I have lived in Las Vegas my whole life, and often the only time I'm around snow is when it's for a sporting purpose. I've never lived someplace cold and when I visit cold places I'm often indoors at almost all times. My girlfriend's family lives 45 minutes outside Detroit, for example, and it's plenty cold there. When we visit in the winter (as we will for Christmas), however, we're always inside visiting with family and friends. In Chicago this will not be the case: we're there for a vacation and have no friends in the city.

I have a wardrobe that consists of denim, lightweight sweaters and button-down shirts. The lightweight sweaters already in my wardrobe are all cotton, as is nearly everything else. I have some cold-weather gear that I've used while in the Marine Corps but it isn't really for walking around on the streets (all green and tan, and obviously military in nature). However, I do have some black wool 3/4-length baselayer pants I can wear under my jeans. I also have plenty of wool socks.

I have purchased a heavy-ish wool trench coat for this trip as well as a pair of lambswool-lined, thinsulate-insulated leather gloves, some merino V-neck sweaters to wear over my button-downs and a cashmere scarf/beanie.

Our hotel is the Tremont Chicago, right near the water, and I have heard from many people that not only is it cold as hell in the winter, the closer to the water you get the worse it becomes.

Will my current acquisitions be enough? It won't get below 40°F (4°C) here in Las Vegas for me to test out the coat I've bought or the warmth level of my sweaters with it. I can always shop once I get to Chicago of course, but that won't give me a chance to look for better prices or styles — I'll just be stuck paying whatever they're asking for whatever they're offering.

We will be in Chicago from the 28th of December to the 2nd of January.

  • One thing specific to Chicago is its metro system is elevated, so there is usually cold wind when you are waiting for your train. – Vince Nov 25 '14 at 18:34

You're right that next to the water it's worse.

I live in northern Sweden next to a massive lake and it regularly gets -30C here at times in the winter. The humidity makes it worse - it's painful to breathe. However, Chicago is apparently more like -10C in the winter, which is really not so hard to deal with! Although I get that it's scary for a desert dweller ;)

I have never gone wrong with some base layer pants (otherwise known as longjohns), a thick jumper, thick coat, gloves, hat, scarf, and TWO pairs of socks.

So yes, everything you listed sounds perfectly fine to me. The important thing is to pack a couple of extra layers so you can remove or add layers according to comfort. You will find as well that when you go inside (like a department store or whatever), you will roast your ass off.

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  • 2
    What's a jumper? – Bryson Dec 7 '11 at 21:16
  • So basically an extra sweater that is rather heavy? I have a zip-front medium-weight wool sweater I can (and should?) wear under my heavier wool coat easily. – Bryson Dec 14 '11 at 10:15
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    A jumper is just British English for sweater. If you have a thick, good quality coat, then a medium/light-weight sweater should be fine. Like I said, the key is to have a couple of different choices for your mid-layer (the sweater), so that you can adjust as needed. – victoriah Dec 14 '11 at 19:43

I realized there is already an accepted answer but I figure I would add my 2 cents. Having lived in Chicago for 6 years and enjoyed the winters. For regular walking about when it is >0F, especially if you plan on going indoors at all, ex. shopping then I usually wear wool socks, non-insulated boots, jeans, t-shirt, heavy cloth button down shirt or sweater, a down/synthetic puffy jacket, light gloves and wool hat. You might get a bit cold if its windy but with this you can go inside without roasting.

If you want to stay outside, particularly if you want to stand outside on navy pier on the lakeshore until midnight to watch fireworks then you should dress warm. I did this once and it was cold, although I was much better prepared than many of the others who constantly went inside. I wore thick wool socks, insulated boots, long johns, pants, heavy base layer/t-shirt, wool/synthetic fleece sweater, down jacket, warm gloves, wool hat. I stayed nice and warm with my heavy down jacket and long johns. The water does make it feel cold. Have fun

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