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Forget all season tires in Chicago. They will not get you home safely. We have used Pirelli Scorpions winter tire and the Bridgstone Dueler HP All season for the rest of the year. There is no substitute for winter tires on a Cayenne. Don't even think about it!
I always subscribed to that policy until recently when I put the Conti DWS on my SUV. I had absolutely no issues in the deep snow in Colorado and was very pleased with the winter performance. Summer performance in the dry is compromised, however (see my earlier post about stopping distances).
If you drive your SUV like a sports car, then get two sets of tires--one summer and one winter. If you drive your SUV like an SUV, I think you can get away with a good compromise like the DWS.
Touche...for most of us, though, life is full of compromises. No one "needs" a P!G. We drive 'em because we need an SUV and want a sports car.
No need for compromise here with a winter low of around 10C (nights) I'm on summer tyres all year round. Just changed out 2 (rear) of my 4 275/45 19 Michelin Lattitude SPs after 40,000km and I figure the fronts are a little over half worn. This is on the CTT daily driver which doesn't take the same abuse as I give the GTS. Conversely a friend with a 4 litre Pathfinder gets 100,000km out of a set of Bridgestone Duellers.