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.

[Brie Schmidt]

@Grayson Schiller - The ordinance which passed a few years ago said if you have a 2-4 unit property you can only do STR in the unit you live in. Now, that was never enforced and as long as you only had 1 per address you could still do it. This spring the city cracked down and delisted hundreds of listings and made them provide proof to get approved. If it is not the unit you live in you have to apply for a commissioners adjustment, which I am hearing is taking months and unless you can prove financial hardship it is getting denied