The Ultimate Winter Packing List Chicago Edition For 2026

Updated: January 2026

Wondering what to pack for Your Winter Trip To Chicago?

I’m about to break down what I consider the non-negotiables for your packing list for Chicago, specifically in winter.

As a native of Illinois for the past 20+ years, trust me when I say Chicago is a very cold city in winter.

If you’ve never experienced a real winter in Chicago, you may not be aware of all the winter clothing essentials we Illinoisans deem necessary not only for ourselves but also for visitors during our coldest months.

In this post, I’ll share with you what I recommend and personally wear as an Illinois native. From base layers to outerwear and accessories, I’ll share my best recommendations, so let’s get started!

Like it? Pin it!

Packing list for Chicago

Winter Packing List: Chicago Edition

Packing list for Chicago: Outerwear

The best parka for Chicago winter: The North Face Hydrenalite Down Parka

This is not only a recommendation. It is a necessity.

As you know, Chicago holds the records for having some of the coldest winters in the U.S., so don’t play when finding a quality jacket or coat that will keep you warm as you explore the city. 

My favorite outerwear/jacket brand is The North Face, and I will recommend it for your visit to Chicago. 

The reasons why I recommend The North Face brand over others:

• The quality is worth the price, and even if you can get a cheaper jacket, trust me, it won’t do you any good in really cold temperatures.
• The North Face’s variety of styles and colors is available.
• You can buy one anywhere from ASOS to, of course, The North Face.
• Many North Face Jackets are not bulky or stiff, yet warm – this I can attest to! 
• It’s the only brand I’ve used to endure Chicago winters in my 20+ years living in Illinois.

The Women’s Hydrenalite Down Parka is great because:

• It has a multi-functional hat that is perfect for cold or wind.
• It’s water-repellent, which is great if you visit Chicago when it’s snowing or raining/snowing.
• It’s also. 600 down fill, which makes for a pretty warm jacket.
• It’s not too bulky, but definitely warm enough.

💡Pro tip: Take a look at both the temperature and the wind chill/sensation because you may see that the temperature for the weekend in Chicago may be 35 degrees Fahrenheit, but the wind chill may be 15 degrees Fahrenheit. 

The Women’s Arctic Bomber is great because:

• It has 600-fill recycled waterfowl down, providing serious warmth without excessive bulk.
• It’s windproof and waterproof, thanks to its DryVent shell.
• The removable faux fur-trimmed hood helps block the icy wind.
• Its ribbed cuffs and hem help seal in warmth, keeping cold air out.
• The shorter length makes it less bulky and easier to move around.
• It has secure pockets to keep your hands warm and store essentials like gloves or a phone.

❄️ Buy The North Face Women’s Hydrenalite Down Parka

❄️Buy the Women’s Arctic Bomber Jacket

>> Read More: The 11 Coziest and Best Coats for Chicago Winter in 2026

The best winter boots for Chicago winter: The North Face Chilkat V 400 Waterproof Boots 

Whether it’s snow boots or ankle boots, I recommend packing boots for ultimate warmth over sneakers or other shoes when planning your winter packing list for Chicago.

Regardless of whether it snows or not, a snow boot will keep you warm, dry, and comfortable as you walk around Chicago —which we love!

The North Face also has a few great options, which I have tried myself and can attest to their quality.

However, these shoes are great for grip and walking on snow and slippery surfaces, but in terms of warmth, I’d still go with the Uggs.

The North Face boots offer great warmth, don’t get me wrong, but the Uggs seem to keep your feet a little bit warmer throughout the day. Both are great options!

My personal favorite from The North Face is the Women’s Chilkat V 400 Waterproof Boots, tall winter boots designed for walking in snow and frigid temperatures, which you may get depending on which winter month you visit Chicago.

What I love about this boot is its grip, which helps ensure you won’t slip on ice. It’s waterproof, extremely comfortable, and supportive, and it’s designed with extra padding to keep your foot warm for all-day exploring. 

Chicago, again, is a city best seen on foot, so trust me, a comfortable shoe will be necessary, and one that will help you trek any snow or ice you may encounter if you visit during the winter.

The weather is unpredictable here in Chicago!

❄️ Buy the Women’s Chilkat V 400 Waterproof Boots

The UGG Women’s Adirondack XXV Boot is great because

My personal favorite brand of boots to keep you warm is Ugg.

Yes, I know it’s basic, but if you want warmth, the Uggs won’t let you down. I promise you that.

