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Hi, we're Georgina and Nathan, college friends turned travel partners. We're coffee and animal-loving adventure enthusiasts here to share our favorite travel tips with you! Our goal is to inspire others to get out and explore this wild planet by camping, hiking, or wandering around a fun new city!

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  • Georgina D'Angelo

What to Wear in Chicago Winter

Updated: Feb 8

Stay Warm While Visiting Chicago in Winter. FREE Printable Packing List Below.

What to Wear in Chicago Winter

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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!

Winter Coat

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.

How to Dress for Chicago Winter - Wear a Winter Coat

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.

What to Wear in Chicago Winter - Sweaters and Beanies

Long Sleeve

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.

Thick Socks

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.

Grab some warm socks here.


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.

What to Wear in Chicago Winter - Boots and Long Pants


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.

Shop colorful beanies here.

How to Dress for Chicago Winter - Alpacka My Bags

Long Pants

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.

Buy trendy pants here.


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!

Shop sunglasses here.

Recap: What to Wear in Chicago Winter

  • Winter Coat

  • Fleece Liner

  • Sweater

  • Long Sleeve

  • Thick Socks

  • Boots

  • Gloves

  • Scarf

  • Beanie

  • Long Pants

  • Thermals

  • Sunglasses

Chicago Skyline - How to Dress 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!

Chicago Winter Packing List
Download • 79KB

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We're Georgina and Nathan, two adventure enthusiasts and creators of Alpacka My Bags. We're here for all of your travel and adventure planning needs! 


We've been exploring this insane planet that we call home together for over 3 years now. After college, we knew the "traditional career path" was not for us, and honestly the "traditional life path", in general, just wasn't for us.


We needed to travel and explore what this world has to offer, it sounds cliché but you do only live once. So we made going on adventures a priority, and soon realized that we wanted to share them with others so they can enjoy them too! 

Our passion is spreading the travel bug and showing others that travel is attainable and so worth it. From itineraries to camping tips to packing lists, Alpacka My Bags has you covered!

Join us, and often our dog, JoJo, as we find exciting adventures and travel recommendations for you! If you've been bit by the travel bug just as we have, we hope you find our tips useful for any and all of your future travels.

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