I don’t mean to defend Chicago, there is really no way I’d consider moving there. I just don’t think “the people” is why I choose to stay in California. The weather, the things to do, the weather, the topography, the sunshine (starting to sound like a broken record)…
I’d take almost any major midwestern city before Chicago, because it’s just too damn big and expensive. If I went back to Cleveland it’s more that “provincially speaking” I fit in a little better, lifestyle is a tad slower, and you don’t have to live so far out of town, to find an affordable but good community. There are some really expensive burbs near the city in greater Chicago.