It really depends on what you are looking for, and all of the points you made are true. However, Chicago has some great things going for it IF you like living I

It really depends on what you are looking for, and all of the points you made are true. However, Chicago has some great things going for it IF you like living IN the city. Chicago's winters are brutal, but the rest of the year is gorgeous. Chicago overall has much better weather than San Fran, though much worse than the rest of the Bay Area. If you want to raise a family, while living in the city, it is both doable and affordable here. Areas like Wicker Park and Lakeview have pretty tree lined streets, brick 3-flats, amazing restraunts, coffee shops, record stores etc etc. The bars are amazing, good music venues, oh and you will never have to get behind the wheel drunk because you cannot walk 5 feet without seeing a cab for hire. There are great artist and developer communities here, as well as a budding startup scene. I am not saying you should rush out of San Fran for Chicago, but if you are considering moving here you should give it serious consideration. One caveat, for the love of god don't move to the suburbs. They are filled with mid-westerners. scary.