Chicago bean covered in snow

Chicago Winter Boots: Top Recommendations from A Local

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Wondering which Chicago winter boots to invest in? 

As a Chicago native, I’ve spent most winters of my life right here in Chicago. And yes, it’s as cold and brutal as you might’ve heard. One thing that makes it bearable is having the right gear, and proper Chicago winter boots are a key part of the equation. 

The winter conditions in Chicago are unique to winters elsewhere, and winter shoes that work in one city might not serve you as well here. In this guide I’ll explain what to look for when buying boots for Chicago winters, as well as some specific recommendations.

Top 3 Picks: Chicago Winter Boots


Sorel Joan of Arctic Boots
✔️ Waterproof Suede
✔️ Slip-resistant Sole
✔️ Tall or Ankle Length


Hunter Intrepid Nebula
✔️ Quilted Stylish Look
✔️ Made w/Recycled Materials


Columbia Ice Maiden II
✔️ Well-Insulated
✔️ Durable

9 Best Chicago Winter Boots for Women

What you really want to look for are boots that are warm, waterproof and slip resistant. 

Sorel: Women’s Joan of Arctic Boot

Sorel is one of the most popular and reliable winter boot brands. Sorel’s Joan of Arctic boot is an ideal choice for braving Chicago’s harsh winters. With its waterproof suede upper and seam-sealed construction, it keeps your feet dry even in the wettest conditions. 

The rugged rubber sole provides excellent grip on slippery surfaces, making it a must-have for both functionality and style in the Windy City’s winter months.

You can also consider the Joan of Arctic Next for similar protection but in an ankle length style. Both options are heavy duty without weighing down your feet so you can still walk comfortably. 

You’re sure to spot many Sorel boots around town in Chicago during winter, so you’ll fit right in with a pair.

👉 Click here for Sorel’s Joan of Arctic Boot

Hunter Intrepid Nebula Knee High Boot

Another great option if you’re gearing up for a Chicago winter is this iridescent quilted boot. Not only does it add a stylish touch with its drawcord cuff, but it’s also designed to keep your feet toasty warm.

Thanks to its waterproof feature, you can confidently tackle rainy days, puddles and slush while keeping your feet dry and comfortable. You’re sure to come across all these conditions during winter in Chicago, so this versatile boot is a solid investment.

Plus, with a modest 1 1/2″ heel and a 1″ platform, these boots effortlessly blend fashion and functionality. They offer ample coverage with their tall shaft, making them ideal for navigating snowy sidewalks.

They’re eventemperature-rated to handle Chicago’s chilly weather, keeping you cozy even on those inevitable frigid days.

For added comfort, these boots come equipped with an OrthoLite® footbed and a removable cushioned insole with arch support.

Crafted from a combination of textile and synthetic materials, with a recycled textile lining and rubber sole, these boots are also environmentally conscious.

👉 Get the Hunter Intrepid Nebula High Knee Boot here

North Face Shellista IV Luxe Waterproof Boots

The North Face Women’s Shellista IV Luxe Waterproof Boots are a fantastic, heavy duty choice. They blend waterproof full-grain leather with recycled P.E.T. ripstop for durability. Plus, the faux-fur collar lining adds warmth and style.

These boots are built to handle winter’s tougher challenges. The 200g Heatseeker™ Eco Pro insulation makes them eco-friendly and cozy. The rubber outsole offers great traction, and the OrthoLite® sockliner adds comfort.

Consider going up half a size or even a full size in these, as some have said they tend to run small. 

👉 Click here for the North Face Shellista Luxe Boots

Baffin Chloe Boot

CHLOE is a stylish yet functional choice for everyday winter wear. These boots are tested and rated for tundra conditions, so you can trust them in Chicago’s snow-covered streets.

They come equipped with a removable Comfort-Fit inner boot for warmth and a B-Tek™ Dry Waterproof Base to keep your feet dry. The suede leather upper with a faux fur collar adds a fashionable touch.

CHLOE also features top-notch insulation technology, ensuring your feet stay cozy. The Arctic™ Rubber shell provides flexibility and cold resistance, while the Polar Rubber® outsole maximizes grip in cold temperatures.

At 11 inches tall and weighing 4.6 pounds per pair, they’re protective without being bulky.

👉 Get the CHLOE Boots here

WindRiver Ice Queen IceFX T-Max Insulated Waterproof Leather Boots

These boots are designed to keep your feet warm, dry and fresh in the city’s chilly conditions. Their standout feature is the tarantula iceFX rubber outsole, offering enhanced traction on icy surfaces to make winter walks safer.

Duraguard protection makes the boots durable enough to last through multiple winters. If you’re looking for a comfortable, slip-resistant, and long-lasting winter boot this is it. 