Believe it or not, Ugg boots have elevated their style beyond the classic boot we all once had in middle and high school.

Reasons why the UGG Women’s Adirondack III Boot is a great addition to your winter Chicago packing list:

• They are waterproof and feature waterproof leather.
• They’re rated for temperatures as low as -25 Farenheight
• They are casual yet very warm and will go with most Chicago outfits you have planned.
• It has a UGGpure wool lining and insole, which adds extra warmth and comfort for long walks around the city.
• The rubber outsole has great traction.
• It’s lightweight yet super warm, so your feet stay cozy without feeling weighed down.

❄️ Buy the UGG Women’s Adirondack III Boot

Packing list for Chicago: Warm Layers

Cozy Sweaters

When packing for your weekend or week in Chicago, sweaters will most likely make up 85% of your tops because the cold demands them.

I don’t have a specific brand of sweaters I like, but I usually go for materials that keep me warm but are also breathable, like cotton, fleece, flannel, or cashmere.

Wool is a popular, warm material to consider when shopping for sweaters. 

ASOS, Mango, and Uniqlo have some great options for every budget, luggage space, and style. 

❄️ Click here to check out more warm sweaters ideal for winter sightseeing ❄️

Extra Warm Socks

Whether you bring warm boots or pack sneakers, I recommend packing a few extra pairs of warm socks.

They will not only add another layer of warmth but also provide extra comfort and support inside your shoes for long hours of walking and sightseeing in Chicago.

Long socks like these are perfect because they are plush, cozy, and long, which is great for boots. After all, if they’re short, they’ll be falling off your foot, and other than the cold wind, there is no other worse feeling than that.

Speaking of, if you want to make your sneaker or ankle boot even more comfortable, I recommend getting some gel insole shoe inserts. I’ve done this, and it really makes a world of difference.

And if you’re looking for a comfortable, warm shoe insert, Ugg and other stores sell shearling and sheepskin inserts for just $20! So, you can get both comfort and warmth in whatever footwear you decide to pack!

❄️ Click here to browse warm socks ideal for frigid weather ❄️

Don’t forget to grab your FREE printable packing list!

👇🏽👇🏽

Long-Sleeved Thermal Tops

If you are running low on space and can’t pack all the sweaters you’d like, long-sleeved thermal tops are the next best thing. 

Some of my favorite thermal tops are from Uniqlo’s HEATTECH line.

These tops come in different colors and cuts and offer 3 heat levels, depending on your activity and destination.

They are perfect for layering without feeling bulky, soft, and incredibly comfortable. As someone from Chicago, I give it my stamp of approval.

❄️ Click here to buy Uniqlo HEATTECH Thermal Tops

A few other staple travel tops that I love come from Lululemon.

Even though, at first, it may seem ridiculous to pay 2-3x more than you would for a basic-looking T-shirt at another store (I know, this was me not too long ago), I have to share how amazing they are for travel and comfort.

I especially love the Classic-Fit Cotton-Blend Long-Sleeve Shirt, which combines sweat-wicking materials to keep you dry and cotton, lyocell, and linen to make the shirt incredibly soft and stretchy. 

>> Read More: 7 Of The Best Lululemon Travel Essentials

You don’t have to buy from Lululemon to get similar sweat-wicking long-sleeve shirts designed for movement; you can also check out Athleta or other active or sportswear brands with long-sleeve shirts that look like regular long sleeves and offer that sportswear comfort.

Warm Bottoms

I know leggings are a popular option amongst tourists and even locals.

Still, I find the materials are often too thin, so you’ll feel every wind gust. I wouldn’t recommend them, especially if you’re going to be spending a significant part of your day outside sightseeing in Chicago.

I wouldn’t just bring those unless you want to opt for fleece-lined leggings. 

I would recommend a looser-fitting bottom so you can comfortably layer a thermal base layer underneath.

Anything from wide-leg jeans to loose-fitting trouser pants will look great and stay warm thanks to the base layer underneath. 

I love and use Lululemon’s trouser pants because they are soft and stretchy yet still look put together.

I know I keep mentioning a specific group of brands, and even though they do not sponsor me to write and share their products, I vouch for them because I use them. Regarding travel clothes, especially winter clothing, I think investing in a few key pieces is essential. So, as an additional disclaimer, I am not being sponsored or gifted any of these products—they’re just that good and appropriate for cold temperatures, in my opinion.

