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Hi, I'm Georgina! A coffee-loving adventure enthusiast here to share my favorite travel tips with you! My 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 in Winter

Updated: Jan 11

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 this amazing city for three years, I learned just what you need to stay warm and comfortable while exploring. 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!

What to Wear in Chicago in Winter | Alpacka My Bags Packing List

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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!

Winter Coat

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.

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.


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.

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.

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, and other long pants are the best options to keep your legs warm during a winter trip to Chicago.


Having gloves to keep your hands warm is a must. 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. Trust me when I say you want gloves to comfortably explore Chicago in winter.

Keep your hands warm with thick, touchscreen gloves or a pair of Merino wool glove liners.


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 it around your head and neck to protect them from the cold. A scarf can come in handy while exploring indoors too; wrap it around your shoulders like a shawl!

Beanie or Warm 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. Even if you do have a hood, pack a beanie or two. Beanies are cool and they come in so many colors so you can match them to every outfit.


It can get surprisingly sunny during winter in Chicago. Sunglasses are great to have to protect your eyes from the bright reflection off the snow-covered ground. 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!

What Shoes to Wear in Chicago Winter

Shoes are very important to think about when packing for Chicago in winter. Remember there will likely be snow covering the ground this time of year. Pack warm, water-resistant shoes to keep your feet dry and warm while exploring the winter wonderland of Chicago.

Bring at least one pair of boots when visiting Chicago in the winter. Try to get fur-lined, water resistant boots to keep your feet warmer and wear a thicker pair of socks.

Couple sitting in giant Adirondack chairs - What Shoes to Wear in Chicago Winter
What Shoes to Wear in Chicago Winter

Ankle Boots

Boots are the best shoes to wear to explore Chicago in winter. They salt the streets and sidewalks to melt the snow, so you'll encounter many salty patches and snowy patches to walk through. Water-resistant, warm boots are my top recommendation. Shop the best winter boots below!

What Shoes to Wear in Chicago Winter:

Other Shoes to Wear in Chicago in Winter

I highly recommend bringing at least one pair of boots on your Chicago winter trip. They are the warmest and best for walking in the snow. You can also bring a pair of sneakers, but you will want to make sure you have very warm socks on.

Rain boots are also a great way to keep dry in the snow, but they don't provide any warmth. If you opt for rain boots, pack a pair of extra warm socks to keep your feet warm. Make sure you can comfortably wear your thick socks and rain boots together before you head out to explore Chicago.

Extras to Pack for Chicago in Winter

Besides knowing how to dress in Chicago in winter, you'll want to pack a few other essentials to make the most of your winter city trip. Don't forget to pack these items for your adventure to Chicago in winter.


You can use your phone, or you can invest in this recommended Sony digital camera. Either way, you'll want to take photos to remember your winter trip to Chicago!

Lip Balm and Lotion

With very cold and snowy winter weather comes very dry skin. Pack a lip balm and a travel bottle of lotion to keep your skin hydrated in the cold weather. It would be hard to enjoy your trip with super chapped lips and dry, cracking hands.

Day Bag or Backpack

To make it easier to explore Chicago all day, bring a day bag or small backpack on your trip. You can put any winter layers you might not need at the moment in it, or keep a water bottle with you, etc. I recommend this antitheft backpack purse.

Packing Cubes

Compression packing cubes make it so much easier to pack. Keep your clothes organized with separate cubes and fit more in your bag with the compression feature. This is so helpful with bulky winter clothes!

Travel Size Toiletry Bottles

If you're flying to Chicago this winter, make sure your carry-on liquids meet airline requirements. These travel-size toiletry bottles make it easy to bring all your favorite skin and beauty supplies on the plane.

How to Dress for Chicago Winter - Alpacka My Bags
What to Wear in Chicago in Winter

What to Wear in Chicago in Winter FAQ

Do you need winter boots in Chicago?

Winter boots are the best shoes to wear in Chicago in winter. The ground is snowy, and the temperatures are very low this time of year. To keep your feet warm and dry, pack a pair of winter boots, or water-resistant ankle boots.

Do I need a parka in Chicago?

A long winter coat is the best for winter in Chicago. A short coat is okay, but the longer it is, the warmer you will be. Try to get a coat that at least covers your butt and the cold wind won't have as great an effect on your warmth.

Do you need thermals in Chicago?

It's a good idea to pack a pair of thermals for a trip to Chicago in winter. You can wear them under your clothes when temperatures are in the 10s or even lower. A set of thermals also doubles as warm pajamas, which are perfect in winter.

How should I dress for Chicago weather?

To stay warm in Chicago in winter, make sure you wear the following items:

How to Dress in Chicago in Winter

  • Winter Coat

  • Fleece Liner

  • Sweater

  • Long Sleeve

  • Thick Socks

  • Boots

  • Gloves

  • Scarf

  • Beanie

  • Long Pants

  • Thermals

Chicago Skyline - How to Dress in Chicago Winter

Winter is a great time to visit Chicago, especially if you want to celebrate the holidays here, but it does get very cold! Knowing how to dress in Chicago in winter will help you stay warm and explore the Windy City comfortably.

Now you know what to pack for Chicago in winter, it's time to get your suitcase out and make sure you have all these essentials. Bring layers so you can dress warmer or cooler if you need to. Don't forget a long winter coat, gloves, a beanie, and a scarf. And plan to wear boots.

What is the coldest place you have visited? Or will Chicago be taking that number one spot? Download the Chicago winter packing list printable below!

What to Wear in Chicago in Winter Packing List Printable - Alpacka My Bags

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Hi, I'm Georgina, adventure enthusiast and creator of Alpacka My Bags. I'm here for all of your travel and adventure planning needs! 


I've been exploring this beautiful planet since I was a child, so I decided it was time to share my travel tips with others to enjoy. After college, I knew the "traditional career path" was not for me.


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

My 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 me, and often my partner and my dog, as we find exciting adventures and travel recommendations for you! If you've been bit by the travel bug just as I have, I hope you find my tips useful for all of your future travels.

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