"I would put it this way: there are many ways to impose a Georgist land tax, fiscal insolvency being one of them. Very wealthy people and institutions know that if they relocate to Chicago, they will be required to ante up for the final bill. And so they stay away. For a city of its size and import, Chicago just doesn’t have that many billionaires, nor do I think a rational billionaire should consider moving there.
In other words, there is a pending wealth tax. Either directly or indirectly, this will place fiscal burdens on Chicago land, the immobile factor. And this keeps down rents in Chicago now."
Have you checked the recent rent surges? I'm not sure if it's the summer, but any hotel room in the loop is $300+ per night. Airbnb is just a scam there.