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Are you actually moving to Chicago, or to the suburbs. I live in the suburbs and T-Mobile loses connection some places. It's just fine in chicago and within about 50 mile radius around it. You can get a good connection on the highways though. I don't really know how cingular performs, but if you will be moving to chicago connection will not be a problem, so I'd just compare the plans and get the best deal.
BTW, I also don't know how cingular compares, but I think T-Mobile has a great customer support.
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If you multiply that by infinity and take it to the depths of forever, you will, perhaps, get just a glimpse of what I am talking about. --Meet Joe Black--
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