I'm visiting Boston from the first time in mid-August and staying near at the Hilton near the convention center for a total of five days (Thursday-Tuesday). I am coming from Chicago. I will have no car, but am fine with cabs, public transit, and wandering around on foot assuming it's reasonably easy to figure out.
I'm basically looking for suggestions from across the board - the sole restriction is relative ease of getting there from the area. Solid ethnic one day, chowder another, multi course fine dining another, a gastropub the next - I'm game for anything, no real budget restrictions assuming there's a variety, and not the five most expensive places in Boston suggested.
Small plates and and interesting cocktails would be welcome as well. Something unique and unavailable in Chicago is preferred (for example, I see no reason to visit a steakhouse unless something is exceptional).
I prefer, but do not require, bar type seating for lunch as I'll be doing most of those alone, but dinners will be with people.
Right now, the only thing I have my eye on is a meal at Top of the Pub and probably a stop at Cheers just to do it.