[derekp7]

Overall it's really not as bad as people make it out to be. Of course I've lived here all my life. There are periodic cold snaps where it gets way below freezing, but typically it is in the 20's (F). The trick for winter is to embrace it, and wear appropriate clothing. For snow removal you may need heavy machinery (I just use a sleigh shovel, works great). For clothing, a good flannel shirt with a vest jacket and hat goes a long way (keeps you from getting too warm, and your body acclimates to the temps).

[SOLAR_FIELDS]

I lived in Chicago for several years and while the temperature and snow is a lot more extreme in Chicago the winter is a hell of a lot more tolerable than in Sweden where I live now. This is because where I live in Sweden is moderate temperature wise compared to Chicago but the sun basically just never comes out and you have constant cold rain for about 7 months. Chicago will definitely see enough sunshine during the winter to keep you in reasonably good spirits.

Also you forgot to mention for clothing to wear something under your jeans (my trick was sweatpants) to protect yourself from that Chicago wind whipping through them :)