I'm sorry if Chicago beat you up and took your lunch money.
I've never tried living there, but it's a great place to visit. Great food, great museums, great parks, Great Lake. Blues music. You can get there on a train from many places.
If you think Chicago has "great food" then you need to try some real restaurant towns (i.e. SF and NYC). Chicago's idea of great food is thick-crust pizza. The parks don't compare to most other cities', and if you want genuine blues music, you need to head south. The blues wasn't born up north.
37 Signals: well, a couple of people live there, yeah. The founder, who was born there and apparently doesn't know that you don't have to live in a crappy town, and DHH, who is from Denmark -- same exact climate, so I'm sure he feels right at home.
Chicago has no soul. It's a bunch of buildings. Visit a town with personality and you'll see what I mean.
I've never tried living there, but it's a great place to visit. Great food, great museums, great parks, Great Lake. Blues music. You can get there on a train from many places.
Also, 37 Signals seems to be doing OK there.