I'm here for less than 48 hours, and most of my time is being spent either in workshops or asleep here at my hotel. The only local attraction I've been able to see is Navy Pier, which is within easy walking distance (those short lake cruises that depart from the pier are actually rather enjoyable). So I really can't pass much judgement on Chicago.
But: the people seem to be friendly, the street life here in downtown is good, the mass transit system is excellent (if not worn), the food is decent and the beer isn't too expensive.
I'll definitely have to come back when I have time actually do some sightseeing. But my initial impression of the Windy City is good and, at the very least, I can scratch another name off my "important cities I've never visited" list. Which still has a lot of names on it, though: Boston, Philadelphia, St. Louis, San Francisco, Seattle, San Diego... Damn, I'm lame.
Anyway, these workshops wrap up tomorrow afternoon, and then it's off to New Orleans for a few days of eating and drinking in the French Quarter.