I'm from Cleveland, so pretty much any city I visit is cooler than the one in which I live. Having said that, Cleveland's actually pretty darn good. The cost of living is quite cheap, there is abundant fresh water (which is becoming a growing problem elsewhere) and the weather generally mild. Yeah, we have a pretty long winter, but it's generally not too bad; not as cold as Minneapolis or Chicago, not as snowy as Buffalo, not as icy as NYC. Also, summers are really nice. Not too hot to go outside, like in the south, but cool enough where you can survive without AC. And we're not prone to natural disasters. Big snowfalls are the worst we ever seem to get (and tornados, but only away from the city), but the worst I ever remember was about two feet, and that didn't even shut the city down. It slowed things down for a couple of days, but that was it.
The bad parts of Cleveland are the job market, unless you're in health care.
Of the cities I've visited, San Francisco and Ithaca, NY, were my favorites.