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You're entitled to your opinion, of course, but I don't think too many people will agree on these points.
Even people voting for Chicago will not be likely to say it's because of "laid back people", "seasons", or "beaches". I mean, Pacific vs. a Lake, January in Chicago is a selling point, and Chicago is some laid back town? Definitely no. And really neither city is known for attractive people, but Bay Area is much, much healthier and fit.
And transportation and downtown is a wash, IMO.
Definitely everyone has opinions and we're all entitled to posting them.
Laid back people? Yes. Chicago is more laid back. Not in terms of being a small town, but that people are actually friendly and not so judgmental. They're nicer and it's a genuine niceness. SF is a rude city full of very cold people.
Seasons? That's all personal opinion. Though SF is just cold, windy, and foggy for a lot of the year with very few days comfortable enough to wear a T-shirt, let alone a T-shirt and shorts!
Beaches? Yeah the Pacific is prettier to look at. But in terms of functionality, you can actually swim in Lake Michigan comfortably in the summer. I prefer that. Ocean Beach is cold, windy, and foggy almost year round. When it's actually sunny in SF, you still can't comfortably swim in the ocean. Chicago gets warm in the summer (maybe too warm for some people's liking) like in the 80s and 90s and the lake warms up so you can have a nice beach day. It's impossible to do that in SF. You can sit out on the sand when it's warm (which is rare on that side of the city), but you can never swim comfortably.
SF is definitely more fit and healthier, but I'd rather have someone with an attractive face, nice personality, and just average fitness over a butter face with weird/gross hipster attributes/piercings/accessories, a terrible/cold personality and a perfect body.
Transportation in Chicago is way better. It's open 24/7 and the L actually reaches a majority of the residents. Unless you live along Market Street, in the Castro, or in the Mission, you'll be stuck riding buses that are consistently rated the slowest in the nation. It takes me 45 minutes to get downtown. It's 3-4 miles. Because the buses sit in traffic. The L moves quickly above and below ground making it much easier to get around the city.
There is simply no comparison between the size of downtown Chicago and SF, none. Anyone who says otherwise is simply ignorant of one of the two cities. Chicago is just plain massive compared to SF. Other than NYC you won't find any city that has a CBD that compares to Chicago in the US. Transportation in Chicago is also far better than SF. BART is one of those weird hybrid systems that drops off in service as you get outside the city center, while the CTA has comprehensive service for many miles outside the city center (combined with a dedicated commuter rail service in Metra). There's also no comparison on that front.
SF is simply a lot smaller and more homogenous than Chicago. That can be a very good thing for many people, but if you want to create that same thing in Chicago you can stick to the lakefront between the Loop and Foster and have the same experience (in an area that has a larger population). The thing is, that is a small portion of Chicago, there's much more to explore if you have the desire to do so - if not you can still have a large area/population to explore. And in general Chicago is very "gay friendly". That's an evolving term these days, but nowadays in Chicago that means that the vast majority people who you meet will support gay marriage, but you might be pushing against the tide if you're fighting against "sexed" bathrooms for the Trans community.
There is simply no comparison between the size of downtown Chicago and SF, none. Anyone who says otherwise is simply ignorant of one of the two cities. Chicago is just plain massive compared to SF. Other than NYC you won't find any city that has a CBD that compares to Chicago in the US. Transportation in Chicago is also far better than SF. BART is one of those weird hybrid systems that drops off in service as you get outside the city center, while the CTA has comprehensive service for many miles outside the city center (combined with a dedicated commuter rail service in Metra). There's also no comparison on that front.
SF is simply a lot smaller and more homogenous than Chicago. That can be a very good thing for many people, but if you want to create that same thing in Chicago you can stick to the lakefront between the Loop and Foster and have the same experience (in an area that has a larger population). The thing is, that is a small portion of Chicago, there's much more to explore if you have the desire to do so - if not you can still have a large area/population to explore. And in general Chicago is very "gay friendly". That's an evolving term these days, but nowadays in Chicago that means that the vast majority people who you meet will support gay marriage, but you might be pushing against the tide if you're fighting against "sexed" bathrooms for the Trans community.
