The Ultimate Winter Packing List: Chicago Edition

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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’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 40’s and 50’s, but expect some rainy days especially in April if you’re planning a visit then.

How do people dress in Chicago in the winter?

girl with winter coat standing next to Chicago cloudgate

Now that you know the winter temperature averages, you can better get an 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 getting a lay of the land. Click here to learn morea bout tickets and tour details!

Some of my favorite other tours to experience in the city…

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

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, 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. 

Winter Packing List: Chicago Edition

Outerwear –

A Warm Coat

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 brand of jackets is The North Face, and that is the jacket that I will be recommending for your visit to Chicago. 

The reason why I recommend this brand over others is because of the quality, variety of styles available, you can buy one anywhere from Asos to Nordstrom and of course, The North Face store, the jackets are not bulky or stiff, yet very warm – this I can attest to! 

I currently own the Metropolis Parka, which is a longer length jacket (which if you’re especially not good with cold weather, and you plan to travel to future cold destinations, I recommend getting a longer jacket), and it’s a jacket that is warm, figure-flattering (which aside from looks, keeps you warm because the wind doesn’t get inside your jacket), and more. 

I also own the Aconcagua Jacket, which is great if you’re trying to save even more space, and you’re possibly traveling in slightly warmer temperatures. It’s a great option that will keep you warm, keep you light, dry, and very comfortable. 

This is the jacket that I took with me when I moved to Madrid to teach English, and it was so easy to travel with it!

Warm Footwear 

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

Regardless of if it snows or not, a snow boot will do the job as you’re walking around Chicago in keeping you warm, dry, and comfortable.  

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!

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

Other than the warmth, I really love Ugg boots because they have a variety of styles, that go beyond the basic image of Ugg boots that I am sure we are all thinking at first.

I personally love the Harrison Lace boots that are not only snow-ready but also rain-ready – which again, with the unpredictable weather in Chicago, is not a bad thing to have!

I love that it comes with a heel, so you can dress it up or down as you like, it’s extremely comfortable to walk around the whole city.

I also love the fact that it doesn’t have any flashy brands etched on the boot itself, so if you’re all about minimal outfits, this is the perfect winter boot for you. 

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 to walk 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 Shellista IV Mid WP, 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, it’s designed with extra padding to keep your foot warm for all-day exploring. 

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.

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 & Other Stories), 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 have some really great options for every budget, luggage space, and style you may have. 

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!

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



Long-Sleeved Tops

If you are running low on space, and you 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. 

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 being 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. 

Warm Underwear 

Not literally – I mean 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. 

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, 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. 

Read More: First-Time Traveler Tips That Could Come In Handy To Know

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! 

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 in, 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 is 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 CHICAGO WINTER TRAVEL CHECKLIST FREEBIE – a printable packing list for braving the cold Chicago weather. Feel prepped, and grab your winter travel packing list. 



To more travel moments like this,

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