A Local’s Guide to the 21 Best Chicago Winter Boots

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Looking for the best Chicago winter boots for your upcoming trip? You’ve come to the right place! 

In this post, I will be sharing the best women’s boots for Chicago winter, that will surely help guide you in choosing not only the best stylish winter boots, but also the warmest, and most comfortable.

Packing a warm pair of winter boot when visiting Chicago is ideal to experience (and walk through) the epic Windy City’s infamous winter weather and frigid wind chill! 

My Pick

The North Face Women’s Chilkat V 400 Waterproof Boots

👢400 grams of insulation (the warmest!)

👢 Waterproof exterior

👢 Very lightweight with great traction for slushy and slippery conditions

My Pick

UGG Women’s Adirondack III Boot

👢 Waterproof external shell

👢 Able to withstand down to -32 degrees F

👢 Cushioned insole (perfect for long distance sightseeing and walking!)

Quick tips on shopping for the best Chicago winter boots

Before jumping into the rest of the list, here are a few things to consider and keep in mind when shopping for the best winter boot suited based on what you’re looking for. 

I’m sure after reading this post, you’ll not only know which winter boots are the real deal, but what to look for.

What is the difference between snow boots and snow shoes?

It used to be that some snow boots were designed for snow, rain, and basically all types of wet conditions, and are therefore waterproof, while some winter boots were designed to prioritize heat and insulation over waterproofing. 

While this is still true to a certain degree, as you’ll see on this list, there are plenty of winter shoes that combine waterproof materials and great insulation, so you don’t have to sacrifice one over the other when shopping for the best Chicago winter boots.

For your trip to Chicago, both things are important (insulation and waterproof).

Since you never know how much snow/how low the temperature will drop while visiting, it’s best to cover all your bases, and look for these two things when boot shopping, whether you’re looking for “snow” or “winter” boots in specific. 

Insulation grams – what do they mean and why it matters when winter boot shopping

You’ll see as you start reading the winter boot recommendations that I mention numbers that look like the following: 

100g – least warm boots

200g – low-mid warm

300g – mid-high warm

400g – best warm boots 

They are a specific rating that determine how many grams of insulation (down, and other fill) is in the winter boot.

This is important to know so you can make the best purchase based on how much warmth you want, and/or if you want to keep under a certain budget. 

The rating starts out with 100g as the lowest and goes up to 400g and even up to 600g, but that’s for activities where you’ll be exposed to dangerously cold winds and climate.

In Chicago, you’ll be ducking in and out of buildings, so you don’t need that much insulation. 

💡 Local tip: I’d say that anywhere between 100g-400g of insulation is a good place to start, and choose depending on how warm you want to be while exploring the Windy City.

As the grams rise, you’ll notice that the price does too, so if it’s not in your budget to spend above a certain limit, you can purchase a great winter boot with 100g and buy a great pair of warm socks (like these from Uniqlo!) to complete the warmth perfectly.

Can I wear normal boots in snow?

I strongly recommend getting appropriate footwear especially when paying a visit to Chicago in the winter.

You (and your feet) will thank you later when you’re walking through slush and dipping temperatures, especially in Chicago.

Because the city is located next to Lake Michigan, the weather and temperature drops quite often, and the windchill adds on a special extra layer of coldness in the wind that you’ll soon experience. 

So if you can prepare by getting the best warm jackets best warm boots, and other warm accessories, you’ll be absolutely set! 

For these reasons, I don’t recommend any “normal” boot to visit Chicago, but rather a proper winter boot, like the ones I share on this list! 

How can you tell if boots are good in snow?

A good way to determine that your boots are good in snow is to look at a few things when shopping for them. 

  • What kind of outer sole does it have? A good rubber sole creates good traction.
  • What kind of material is used in the structure of the boot? Leather, suede, plastic? If it’s only plastic, it’s a “winter” boot red flag!
  • Is it waterproof? It has to explicitly say that it’s waterproof! 
  • Some winter boots make great rain boots, but that doesn’t necessarily mean that rain boots make great winter boots. Snow requires specific features. 

