Downtown San Francisco vs Chicago (better, compared, population, life)
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Setting/aesthetics/features
Physical size
Vibrancy/crowds (day and night)
Safety
Variety/interestingness of neighbourhoods
Architecture
Walkability/navigability
Transport (ease of travel, service)
Tourist attractions/points of interest
History
Parks
Shopping (low end, high end, fashion, markets)
Dining
Bars, clubs, nightlife
Museums, galleries
Sports
I am not ure what your boundaries so will go off my experience
Compare in all aspects:
Setting/aesthetics/features: Setting SF (bay with hills and mountains more dramatic than lake, Aesthetics Chicago (Chicago Sklyline is my favorite in the US, better overall architecture), Features (Chicago (it just has more DT IMHO, see physical size)
Physical size: Chicago is larger
Vibrancy/crowds (day and night) Close am going to have to say draw - both excel on this aspect IMHO
Safety Both pretty good, on DT to me Chciago actually, SF has some sketchier parts in closer than does Chciago
Variety/interestingness of neighbourhoods: SF more interesting nabes in close IMHO
Architecture: Chicago
Walkability/navigability: Both very good, draw
Transport (ease of travel, service): Chicago better PT
Tourist attractions/points of interest: Draw, both excellent
History: Draw again
Parks: Chicago (GGP is no DT whereas Milennium is)
Shopping (low end, high end, fashion, markets): Slight Edge Chicage but they a pretty comparable overall
Dining: Tough one, they are really close, splitting hairs here
Bars, clubs, nightlife: Edge Chicago here
Museums, galleries: Edge Chicago
Sports: Chicago
Etc
Which downtown do you prefer overall? Love both (both among my top 5)
Which to visit, which to live in? (Hard one, love both always wanted to live in Chciago so will say that)
This one is very hard to do... way harder than SF or Chicago vs say, NYC.
Setting/aesthetics/features SF has the better setting, Chicago is physically more beautiful.
Physical size Chicago easily larger.
Vibrancy/crowds (day and night) Slight edge to SF
Safety Chicago
Variety/interestingness of neighbourhoods SF, more of their interesting neighborhoods are around dt, Chicago dt is a bit too commercial for me. It could prove interesting to other people though, but just too many chains really.
Architecture Chicago easily
Walkability/navigability SF has less dead zones in a circular route.
Transport (ease of travel, service) Chicago has better bus/subway transit
Tourist attractions/points of interest Chicago probably has more of these in DT than SF
History tie
Parks Chicago easily, the feature parks are right in or around DT
Shopping (low end, high end, fashion, markets) Slight edge to SF, again...more boutique and interesting stuff, Chicago has more of big name stuff. Just my personal preference.
Dining SF has better restaurants imo in and around DT, again, Chicago's offering are too chain oriented for the most part in the downtown area in comparison
Bars, clubs, nightlife SF by a hair, again in DT only, city wise, Chicago charges ahead pretty far.
Museums, galleries Chicago tends to have better museums than SF, and most are in DT
Sports Hmmm... Soldier Field vs ATT Park, I'd go with ATT Park, great baseball setting.
I'd give the slight edge to SF's downtown as it does feel a hair more interesting/vibrant at all hours of the day, Chicago is larger though, and more stuff going on once you get out of the downtown area. Chicago over SF for the whole city. Both DT's have touristy aspects, but I feel Chicago's DT is more geared to 9-5 office workers and tourists more so than SF is in terms of the amenities contained there.
I've lived *in* Chicago's physical DT and commuted to SF's.
As a resident, I'd prefer downtown San Francisco, it just feels a bit more lived in and less commercial. It's not just a business district, but it also sort of feels like a neighborhood too. I think its downtown compares better to Philadelphia's or Boston's in that respect. Chicago's downtown is more of just a business district and tourist destination, more comparable to Manhattan's. Though, I will say that downtown Chicago is a much grander, more impressive sight than downtown San Francisco.
