How to bundle up for a Chicago winter

Living in Chicago means living up to the hardiness that others outside Chicago, especially people from the South and West, and often other countries.

I’ve heard questions about how to dress for Chicago, how to prepare yourself for it.

Preparation Tip #1: the City of Chicago does not shut down for snow or cold. Another part is mental. Don’t let this ruin your visit. Locals don’t let it stop their day, and you’re already here. No one stays home. Visit DC on a day when the federal government is closed for weather and you won’t find any locals out.

Frozen Chicago River

Assuming you aren’t coming during a polar vortex, here are a few tips for preparing to come to Chicago.

Preparation Tip #2: Warm clothes – if you ski or snowboard you already have the layers.

Some of this depends on where you come from but here’s a little break down of how Chicagoans treat winter weather:

  • 50°: Spring is here! Turn on the grill; ask for outdoor seating!
    If there’s been a cold snap you’ll likely see people in shorts and sandals.
  • 40°: It’s practically spring
  • 30°: Eh, which coat should I wear
  • 20°: Add hat and gloves, maybe a scarf
  • 10°: Why do I live here again?
  • 0°: Fine – I’ll wear long johns under my pants.
  • Anything colder: Pile on the layers and hope you have enough in your kitchen so you don’t have to go out more than necessary.

We layer up.

My suggestions: thermal layers, wool socks, good boots, and learn to use a scarf to keep you warm (this means wrap it around your neck, don’t drape it over your coat looking pretty).

Gloves: not bulky so you can grab your phone or Ventra card. I wear those one size fits all gloves – sometimes I wear two pairs. And sometimes I wear a pair with fleece lined wool mittens. For when it’s not that cold out (see above) I wear fingerless gloves.

Here’s my brief soapbox about why hats are better than earmuffs:
You lose 20% of your body heat off your head. You will actually feel warmer if you wear a hat. And if it’s somewhere around zero, your ears will thank you.

Buy good boots. This was the biggest thing for me to tackle when I moved back. In DC the most I needed was rain boots. Get something that is waterproof, lined or includes temperature rating. You should be able to wear thick socks with them and be comfortable. I have learned the extent to which my Sorel boots work: three pairs of socks in -20°. I think they are rated to about 0-10°so I can’t ask for much more than that.

Look for temperature ratings for boots and coats. Read the reviews to see who is buying them and where they live. My Sorel boots aren’t temperature rated, but the Joan of Artictic are tested for up to -20° without issue.

I also have Bean Boots that I love for when there is just a dusting of snow, but it’s not really cold out. They’re also great for warmer days when the snow is a melty mess. I use my rain boots more for spring and summer when I don’t need to fit bulky socks in them.

Bean boots buried

If you are looking to move to Chicago, you do adapt to the cold at some point.

Preparation Tip #3: Know what to expect. Winter here runs from November (sometimes October) until the end of March (sometimes April). If you’re thinking of visiting Chicago in winter the best advice I can give you is: Do. Not. Come. In. January. Or. February. Come in November, come in December, come in summer or for a baseball game in the spring or fall. Just avoid those two months, and you’ll want to come back.

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