These are some of the things I’d look for in determining if my boots are good in snow.

Should winter boots be snug or loose?

I would recommend that your winter boots be a bit loose, because like with any other shoe, when you walk for some distance, feet tend to swell, so you want to accommodate for any swelling, plus overall comfort. 

Also, depending on if you get a lower insulation winter boot, you may want to go up a size to make room for thick wool socks for extra warmth. 

When shopping for boots, you may find that you may need to size up for these reasons, so browse through reviews, ask questions, and read what the brand has to say about fit. Most have recommendations. 

Who am I to give you all this advice on the best Chicago winter boots?

As an Illinois local of 20+ years, and going to school in downtown Chicago, I’ve had my fair share of bone-chilling winters commuting and walking downtown for those early morning classes, to trudging back home through slick winter conditions and snow in the evening Chicago rush hour. 

Throughout my time living in Illinois, I’ve learned which winter shoes are the best winter boots for Chicago, as well as the best warm boots for winter that will keep all your toes warm in Chiberia (our city’s nickname for when the winter gets unbearably cold).

So if you’re visiting Chicago in the winter, you’ll definitely want to come prepared for it! 

A Local’s Guide to the Best Chicago Winter Boots

1. North Face Women’s Chilkat V 400 Waterproof Boots

Known as one of the makers of the best winter boots, the North Face does no wrong when it comes to outdoor gear, specifically creating good products to brace the strong Chicago winters.  

Case in point, the ultra warm North Face Women’s Chilkat V 400 Waterproof Boots. 

Known for their lightweight feature, and created with the North Face’s Heatseeker™ insulator (their unique fill that surrounds the material fibers) these boots are considered amongst the warmest snow boots in stock, designed for slush, snow, rain, and subzero temperatures. 

These boots have 400g insulation, making them one of the best boots for winter, for their warmth ranking. 

The hardware of the boots are made with anti-rust material, the inside has a warm sherpa lining, and the exterior has full-grain waterproof leather and suede.

These boots go to about mid-calf. 

These North Face Women’s Chilkat V 400 Waterproof Boots come in a black/gray color combo, as well as a cute brown/black with pink sherpa lining. 

The bottom of the shoes has great grip, which is ideal for great traction, and fewer chances of accidents like slipping on ice. 

Personally, the North Face is my go-to when it comes to the best warm winter boots, and cold weather gear, whether it’s looking for the best winter jacket for Chicago weather or the best options for the best Chicago winter boots. 

“These are incredibly warm boots with great traction on snow and ice. Perfect for a winter hike in the snow or walking through city snow and slush. I couldn’t be happier and highly recommend them.”

More reviews on The North Face

❄️👢Click here to buy the North Face Women’s Chilkat V 400 Waterproof Boots

>> Read More: The Best Coats for Chicago Winter

2. Columbia Women’s Minx™ Shorty III Boot

If you’re looking for short Columbia winter boots for Chicago weather, you can’t go wrong with the Columbia Women’s Minx Short III Boot!

Don’t be fooled that only good Chicago winter boots should be tall, because these thermal lined snow booties offer just as much heat to keep your toes and foot warm, as well as dry inside the breathable and waterproof material (Omni-Tech™), and more.

These short boots come with 200g insulation, which is pretty great for a short boot. Some tall ones have less, so make sure to look at this detail when boot shopping!

Another benefit of these Columbia winter boots is that they are very lightweight (each shoe weighs around 11oz), and do the job of keeping your feet warm, as well as comfortable, as you stride all throughout Chicago’s unmissable sights, or if you plan to do one of many day trips from Chicago! 

What I also love about these Columbia Women’s Minx Short III Boot is that they are built with Omni-Grip™ which is Columbia’s best traction and grip features used on its best-selling hiking boots, and yes, walking amongst frosty and slippery conditions, no matter how cold it is!

Short, lightweight, and coming in various colors, this shoe is the perfect addition to your Chicago winter essentials checklist, especially if you’re trying to travel light in the winter.

