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The popularity of urbanity threads around here got me thinking about this.
I was surprised that I didn't find a thread here just for this topic, as they both have a case for being the second most urban city in the country after NYC.
Ooooh, this is gonna be a tough one! Im giving Chicago the SLIGHT edge here. And by slight, I mean slight. For San Fran's size, it packs an amazing amount of urbanity. This was tough.
Chicago is larger, has a larger/thicker downtown, has always been larger and that shows, etc etc. So there are characteristics of all of this that may lead some to say it is more urban.
San Francisco is perhaps the only other city outside of a large swath of NYC (and Philly) to be pretty much fully built to the curb and it doesn't have the "gaps" that a Chicago has, and feels more crowded. SF to me seems more consistently vibrant and has more of that international/liberal/free-spirited vibe that you find in certain cities that draws people out, year round, to parties, events, and the like. I think it's largely a function of being coastal. It feels more "stimulating" to me with a better street scene, though it's a smaller city with less of a transit system and less of a "grandiose" feel.
I could swing either way and I don't care to vote as a result. These are the two cities that are/could be easily my favorite cities in the US, at different times of my life, along with New York. At this point, I wouldn't consider living elsewhere.
I could say with a straight face that these are the two most urban cities in the US well after NYC.
Chicago by a long shot. It's larger, bigger, taller and has better transportation in the urban area, later last call which mean people are out longer at night, etc
I visited San Fran last Dec. I was very impressed. A lot safer than Chicago. However the transportation is the reason why I voted Chicago. If I had some wicked powers I would remove San Francisco from the West Coast and place it on the East Coast. Placed just North of Virginia Beach somewhere along hgwy 13.
Overall, Chicago. Pound for Pound, San Francisco. Chicago is massive, and has some amazing urban canyons with its perfect grid and taller buildings.
However, Chicago's vibrancy is really concentrated in certain areas. I've traveled these two cities more than any other cities in the U.S. not including my home town, and in SF, you will see pedestrian activity that IMO, is only surpassed by NYC. It's also much more evenly spread throughout the city. Always people out strolling, buying groceries, etc. SF is much more compact and walkable than Chicago, despite its hills.
Also, Chicago turns into single family residences shockingly fast when traveling west from downtown. San Francisco's built form and density travels in all directions and for the majority of its city limits. Just look at an aerial of SF and you will see what I mean.
Honestly, for me, it's really close. But I'll give the edge to San Francisco.
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