Concept preview prepared for The Dream Rentals
The Chicago River and downtown towers from the Riverwalk

Property management in Chicago.

Our home market since 2019. Furnished short-term and mid-term rentals from the South Loop to the lakefront.

Where we operate in Chicago

  • South Loop
  • Edgewater
  • River West
  • Wicker Park–Bucktown
  • Pilsen
  • Near West Side
  • River North
  • Lakeview
  • Ukrainian Village
  • Gold Coast
  • West Lawn
  • Loop

Plus the suburbs: Forest Park and Skokie.

A Dream Rentals-managed home in downtown Chicago

The rules, in plain English

As of October 2026.

  • Every short-term rental needs a city registration (Shared Housing Unit registration from the Department of Business Affairs and Consumer Protection), and the registration number has to appear on every listing.
  • In buildings with one to four units, the host generally has to live there, and only one unit per building can be registered.
  • In buildings with five or more units, owners don't have to live on site, but only a limited share of the units can be registered.
  • Some buildings are on the city's Prohibited Buildings List, and a growing number of precincts have voted to restrict new rentals.
  • Stays of 32 nights or more aren't short-term rentals under the ordinance.
  • Suburbs differ: Skokie doesn't allow new investor-owned short-term rentals; Forest Park is still studying an ordinance.

We check your exact address before we propose anything.

What that means for your property

If your unit qualifies, we run it nightly. If it doesn't, we run it as a furnished monthly rental for traveling nurses, consultants and families between homes. Either way, same team, same reporting.

Demand

  • McCormick Place, North America's largest convention center, draws conventions and trade shows to the Near South Side.
  • The United Center draws event-night demand on the Near West Side.
  • Chicago's academic-medical corridor — Northwestern Memorial, Rush, UIC and University of Chicago Medicine — supports steady demand from traveling clinicians and patient families.

A whole building, run as one hotel.

The Plymouth in Printer's Row is 30 furnished suites, from studios to four-bedrooms, operated by Dream Rentals with its own booking site and brand.

Owner-supplied · not final

Occupancy, average nightly rate and owner revenue before/after — needs client permission.

A furnished suite at The Plymouth, Printer's Row

Know the number before you sign anything.

Send us the address and the unit mix. We'll send back a revenue projection built the way we underwrite our own launches. Free, and no obligation.