City Files Suit Over Hundreds of Alleged Violations
The City of Chicago filed a lawsuit in Cook County Circuit Court on June 23, 2026, against Airbnb Inc., Airbnb Living LLC, a host company called Slumber Stay LLC, and its manager, Milan Rubenstein, according to the City of Chicago’s own press release. The suit alleges the defendants ran a large-scale short-term rental operation that repeatedly violated the city’s Shared Housing Ordinance and consumer protection laws.
According to the city, Slumber Stay racked up nearly 200 citations in 2024 and 2025 for failing to properly register rental units. Reporting from WBEZ found the company operated 156 total short-term rental listings, including 95 in Chicago concentrated in the Near South Side, and that the operation allegedly used a single nontransferable hotel license to cover multiple, unrelated properties instead of registering each one individually. Block Club Chicago reported the city describes Rubenstein as one of the most active short-term rental hosts it has tracked.
The city’s complaint contends the pattern continued even after fines were issued, and that Airbnb kept processing bookings and collecting fees for the unregistered units rather than pulling the listings. CBS Chicago’s coverage of the filing notes the city is also accusing the platform of failing to cooperate with a city data-verification portal meant to confirm which listings are properly licensed.
Officials Want Fines, Not Just a Cease-and-Desist
Mary Richardson-Lowry, the city’s Corporation Counsel, said, according to WBEZ, that “the city has been in discussions with [Airbnb and Rubenstein] for years, and they continue non-compliance,” adding that the unregistered units affect “inhabitant safety.” Mayor Brandon Johnson said “requiring short-term rental companies to follow the same rules as everyone else is critical,” per the same report.
The city’s remedies sought include monetary fines, an order compelling Airbnb to surrender profits collected from the improperly listed units, and an injunction barring the platform from continuing to book unregistered Chicago properties. This is a materially different ask than the fines Chicago has issued in the past, which the city says the defendants simply absorbed as a cost of doing business rather than a reason to comply.
Airbnb pushed back on the suit. A company spokesperson told CBS Chicago the platform is “proud to provide everyday Chicagoans with economic opportunity at a time when costs continue to rise for them,” and the company has said it generates roughly $777 million a year for Chicago’s economy while supporting about 8,000 local jobs. The case is now pending in Cook County Circuit Court, where the city is asking a judge to impose penalties steep enough, officials say, to actually change behavior rather than simply get treated as overhead.
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