Crime is bad, but concentrated in some parts of the city. Sure, I can't leave my bike with a cheap lock, but I've also lived in some questionable areas and never had real issues - nor have 95%+ of people I know, about the same rate as friends in other major cities (Philly, DC, etc.)
Public schools are dysfunctional - yea, I guess I'm young, but isn't that similar in most major cities?
Taxes are bad - yes, but so is NY/SF. Getting worse - fair point. Agree there.
Weather - yea, fair. Sucks hard.
Travel - yes, nothing close - but it's also an airline hub for 2/3 major airlines, and it's easy to get $100 tix to cool places.
I guess I may have just been too young much of the time to "get it." But it has so many great things, too - the summers, the restaurants, the colleges, the neighborhood variety & subcultures.
I kinda just wish I could buy long-term Calls on Chicago.