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Winter tire season for me is November through mid April.
I also happen to avoid driving the car from November through April... however, I still put the winter tires on just in case. It's not just for my safety, but the safety of those around me - with a little one in the car, it's an easy expense to justify.
Also, don't cheap out on the winter tires - I make the drive from the city all the way up to Waukegan Tire to get Nokian winters for my wife's car (which is the one that gets driven a lot... neither of us drive to work, but groceries and the gym...)
Also, if you're ever heading into the city, public transportation is pretty good here! It won't get you everywhere, but I commuted from the far north suburbs for 9 years. It's sooo much nicer than driving - especially in the winter! I did have to drive to the station. Now I walk.
Welcome to town.
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