The city of Chicago has filed a lawsuit accusing short-term rental home company Airbnb and one of its hosts of improperly listing numerous properties.
The complaint filed Monday in Cook County Circuit Court alleged that real estate broker Milan Rubenstein and his company, Slumber Stay LLC, did not properly register his short-term rentals and used a single nontransferable hotel license for multiple listings — then kept renting those units after being issued citations.
Airbnb was accused of profiting from those allegedly unlawful rentals rather than working with the city to ensure compliance with the Shared Housing Ordinance.
According to the lawsuit, the city issued Rubenstein and Slumber Stay LLC nearly 200 violations in 2024 and 2025. The lawsuit alleged that Airbnb was aware of those violations but chose to “prioritize profits over compliance with City law.”
Mary Richardson-Lowry, City Hall’s top lawyer, said “the city has been in discussions with [Airbnb and Rubenstein] for a number of years now, and they continue to not bring themselves in compliance. It affects the safety of those who inhabit those units,” as well as the affordability of long-term rentals in the city’s neighborhoods.
Mayor Brandon Johnson said in a statement that the lawsuit aims to prioritize Chicagoans “at a time when affordability remains front of mind.”
“Requiring short-term rental companies to follow the same rules as everyone else is critical to our work of building a safer, more affordable Chicago,” he said.
Airbnb representatives said they had not yet seen the court filing. Rubenstein did not respond to WBEZ’s requests for comment.
The city’s Shared Housing Ordinance, passed in 2016 and amended in 2020, limits the number of short-term rentals in a building, restricts short-term rentals in certain neighborhoods and requires registration with the city’s Business Affairs and Consumer Protection Department.
The ordinance was intended to address concerns that the prevalence of Airbnb rentals hurts the availability of affordable housing. WBEZ previously reported on the increase in short-term rental licenses in Woodlawn near the Obama Presidential Center and the struggles of renters looking for affordable units in the neighborhood.
The lawsuit said hosts such as Rubenstein who “engage in unlawful renting are able to avoid City detection through re-listing, approximate locations, and fake names, among other tactics.” While Airbnb provides the city with some data on the listings and the ability to take down a problematic listing, any host can put up a new listing under a different title, host name and registration number, the complaint said.
“The city cannot determine from Airbnb’s provided data alone whether a given unit is being rented unlawfully,” the lawsuit reads. “Because Airbnb does not provide exact address information either publicly on its platform or in its reports, the city cannot ensure that a listed license or registration number matches a licensed or registered property approved by the city.”
In the case of Rubenstein and Slumber Stay, after being cited for multiple violations and paying fines starting in 2022, the company continued to list short-term rentals using different host names and on its own website, slumberstay.com, the lawsuit said.
On Monday evening, Slumber Stay’s website showed 156 short-term rental listings, including 95 in Chicago — mostly in the Near South Side neighborhood. By Tuesday morning, the website was no longer available. The webpage for another company that Rubinstein founded was also down Tuesday after it was mentioned in the complaint but not named as a defendant.
The city is seeking fines and fees, as well as injunctive relief to prevent Airbnb and Slumber Stay from renting illegal short-term units.