Question, how is San Francisco "homogenous"? I don't have a dog in this fight but I just found that statement totally weird.
There is simply no comparison between the size of downtown Chicago and SF, none. Anyone who says otherwise is simply ignorant of one of the two cities. Chicago is just plain massive compared to SF. Other than NYC you won't find any city that has a CBD that compares to Chicago in the US. Transportation in Chicago is also far better than SF. BART is one of those weird hybrid systems that drops off in service as you get outside the city center, while the CTA has comprehensive service for many miles outside the city center (combined with a dedicated commuter rail service in Metra). There's also no comparison on that front.
SF is simply a lot smaller and more homogenous than Chicago. That can be a very good thing for many people, but if you want to create that same thing in Chicago you can stick to the lakefront between the Loop and Foster and have the same experience (in an area that has a larger population). The thing is, that is a small portion of Chicago, there's much more to explore if you have the desire to do so - if not you can still have a large area/population to explore. And in general Chicago is very "gay friendly". That's an evolving term these days, but nowadays in Chicago that means that the vast majority people who you meet will support gay marriage, but you might be pushing against the tide if you're fighting against "sexed" bathrooms for the Trans community.
The first time I saw Chicago in person, I was completely blown away by the size of the downtown area! BART stops running quite early as well. It doesn't actually serve the majority of the city of SF. Ironically, the abbreviation is for Bay Area Rapid Transit. Rapid, to me, doesn't mean 15 minute wait times during the middle of the day. And Muni Metro? They look like toy plastic trains, sometimes coming as only a single car.
SF is extremely small. Additionally, the Sunset District, Hunters Point/Bay View, Balboa Park, Twin Peaks, the Richmond District, Crocker Amazon, Visitacion Valley, and Noe Valley make up a huge chunk of the city and are quite boring, quiet, and residential. Well some aren't quiet if you count gun shots and sirens, but quiet in terms of things to do. The actual cool, fun, active part of the city is even smaller than the 7x7 box SF is known for. There's just way more to do in Chicago. As for being gay friendly, obviously no city can beat SF, but Chicago is by no means some conservative Midwest city.
Question, how is San Francisco "homogenous"? I don't have a dog in this fight but I just found that statement totally weird.
Agreed - that is a weird thing to say, but I do believe it. I don't think there's really a large Gay/Straight split in any large urban area any more, and there are probably more splits within the gay community in SF than there are between the straight and gay community even in cities like Indianapolis. SF is also one of the few cities to have a white population close to 50%, combined with a very large Asian population. Consider these numbers:
I've lived in both cities, and while SF has a larger Asian population, the biggest divisions we have in the US are not between Whites and Asian (which account for more than 75% of SF population), they are between Whites, Hispanics, and African Americans. Combine that with the fact that much of the White population in Chicago is made of Eastern Europeans, the geographical barriers in SF vs. Chicago, and SF has a homogenous feel to me that I don't have in Chicago.
Are you meaning to say you find SF more segregated? Homogenous, I have to disagree with you there. They're about equal. Segregated, they're about equal in certain ways. In most cities, the gays want to be accepted. In SF, the gays enjoy being cliquey in the Castro and are not welcoming to outsiders.
One thing about those percentages is that in SF, the whites are just "white". Besides the Russian community in the Richmond District, there's no "white diversity". In Chicago, there are communities of Europeans all over. Italians, Poles, Russians, Greeks, Irish, etc. In SF, the Asians are almost entirely Chinese. Aside from Japantown which is a joke and a small Vietnamese community the Tenderloin, almost every Asian is Chinese.
The Latino and black communities of SF are virtually non-existent anymore. The Mission is gentrified in some areas beyond recognition and nearly all the blacks have moved out.