“These boots are not only but very comfortable. They keep your feet warm in the cold and extreme cold.”

More reviews at Columbia.com

Psst! If you are however looking for the tall boot version of the Minx Shorty, you can check out the Minx III Mid Boot!

❄️👢Click here to buy the Columbia Women’s Minx Shorty III Boot

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3. Kamik Rogue 10 Snow Boot

Face the winter conditions in Chicago while wearing the amazingly-built Kamik Rogue 10 Snow Boot, engineered with a single-seam structure to ensure feet stay warm and dry, as well as comfortable with the footbed with round toe

When looking for the best winter boots for Chicago, you want gear that also features other bonuses like odor-eliminating properties like these do, with Kamik’s special Cleansport NXT™ EVA insole and fleece lining inside. 

The Kamik Rogeu 10 Snow Boot has 200g of not just any insulation, but 200B 3M™ Thinsulate™ insulation, which is a special insulation designed to withstand down to -22 Farenheight/ -30 Celcius.

This blend is proven to feel 1.5 times warmer than traditional down. 

Not to mention, the rubber sole is made of natural materials, making this boot one of the best winter walking boots to invest in. 

“These boots are comfortable & stylish. They keep your feet snug and warm (without sweating). “ 

More reviews at DSW.com

❄️👢Click here to buy the Kamik Rogue 10 Snow Boot

4. Sorel Women’s Tivoli  IV Tall Boot

Sorel is a very popular brand of snow boots here in Chicago, and many other snowy destinations, more specifically, to brave sub-zero conditions and snowy sidewalks in the city, the Sorel Women’s Tivoli IV Tall Boot is a great option!

These sorel winter boots have 100g of insulation, which is the boot with the least insulation thus far on the list, however don’t rule them out yet, as they are waterproof, they have a stylish and warm faux fur collar, and microfleece lining throughout the boot. 

The boot reaches just below the knee and has laces, but owners of the boot report that they are easy to put on and take off. 

Though these boots are designed for lighter snow conditions, they are a great option to consider when winter boot shopping. 

While we get an average of 37-40 inches of snow throughout the winter season, as a local, I can tell you that the city does a good job of keeping sidewalks and specifically, tourist destinations throughout the city clean during the winter. 

You definitely won’t be treading foot-long snow accumulations, so as long as the winter boot is warm, waterproof, and slip-resistant, all of which the Sorel Women’s Tivoli IV Tall Boot has, you’re good! 

“Extremely warm and comfortable. So much better than I ever expected.” – Lisa

Read more reviews at Sorel.com

❄️👢Click here to buy the Sorel Women’s Tivoli IV Tall Boot

5. Columbia Moritza Shield Omni-Heat Boots 

Don’t worry about slushy conditions, rain, snow, or slippery conditions in Chicago, because with the Columbia Moritza Shield Omni-Heat Boots, you’ll be more than ready for whatever Chicago throws at you!

One of the things that makes this boot one of the best boots for Chicago winter is that the bottom of the boot has a rubber-made duck base that makes it easy for the slush to slide off and clean afterward, and the top of the boot is made with waterproof leather and suede for ultimate warmth and style. 

The Columbia Moritza Shield Omni-Heat Boots are made with 200g of insulation, making them one of the warmest winter shoes that are also made with Columbia’s special Techlite™ technology in the midsoles – ideal for long-distance comfort walking. 

The boot’s grip is also perfect for trekking in icy conditions, thanks to its rubber outsoles. 

Each shoe weighs about 1lb, reaches around mid-calf, and comes in 4 colors: brown, white, black, and sage.

“Love the look and feel of these boots. A must if you’re anticipating slushy and cold conditions. The fit is great and the materials are what I expect from Columbia.”

Read more reviews at Columbia.com

❄️👢Click here to buy the Columbia Moritza Shield Omni-Heat Boots

>> Read More: The Ultimate Winter Packing List Chicago Edition For 2024

6. Columbia Ice Maiden II

A rain boot and snow boot in one, the Columbia Ice Maiden II is a great snow shoe that provides warmth, anti-slip rubber soles, and goes just above the ankle, perfect to wear all around Chicago!

