German Shepherd Dallas

How is winter in Chicago for a big dog?
I'm thinking about moving to Chicago in a year or so for the school and of course I bring along my "best friend". I have a German Shepherd / Chow mix, who is 5 years old and 60 pounds. Will you be able to withstand Chicago winters? Are the larger dogs to enjoy the winter? We are in Dallas, and I know that no fan of the series. I will be a busy student when I move, so I want to make sure I get plenty of exercise outdoors while I'm gone. I would hate to only be able to take out for 10 minutes at a time because it is too cold. I've heard of dog booties .. How well do they work? Any tips and things to consider would be greatly appreciated!
I just hope you live in suburbs because that would be just cruel to keep ur dog in a small yard and I hope he'll get a great dog house for not too cold and there is no comparison with winter winters in IL tx !!!!!! is freaking cold, so if you have that opportunity, leave your friend TX!