What's the best way to stay warm for my first Chicago winter?

Oh my gosh, how fun. I hope you have a great time. I personally would purchase a good pair of long johns and wear a good coat. I've never been personally so I don't know if it will be wet, snowy, or just windy but in general a good waterproof wind jacket with a fleece interior would be best. Personally I think long johns would be key. Something lightweight and thin so you can wear your jeans over them.

Reply · Send thanks · posted 217 days ago

My boyfriend just bought a "Dual Commuter" jacket from Columbia. After taxes it was about $300, which is pretty reasonable for such a nice jacket and to know he won't be freezing his ass off all winter.
It is pretty heavy but it also stylish... not just a big bulky coat. It actually looks nice.
There is no hood on this jacket, but he plans on layering under it with a hoodie, so he'll be good and toasty all winter!

Reply · Send thanks · posted 233 days ago

If you want to stay warm this winter there is really only one thing you can do: move away from Chicago and go somewhere nice like Florida. Otherwise, you will definitely be cold.

Reply · Send thanks · posted 233 days ago

I would say spend some cash and get yourself a North Face or Columbia jacket. Like Cassandra said, make sure it is waterproof and windproof. There's not really any way around it, or any tricks. You just need a really warm jacket with a hood. Get yourself a scarf and a warm hat.
Sometimes the wind is so cold it actually hurts your face to be outside, so some people wear those ski mask things... or anything that will cover your face. A scarf will work, too.

Reply · Send thanks · posted 233 days ago

Oh man good luck with that! I would say layers, layers, layers. Definitely make sure you have a waterproof, windproof jacket or shell of some sort. This is key. There is a lot of wind and precipitation in that part of the country!
Any sort of long underwear or thermal will help. Under everything you wear can be a thermal layer.
Under Armor will do the trick, too.