Chicago Magazine has an interesting list of "Ten Modern Masterpieces" of architecture that have apparently revived the city from state of structural staleness in the early 2000's. I'll have to add some of these to the list of buildings I have yet to see, but my personal favorite of these that I have been to is the State Street Village on the IIT campus. Chances are, if you visit me in Chicago I'll drag you to see it... on the way to the Rem Koolhaas campus center of course.

We [Chicago] have powerful politics, which count when you are trying to build an ambitious building. We have a public that knows about architecture. Most important, Chicago harbors a preternatural distrust of "style," a word that, in architecture, refers to a set of formal characteristics that can be imitated and later discarded. Here, passing fashions are a distant second to the pure pleasure of a well-built building.