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Check out Craigslist first, and make sure to post a "Housing Wanted" ad for yourself. Ads in the newspapers or online referral services tend to be VERY overpriced, so look for a word-of-mouth referral or a less known site like Craigslist.
That said, there hasn't been anything "cheap" in the Bay Area for a decade. People in the Bay Area who want "affordable housing" typically find it by moving OUT of the Bay Area...they endure grueling commutes (sometimes 4-5 hours a day) but save hundreds of thousands on purchased homes and 50-75% on rents. A few years back a friend of mine was paying $2,000 a month for a studio in Los Gatos, until he finally got sick of it an rented a 2BR apartment in Concord for $650 a month. The daily commute from Concord to San Jose can be over 2 hours each way when traffic is bad (and it often is), but he's never looked back.
The trick is really to keep your eyes out and jump on the deals when you spot them. If you are moving out here blind, make sure you have the money for TWO deposits...one for the overpriced place you're going to move into first, and the second for the better priced place you'll eventually find if you keep looking and move fast.
Avoid Palo Alto, Newark, and Oakland. You'll see lower rents there, but they're lower for a reason.
Oh, and since you're from Chicago I'll also point out that you'll need a good car out here. My last boss apparently never owned her own car until she moved out here from Chicago at 40 years old...a fact that she complained incessantly about. She, like most people from large eastern and midwestern cities, was amazed at the utter lack of public transportation that exists in the SF Bay Area. The public transportation that does exist works well, but it only covers a small portion of the region. Many people have moved out here expecting to catch a bus or train to work, only to be suprised when they discovered that they don't exist in most of the region.
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