The Ultimate Winter Packing List Chicago Edition For 2023

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Updated: January 2023

Wondering what to pack for Your Winter Trip To Chicago?

I’m about to break down what I deem are the non-negotiables when it comes to your packing list for Chicago, specifically in the winter.

Chicago is a very cold city in the wintertime.

Whether you’re a tourist and you’ve never been to Chicago, or you’re a local who wants to find ways to keep warm as you wander the beautiful streets of Michigan Ave. and State Street – then keep on reading because, in today’s post, I’ll share with you what I recommend and personally wear as an Illinois native.

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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 the month of December, you can expect temperatures to range around the 30’s-20 degrees Fahrenheit, while in January and February, those numbers drop, and can drop into the single digits, and even feel like it’s in the negatives Farenheight.

In March and April, you can expect the temperatures to rise slightly more to the 40s and 50s, but expect some rainy days especially in April if you’re planning a visit then.

How to dress for Chicago winter

girl with winter coat standing next to Chicago cloudgate

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

If you are going to be spending the day out walking around Chicago, hitting up the Art Institute, Millenium Park, or Lincoln Park Zoo (yes, it’s still open in the winter) you have to know how to best keep warm and comfortable so you can withstand some of those frigid temperatures and strong gusts of wind!

And before you start thinking to yourself if Winter is a good time to visit Chicago at all, the answer is YES!

It’s just a different experience from say, Summer for obvious reasons, but nonetheless, 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, as well as 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 cities across the U.S. that experience a brutal winter, with harsh winds, and snow storms, we dress in a way to prioritize comfort and warmth when it comes to picking 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, and a piece of clothing that you should probably consider packing in your winter packing list for Chicago. 

Athleisure pieces I recommend for added comfort:

>> 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 want to wear shoes that can cover the most, and that truly can keep your feet warm. 

Boots are going to 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 and 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 boot you’re getting, it’s up to personal comfort – remember you’re walking a while in these!

When picking out winter shoes/boots, I usually browse online to see other people’s recommendations, and I make a decision based on what I am going to need the shoe for. 

Maybe it’s walking a lot/sightseeing, in that case, Uggs make really cute boots (they’ve come a LONG way since the classic ugg boot) and they now have different boots with chic, minimalistic, stylish designs that WILL keep your foot warm. 

❄️ Check out warm UGG boots for your trip to Chicago in the winter ❄️

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. 

❄️ Check out warm and slip-free boots for your trip to Chicago in the winter ❄️

What should you not wear in Chicago in the winter?

Downtown Chicago is best explored on foot, therefore coming to the city during the winter is going to require some extra duty, and next-level warm clothes. 

My recommendation is that whatever you end up wearing, you are aware that you have to pack and dress for wind chill, possible snow, and/or sleet. Chicago winters are brutal, and a bit deceiving so bundle up even if it’s sunny!

A simple hoodie alone won’t cut it, or a thin bomber jacket won’t be enough to keep you warm.

Read below to learn what are some of my recommended Chicago winter essentials – as a local. 

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. Especially Chicago being so close to Lake Michigan, we often get our famed “crazy, unpredictable” weather and snow due to the city’s proximity to Lake Michigan. 

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

Packing list for Chicago

Winter Packing List: Chicago Edition

Packing list for Chicago: Outerwear

The best parka for Chicago winter: The North Face Metropolis Parks

This is not only a recommendation, this 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 it comes to finding a quality jacket or coat that will keep you warm as you are exploring the city. 

A quick word to the wise as you plan your winter outfits for Chicago: Take a look at both the temperature, but also 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. 

My personal favorite outerwear/jacket brand is The North Face, and that is the brand that I will be recommending 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 when I say it won’t do anything for you in really cold temperatures.
  • The North Face’s variety of styles and colors are available.
  • You can buy one anywhere from Asos to Nordstrom and of course, The North Face.
  • A lot of The North Face Jackets are not bulky or stiff, and yet they are warm – this I can attest to! 

I currently own the Metropolis Parka, which is a longer-length jacket that I have been wearing for the past 4 years, and it’s still in great condition.

The reasons why I love the Women’s Metropolis Parka:

  • I love the longer length, and find that it helps with keeping more of you warm especially against cold wind gusts, which if you don’t know, Chicago ain’t the Windy City for nothin’!
  • It is 550 fill-down, which means that it ranges within medium on the warmth scale for winter jackets.
  • It’s figure flattering ⌛️ which in and of itself is great on its own, however, I find that the more fitted your jacket is, the warmer it will keep you because the wind won’t be able to get inside.

If you’re looking for something on the shorter side, I also highly recommend the short version of the parka I just mentioned, called the Women’s Metropolis Jacket or the Belleview Stretch Down Jacket.

The Women’s Metropolis Jacket is great because:

  • It has a hood that covers your whole head and will also stay on when the wind hits you.
  • It’s a slim fit, which we love for ⌛️ but also for warmth 👍🏽
  • It’s also a 550 fill-down.
  • It has pockets on the inside, and outside.
  • The North Face logo is the same color as the jacket, so if you don’t want to seem flashy with the logo, this and the longer parka have the logos blend in with the color of the jacket.

