What to Wear in Chicago in Winter

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Chicago is a beautiful city owing to its glorious skyscapes and an atmosphere that can make anyone fall in love. But Chicago ushers some of the harshest winters hailing the Snow Queen into the city.

However, even with such freezing temperatures, Chicago holds its reign upon millions of hearts! And, sees all of its people coming together for spiritedly celebrating the season’s festivities.

But, for enjoying this wonderful yet unyielding climate, you need to know what to wear in Chicago in Winter.

And, if you’re gearing up for just the thing we’ve got you covered on this one!

Because in this guide, we’ve compiled a list of all that you should carry along on your awaited Chicago winter trip!


… to always invest in superior fabric materials and avoid cheaper, poor quality things. Why? Because it can get uncomfortable quickly if you end up with clothing that does not keep you warm. This is because the winters in Chicago can be frigid and formidable with blizzards and snowstorms.

So, consider keeping the following things about you to enjoy your trip in peace.

1. Layering

Layering is key to staying warm in the harsh winter climate. You should wear:

Base Layer – A long-sleeved top will help insulate your body and wick moisture from your skin. Pair this with thermal underwear/pants and you’ll be cozy. 

Mid Layer – This is the main insulating layer, fleece or insulated jacket is best suited to use as a winter mid layer.

Outer Layer – This is the layer that protects you from the weather; wind, rain, snow, sleet, etc. A Parka is the most suited coat for the Chicago winter thanks to its insulation and longer length.

Here the mean temperature drops below 20 degrees Fahrenheit. If you don’t have sufficient layers of insulation going on underneath your outfit, the chill can hit hard, barely giving you time to adjust to the climatic conditions. Better to be too warm than too cold, the beauty of layering is that you can peel them off or add more to regulate your body temperature. 

2. Keeping your Extremities Warm

You’d be surprised at the amount of heat lost through your extremities. Keeping your head, neck, hands, and feet warm and dry are paramount to keeping you warm. A hat and scarf might not cut it in the extreme cold so investing in a neck gaiter can do you wonders. You should look at buying:

  • Hat
  • Scarf/Neck Gaiter
  • Gloves
  • Thermal Socks

3. For your lower body

Although most people would just overlook the importance of a good lower body warmer, know that your favorite pair of jeans won’t make the cut. As mentioned in the layering guide above you should wear thermal underwear that will reach down to your ankles.

4. Covering your hands and feet

Your standard fabric gloves will not be of much use against the Chicago cold. But, they can be ideal second layers which you could wear under thicker, water-resistant gloves! You could also go for comfortable mittens that would keep your hands warm and snug, protecting them from frostbite.

It’s also a good idea to wear an extra pair of socks over your normal ones (make sure they are a larger size than the first pair). When you put them on, pull the seams of socks above the ankles of your thermal underwear, so that none of the skin gets exposed while walking.

The shoes you put on daily will never hold up against this weather, and if you find yourself surrounded by two inches of snow, then you might as well close the door on your travel plans until you get sturdy hiking boots. Because, not only will your shoes get thoroughly ruined in that kind of weather, but you would also expose yourself to the risk of ending up with frostbite as it clenches around ankles and up.

Invest in a pair of the most durable waterproof winter boots you can find and make sure they go at least halfway to your knees.

5. Proper sunglasses, moisturizer, and sunscreen

As much as you need protective clothing for vicious winters, your skin needs intensive protection to battle the onslaughts of such climatic conditions.

If you didn’t know this already, the winter sun dips closer to the earth reflecting an immense amount of UVA and UVB rays that could cause tremendous harm to the eyes and skin.

Invest in a good pair of UV protective shades to shield your eyes from the harmful rays of the sun.

Also, you can’t just go without wearing sunscreen and expose your skin to sun damage. Hence, it’s more important to get a good sunscreen with proper UV protective factors that will safeguard your skin from the aging and damaging rays of the sun.

And, on the same line, it is important for you to get an appropriate, thick moisturizer that would prevent the frigid weather from stripping away the moisture from your skin by creating a barrier between them.

Conclusion – What to Wear in Chicago in Winter

So this was all about how to battle the ferociously cold winters of Chicago! 

We wish you all the very best of Chicago winter tripping!

Till next time!

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