<p>Having lived in Chicago, NYC, Boston, and Washington and with a daughter now going to school just outside Philadelphia, I’d pick New York as the place to live if I didn’t need to worry about money. It has the absolute best and the absolute worst of everything, but money can shield you from the worst, and it can make the best accessible. If money is an issue, which it will be when I retire, I’d choose Chicago which has everything and often the second-best of everything, but at a more affordable cost.</p>
<p>As a place to visit among the cities named by the OP, if you need to choose just one, I’d say . . . it depends. Your dollar will go farther in DC due to all the amazing free things you can see and do. A few things require you to pay. For art, the National Gallery and other federal museums offer of a free look at greatness, but there’s also the private Phillips Collection which is a must-see for people who are serious about art. For history, there are all the usual national shrines and still-operating institutions on the free side, but you’ll need to pay to see Mount Vernon which is well worth a visit.</p>
<p>For history, though, Philadelphia and Boston beat Washington hands down. In Boston, walk the Freedom Trail, some sites free, some paid, but on the whole it’s inspiring. In Philadelphia everything centers on Independence Mall; the federal sites are free, some others are not, but it’s equally inspirational. For the history buff I’d rate the two a toss-up, but better than New York or Washington. For art, no question it’s New York (at a price), then Washington in my estimation (with much of it free), then I’d actually give Philadelphia a slight edge over Boston but mainly due to personal preferences in periods, styles, and artists represented. For theater, New York clobbers the others, but among the also-rans Washington seems to me more lively and original than Boston or Philadelphia (though Chicago would run a moderately strong second to NY, well ahead of Boston, Philadelphia, or Washington). For food, whether serious high-end foodie stuff or more down-home ethnic fare, it’s also New York by a country mile, but again I’d rate Washington second, and Boston and Philly tied for a distant third (but not bad by national standards, but Chicago would rank well ahead of any of the three). The qualification here is that for seafood, New England is outstanding; but the best deals are not to be found in Boston proper.</p>
<p>Bottom line: if money is no object, I’d say New York, but expect to spend a small fortune. If you’re on a budget, Washington gives you the most bang for your buck. Boston and Philadelphia are both well worth a look, but I’d place both in a second tier, places well worth visiting on a second trip.</p>