Maybe I should just sit tight and hope for $105K off the waitlist like this person
Yes, this. I was looking at the waitlist thread a few months ago (it was still going when apps for this cycle opened lol) and I think it goes something like this:
1) Out of the blue in June or July you get an email from a junior member of the admissions staff asking if you're still interested, any updates etc. If you haven't interviewed, you might get an interview invite. If you have already interviewed, she'll just say that Dean Perry would like to have a five minute chat.
2) You have a five minute chat with Dean Perry. This is basically a YP interview; she'll say you can't request a deferral etc.
3) A day or two later you get the Welcome to Chicago email, giving you a deposit deadline a few weeks out
4) A few days after that you get a scholarship offer via email that will make all the RD admits jealous
5) You deposit, and you won't have missed anything because Chicago's fall quarter starts a month after everyone else