As for best place to shop for insurance, I always try Kanetix before I buy any car (new or used), and every year before my insurance is up for renewal. For the past 4 years TD has been the cheapest for me, but that doesn't mean it'll be cheaper for everyone. It depends on how many cars/drivers you insure, if you insure property, and of course it depends on your record, experience, etc.
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We know driving in Toronto can be challenging, from the Gardiner’s morning gridlock to the crowded parking spots of Bloor. That’s why you need a car insurance plan built for city driving – one suited for the ever-changing road conditions, the speedy freeways and the diverse neighbourhoods. And we take that need very seriously. As a car insurance broker, we shop at up to nine car insurance companies to make sure you get the best rates for your specific driving situation. We’re also available 24/7 to help you with any claims.
As of January 1st 2016, the Ontario government passed a law mandating that insurance companies give drivers a discount on their insurance if they buy and install winter tires on their cars for the winter months. The discount is usually around 5% of your collision coverage, or $72 per vehicle per year, but you will not necessarily get this discount immediately. Some companies make you wait until your policy renews, so make sure you call your insurer to find out how they handle it.