Buying STR in city of Chicago

[Tara Sonnabend]

Hi all, new to the group. I own a few investment properties and would like to expand to a STR in the city of Chicago. I am aware of the city's licensing requirements, but so far, what seems most problematic is the lack of condo buildings willing to accept leases/stays less than 6 months. In searching existing STRs, it is very clear this happens in practice, but I am not willing to buy a property and gamble that we can do an STR. One piece of advice I heard from a realtor friend was to search for a single family or row home so an association isn't involved, but those are both outside of the price range for what would make sense. Does anyone have advice/experience in the Chicago market? Thanks in advance!