Also, pros: world-class architecture, fun music scene, great museums and of course The Art Institute, top universities and everything that comes with that, great restaurants from every cuisine under the sun, very immigrant-friendly city, lovely tree-lined streets with block parties, I could go on and on. Oh, and living is affordable and people are Midwest Nice.
Cons: it's the great flatness - you have to drive for hours to see hills. Tech industry is ok but very b2b and fintech focused and not a lot of consumer or entertainment stuff. Also as a very liberal city it's a favorite target of culture warrior types.
Tie: winter. Yeah, it gets cold and snowy. But also, it's "just weather". It's the same every year and people deal with it pretty easily.
As a life long Chicagoan I really think you're underselling how bad the winter is. Combined with the flatness it means that most people just don't spend any time at all outside december-april. I think this is why Chicago has such a strong drinking culture, there's just not much else to do in the winter, certainly not 5 months worth of stuff.
I've only visited Chicago once. It was nice, but I'd never thought architecture would be a selling point. Do you have examples of where I should look, the next time I'm there?
Cons: it's the great flatness - you have to drive for hours to see hills. Tech industry is ok but very b2b and fintech focused and not a lot of consumer or entertainment stuff. Also as a very liberal city it's a favorite target of culture warrior types.
Tie: winter. Yeah, it gets cold and snowy. But also, it's "just weather". It's the same every year and people deal with it pretty easily.