I don't hold any particular brief for Chicago. My denomination has its headquarters, main 4-year college, and seminary there (North Park), so I have lots of friends who are attached to the place. I've been there, in-and-out.
It was "Laconia" that caught my eye when I clicked through the Maggie's link. Not many famous people from NH Lakes Region, though a lot spend their summers there.
The article about how "elite" various cities are is interesting.