Your opinions on Chicago always amuse me. I've never lived in Chicago, and don't feel any particular affinity for it, but c'mon, really? It's an incredibly cosmopolitan and multicultural global powerhouse with *some* of your typical midwestern fatties. NYC has its own trashy native contingent, with the long-mocked guidos merely topping the list of the many tri-state undesirables. Just take a gander next time you're in Murray Hill if you want to see the jersey-wearing douche crowd. The funny thing about NYC is most of its "cool" areas (LES, Williamsburg/Greenpoint, Bushwick) are full of midwestern art and music students who went to live the hipster life in the big city. Your viewpoint on Chicago really reflects the someone ironic ignorance that comes with NYC provincialism. You hang your hat on it being the center of the universe, and while it still dominates the American scene to a waning extent, a handful of Asian cities now make it feel like a sleepy hamlet. If I wanted to live in a reasonably priced city that offered world-class amenities, I'd choose Chicago. If I wanted to live in a vibrant, exciting, modern city that isn't merely resting on its laurels, I'd go with Tokyo, Seoul, Shanghai, Hong Kong, etc. With international travel becoming more the norm, there are fewer reasons to go to NYC every year (especially after 2008). It's starting to feel like a combination of Paris, which is nearing the end of its journey to becoming a dull museum to its past greatness, and Disney World.
And Chicago, while being basically an overgrown cow town full of big 10 fatties (that wear sports jerseys when they "go out on the town") and people who couldn't make it in a real city, at least it has some things to do.
Contrast this with Mississippi, which is appropriately in the bottom. Not only is it practically tropical in climate, there is nothing to do there (outside of riverboat casinos), and god help you if you're poor and/or non-white. And since there are only about 3 rich people in MS, poor and/or non-white probably describes you if you grew up there. Really, the bottom 5 oughta be all Southern states, there really isn't anywhere below the Mason-Dixon a civilized person would choose to live. I mean, sure, there's New Orleans, but I don't know any sane person that would actually want to live in that dump, although it can be fun for a week. And Miami isn't part of the South, IMO. The rest of the South's "cities" are either wholly unremarkable, like Raleigh, or are sprawling dismal places, like Atlanta.
Loony leftists or not, I think San Francisco is easily the most desirable metro area in the country. The Redwoods, Sierras, Lake Tahoe, Pacific Ocean all nearby, a magical Mediterranean climate, fresh produce year-round with one of the best food scenes and the best wine and beer producing regions in the country, all anchored by a vibrant, historical city. Also, do people still talk about hippies? I mean, I think they exist in some college towns, PIRG campaigns and the Haight, but most urban culture is no dominated by the undefined "hipster" aesthetic.
Finally, CA at #1 baffles me. I don't get what people dislike about it. Is it the Mexicans? I mean, well, that describes practically the entire Southwest, so that can't be it. Is it the Hollywood Jews? Well, that can't be it either, cause NY isn't on the top 5. Maybe it's all the SF hippies, and while hippies are indeed some of Earth's scum, you're gonna run into hippies in practically every coastal city. That and SF's ideal weather makes up for the hippies. Not to mention there is a vibrant finance industry in SF, so you can isolate yourself from the leftists if you so choose.