Airbnb in Chicago- Is it legal/ worth it?

[Grayson Schiller]

Who here is working the short-term rental market in Chicago? I am a Chicago native, working in development for the last six years. I'd like to expand my investment portfolio into STRS, but it's been challenging to get consistent information. For example, some brokers I've talked to have been insistent that if I don't live on the property my permits will be denied to legally run a STR. Other brokers have told me basically the opposite answer.
Without a doubt Chicago is a highly restricted place to try to launch an STR, but is it possible/ worth it? Let’s talk.