The tax situation is not great, but for tech workers, it ultimately just means that Chicago is not as advantaged over NYC and SFBA as it could be; the cost of living here is so much lower that it's hard for me to think of a scenario where you wouldn't come out substantially ahead. My kid brother is buying a starter home, in a relatively (obnoxiously) expensive part of Chicagoland, and to get the same house within an hour's drive of San Francisco he'd be looking at 4-5x the outlay.

The property tax situation does mean that Chicago houses aren't mortal-lock speculative investments the way SFBA houses are, so there's that to contend with.

This is a fair point. Long term tax issues could def be a factor. Even beyond the abstract potential bankruptcy: who wants to buy a house when 90-110% of appreciation will be eaten by the inevitable tax increases?

In what way is Chicago’s tax situation worse than SF or NY?

Illinois is generally in the bottom three of states for pensions being underfunded, and Chicago is normally the city with the highest or second highest sales tax in the US. As an Illinois resident I'm concerned about the high percentage of taxes over the next several decades that will go to service debt, and therefore not provide other services. I think this causes issues which scare away established employers as well as entrepreneurs (high crime rates, struggling public schools, etc). This will then drive away young people who are looking for good jobs, and therefore Illinois misses out on the taxes those people would pay over their careers and thus the situation spirals down further.

https://taxfoundation.org/state-pension-funding/

https://www.taxjar.com/blog/cities-and-states-have-the-highe...

Boeing left because their tax break ended for what it's worth.

A few years ago the Citadel CEO went through a very public and extremely acrimonious divorce, during which the wife and kids left Chicago for the east coast and refused to come back. So now, he's all alone, and seemingly getting angrier by the day. His politics are increasingly distanced from what people in the area are interested in, etc.

Moving to a location where he might see his kids more often might just make him a lot happier and less angry. If so, that's good for him.

Boeing was barely here to begin with. They consistently missed their job targets, despite being allowed to count contractors towards the anemic targets they were meant to hit. Citadel is a body blow, but Boeing? Who cares.