Where would you rather live

Chicago has a lot going for it (and tons of women I hear), but it is fucking COLD for most of the year. San Fran is a little warmer, but still doesn't have fantastic weather. I think cost of living is probably pretty comparable. San Fran has a lot of young people and a pretty good food/bar scene. There's also the whole tech/Silicon Valley subculture if you're into that.

San Francisco, in my opinion.

If the year only ran from April to October, Chicago would win hands down for the friendlier people, lower income taxes, the beach 1/2 mile from the CBOT, and small town in the big city feel. But the winter ruins everything.

Still think Chicago beats NYC, Boston, and Philly, though.

If those are your only criteria I would recommend Austin, though much more VC than PE oriented.

June - October Chicago is quite possibly the best city on Earth, it is a non-stop party. November and December are also great in Chicago with the holidays. I can't lie, the rest of the year, weather wise, can be brutal, but if you are single, and like the bar scene I can't think of a better city for you. Also, there are plenty of hot girls, no clue what some of you are talking about. Cost of living is also lower in Chicago, but if you are working in PE, I doubt this is much of a deal breaker for you.

I would rather put a gun in my mouth and pull the trigger than live in Chicago

This question was totally framed to support OP's decision of choosing SF over Chicago.

Its like saying... where would you rather live LA or NY... considering quality of mass transit, access to variety of different scenes, round the clock party scenes, exposure to high powered financiers, etc...

vs.

where would you rather live LA or NY... considering cost of living, weather, quality of life (i.e. laid back lifestyle), proximity to beaches, etc...

Would take SF any day of the week over Chicago; SF is the nicest city in the US in my opinion and I cannot think of a more fun place to start a career. SF is a big step up from Chicago in nearly every category, in my view.

Haha Marcus you got me, I am leaning towards SF. I'm actually from Chicago, so I'm considering b/c of lower cost of living and proximity to friends and family.

I guess what I really wanted was to get some insight on things that aren't immediately obvious, like the type of people in the city/types of people who go the bars, the financial community (is it a tight community?), any career advantage for PE from being in one city over another, amount/variety of things to do on the weekends (all 10 of them probably), etc.

Thanks for all the comments guys, this is really helpful. Thought this might be an interesting discussion for other readers as well.

SF has more personality IMO, also has great wine.

Haven't spent a meaningful amount of time in Chicago though, so take my perspective with a grain of salt.

Theres CA and NY.... and then there's every other region

Where would I really rather live?

In Tahiti!

Everything else is a gulag by comparison.

As somebody that's from San Francisco but who has lived in Chicago for years, I have to say that these are my top two cities I'd choose to live in among all of the major financial hubs in the U.S. That said, there are huge differences between the two, so I'll try to address your points one at a time:

Career/networking opportunities - This is highly dependent on what you want to do. If you want to work in technology or venture capital, then SF will obviously be the place you want to be. If you want to work at a private equity firm that focuses on industrial companies or in trading then Chicago is better. Overall, SF has a much higher proportion of what many people would consider to be "sexy" career options.

Weather - SF wins this one by a landslide, mostly due to Chicago winters. SF is both warm enough in the winter and cool enough in the summer to run, bike, or hike year-round without worrying about freezing or passing out from heat exhaustion. That said, if you like beach weather in the summertime, then Chicago will offer that while SF only has the occasional Indian Summer in October or November.

Cost of living - Chicago wins this by a landslide. SF cost of living is similar to NYC, which means that you'll be paying 2-3 times the rent or real estate that you would be in Chicago.

Lifestyle (lots of young people, bars, fun things to do) - As far as young people and bars are concerned, I'll take Chicago over SF any day of the week. Because Chicago is so much less expensive than SF, it draws a much higher concentration of young people to fun neighborhoods than SF does, where young people tend to be less centralized in certain neighborhoods and often live outside of the city to be closer to where they work.

As far as the singles scene is concerned, Chicago is much, much better than SF. SF is an awful place for single guys. The population of good looking girls in SF is very small (both in numbers and in proportion of attractive to ugly girls), the bar scene is much smaller, and everything shuts down earlier than in Chicago. While the weather in Chicago does suck during the winter, the summertime scene in Chicago is dominated by the beach, by big street festivals (which are essentially huge outdoor parties) every weekend, by a stronger influence of sports on the city's pulse (I'm a Giants fan and love going to games at AT&T, but the day game experience before, during, and after a Cubs game is unique in baseball).

Location in the United States - This, along with the weather, is where SF is the clear winner. SF is right on the Pacific, has easy access to hiking, running, and biking in the hills, has numerous state and national parks a short drive away, great skiing a 3-4 hour drive away, golf year round, etc. Chicago is surrounded by flat lands with little geography. Good skiing requires getting on a plane. It does have Lake Michigan right next to it and there are nice little beach towns in Indiana and Michigan, but it's a far cry from many of the weekend getaway offerings on the west coast.

Damn indentured, thanks for the detailed breakdown. Now its gonna be really hard to choose between these two cities, though at least I'll be informed.

Since you're so indecisive between the two cities, I have an ingenious idea. How about you base your decision on what the actual fucking JOB is, since that will have 100x more influence on your quality of life than the city you're in, especially given that SF and Chicago both have plenty to offer.

Even if it's with the same firm, the culture and work varies from office to office.

Tough one. I'm from Chicago as well and I love the Chicago summers. However, winter is a bitch and that last winter shitstorm was proof enough. The cost of living is cheaper in Chicago. I'm a foodie and while Chicago has some really good restaurants, SF is still better.

It does come down to what you want to do. Trading? Probably Chicago. But for PE/VC, especially in tech, SF hands down. I'd love to transition into PE or VC because of the tech scene. At this point in my life, I'd go SF.

I have several friends in both cities. When you compare the prime areas that young people want to live, SF is far more expensive as far as rent goes. It really isn't even close. Remember you can't just compare what people are spending, you also need to compare what they are getting for their $.

SF!