You should definitely plan another trip when eating can be a higher priority than work. Stay an extra day or go a day early or something. It’s hard in an unfamiliar city when you are rushed and don’t know exactly where to go.
I am going to Chicago for Valentine’s Day weekend. My wife is thinking of it as a romantic trip. I am just looking to find as many good meals as possible (as Homer Simpson once said, "I discovered a meal between breakfast and brunch"). We already have reservations at Greek Islands for the 13th and a newer place called Keefer’s on Valentine’s Day (has anyone here ever been?). I figure that should take care of the sit down places. The rest of the time, I plan on finding a good Chicago dog, a good pizza, an Italian beef, etc. At least you got to try some of the things on your list. And now you have a good excuse to go back.