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.