I use Meloche. I know if you're a former U of C student you get a great deal through the Alumni Association. Just tell Meloche you're a U of C grad (might work for more universities, I don't know) and they cut you an even better deal.
I've only had a car for 2 years, and my insurance (youngish male) is below $500 per year (recent legislation also realllly helped me out).
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