As city officials call for better enforcement of Chicago’s vacation rental ordinance, renting out rooms could get more complicated for hosts. Aldermen Michele Smith (43rd Ward), Brian Hopkins (Second), and Brendan Reilly (42nd) have called  for a crackdown on violations of the city’s existing vacation rental ordinance. Though Smith said doing so could bring in an estimated $2 million annually, it’s not clear if the city can effectively enforce the ordinance.  

Since 2011, BACP has investigated 199 rental locations, which resulted in 832 citations, Stambaugh said in an e-mail. After the agency cited HomeAway and FlipKey, both rental companies agreed to provide information about Chicago’s regulations to prospective hosts.

“You really have to go into the fine print of Airbnb’s website to see that there might be regulations that govern it,” she said.

Enforcement may also be difficult because some hosts aren’t sure how to become compliant until after they are faced with costly citations. Sattar said he was confronted with the city’s regulations after a neighbor complained about a guest taking photographs of the neighbor’s garden.

Host Ryanne Maldonado said she wouldn’t mind complying with the city’s regulations as long as the cost of doing so doesn’t increase too much. Hosting guests in her home has allowed her to leave her previous job as an office manager for a large hospitality group and pursue art full-time.