The Women’s Belleview Stretch Down Jacket is great because:

  • It doesn’t have a hood for those who don’t want a jacket with one.
  • It’s a slim fit
  • Super lightweight
  • It’s a 3 (the warmest) on The North Face’s warmth scale
  • Added stretch in the armpit area to provide more range of motion and breathability.
  • Adjustable cords at the hem to customize the fit.
  • Really pretty color options.

The Belleview Stretch Down Jacket is the jacket most similar to the one that I took with me when I moved to Madrid to teach English, and it was so easy to travel with because of how packable it is.

❄️ Click here to browse The North Face Metropolis Parka and other warm jackets ❄️

>> Read More: The 25 Coziest and Best Coats for Chicago Winter in 2023

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

Whether it’s snow boots, ankle boots, or whatever it is, I personally recommend packing boots for ultimate warmth over sneakers, or any other type of shoe when planning your winter packing list for Chicago.

Regardless of if it snows or not, a snow boot will do the job as you’re walking around Chicago keeping you warm, dry, and comfortable – which we love!

My personal favorite brand of boots to keep you warm are Uggs – yes, I know super basic, but if you want warmth, the Uggs will NOT fail you, I promise you that.

Believe it or not, Uggs have elevated their style beyond the classic boot we all once had in middle school and high school. For a stylish and winter-ready boot, I would recommend the Harrison Lace Boots.

Reasons why UGG boots are a great addition to your winter Chicago packing list:

  • They are waterproof and feature waterproof leather.
  • They have a 1.5″ heel height.
  • They are casual, yet very warm and will go with most Chicago outfits you have planned.
  • they have cotton laces, making them easy to wash.
  • They are very warm.
  • They don’t have a flashy UGG brand logo, so it’s perfect for the minimalist traveler!

The North Face also has a few great options to look at, which I have also tried myself and can also attest to how great they are.

I will say, 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 foot 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, which are tall winter boots designed for walking in snow and in frigid temperatures – which you may get depending on which winter month you visit Chicago.

What I love about this boot is the grip that it has which will help ensure that you won’t easily slip on ice, it’s waterproof, it’s 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 that is 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 come across if you visit during the winter.

The weather is unpredictable here in Chicago!

In years past, I’ve purchased my boots from Nordstrom, regardless of the brand, and I especially love the fact that at Nordstrom you can get a dozen different quality snow boot brands under one roof. The reason why I mention them is because of their Satisfaction Guarantee policy, which has to be one of the most flexible ones out there. Basically, if you’re not happy with your purchase, even after using the boots out in the snow and walking all over Chicago in the winter, you can return the shoes (or any product purchased from them) and more than likely get a full refund. You can read the full Satisfaction Guaranteed policy here, and read some of these details.

Packing list for Chicago: Warm Layers

Cozy Sweaters

Sweaters will most likely make up 85% of your tops when packing for your weekend or week in Chicago because the cold simply demands it.

I don’t have a specific brand of sweaters that I like, but I usually go for any material that will keep me warm but is also breathable, like cotton (like this one from Nordstrom), fleece, flannel, or even cashmere.

I don’t have cashmere, but if you’re interested to know, it’s a good fabric that will keep you warm!

Wool is a popular warm material that you can also consider when shopping for warm sweaters. 

Nordstrom and Asos and Mango have some really great options for every budget, luggage space, and style you may have. 

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

Extra Warm Socks

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

Not only will they add another layer of warmth, but they’ll also add extra comfort and support to inside your shoe for long hours of walking and sightseeing in Chicago.

Long socks like these are perfect because they are plush, cozy, and long – which are great for boots because 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 insoles shoe inserts, which is something I’ve done and really makes a world of a difference.

And if you’re looking for an insole shoe insert that is both comfortable and warm, Ugg and other stores make shearling and sheepskin insole shoe inserts for only $20! Get both comfort and warmth in whatever footwear you decide to pack in!

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

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

👇🏽👇🏽

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Long-Sleeved Tops

If you are running low on space, and can’t pack all the sweaters you wish you could – long-sleeved tops are the next best thing to pack. 

Something I want to mention that I haven’t said throughout the post yet is this: just because it may be really cold outside, and you’re looking to keep warm (understandably) it doesn’t mean that you won’t sweat from all the walking and sightseeing you’re going to be doing. For this reason, I recommend that you consider long-sleeve shirts that are made with breathable material that is sweat-wicking, quick-drying, and unbelievably soft.  

Some of my favorite staple travel tops come from Lululemon, and 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 beautifully combines sweat-wicking materials to keep you dry, as well as cotton, lyocell, and linen to make the shirt incredibly soft and stretchy. 

❄️ Click here to find more warm, long-sleeved shirts ❄️

>> 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 Nike, Athleta, or other active or sportswear brands with shirts that look like regular long sleeves and that will give you that sportswear comfortability.

