Mayor Targets Platform Profits in Short-Term Rental Crackdown
Chicago filed a lawsuit Monday against Airbnb and real estate broker Milan Rubenstein’s Slumber Stay LLC, alleging the host company failed to register short-term rentals properly and continued operating after receiving nearly 200 violations in 2024 and 2025. Rubenstein allegedly used a single nontransferable hotel license for multiple listings and evaded enforcement by re-listing units under different host names and registration numbers. Airbnb is accused of profiting from the unlawful rentals and refusing to help the city enforce its Shared Housing Ordinance. Mayor Brandon Johnson said the lawsuit addresses affordability concerns at a time when housing costs remain a priority for residents.
City officials say Airbnb’s data-sharing practices prevent enforcement. The platform provides some listing data and can remove problematic units, but hosts can immediately create new listings under different titles and names. Airbnb does not share exact addresses publicly or in reports to the city, making it impossible for officials to verify whether a listed registration number matches an approved property. By Monday evening, Slumber Stay’s website displayed 156 rental listings, including 95 in Chicago concentrated on the Near South Side; by Tuesday morning the site was down.
Chicago’s Shared Housing Ordinance, passed in 2016 and amended in 2020, limits short-term rentals per building and restricts them in certain neighborhoods to protect affordable housing. The city previously documented a surge in short-term rental licenses in Woodlawn near the Obama Presidential Center, where renters reported difficulty finding affordable long-term units. The lawsuit seeks fines, fees, and injunctive relief to stop Airbnb and Slumber Stay from listing unregistered properties. Chicago has been in discussions with both defendants for several years, according to corporation counsel Mary Richardson-Lowry.
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