❄️ Best Chicago winter travel trouser pant options ❄️

>> Read More: What to do in Chicago during the Holidays

Warm Baselayers 

The essential base layers and thermals, like a base top and pants, to layer under your bottoms and sweaters/jackets.

They will make a difference, especially if you’re visiting Chicago in the middle of winter when the temperature is in the single digits.

I use 32 Degrees base layer top and bottom, as they are thin enough to layer under your clothes without feeling bulky, and they manage to keep you warm.

Another great alternative is Under Armour’s ColdGear Authentics Crew, which is amazingly warm, sweat-wicking, and thick enough to wear as a top on its own.

Uniqlo’s branded HEATTECH thermal clothing is also a favorite among those who live and travel to cold destinations.

It’s a great piece to pack if you plan on visiting more than one cold destination. 

❄️ Buy the best base layers to survive a Chicago winter❄️

Packing list for Chicago: Warmth Accessories – Hats, Gloves, Scarves – Repeat!

You need all of these, no questions asked.

Especially in a city dubbed “The Windy City,” that lake-effect wind is no joke!

One pair of each suffices; when looking for these accessories, consider warm materials such as wool, sherpa, or other breathable options. 

The North Face and UNIQLO are my favorite go-to brands for all things winter accessories.

• Gloves – It’s ideal to wear gloves that aren’t too bulky, let you use your smartphone, and are warm. Look for a fleece-lined or faux leather exterior.
• Scarves – Any thick scarf will do, but cashmere and wool are good options if you’re looking for ultimate warmth.
• Hats – A warm beanie does the job well.

In my opinion, I don’t recommend mittens because they’re not functional enough for using your cell phone or other touchscreen devices. 

❄️ Click here to find more warm, winter weather accessories and sets ❄️

>> Read More: Planning A Trip To Chicago? Here Are 10 VERY Useful Things To Consider First!

My go-to winter hair and skin care staple items for Chicago winters 

The winter and the wind chill in Chicago are no joke yall, even if you say it’s not that bad, your skin and hair will say otherwise if you don’t take proper care of them while you’re out and about in chilly Chicago.

Here are a few of my recommendations for hydrating moisturizers for hair and skin. As someone who has experienced more than a few Chicago winters, thank me later.

• Almond Oil for your face – I use it as my evening moisturizer to help moisture seep into the skin.
• Giovanni 2-Chic Ultra Moisture Care Shampoo and Conditioner – the absolute BEST shampoo and conditioner – this brand is amazing!
• Giovanni Ultra Moisture Leave-In Conditioner – give your hair lasting TLC on cold days.
• Ultra-hydrating chapstick
• SPF for your face – the sun rays bouncing off the snow are no joke, even on a cloudy day.
• Hydrating body lotion

What are the winter months in Chicago like? What’s the average temperature in Chicago in the winter?

Winter is officially from December 21st-March 20th in the U.S. If you visit during December, you can expect temperatures to range around 30-20 degrees Fahrenheit, while in January and February, those numbers drop and can even dip into the single digits, and it can feel like it’s in the negatives Farenheight.

In March and April, temperatures will rise slightly into the 40s and 50s, but if you’re planning a visit, expect some rainy days.

How to dress for Chicago winter

Now that you know the winter temperature averages, let’s go over how to dress for Chicago winter by getting a better idea of what to pack and what to bring along on your trip to Chicago.

If you are going to spend the day walking around Chicago, visit the Art Institute, Millennium Park, or Lincoln Park Zoo (yes, it’s still open in the winter).

In that case, you have to know how to stay warm and comfortable so you can withstand frigid temperatures and strong gusts of wind!

Before considering whether winter is a good time to visit Chicago, the answer is yes!

It’s just a different experience from, say, Summer for obvious reasons, but it’s still uniquely beautiful to experience a wintery trip to Chicago.

Looking for things to do while in Chicago and places to eat? Why not combine both and sign up for the Chicago Favorites Ultimate Food & Walking Tour! Try local Chicago classic dishes and get a lay of the land.

>> Read More: The Best Places To Eat Deep Dish Pizza in Chicago

​​What do people wear in Chicago in winter?

In Chicago, as in many other U.S. cities that experience a brutal winter with harsh winds and snowstorms, we dress to prioritize comfort and warmth when choosing our Chicago winter clothes.

That’s why, depending on how cold it is, if you’re strolling down the streets of Chicago, you’ll find people wearing coats and outerwear, typically from brands like The North Face, Patagonia, Canada Goose, Columbia, mixed in with a few other pieces that add layers of warmth, comfort, breathability, and flexibility. 

