The contention among some folks is that since real estate is the only captive taxation target (people, and businesses, can leave) for Chicago, the only realistic future scenario for resolving Chicago and Illinois’s pension insolvency is to dramatically raise property taxes. That, in turn, suppresses demand for assumed in-future-more-expensive real estate.
Well I, for one, grew up in Chicago, great city, but wouldn’t consider buying real estate there specifically because of the fiscal situation, so you’ve got one data point for reduced demand.
Okay, but I know 50 other people who have bought real estate there. We would as well, if we weren't on the East coast for my job. I don't see any indication that Chicago is cooling as a property market.