Setting/aesthetics/features - Chicago because it has a beach, is much CLEANER, and has far less homeless people.
Physical size - Chicago
Vibrancy/crowds (day and night) - Tie
Safety - Chicago
Variety/interestingness of neighbourhoods - SF (Chinatown is pretty unique compared to anything around DT Chicago)
Architecture - SF, not that impressed with Chicago's architecture as some.
Walkability/navigability - Chicago because it's flat ad on a grid. Downtown SF is split into two seperate grids by Market St and a pain to drive around.
Transport (ease of travel, service) - Chicago
Tourist attractions/points of interest - Chicago (Navy Pier, Millenium Park, Married With Children fountain lol)
History - Tie
Parks - Chicago
Shopping (low end, high end, fashion, markets) - SF
Dining - SF
Bars, clubs, nightlife - Chicago (River North is better than anything offered in DT SF)
Museums, galleries - Chicago
Sports - SF for the stadium, Chicago for the fans. (I hate Giants fans lol)
Which downtown do you prefer overall? Very close imo but maybe a slight edge to Chicago since it seems to offer pretty much everything SF does plus for the fact they have a beach (I like beaches lol), seems more family friendly, and is cleaner.
SF is definitely more lived in and has been for longer, the growth of residential in at least Chicago Loop is fairly recent. For instance it doubled in population from 2000-2010... the neighborhood fill/local restaurants/established bars still have to come. Near North Side grew at 10%. As far back as 1950 when Chicago had almost a million more people than it currently does, only 7000 people lived in the loop, it's always just been more of a business hub.
Setting/aesthetics/features - San Francisco is much prettier overall and is always pleasant to walk.
Physical size - Chicago
Vibrancy/crowds (day and night) - San Francisco is more vibrant/packed than Chicago, all year round.
Safety - Both are fine.
Variety/interestingness of neighbourhoods - San Francisco has more packed in a smaller area. Chicagos are spread.
Architecture - Overall Chicago, but SF brings bridges into the equation.
Walkability/navigability - Same, both good although SF is tighter in density.
Transport (ease of travel, service) - Chicago
Tourist attractions/points of interest - San Franciso
History - Tie
Parks - Chicago immediately DT
Shopping (low end, high end, fashion, markets) - SF
Dining - SF, both are great though
Bars, clubs, nightlife - Tie
Museums, galleries - Tie
Sports - Niners.
Which downtown do you prefer overall?
San Francisco.
Setting/aesthetics/features - San Francisco is much prettier overall and is always pleasant to walk.
Physical size - Chicago
Vibrancy/crowds (day and night) - San Francisco is more vibrant/packed than Chicago, all year round.
Safety - Both are fine.
Variety/interestingness of neighbourhoods - San Francisco has more packed in a smaller area. Chicagos are spread.
Architecture - Overall Chicago, but SF brings bridges into the equation.
Walkability/navigability - Same, both good although SF is tighter in density.
Transport (ease of travel, service) - Chicago
Tourist attractions/points of interest - San Franciso
History - Tie
Parks - Chicago immediately DT
Shopping (low end, high end, fashion, markets) - SF
Dining - SF, both are great though
Bars, clubs, nightlife - Tie
Museums, galleries - Tie
Sports - Niners.
Which downtown do you prefer overall?
San Francisco.
Setting/aesthetics/features-Chicago
Physical size-Chicago
Vibrancy/crowds (day and night)-Chicago, during winter not too vibrant
Safety-Chicago
Variety/interestingness of neighbourhoods-SF
Architecture-SF
Walkability/navigability-Chicago
Transport (ease of travel, service)-Chicago
Tourist attractions/points of interest-Chicago
History-Chicago
Parks-Chicago
Shopping (low end, high end, fashion, markets)-More shopping
Dining-Chicago
Bars, clubs, nightlife-Chicago
Museums, galleries-Chicago
Sports-Chicago
Etc
Which downtown do you prefer overall?
SF
Which to visit, which to live in?
My answers are above.
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