Let’s talk about athleisure, which essentially is workout clothes designed to be worn in the gym, as much as they are meant to also transition into everyday staple items to wear because of their chic, figure-flattering, and comfortable styles – it’s the gym clothes that don’t look like traditional gym clothes and add all the comfortability you’d want, especially in winter.

Athleisure is big in Chicago, so you should probably consider adding your favorites in your winter packing list for Chicago. 

Athleisure pieces I recommend for added comfort:

• Softstreme High-Rise Pant Regular
• Rain Rebel Insulated Jacket RepelShell
• Everywhere Belt Bag 1L
• The Love Crew Long Sleeve
• Scuba Oversized Funnel Neck Half Zip

>> Read More: 11 Amazing Lululemon Travel Accessories and Essentials Worth The Money

What shoes do you wear in Chicago winter?

When it comes to shoes, it’s very important to wear ones that cover the most and truly keep your feet warm. 

Winter boots will become your staple item, whether you’re traveling in early December or the middle of February. 

WINTER BOOT Q&A: These are the common questions and things I keep in mind when I ask myself what shoes to wear in Chicago winter, and can help you pick the right winter boot for you:

• How warm are the boots? What kind of interior lining do they have? Fleece and shearling are good materials to keep warm. 
• What is the material? You want to look for heavy-duty nylon or leather that is waterproof.
• Are they breathable? The shearling fleece interior makes for good breathability. 
• Will I be able to wear thick socks with the size of boots I’m getting? Maybe size up!
• How tall are they? If you’re walking through snow, you’ll want high boots up to your knees. If you’re walking in the city, any length above your ankle is good!
• Do they have a zipper, or are they slip-on? Depending on the length of the boot you’re getting, it’s up to personal comfort – remember you’re walking a while in these!

When picking out winter shoes or boots, I usually browse online to see other people’s recommendations and decide based on what I will need the shoes for. 

Maybe you’re walking a lot or sightseeing. In that case, Ugg boots make really cute boots (they’ve come a long way since the classic Ugg boot). They now have different boots with chic, minimalistic, stylish designs that WILL keep your feet warm. 

The North Face also has a few good pairs, especially great if you’re going to be in colder temperatures or walking on snow/ the sidewalks are slippery with black ice. 

>> Read More: A Local’s Guide to the 21 Best Chicago Winter Boots

What should you not wear in Chicago in the winter?

Downtown Chicago is best explored on foot; therefore, visiting during the winter will require extra effort and next-level warm clothes. 

Whatever you wear, you must pack and dress for wind chill, possible snow, and/or sleet. Chicago winters are brutal and deceiving, so bundle up even if it’s sunny!

A simple hoodie alone will not keep you warm, and neither will a thin bomber jacket.

What should I pack for a Chicago winter?

To withstand the famous frigid temperatures of Chicago, it is essential to pack for the weather because, as a native, it’s no joke.

Chicago, especially, is so close to Lake Michigan that we often get our famed “crazy, unpredictable” weather and snow. 

To brave the Windy City’s cold, consider packing the following:

• A good quality winter coat/jacket
• A warm pair of boots/walking shoes
• Warm and comfortable layers
• Cozy sweaters
• Warm and sweat-wicking socks
• Warm bottoms
• Warm underclothing layers
• Winter accessories

What should I wear in Chicago in early December?

The weather in Chicago in early December is typically cold, often 40 degrees Fahrenheit or below. 

But keep in mind that this does not account for the wind chill from Lake Michigan, which makes it feel colder, dropping to 20-25 degrees Fahrenheit. 

That said, I recommend using this Chicago winter packing list as a guide to help you select a few items to add to your winter capsule wardrobe for Chicago if you plan to travel there in early December.

Do we get snow in early December? It’s not so common, but it has happened in the past. If you plan on traveling to Chicago in early December, check the weather a week or a week and a half in advance to see if snow is on the horizon during your stay.

If so, I know these winter accessories for Chicago will help you stay warm!

What should I wear in Chicago in February?

February in Chicago is still peak winter, so you will most definitely have to bundle up for extra warmth.

Especially if you’re going to be sightseeing and spending time outside, I cannot recommend layering enough. 

Layer your outfits with warm underclothing, bring a hat, scarf, and gloves (very important, people seem to forget gloves for some reason), and of course, a good jacket is a no-brainer. 

