I'm going to Virginia this August and will also be going to Washington DC. But I'd like to go to another place for 2-3 nights so I'm thinking of one of those 3 places. Chicago looks appealing for the food and culture but Boston looks fancy. Don't know much about Philadelphia
I have never been to any of these cities, but.
I have a friend in Chicago who does say the variety and quality the restraunts there are unurpassed!
I have a friend in Boston, which of course is great for history buffs. Boston is still on my bucket list so that I can stand before the green monster at Fenway. (Don't judge me!)
My step-mother is from Philly. It is also great for history buffs. Though I don't know too much else about it.
Philly and Boston are close enough together you could hit both in one 1 trip if you wanted to be hardcore.
But if I had a choice of only one....Boston would be the winner. Great for the history buff side of me, get to see my Bostonian friends (short bus 4 life), Fenway Park, and good food. Can't be beat imho!