But let's be honest, the North Side is white and the South Side is black. There's no denying that in Chicago. However, I do find SF to be very cliquey. People of certain races only hang out with their race, sometimes even their own nationality. I have no problems with any race, but I sometimes feel left out from things simply because I'm white. In fact, I've been told that before.
Agreed - that is a weird thing to say, but I do believe it. I don't think there's really a large Gay/Straight split in any large urban area any more, and there are probably more splits within the gay community in SF than there are between the straight and gay community even in cities like Indianapolis. SF is also one of the few cities to have a white population close to 50%, combined with a very large Asian population. Consider these numbers:
Chicago:
White: 31.7%
Asian: 5.5%
Hispanic: 28.9%
African American: 32.9%
I've lived in both cities, and while SF has a larger Asian population, the biggest divisions we have in the US are not between Whites and Asian (which account for more than 75% of SF population), they are between Whites, Hispanics, and African Americans. Combine that with the fact that much of the White population in Chicago is made of Eastern Europeans, the geographical barriers in SF vs. Chicago, and SF has a homogenous feel to me that I don't have in Chicago.
So you're discrediting or knocking off points off San Francisco because whites and Asians (a race Chicago severely lacks) tend to get along better There's also been talk of SF as a "small" city, but really city borders are arbitrary as I'm sure you guys know, Oakland and Berkeley add to the overall urban footprint which are also very diverse, with a CSA of over 8 million people and a larger economy than Chicago's there's nothing small about it, and may have well surpassed Chicago as the third most important metropolitan area
Wrigleyville is probably the "coolest" neighborhood for young urban professionals.
LOL! Oh god..while it's a popular hood for younger people just out of school with decent paying jobs, it's in no way considered a hip or cool neighborhood for a young professional. River North, West Loop, and Wicker Park is.
Lincoln Park may be Chicago's trendiest neighborhood at the moment.
Not even close to trendiest. Ukrainian Village, East Ukrainian Village, Noble Square, Wicker Park, Logan Square, Bucktown, Gold Coast, River North, Pilsen, Bridgeport, Avondale, etc....all trendier than LP unless you consider North Face jackets trendy then I guess Lincoln Park is your place.
So you're discrediting or knocking off points off San Francisco because whites and Asians (a race Chicago severely lacks) tend to get along better There's also been talk of SF as a "small" city, but really city borders are arbitrary as I'm sure you guys know, Oakland and Berkeley add to the overall urban footprint which are also very diverse, with a CSA of over 8 million people and a larger economy than Chicago's there's nothing small about it, and may have well surpassed Chicago as the third most important metropolitan area
SF is small. Sorry. Like I said before, the actual "fun" and "vibrant" parts of SF are small, and the actual city is already small. The Richmond, The Sunset, Twin Peaks, Noe Valley, etc. feel quite suburban yet take up probably half of the 47 sq mi. Oakland and Berkeley add to the urban footprint, but let's be honest. Getting to/from those cities is not fun or easy. BART doesn't run all night like the L and the Bay Bridge is hell at any time of day. Then once you're there, there's not much to do. I mean yeah there's stuff to do, but they're both clearly suburbs of SF. Don't get me wrong, I like Berkeley, but it's not really that happening. And if we're talking about the CSA, let's not forget that San Jose has to be the most boring large city in America, on par with Phoenix. It's as suburban and sprawling as can be with nothing to do besides walk Santana Row. But let's give SF the benefit of the doubt and include Oak and Berk. According to data on Wiki, SF+Oak+Berk has 1,342,006 people with a density of 11,862.51/sq mi. Chicago has 2,714,856 with 11,864.4/sq mi. That right there should prove something. Over an area twice the size, Chicago is still denser.
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There's also been talk of SF as a "small" city, but really city borders are arbitrary as I'm sure you guys know, Oakland and Berkeley add to the overall urban footprint which are also very diverse, with a CSA of over 8 million people and a larger economy than Chicago's there's nothing small about it, and may have well surpassed Chicago as the third most important metropolitan area 
