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Out of these probably SF/Seattle, but they're still less similar than many people think. The northern 1/5 of Seattle in particular feels nothing like anywhere in SF (not "suburban" exactly but more of a less-developed feeling --- huge old-growth conifers, few sidewalks, poorly maintained streets, old-school white working-class vibe, and still in the city limits).
Although the culture in the core areas of Seattle is still very type-A, wealth-driven, largely tech, I think that extends much less over the whole city than it does in SF. Areas like South Seattle and Georgetown in particular have more of a relaxed, hipster vibe still.
Though there is a massive size difference, I'd say the built environment of Philadelphia/New York City has more similarities than Philadelphia/Boston. Culturally, Philadelphia/Boston have a good bit in common.
I voted Midwest (Chicago, Milwaukee) since their urban areas blend in to each other and form a sort of megaregion. Similar ethnic makeup and culture, etc.
The one that really sticks out here is West (San Francisco, Seattle). These two cities and regions are not similar at all. The only thing they have in common is a tech scene. The culture and attitudes are completely different.
I spend a lot of time in Milwaukee and live in Chicago and it always confuses me when people talk about how Chicago is just a bigger version of Milwaukee. There are similarities but the cultural and political roots of the cities are pretty distinct and honestly they don't really have the same feel at all. Milwaukee reminds me much more of like a more progressive and outdoorsy version of Pittsburgh, St. Louis or Cincinnati than anything to do with Chicago.
I spend a lot of time in Milwaukee and live in Chicago and it always confuses me when people talk about how Chicago is just a bigger version of Milwaukee. There are similarities but the cultural and political roots of the cities are pretty distinct and honestly they don't really have the same feel at all. Milwaukee reminds me much more of like a more progressive and outdoorsy version of Pittsburgh, St. Louis or Cincinnati than anything to do with Chicago.
Yes, I agree they are pretty different culturally. People say they are similar because they are both giant grids up against Lake Michigan. But I gotta say what was really similar is much of the North Side of Milwaukee looks and feels a lot like say Englewood or Austin in Chicago. So this is the pair I voted for for that reason
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