Warm Bottoms

I know leggings are a popular option amongst tourists and even locals, but I find that the materials are often too thin that you’ll feel every wind gust – so I personally wouldn’t recommend them especially if you’re going to be spending a significant part of your day outside sightseeing Chicago. Unless you want to opt for fleece-lined leggings, but even then, I wouldn’t just bring those. 

What I would recommend is actually a looser fitting bottom so that you’re able to comfortably layer a thermal base layer underneath.

Anything from stretchy jeans, to joggers or loose-fitting trouser pants, will not only look great but also be warm because of the base layer underneath. 

I personally love and use Lululemon’s jogger pants because of their soft materials, sweat-wicking material, and variety of colors and styles they come in.

Click here to check out why these pants are the new “travel pant”.

I know I keep mentioning a specific group of brands, and even though I am not sponsored by them to write and share their products, I vouch for them because I personally use them. When it comes to travel clothes and especially winter clothing – I think it’s important to start investing in a few key pieces. So, as an additional disclaimer, I am not being sponsored or gifted any of these products – they’re really just that good and appropriate for the cold temperatures in my opinion.

❄️ Click here to find more travel joggers and 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 such a difference, especially if you’re visiting Chicago during one of its *quirky* single-digit weather days. 

I personally use 32 Degrees base layer top and bottom, as they are thin enough to layer under your clothes without feeling bulky, and manage to keep you warm, or Under Armour’s ColdGear Authentics Crew which is amazingly warm, and good enough to wear as a top on its own because of how thick it is.

I like this thermal because it is also sweat-wicking and keeps you warm and dry.

Definitely a great piece to have if you plan on visiting more than one cold destination. 

❄️ Click here to browse through more thermal underclothing options for all budgets and styles ❄️

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 not a joke!

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

My personal favorite brands for hats, gloves, and scarves that I own are The North Face classic beanie, for scarves anything that is knit, chunky, or fleece, and for gloves, anything with exterior recycled polyester like these and fleece-lined, or faux leather exterior.

I don’t recommend mittens just because they’re not functional in my opinion to use your cell phone or other touch screen surfaces. 

❄️ 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 definitely 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 personal recommendations for hydrating moisturizers for your hair and skin, as someone who has experienced more than a few Chicago winters – thank me later.

What should I wear in Chicago in early December?

The weather in Chicago in early December is typically already cold, typically ranging between 40 degrees Fahrenheit and below. 

But keep in mind this is not considering the wind chill from Lake Michigan, which makes it feel colder – dropping down to 20 – 25 degrees Fahrenheit. 

That being said, I recommend using this Chicago winter packing list as a guide to help you select a few items that you can add to your winter capsule wardrobe for Chicago if you’re planning on traveling to Chicago in early December.

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

If it is, I know these winter accessories for Chicago will help you keep warm!

What should I wear in Chicago in February?

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

Especially if you’re going to be sightseeing, and outside, I cannot recommend enough to layer up. 

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 it comes to figuring out what to wear in Chicago in February, my biggest piece of advice is to truly dress for the weather. This is the month in Chicago where you can have 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 that specialize 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’re not burning up or sweating too much as you pop into 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 just drains your phone’s battery, so between using it for Google maps, and the cold draining the battery, you’re going to want to get an external phone battery.
  • Hand warmers – if you’re going to be outside for an extended amount of time, for instance, you’re visiting Lincoln Park Zoo for the Zoo Lights, or you’re 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 a great deal to keep your hands warm, especially your fingers.

>> 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?

The best shoes to bring to Chicago are by far snow boots, or insulated boots to help keep warmth in your feet.

Look for boots that have a warm inner lining, from fleece, faux fur, down-fill, or other soft and warm materials. My personal brand recommendations are always going to be boots/shoes from The North Face or UGGS for their durability, design for cold climates, warmth, and comfortability, which you will need 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, which may be possible.

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 much more 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 how to dress for Chicago winter, I suggest looking ahead at what the weather says will be like during the time of the year you’ll be visiting.

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

Bring lotion, chapstick, hair oil, and other types of 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 you want an extra layer, or you get warm and you feel stuffy and hot so you can remove layers.

Bring an extra hat, scarf, and different-thickness gloves, so that you can alternate between accessories in case they get dirty, or start to smell.

Bringing different thickness gloves is a good idea so that you can alternate between using thicker gloves for those days when you may be ice skating or walking outdoors, and using thinner gloves for slightly warmer days, or if you need to use your phone.

Concluding thoughts: Winter Packing List: Chicago Edition

girl standing next to "Greetings from Chicago" mural in Chicago, IL.

I hope this list gave you some inspiration on what to pack when you come to Chicago, as well as 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, just a poorly chosen outfit.

But in all seriousness, I hope this post helped you get a better idea as to 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 personally use and products I trust, but this by no means, means you have to buy these products and these products only.

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

Don’t forget 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. 

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