👉 Get the Ice Queen IceFX T-Max Insulated Leather Boots

UGG Adirondack III Waterproof Tall Boot

When it comes to surviving a chilly Chicago winter, this lace-up boot is a real champ. It can handle bone-chilling temperatures as low as -25º Fahrenheit, so your feet stay toasty warm.

The waterproof leather upper keeps the slush and snow out, ensuring you arrive at your destination dry.

Inside, there’s a super cozy lining called UGGpure. It’s made from wool, but feels and wears like shearling. Whether you’re exploring the snowy streets or tackling icy sidewalks, these boots are up for the challenge. 

The outsole has a special lug pattern that provides solid grip on slippery surfaces. These boots are built to last, and they maximize contact with the ground, so you won’t be doing any accidental ice skating. 

👉 Click here to get the UGG Adirondack III Tall Boot

Women’s Bean Boots, 8″ Shearling-Lined Insulated

These boots are crafted from soft leather and lined with plush shearling, offering both style and warmth.

Handmade in Maine by skilled craftspeople for more than a century, they are a timeless choice. The leather is rich and the shearling lining is cozy, making each step comfortable.

Functionally, these boots are top-notch. The waterproof rubber bottom keeps your feet dry in wet or snowy conditions, and they provide insulation for extra warmth.

The lace-up design allows for a secure fit, and the chain-tread outsole ensures reliable traction on wet or icy surfaces.

👉 Get the Bean Boots here

Columbia Ice Maiden II

The Columbia Ice Maiden II boots are well-equipped for tackling a Chicago winter with their blend of practicality and style. Rated for frigid temperatures and featuring great insulation, these boots keep your feet warm and cozy.

The design balances function and fashion, offering a waterproof woven synthetic textile upper with suede overlays for durability and support. 

The Omni-Grip™ non-marking rubber outsole offers traction to make the boots slip resistant on snowy, icy streets. And, of course, Columbia is a timelessly reliable brand. The Columbia Ice Maiden II boots are a sensible choice for staying warm and comfortable while facing a Chicago winter.

👉 Get the Columbia Ice Maiden II Boots here

Kamik Rogue 10 Snow Boot

The Rogue 10 snow boot from Kamik delivers comfort and coziness to brave the Windy City chill. With seam-sealed construction and a waterproof leather upper, these lace-up boots are ready to tackle whatever winter brings.

They offer serious cold resistance with a -30 degree C cold rating and 200g of 3M™ Thinsulate™ insulation for an extra layer of warmth. 

On top of it all, these boots are durable, comfortable and stylish, ticking all the boxes for a Chicago winter. 

👉 Click here for the Kamik Rogue 10 Snow Boots

Chicago Winter Boots to Survive the Season

As you prepare to experience Chicago in winter, you might also be wondering: 

Do you need boots for Chicago winter?

Want to stay warm and dry? Then the answer is yes, you need a quality pair of Chicago winter boots. Most Chicagoans have a variety of winter boots of different lengths and materials to fit the various weather conditions and occasions this season brings. 

In my closet, you’ll find ankle boots for warmth and dryness, longer boots for slippery snow days and dressy boots for formal occasions. 

It’s not unusual for commuters to wear one type of winter boot on the way to and from work, changing into a lighter weight pair of shoes once in the office. 

Do I need snow boots in Chicago?

This really depends on your chances of experiencing snow while in Chicago. If you’ll be living here, and going out and about often, definitely yes. If you’re visiting for a weekend, you may or may not need snow boots depending on the weather forecast. 

One thing is for certain, it will for sure snow at some point in Chicago during winter. However, over the years with shifts in climate I’ve noticed the winters are (though still harsh) a bit less snowy than they were growing up. 

When it does snow, the city is pretty good about getting it cleaned up and salting the streets to encourage ice to melt quickly. However, as a local I still wouldn’t be caught without a pair of boots that can withstand the snow. 

What is the warmest boot for winter?

The warmest boots for winter offer quality insulation, as many of the boots listed above do. For extra warmth, look for boots lined with shearling. 

What shoes to wear in Chicago in December?

Shoes that are waterproof, slip-resistant and lined with shearling for warmth are ideal to wear in Chicago in December. 

How Cold is Chicago in the winter?

On average, the low is around 20 degrees F and the high is just below 40 degrees F in Chicago in the winter. However, it’s not uncommon to see much lower temperatures throughout the season as well. 

How much snow does Chicago get?

According to the National Weather Service, Chicago averages approximately 38 inches of snowfall annually. 

Conclusion: Chicago Winter Boots

Whether you’re planning a brief Chicago trip in winter or have moved here and are looking for ways to stay warm this season, the Chicago winter boots outlined in this post are sure to keep your feet protected.