Meh, it doesn't have the geographic limits that you get on the coast. The only geographical feature hemming in the city is the lake. You have essentially unlimited space to expand in all other directions. It would be hard to get skyrocketing rents outside of the immediate downtown area.

But mostly Chicago just sucks. Its all the shitty parts of the midwest without any of the good ones. What you really want is Indianapolis, Columbus, Minneapolis, Louisville, etc...