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You can search this thread for answers to most of this, but here's the synopsis:
Chicago is great, it's affordable if you are coming from LA or NYC, but not if you are coming from a small town...just depends on definition of affordable, the level of experience you have in marketing, etc will impact your about of job opportunities. I have friends who are going to be college grads in marketing in 2008 and already have jobs lined up for when they graduate...but will only be making about 30K or slightly less. My advice would be to start looking for jobs to feel out the market based on your interests in your experience.
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