San Fransico V Chicago (cost, better, place, bigger)
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It really all depends on what you're after. Chicago is an older and much more climatologically varied than San Francisco, while San Francisco is a newer and much less climatologically varied city. Both are filled with culture and character. For me personally, I would choose Chicago because I like snow, and while St. Louis gets enough, the more snow for me, the better.
I personally love San Francisco. Don't know about the schools there though. Housing is much less affordable there than in Chicago. Chicago schools suck; would have to live in the suburbs and then trek for the fun stuff. I think there are more options in Chicago but, as I say, you may have to travel to get to them.
San Francisco is probably the greatest city in the country to visit and spend time in. Unfortunately, it is an obscenely expensive place to buy a house and raise a family in. I think it was once a wonderful place to raise a family before the costs went through the roof. I worry now that even if one could afford it, the fact that so many rich people live there would skew the values of the children you raise in that environment.
Chicago, on the other hand, is much more affordable. And it is a pretty great city in its own right. Cost being equal, I would choose SF. But with a family and with college costs to pay for someday, I would happily choose Chi-Town.
I have to go with Chicago just based on the COL factor alone. I cannot imagine trying to eek out a decent quality of life for myself alone in San Fran, much less trying to provide for an entire family.
I have a friend in Oakland Ca. (across the bay from SF) He has a wife and two girls. They live in a 900 sq. ft. house that is worth upwards of $700,000 and he can not afford to moved into a larger house. Chicago is much more realistic and a great city.
I understand you're trying to get basic info on the forum but you have a lot of more serious homework to do before moving here with 2 kids and an uncertain job.
To live? If you are single, it is basically a toss up. Chicago is a much bigger city, but SF has much better weather and is near numerous outdoor activities. To raise kids? I'd say Chicago. It is almost impossible to raise kids in SF- and I'm not sure it's a good idea to do so. Marin county would be an OK place to raise kids. A lot of the Bay Area has some very ugly suburban towns (with some nice very expensive ones too). If you can afford at LEAST a 1 millon dollar home and don't mind a long commute, SF would rate higher for me because of the weather. If you cannot afford a millon dollar house, you have to choose Chicago if you want to raise kids.
SF is not a place for kids, nor is it a huge city like Chicago.
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