467
    Triplexes 315
    Quadplexes 139
    Short term rental properties 21

    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 average listing prices of real estate assets

    Neighborhood Average Price
    60621 $411K
    60647 $549K
    60619 $595K
    60649 $749.9K
    60637 $794.5K

    Taxes & Financing

    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Cook County

    New Delisted

    Property Size Breakdown

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

    How Realmo verifies these figures

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    Browse Short term rental properties for Sale Near Chicago, IL

    Popular Searches in Chicago, IL

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    Most Searched ZIP Codes in Chicago, IL

    • 60618
    • 60637
    • 60619
    • 60622
    • 60647
    • 60649
    • 60611
    • 60614
    • 60615
    • 60621
    • 60642
    • 60660

    Featured Chicago Real Estate Agencies

    Realmo connects you with licensed Chicago CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Dream Town Realty
    1950 North Sedgwick Chicago, IL 60614
    Phone: 13122658000
    www.dreamtown.com
    Chicago Real Estate Resources
    932 W. Grace Street Chicago, IL 60613
    Phone: 17733279300
    www.crer.com
    American International Realty Corp.
    6138 N.Lincoln Ave. Chicago, IL 60659
    Phone: 17735099493
    www.airealtyco.com
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