When figuring out what to wear in Chicago in February, my biggest advice is to dress for the weather.

This is the month in Chicago where there is a lot of snowfall and chilly wind, and the temperature can drop into the teens and even single digits with wind chill. 

So, please, I ask of you don’t…

• Wear thin coats (this is why I only purchase coats and jackets from brands specializing in winter coats – you wouldn’t buy a long-lasting computer at a grocery store, would you?) 
• Expose your ankles 
• Expose your neck (wear a scarf!)
• Wear layers so you won’t burn or sweat too much when you visit stores, museums, and other warm places. 
• Forget your gloves 
• Wear cheap shoes – you’ll lose feeling in your feet after walking a few hours outdoors.

Extra accessories that you’ll want to pack for your Chicago winter trip:

• External phone battery – something about the cold that drains your phone’s battery, so you will want to get an external phone battery.
• Hand warmers – if you’re going to be outside for an extended amount of time, for instance, visiting Lincoln Park Zoo for the Zoo Lights or walking down the beautifully lit Michigan Avenue in December, packing a set of hand warmers wouldn’t hurt. They’re small, fit anywhere, and can help keep your hands, especially your fingers, warm.

>> 5 Fun And Different Ways You Can Experience The Holidays In Chicago And Nearby Suburbs

Chicago Winter Clothing and Packing Tips:

What shoes should I wear in Chicago winter?

By far, the best shoes to bring to Chicago are snow or insulated boots that help keep your feet warm.

Look for boots with a warm inner lining made from fleece, faux fur, down fill, or other soft, warm materials.

My brand recommendations will always be boots or shoes from The North Face or UGGs because of their durability, cold-weather design, warmth, and comfort, which are essential for walking long distances.

Is Chicago too cold in December?

The average temperature in Chicago in December is around mid- to high-30s Fahrenheit. However, some days may feel chillier if the wind picks up.

December is a good month to visit Chicago for many reasons, including seeing the Chicago holiday festivities in full action. It’s not too cold yet, and you may get snow. If you want to see snow, the possibility increases in January.

So come prepared with your good jacket, gloves, hat, scarf, and other winter essentials.

How do I prepare for Chicago winter?

When planning what to wear in Chicago in winter, I suggest looking ahead at what the weather is expected to be like during the time of year you’ll be visiting.

Be sure to bring (if possible) different options for jackets, sweaters, and winter accessories like hats, gloves, and socks, so you can switch them out if they get dirty or wet from the snow.

Bring lotion, chapstick, hair oil, and other moisturizing products because the winter and the wind, especially in Chicago, are no joke.

Exposed skin will feel the chill and the dryness, which is not fun, so pack up those items well!

Chicago Winter Clothing Tips

Adding layers to your Chicago winter outfits is very helpful, whether you get cold and want an extra layer or you get warm and feel stuffy and hot, so that you can remove layers.

Bring an extra hat, scarf, and gloves to alternate between accessories in case they get dirty or start to smell.

Bringing gloves of different thicknesses is a good idea so you can alternate between thicker gloves for ice skating or walking outdoors and thinner gloves for slightly warmer days or when you need to use your phone.

Concluding thoughts: Winter Packing List: Chicago Edition

I hope this list inspired you to pack what to bring when you come to Chicago and provides a few items to create some Chicago winter outfits! 

As a recap, here are my top 8 winter packing list Chicago essentials:

• Winter shoes
• Warm jacket/coat
• Warm socks
• Long-sleeved tops
• Warm bottom
• Warm base-layer
• Hats, gloves, scarves
• Moisturizing products

Don’t feel intimidated by cold-weather travel. As someone once said, there’s no such thing as cold weather; it’s just a poorly chosen outfit.

But in all seriousness, I hope this post helped you get a better idea of what winter travel essentials are helpful to pack from a local, and that this helps you enjoy and maximize your endurance outside sightseeing in Chicago.

I recommended specific brands and pieces in today’s post because they are brands I use and products I trust, but this does not mean you have to buy only these products.

These are just the pieces and brands I recommend, but the rule of thumb is to pack clothes that you feel comfortable wearing and that will keep you warm.

Remember to download your copy of the WINTER CLOTHING CHICAGO TRAVEL CHECKLIST FREEBIE—a printable winter packing list for cold weather in Chicago. Feel prepped, and grab your winter travel packing list. 

👇🏽👇🏽

To more travel moments like this,

Like it? Pin it!