I've been to some pretty lousy cities but the one that constantly takes the cake for me is Chicago. Chicago offers some pretty amazing things (as well as high expectations of it being a premiere US city destination) but then washes all of that away with insane prices, rude ass people and ridiculous traffic. It is absurd how expensive shit is in Chicago...after having been to many other major US cities, Chicago constantly takes the cake as one of the costliest places I've been...and often for no reason. Gas, parking, food, hotels...often some of the highest prices I've ever paid anywhere. Couple that to the rude/miserable motherfuckers around every corner and it makes for a place I more than often dread rather than look forward to visiting.
just posting here to point out how much of a pussy smokehouse is.
Chicago is a fucking great city. It's a city so it has city problems (people who don't give a fuck about you and don't share your stupid small town mentality ["rude people"] for instance) It kind of blows my mind in general how stupid some suburbanite assholes are who think every crazy and/or black person outside is trying to stab them and that their life is going to end on public transit systems at night.
Also, having lived in the country, and having lived in one of the cheapest cities to live in in PA, it's not that expensive here. Grocery store has better prices than what I'm used to despite not having as good of a produce selection. Cigs are about as expensive as you'd expect them to be in a major city but not anywhere near as pricy as New York (and you can just go to Indiana and get them for $7 a pack if you really want to) . And again, if you aren't a fucking pussy, the public transit here is very encompassing and cheap as fuck.
GET REAL
EDIT: Worst cities? I'm not the best person to ask, but in Chester (basically a Philadelphia ghetto) when i was a toddler I saw a lady get her head blown off at a stop light and hijacked like it was fucking Grand Theft Auto 3 and my mother worked at the hospital there (Crozer aka Guns & Knives Club) and would come home nearly every night and describe in detail the murders, rapes, teenage pregnancies. My late night schmooze hours with my insane mother were like a Law & Order series.
Lancaster City in PA is a lot worse than you'd think as well. You get a lot of fugitives and nomadic criminals because it is under-policed and placed near/between major cities such as Baltimore, NYC, Philadelphia and nearby is another shit city called York. Definitely some scary streets in Lancaster despite being in the beautiful country.
EDIT 2: (im a serial edit0r) looks like NYC and Chicago have about the same cig prices, but whatev,r they're fuckng cigarettes you should have to pay $11 a pack because they are bad for you