What to Wear in Chicago Winter
Updated: Feb 8
Stay Warm While Visiting Chicago in Winter. FREE Printable Packing List Below.
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Chicago needs to be on your travel list, and winter can be a very fun time to visit. From the Christkindlmarkets to the fully decked out holiday train, Chicago goes all out for the holiday season. But you must pack right if you plan on visiting Chicago in winter! Keep reading to learn how to dress for Chicago winter; this is super important to make your trip enjoyable.
If you’re traveling from a warmer state or country, you probably won’t be prepared for how cold it gets in the Midwest. But lucky for you, we lived in Chicago for three years, and we’re pretty familiar with how to dress for Chicago winter so you stay warm and comfortable.
How to Dress for Chicago Winter
Staying warm will be your first priority when you visit Chicago in winter. So a winter coat is definitely a must. Packing layers for cooler weather is always a good idea, so you can bundle up when you venture outside into the snow, but you can easily lose a few layers when you go back inside again. Keep reading for a free, printable list of what to wear in Chicago winter!
Most importantly, you are going to need a winter coat in order to stay warm while visiting Chicago in winter. It's cold and snowy and windy, but it is oh so beautiful as a winter wonderland. Having a very warm outer layer will make you the most comfortable while you're exploring outside.
Buy the best winter coat here.
Fleece Jacket / Inner Layer
In the heart of winter, you will want another layer of warmth while you’re outside. 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.
Buy my favorite fleece jacket here.
Sweaters will be your best friend when you visit Chicago in winter. They’re the best option for a base layer so you stay comfortable and warm. Plus, they’re cute and you can pick one that matches your style!
Buy a super cute sweater here.
Another layer that’s handy to have is a long sleeve shirt. Layer it 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.
Shop the best long sleeves here.
Socks are a must to keep your feet warm in Chicago winters. It snows a lot in the Midwest, so you definitely need to keep your feet warm and protected. Don’t let your feet freeze, it’s incredibly uncomfortable to walk around Chicago with frozen toes.
Snow boots, or at least sturdy quality boots, are a must to explore Chicago in winter. Remember it snows a whole lot, so your feet will get a little wet, and probably salty. They salt the streets and sidewalks to melt the snow and keep them walkable and drivable.
Buy winter boots to save your feet here.
Beside being snowy and cold, Chicago also gets quite windy, especially downtown. Having gloves to keep your hands warm will be very nice. Chances are you’ll be looking at your phone for directions or a train schedule, so having gloves to keep your hands protected from the wind will be very handy.
Keep your hands warm, get some gloves.
Did I mention it gets windy in Chicago? And in the winter, that wind can be bitter cold. Pack a scarf so you can wrap your head and neck up and protect them from the cold. A scarf can come in handy while exploring indoors too; wrap it around your shoulders like a shawl!
Grab a cute winter scarf here.
Beanie / Hat
Protect your head, protect your ears! Unless you have a great hood on your winter coat, you’ll definitely want to bring a beanie or warm hat with you to Chicago in winter. Plus, beanies are cool and they come in so many colors so you can match them to every outfit.
You do not want to wear shorts, capris, skirts, or dresses in winter in Chicago, unless you’re wearing thermals underneath. Jeans, dress pants, etc. are the best option to keep your legs warm during your outdoor exploring.
If you normally run cold like I do, I highly recommend packing thermals for your Chicago trip in winter. I always wear thermal pants and sometimes a thermal long sleeve under my clothes. This keeps me nice and toasty, and I was always comfortable while outdoors in a Chicago winter, thanks to my thermals! And they double as winter PJs!
Buy some thermals & stay warm.
It can get surprisingly sunny during winter in Chicago. And with white snow all around you, sunglasses are great to have to protect your eyes from the insanely bright reflection off the snow. Plus, sunglasses are a great barrier from the wind. It's not fun to walk head on into a bitter cold wind when you have nothing to protect your eyes!
Recap: What to Wear in Chicago Winter
While winter is a great time to visit Chicago, especially if you want to celebrate the holidays, it does get very cold! But now you know how to dress in Chicago winter, so you can stay warm and explore the Windy City comfortably. Download and print our free list for what to pack in Chicago winter and start packing your bags!
What is the coldest place you have visited? Or will Chicago be taking that number one spot? Let’s chat about it in the comments! And download the Chicago Winter Packing List below!