Most urban city besides NYC (Boston, Chicago, cons, size)
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I make the case for San Francisco, at least pound for pound. Its amazing how much is packed into that city and how urban it feels for a city of only 800,000+.
San Francisco's urbanity is very impressive for a city of under 1 million. Very consistant, packed infrastructure, vibrant. I would choose it over Philly and Boston, no doubt.
But I don't see how anyone would not vote for Chicago here. It is way more vast, its density continues for huge stretches, the scale is on a completely different level than the other choices. Easy. Chicago.
Boston epitomizes my definition of 'urban'; it's the only city on the list that I have been to, so I can't speak on the others; but from pictures I've seen, every city on this list is top tier in terms of 'urbanity'/
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