Chicago Airbnb Properties For Sale

642 N Dearborn St

Chicago, IL 60654

Airbnb Property
Multifamily for Sale
$2,942,253 CAD
6,100 SF

Chicago Multifamily for Sale - River North

This is an income-producing, mixed-use investment opportunity with a projected NOI of $135,514. The highly desirable historical River North property is adjacent to the highly acclaimed Tao restaurant and consists of five units, billboard income, and a shared outdoor garden patio. The property benefits from favorable remaining lease terms, an opportunity for short-term rental management for additional income, and favorable DX-5 zoning permitting a variety of uses. Recent upgrades include a completely updated 3rd floor completed in 2025 and an updated 4th floor completed in 2021. The property is located in the heart of River North, offering exceptional walkability, immediate access to amenities, and easy access to major transport options, including the CTA Red, Brown, and Purple lines and 90/94 Expressway.

Contact:

SVN | Chicago Commercial

Property Subtype:

Apartment

Date on Market:

2025-12-05

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Leavitt Town Lofts

Airbnb Property
Mixed Types for Sale
$12,316,410 CAD
6 Properties | Mixed Types

Chicago Portfolio of properties for Sale - Northwest City

The Leavitt Town Lofts Portfolio represents a rare multi-asset urban assemblage strategically positioned in one of Chicago’s most dynamic infill industrial corridors. Comprising a mix of industrial warehouse, office, event space, and surface parking lots, the portfolio provides highly diversified income streams, tenant profiles, and use cases—creating resiliency and upside within a tightly supplied submarket. This portfolio offers investors stable in-place cash flow with strong repositioning upside—ideal for value-add, industrial expansion, or longer-term hold strategies seeking diversified yield. The portfolio spans four complementary property types: 1. Industrial Warehouse Core stabilized industrial space with below-market rents relative to comparable West-Side and near-downtown submarkets. Strong demand tailwinds from logistics, last-mile distribution, and trades users. Flexible bay sizes that appeal to both small and midsize operators. 2. Office / Flex Space Ancillary administrative and creative office uses support industrial tenancy. Opportunity to modernize and convert select areas into higher-rent flex suites. 3. Event / Specialty Use Space Unique urban event space with character that commands premium short-term rental rates. Seasonal volatility is offset by diversification across the portfolio. 4. Surface Parking Lots Valuable urban land component with low operating costs. Highly adaptable—supports fleet storage, logistics operations, or future redevelopment.

Contact:

33 Realty

Property Subtype:

Mixed Types

Date on Market:

2025-11-19

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5017 S Drexel Blvd

Chicago, IL 60615

Airbnb Property
Multifamily for Sale
$6,431,903 CAD
17,800 SF

Chicago Multifamily for Sale - South Chicago

Nara Advisors has been exclusively engaged to market for sale Drexel House [5017 S Drexel Blvd], an 8-unit, 38-bedroom multifamily property in Chicago's Hyde Park neighborhood. 5017 S Drexel is a gut-rehabbed property showcasing a rare and highly functional unit configuration: [7] spacious five-bedroom apartments and [1] three-bedroom unit, all equipped with three bathrooms. Each residence has been meticulously updated, offering modern, high-end finishes, quality furnishings, private furnaces, and in-unit laundry. These extensive upgrades support strong investment potential and market-leading returns in one of Chicago’s most upward-trending submarkets. The building operates with both short-term rental flexibility and long-term lease stability. The property is situated in close proximity to numerous attractions of Chicago's desirable Hyde Park neighborhood, including The University of Chicago, The Northwestern Medical Center, and the future Obama Presidential Library. The owner has successfully implemented a hybrid long-term/short-term rental strategy that caters to the University of Chicago community. Ownership has achieved high occupancy and strong in-place rental income off their hybrid model.

Contact:

Nara Realty Advisors

Property Subtype:

Apartment

Date on Market:

2025-10-28

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2022-2026 W 95th St

Chicago, IL 60643

Airbnb Property
Office for Sale
$1,361,648 CAD
7,575 SF

Chicago Office for Sale - South Chicago

Fully renovated mixed-use building in the heart of Chicago's Beverly neighborhood, offering a prime investment opportunity. This property features a newly built +/- 2,175 SF turnkey restaurant with a commercial hood, walk-in cooler, and dine-in seating, completed in May 2024. Additionally, a +/- 1,500 SF remodeled office space includes a kitchenette, full bath, private office, and open work area, ideal for various business uses. The spacious +/- 2,575 SF residential unit boasts 4 bedrooms, 3 bathrooms, in-unit laundry, a rooftop balcony, and a gaming room, currently utilized as an Airbnb. A +/- 1,325 SF garage accommodates up to five vehicles or additional storage, perfect for contractors or small warehousing. Recent upgrades include a full roof tear-off and replacement (2024), new restaurant build-out with commercial-grade features, and individual HVAC systems for each unit (2022). Located in a high-demand, walkable area near the Rock Island Metra line, restaurants, and retail shops, this property ensures strong long-term investment potential. Great income producing investment with little maintenance and outstanding financials at11 cap / proforma 6.5 GRM on return.

Contact:

First In Realty, Inc

Property Subtype:

Office/Residential

Date on Market:

2025-02-21

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7-Unit East Garfield Park Portfolio

Airbnb Property
Multifamily for Sale
$2,052,735 CAD
7,192 SF
2 Multifamily Properties

Chicago Portfolio of properties for Sale - Northwest City

Rare chance to acquire 7 fully leased investment properties / Airbnb rentals in East Garfield Park, one of Chicago’s fastest-rising neighborhoods. Each unit is well-maintained and is ideal for investors or owner-occupants seeking steady income with long-term growth potential. Each unit is thoughtfully designed with in-unit laundry, central heat & A/C, and private patios, delivering the comfort and convenience today’s renters demand. Situated on an extra-deep 200’ lot, the property features a sprawling 65-foot backyard, perfect for outdoor enjoyment or future development. Every unit also comes with two tandem parking spaces, a rare bonus in the city. Recent upgrades ensure peace of mind for the next owner, while the prime location, just minutes to the United Center, Downtown, public transit, and expressways, keeps demand strong. Don't miss out on this incredible opportunity to own turn-key investment properties in the heart of East Garfield Park!

Contact:

Compass

Property Subtype:

Multi Family

Date on Market:

2025-10-14

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Airbnb Properties for Sale in Chicago, IL, USA

Chicago Multifamily for Sale - River North

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Chicago Portfolio of properties for Sale - Northwest City

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Chicago Multifamily for Sale - South Chicago

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Chicago Office for Sale - South Chicago

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Chicago Portfolio of properties for Sale - Northwest City

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Airbnb Properties For Sale

Airbnb Properties