I don't know anything about Chicago rates, but I know enough about auto rates to know that there isn't enough information here to answer your questions.
For instance, usually one carrier is better with the 20 somethings, another with the 40's and married, yet another with a few tickets, someone else for a DUI. Then start into things that might lead to discounts and it is a no single answer for everything.
Talk to a local agent, they will help you out.
Dan
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