Chicago and the rest of Illinois are in a dreadful fiscal situation with underfunded pension liabilities. Anyone who buys real estate there will eventually be hit with higher taxes and lower services. Buyers are probably factoring that in.
So the deciding factor becomes something more like, "How much is the job I'm being offered going to pay me vs the cost of living?" They may also think about personal contacts, and the future opportunities a city is likely to provide them? I'd imagine it doesn't go too much further than that though.
Not on the same scale everywhere, and certainly not as bad as KY/NJ/CT/IL. If you’re in the 40% to 80% income in those states, and you have 10+ working years left, it would make a measurable distance to move somewhere else where you can save $5k+ per year in taxes, if not more. Even more if you can go remote with a high salary.
Whether or not the "fair tax" passes will be an important bellwether.
What? The tax increases are just starting. This year, Illinois is voting to change from a flat % income tax to having marginal rates. Anyone earning any decent amount of money should expect to pay more and more every year in income tax, property tax, sales taxes, tolls, fees for car registration, basically anything that can help increase tax revenue since expenses aren't going anywhere but up also for the next couple decades. Unless benefit recipients die earlier than expected.
Just California has Prop 13 protections for land owners.