I am thinking about getting new wheels and tires together for the winter like privat fahren and pilot sports A/S but I live in Chicago and in the winter there are millions of potholes, so do u think I should keep using the stock wheels and just get new tires for the winter? How easy would the new wheels get damaged by the potholes?

 

you definately wont be able to drive with bigger wheels in the snow

you cant even drive with the stock setup...if u wanna do it right buy winter tires for your stock setup

and then after the winter buy your new wheels

 

I bought a complete new set of wheels and tires for the non-snow season and kept the stock wheels and bought some Blizzak winter tires for the snow season. That way I do not have to take the car into the shop twice a year to change the tires on the wheels, plus I have a nice set for the summer and a set that I am not worried about for the winter that still looks nice.