I'd prefer to be as far from any city as possible. Period.... visit or not absolutely no interest. That being said I have been to my share and would only really rate them by how much I enjoyed the food. NOLA Chicago San Fran
I generally dislike cities, though I live in one. But if I'm going, these have been favs: Charleston, Boston, NYC, Chicago, DC. Plenty to do/see, good eats, good accommodations available. Favorite vacation spots is a TOTALLY different set of answers...
I would leave Chicago out of it. Believe me your not missing anything. Unless you support gun grabbers. Plenty of better cities out there. Me I would stick with towns with good BBQ. And KeyWest.
Ha, sounds to me like your going to the wrong neighborhoods. If you really want to find some cool places in Chicago I recommend the smaller neighborhoods like Wicker Park, Old Towne... They have some amazing food!
D.C., lots of stuff to see and do Paris, lived there for a year and was pretty fun Dublin, been there twice, once during St Patty's day, by far favorite place I visited Moscow, yea Russia actually ain't that bad. Also lived there for a year St Louis, jus becsuse go there to watch the Cards and got some good food Most of my experiences are from being stationed overseas for three years and actually been to more big cities outside the US. Been to a lot of airports tho ha