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What to Wear in Chicago in Winter
Updated: Sep 25
Chicago is the perfect place to plan a winter trip. The Windy City is a snowy wonderland from December through February, and there are so many fun holiday activities in Chicago.
The key to making the most of your city trip this time of year is knowing just what to pack for Chicago in winter. If you have the proper clothes on, you'll be able to enjoy all this US city has to offer, snow, cold, and all!
After living in Chicago for three years, I learned how to dress comfortably in the snow. So start planning your trip to Chicago this winter and get your suitcase ready!
Below I'll cover how to dress in Chicago in winter, from the best shoes to the best winter coat, other essentials accessories, and more. Grab the Chicago winter packing list printable too!
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How to Dress for Chicago Winter
Staying warm will be your priority when you visit Chicago in winter. Pack layers of varying warmth as the weather does change in the winter months here. A winter coat is a must as well as a scarf, gloves, and a hat. You should also pack a set of thermals, long pants, sweaters, and boots.
Below is what to pack for Chicago in winter so you can have a great, warm trip! Keep reading for Chicago winter styles women inspiration. Click the links below each image to check the price of an item.
Best Winter Coat for Chicago
Most importantly, you are going to need a winter coat while visiting Chicago in winter. It's cold and snowy and windy, but it is oh so beautiful as a winter wonderland and makes for the perfect US holiday destination.
Having a very warm outer layer will make you the most comfortable while you're exploring outside. When looking for a winter coat make sure it's waterproof, or at least water resistant, long, and has a hood.
Below you'll find my top three picks for the best winter coat for Chicago that will keep you warm and stylish without costing a ton.
Shop: White Coat | Tan Coat | Black Coat
Fleece Jacket
In the heart of winter in Chicago, you will want another warm layer to wear under your coat. The temperature drops down to the teens and often hovers around 0°F in the middle of winter in Chicago. So pack a fleece jacket or warm inner layer to wear under your winter coat.
Shop: Pullover Fleece | Zip Up Fleece
Sweaters
Sweaters will be your best friend when you visit Chicago in winter. They’re the best option for tops so you stay comfortable and warm. Plus, they’re cute and you can pick one that matches your style!
Long Sleeve or Thermals
For extra warmth, pack a long sleeve shirt or set a set of thermals to wear under your clothes. Layer with a sweater for extra warmth, or wear it by itself under your coat. When the temperature is below 20°F in Chicago, you’re going to want several warm layers on.
As someone who lived in Chicago for three years, I can highly recommend wearing a thermal set under your clothes. Especially thermal pants under jeans; you'll stay so much warmer.
Shop: Long Sleeve | Thermal Top & Pants
Thick Socks
Don't forget thick, long socks on your list of what to wear in Chicago in winter. It snows a lot in the Midwest, so you'll want to keep your feet warm and protected. Don’t let your feet freeze, it’s incredibly uncomfortable to walk around Chicago with frozen toes.
