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I worked in downtown Chicago for 3 years. Commuted there weekly from NY, bought an extra car but discovered I didn't NEED it - the Chicago public transportation is so good - usually - "Blue Line" terminates under O'Hare terminal 2. So can't help you with a mechanic. Sorry.
Chicago is not a bad city. Except for the wind. And the snow. And housing prices - the city is almost as bad as NY.
I currently have a set of Vredestein Snowstar studded winter tires on 15" steel rims. This is their last season, I plan to replace 'em, but we haven't even seen snow, yet.
One advantage of the steel wheels is that if /when you bend them they're cheaper to replace than the alloys. Bent wheels are a particular problem in "pothole season", in NYC the potholes actually swallow cars from time to time, I don't think Chicago is much better!
I've averaged 2 bent/destroyed wheels on each of my last 3 cars.
My Volvo owner's manual specifies 185/65x15 winter tires. I recall that Illinois doesn't allow studded tires unless you're an emergency vehicle or a rural mail carrier. It's been a few years, perhaps they changed this law. If studs are not allowed, I'd look at the Michelin Artic Alpin which are unstuddable snows.
I have the "winter package" but the reason I bought it is the TRACS traction control. As to the headlight washers and seat heaters, I don't find them particularly useful, I'd choose a sheepskin for winter if I had leather seats.
My $0.02, worth exactly what you paid!
-Bill the Cat
'98 V70 T5M, 85k, lotsa rock chips
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