Just chiming in. I think a few folks have mentioned in passing but... the residential rental market is nutty. I have less info on it but the purchase market also seems to be rather solid (meaning it doesn't seem to be a product of people renting not buying).
Anywho... this seems rather incongruent with the approved narrative of "Chicago is collapsing".
If Chicago is emptying out it where are all these people applying for apartments coming from??? 
To expand a bit, I've had rental properties for about 8 years and have never seen anything like this. A few quotes from Realtors:
Agent 1: Asked how the rental market is
"Prices are up!"
a min later
"Wayyy up"
Agent 2: Also asked how the rental market is
"Oooh yes! Things are renting fast and are getting expensive."
Agent 3: Regarding a referral finding a place via not them (usually makes agents not happy)
"with how tough the market has been, as long as (renters) find something they're happy with then hooray!"
More data-driven, from what I've teased out of MLS data, rents are up over 10% year-over-year in all in all of the neighborhoods I've had to calc. Back to anecdotal, the few listings I've had have been snapped up incredibly quickly, with big price increases, and a torrent of interest. Also anecdotal, there seem to be more applicants from out of state than there had been pre-pandemic. General demo of those folks seems to be young and highly educated (again this is very anecdotal).
Anyway, seems more "on the ground" indicators like the rental market and
return to office stats (Chicago is now closing in on Dallas for #3 for total week and is already #3 for peak occupancy day) seem to point to Chicago doing pretty well despite the media claiming catastrophe. If anything, I guess this seems normal. I've personally spent the last 8 years freaking out from time to time that Chicago was done for. All the while, residential towers kept going up and rents kept increasing.... Strange how that can work in a city people are "fleeing."