[phil21]

I think it depends on the person quite a bit. For some folks winter is utterly miserable.

For others who generally stay indoors all year anyways, it's pretty easy.

Most are somewhere in between. I will say the winters here can get long some years, but Chicago has to be either the best, or among the best summer cities in the world. Yeah you get a few super hot muggy days, but those almost let you appreciate winter more. It's an absolutely gorgeous and fun city in the summer - and in the winter if drinking is your thing it's not so bad. If you hate drinking, you might not make it.

The one really weird thing about Chicago (coming from MN) is that the house construction is utterly horrible for cold weather. If it hits negative temps you can expect plenty of your friends to have pipes freeze. This may be getting better as units get rehabbed but it really contributes to the misery.