The reality is, the confluence of factors such as availability of VC capital, proximity of Stanford and weather make Bay Area the best place to be if you are a

The reality is, the confluence of factors such as availability of VC capital, proximity of Stanford and weather make Bay Area the best place to be if you are a founder or a very early employee of a startup and you hold a significant stake. If the weather is a big factor for you, then Chicago will never beat Bay Area. But if you are not one of the above, and you don't care about the weather, Chicago beats Bay Area hands down on quality of life, in my opinion