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I guess it depends on what aspects you prioritize- Urban scale-Chicago. It's a big gap from NYC. But, it is clearly the 2nd city when it comes to feeling like a grand urban city. Philly is probably 2nd.
Density/streetlife activity- SF Again a big gap, but SF's NE quadrant just feels packed with people everywhere. Tough call after that as they are all pretty clustered. Chicago obviously has more people across the city, but its kind patchy compared to SF/Bos/Philly.
Architecture- Philly. Parts of NYC can very much look like you are in NY. The architecture is fairly similar. Then its kind of a toss up. Inner-SF can feel like NY in small parts (FiDi, Union Sq, Tenderloin, Chinatown), Boston has some areas that can feel like Brooklyn or a small scale Lower Manhattan, and Chicago's loop has elements of Midtown (with way less streetlife).
Culture-Philly or Boston. Philly's blue collar and arts culture is more like NYC. But, Boston feels safer, more affluent, polished and international than Philly.
I guess it depends on what aspects you prioritize- Urban scale-Chicago. It's a big gap from NYC. But, it is clearly the 2nd city when it comes to feeling like a grand urban city. Philly is probably 2nd.
Density/streetlife activity- SF Again a big gap, but SF's NE quadrant just feels packed with people everywhere. Tough call after that as they are all pretty clustered. Chicago obviously has more people across the city, but its kind patchy compared to SF/Bos/Philly.
Architecture- Philly. Parts of NYC can very much look like you are in NY. The architecture is fairly similar. Then its kind of a toss up. Inner-SF can feel like NY in small parts (FiDi, Union Sq, Tenderloin, Chinatown), Boston has some areas that can feel like Brooklyn or a small scale Lower Manhattan, and Chicago's loop has elements of Midtown (with way less streetlife).
Culture-Philly or Boston. Philly's blue collar and arts culture is more like NYC. But, Boston feels safer, more affluent, polished and international than Philly.
So all in all, I would say Philly.
I feel like Queens/Staten Island/Eastern Brooklyn look a lot more like Boston/Chelsea/Somerville than Philly. Even if Park Slope or whatever looks more like Philly.
The Bronx and a lot of Manhattan look nothing like a most other cities since they don’t have tower blocks almost anywhere else
SF doesn't have large European ethnic enclaves (relatively) and the associated communities built around them that are a staple centers of eastern seaboard cities.
But again, I don't see what that has to do with "urban feel?" Most of these are gone in NYC anyway, especially in Manhattan.
I feel like Queens/Staten Island/Eastern Brooklyn look a lot more like Boston/Chelsea/Somerville than Philly. Even if Park Slope or whatever looks more like Philly.
As in there are tightly-packed houses and single story convenience stores and/or restaurants on the corners of major intersections. Just a lot more wood than brick in the Boston area vs NYC. The styles of houses seem close, though, despite the difference in material. Those definitely aren’t Philly or Baltimore -style townhomes he’s driving by.
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