I worked as an IT consultant for years and spent weeks to years in dozens of different cities.
Houston - I was HQ'ed there for 7 years. If it wasn't for the beautiful women, that place had nothing to offer but sprawl and humidity. I think these country girls all flocked there looking for JR Ewing, but he'd gone broke and they settled for me. I went to pick one up once, drove 60 miles to get there, and never technically left Houston. Dallas was just about as bad; the only difference was the women cared more about what type of car you drove.
Gary was the absolute worst. I was at the US Steel plant there. That whole town just needs to be put to the torch and start over.
Allentown, PA - I was there during the OJ joyride. We called it "Jonestown". Just dead, dead, dead. Worst hotel I ever stayed in. Flew into Newark to get there, got on a shuttle bus to the plane, then found out it was in reality a shuttle bus to Allentown, 3 hours away. Actually said "Bus" in fine print right on the ticket, which was no consolation considering I'd downed an extra-large beer in the terminal and the bus had no john.
Jackson, MS had some beautiful architecture but absolutely nothing to do but stare at it.
Grand Rapids, MI. Actually making a joke here. I was in O'Hare, about to make my first visit to Cedar Rapids, Iowa. Got on the wrong puddle jumper (no one ever looked at my ticket), went to GR, then realized I was in the wrong city at the rental car counter. Turned right around and got back on the same plane I'd just left (Flight crew: "Weren't you just on this flight?" Me: "Err...yeah. I'm an airport inspector. My job is done here") and went back to O'Hare. The client was not amused.