Note - there is a reason housing prices in Chicago are stagnant...people are leaving.
I would not classify Chicago as anything close to an "affordable" housing market. Probably a toss up whether the least affordable area in the midwest to median income earners is Chicago or Minneapolis? Either area, you will be paying through the nose compared to, say, here in Wisconsin.
Buying and selling real estate involves high transaction costs - there are closing costs and transfer taxes on the buy side, and 6% commissions and transfer taxes on the sell side - which means in order to break even, you need to have some amount of appreciation.
Then there's the opportunity cost of living in a home that doesn't appreciate while literally everyone else in the country is getting rich merely by owning homes in states that have increasing populations.
And to top it all off, Chicago homes are not cheap and the property taxes are astronomical, so it's not like you're getting an amazing deal to make up for it.
Secondly, only the people who can afford to live in those high cost of living areas would get rich off of these increasing property values you're talking about. The worst thing a person can do is move somewhere to live beyond their means because "when I sell I'll be making a killing!" Out here in flyover country, unless you live in Chicago or Minneapolis, you're probably not seeing 30% per annum increases in your property values.
Finally, yeah, we in the midwest already know Chicago is not cheap. You buy there because you're well off, and you're going to make those ridiculous returns you were talking about. But the rest of us just deal with the areas we can afford. Which is probably not Tribune Tower.
