As someone who has lived in 13 different cities/towns in 9 different states, including all of the big three (NYC, LA, Chicago) I'd put Chicago in the upper half. Don't know if you've spent a lot of time in the northeast, but it is WAY ahead of NYC/Boston/Philadelphia. The cost of housing in Chicago is dirt cheap for a city that size - a very welcome change from LA and NYC. The women are prettier than NYC/Boston/Philadelphia, that's for sure. The public transportation system makes it really easy to get around, second perhaps only to NYC. Yeah, it has it's fair share of douchebags, but there are douchebags everywhere (less douchebags in NYC, but that's because everybody is broke from the cost of living) and the douchebags are pretty much limited to the fratboys/sorority girls who grew up in the upper middle class suburbs of Chicago and never have lived anywhere else. There are plenty of people here who didn't grow up in the upper middle class suburbs of Chicago who aren't douchebags, you just have to avoid the general Wrigleyville area. And Chicago is driving distance from Wisconsin if you want to get away for the weekend. It's not utopia by any stretch - I'd rather be in Austin or Denver, maybe Nashville or Seattle (Seattle is getting expensive too, and my field doesn't pay enough to live in coastal CA), but I work in a fairly specialized field and there aren't many opportunities in those cities. I've never lived in the "Big 3" but have been to all 3 cities plenty of times. I hate Chicago. The people there are generally jerks. NYC gets that reputation, but it hasn't been my experience at all. But Chicago....doesn't matter if it's the city or burbs, upper, middle, lower class...most everyone is a jerk. Beyond that, I can't explain it, but I just don't like the whole "feel" of the area.