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Both feel very urban, Chicago feels much more monumental with its impressive skyline, river, parks and grand museums on the lake.
I’ll say one thing for certain, Chicago is like 10 times cleaner than San Francisco. I was amazed when we visited early last summer. At least in the Loop I would describe it as the Singapore of the U.S.. One had to strain to find a speck of litter (and no poop whatsoever!) and hardly any homeless, drugged-out vagrants to bother you as is present throughout the city in SF. Chicago is a justifiably very impressive city and much safer feeling than the overblown bad press it gets which in reality is mostly limited to a few select areas.
San Francisco is hugely underrated in urbanity, and is top-tier in its urban ranking, although Chicago is larger and has a larger traditional urban footprint due to its size.
Cosmopolitan is hard to gage. San Francisco has a larger international population, although Chicago is also top-tier in that category as well. The high-end, wealthy tech presence, I guess could boost it in the cosmopolitan category. The reputation for San Francisco being so dirty and unsanitary hurts it on that front, although Chicago's violent crime rep hurts it even more, so Chicago gets more urban and SF gets more cosmopolitan.
Chicago is no slouch in being cosmopolitan though. Especially the look and feel of the downtown neighborhoods, with tons of high-end condos, museums, parks, lounges and art studios, restaurants (including Michelin), lots of high net worth individuals living there (along with diversified industries-law firms, consulting, banking/private equity, tech, medicine).
Been to both, although I have been to SF many more times than I have been to Chicago. I think Chicago overall is more urban. While the financial district/union square in SF is more dense than Chicago’s loop, the loop stretches to a significantly bigger area than the financial district.
As least for me, in terms of the overall cosmopolitan feel of the city, Chicago’s loop is probably only behind Lower/Midtown/Uptown Manhattan of NYC in this country.
But overall though, I still vastly prefer SF over Chicago.
Both feel very urban, Chicago feels much more monumental with its impressive skyline, river, parks and grand museums on the lake.
I’ll say one thing for certain, Chicago is like 10 times cleaner than San Francisco. I was amazed when we visited early last summer. At least in the Loop I would describe it as the Singapore of the U.S.. One had to strain to find a speck of litter (and no poop whatsoever!) and hardly any homeless, drugged-out vagrants to bother you as is present throughout the city in SF. Chicago is a justifiably very impressive city and much safer feeling than the overblown bad press it gets which in reality is mostly limited to a few select areas.
Chicago's downtown is cleaner but I would argue SF's residential neighborhoods are cleaner. There is no equivalent of the West and South sides in SF. Tourists in Chicago don't see that side of the city, which has been woefully neglected for decades. We should also factor in the lack of rain in SF and how the city needs to triple the size of it's street cleaning budget and increase civic pride (which it is doing).
Chicago's downtown is cleaner but I would argue SF's residential neighborhoods are cleaner. There is no equivalent of the West and South sides in SF. Tourists in Chicago don't see that side of the city, which has been woefully neglected for decades. We should also factor in the lack of rain in SF and how the city needs to triple the size of it's street cleaning budget and increase civic pride (which it is doing).
I would go further to say in terms of “niceness” of the residential neighborhoods, places in SF like the North Beach, Presidio, Nob Hill even Marin County are probably among the best residential neighborhoods in the whole country, rivals Santa Monica/Beverly Hills/Malibu here in LA and Upper West Side/Upper East Side of Manhattan, NYC.
Yeah, that's what I would say too. Though both cities are no slouches in either category.
Aspects of SF are actually more urban than Chicago but Chicago has the edge for sheer volume of urbanity. Both are very cosmopolitan but I’d give SF the edge there.
If we are talking CSAs, I would say that the Bay Area edges Chicagoland. In terms of urbanity and cosmopolitanism, Berkeley beats Evanston and there is no equivalent to Oakland in the vicinity of Chicago, but if it is city versus city: Chicago by a large margin. Much better nightlife, equivalent food, much better public transportation, and economies of scale. The Loop smashes downtown San Francisco. SF has the better Chinatown. Lakeview east is much more lively than the Castro. Ditto for Lincoln Park over Nob Hill. I am a middle aged gay guy. I really want to like San Francisco, but compared to Chicago, it always feels sleepy and provincial...
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