gradapplicant1012

Transferring during an American PhD program would be a highly unusual event, and it is quite difficult (though not impossible). Your PhD education is deeply connected to your advisor, and so your research project will not necessarily translate easily to another university. If you really wanted to leave your PhD program for some reason, you would likely have to re-apply to another program and thus you'd have the same chance as any other applicant. This usually will involve completely starting over in the degree program. What is your motivation for transferring? There are different strategies depending on your answer that might work better than considering a transfer.

I would go to the Bay Area, as it seems like you perceive some advantages (climate, industry, etc.) to that route. Interestingly, the rental market has suffered greatly in the Bay Area (while the housing market has remained very strong). This is not the case in Chicago, where the rental market remains fairly competitive. If you can lock in a good 12/24-month rental agreement in SF, it seems like the cost of living will be sustainable with your 60k/yr salary. Of course, Chicago will always be significantly more affordable--so if you want to have lots of discretionary spending, I would still go to U Chicago.