Let me describe the effects of freezing rain on a commute. Freezing rain means that the rain has been superchilled, and it freezes immediately upon contact with something - like the road and your car's windshield. Last time I had to drive through freezing rain, we were only able to drive at around 5mph on the highway, and had to stop every quarter mile to chip the ice off the windshield so we could see.

Let me describe wind, and its effect during a cold day. Wind chill describes the effect of wind on exposed skin, by describing the equivalent effect in pure temperature. At -20 farenheit, you're uncomfortable, but you're able to operate without having your face covered; without having to breathe from a heated air supply. At -20 F with a (for the region) mild breeze of 20mph, the equivalent temperature is -50. Cold enough that you will get frostbite on any exposed skin within 5-10 minutes (i.e. your skin freezes solid and can cause permanent damage).

At -40 (a particularly cold day), with the same wind, it's equivalent to -75 F. That's much more rare, only 1-2 times per winter. You are pretty much trapped indoors on those days.

When I lived in the mid-west, they would shut down the college only when it reached -40 with a still wind, or -110F with wind chill. The college would be shut down an average of 4-5 days out of the winter.

So, yeah. You absolutely can survive it; can live in it. Like all annoying or even painful things, you can even become inured to it - consider it a badge of pride. That doesn't make it pleasant.

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).

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 :)

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.

A few years ago I met a woman from Alaska. She told me she went to college in Chicago and she barely made it through the first winter. Her friends said "What's your problem? You're from Alaska!" She replied "You don't understand. We never get this cold at home."

Of course Alaska is a big state and not all of it is freezing, but still. Chicago winters are impressive.