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In terms of places I'd actually live, probably Los Angeles. San Francisco would be my choice if it wasn't so expensive, Chicago if not for the summers and winters.
My hometown is Montreal and I live in Vancouver and they're both very nice cities, but my very favourite city in the world, and I've visited quite a bit of it, is Prague in the Czech Republic. It's a special, down to earth, magical city with a perfect vibe. Not an overly international alpha city like London, just a fantastic big city with a ton of heritage, down to earth people, great vibe, great things going on. For me, it comes down to that je ne sais quoi of the people who live there, and I guess the Czech people generally (I have no connection to the Czech Republic, i'm just a foreign fan).
US: Philly and San Francisco - Lots of history, very walkable, great architecture, big but not massive. Anywhere: Florence, Italy; Barcelona, Spain; Paris, France - All three have amazing architecture, very very walkable, good transit, beautiful layout. I'd take any of these three over Philly and San Francisco.
I've only left the US a few times, but I really liked Montreal when I did.
Seattle is great for me.
I almost named Montreal, but the weather there is just so bad.
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