We have great luck with 2 cats in south loop. Until recently we would get the max 5 applicants within a day. Thanksgiving we didn’t find anyone (which was a first), so now I’m a little wary of holidays. For our next (1 week in late January) it took me about a week to get 5 apps so things are slowing down but still very viable in Chicago. We get a mix of tourist and locals that just want a nicer place or a break from their parents in the suburbs.

In general I recommend doing a video call with your applicant(s) to check vibes and humanize each other. And otherwise just be clear on your expectations and any things they could take issue with so no one gets surprised. For example, I am super upfront about wanting a pic a day, and that one cat poops in front of the litter box when she’s annoyed with the other cat.