We went to Chicago a few weeks ago. I liked it.
There's an inescapable charm to "real" cities, one that's magnified for me by the fact that I've lived in North Carolina my entire life. When I travel, I almost always find myself wishing I lived somewhere else. Chicago had this effect on me, as did Boston and Manhattan.
One thing I found very interesting about the city was the mix of old and new structures dating back to the late 1800s. The fire, of course, had left Chicago a blank slate of sorts - the truly old structures were mostly destroyed. But the timing proved fairly beneficial to the future of the city - as the old structures were wiped out, new higher density structures moved in to take their place. The internets will in fact tell you that Chicago was home to the world's first skyscraper. Many early skyscrapers were constructed there, many of which still stand today.
When fantasizing about moving, there's an immediate practical concern that can bring things to a swift halt - that is, the cost of housing. In this respect I found Chicago pleasantly surprising - it seemed like mortals could actually live there, whereas Manhattan felt like a playground for tourists and the wealthy. $300k for a 2 bedroom condo in downtown Chicago may not sound like a bargain for somebody used to North Carolina prices, but it's actually workable in theory. Compared to a comparable place in Manhattan, which could run you 7 figures easily, it's downright cheap.
Transit is another concern. Chicago of course has the elevated trains, which seemed pretty functional, but we also got around via car a good bit of the time. I'm a major proponent of mass transit and alternate transportation, so the rail system is a major attraction for me. Such things can only really prosper in areas of high density, which means we'll probably never see such a system in the Raleigh/Durham area.
Anyway, it's something to think about, especially as temperatures creep up to near 100 here in NC in early June. Global warming is only going to make Chicago more attractive and NC less so over time, so now might be a good time to beat the rush...