With 200g of insulation, a comfortable footbed made with Columbia’s TechLite™ memory foam, and great traction with their unique Omni-Grip™ outsole, all in all, make this snow boot perfect for both hiking or walking in snowy and slushy conditions!

Of course, it’s also waterproof and comes in various colors, including black, grey, dark lavender, and brown. The Women’s Ice Maiden III Boot comes to around mid-calf. 

“Absolutely perfect! Cute, comfortable & warm. Went down half a size and they fit great!”

Read more reviews at Columbia.com

❄️👢Click here to buy the Columbia Ice Maiden II 

7. UGG Women’s Adirondack III Boot

Ugg shoes are some of my other favorite warm winter boots when it comes to the best Chicago winter boots, especially for their warmth and waterproof materials, and of course, stylish and sleek boot designs that aren’t sacrificed. 

What I love about the Adirondack III Boot is that is designed to withstand frigid temperatures as far as -32 degrees Fahrenheit (-35 degrees Celcius). 

They will keep your foot not only warm, but dry with its waterproof external shell, as well as ensures good traction, and good comfort with its cushioned insole

Though they are short boots, they do a great job of protecting you from sub-zero temperatures, no matter the messy, wintery conditions that Chicago is known for in winter.

They come in 3 colors: black, chestnut, and mustard seed. 

With all this being said, the UGG Women’s Adirondack III Boots are designed for heavy snow and even heavy rain, so you can use them for any kind of extreme weather. 

  “If you need to commute in blizzards, or slushy conditions then these are your boots.”

More reviews on Ugg.com

Psst! If you’re looking for the tall version, check out the Women’s Adirondack III Tall Boot, which is another popular option, and has the same benefits and features as the short boot, just in tall form. 

❄️👢Click here to buy the UGG Women’s Adirondack III Boot

8. Merrell Women’s Snowcreek Tall Polar Waterproof

Packed with style, warmth, and comfort, especially if you’re looking for a tall winter boot, the Merrell Women’s Snowcreek Tall Polar Waterproof boot is just the ticket!

The perfect shoes for Chicago winter, these boots are packed with 200g of insulation, are designed with Merrell’s signature mountain Quantum Grip™ for great traction, and have overall fleece lining, and a faux fur collar. 

For easy slip-on and slip-off, they come with an easy side zipper, making this boot a great option to get if you’re planning a trip to Chicago!

Not to mention, another unique feature of the Merrell Women’s Snowcreek Tall Polar Waterproof is that the boots are treated with Merrell’s Cleansport NXT™, which helps neutralize odor, and the comfortable footbed features an air cushion in the heel which is great for long-distance walking all around the city, which you need! 

These shoes are a bit heavier, at 2lb per shoe, but if you’re looking for a seriously good boot, this one is a great option! 

“They are so comfortable and I have worn them in all kinds of conditions/temperatures and walk distances in them and they provide good support and are entirely comfortable.” 

Read more reviews on Merrell.com

❄️👢Click here to buy the Merrell Women’s Snowcreek Tall Polar Waterproof

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

Slip on the shearling lined and stylish Bean Boots, designed and created in the state of Maine, and perfect for cold temperatures. 

Made with durability in mind, the full-grain leather is tough on the outside but feels very soft and moves along with you as you begin to wear it.

The waterproof boot is not only going to keep your feet dry but warm as well, in all types of weather. 

From slushy snow to fresh snow, rain, and other slippery conditions, these shoes are winners, and very much worth many of the high reviews they’ve received over the years.

These Women’s Bean Boots are sure to be comfortable for everyone, as they come in a wide range of sizing options, plus foot width options. The boot reaches a little over the ankle.  

“I’ve had these boots for 3 years and they have been through multiple Polar Vortex’s like champions. -25 degrees real temps…”

Read more reviews at L.L. Bean.com

❄️👢Click here to buy the Women’s Bean Boots, 8″ Shearling-Lined Insulated

10. North Face Women’s Yukiona Mid Boots

Get the best winter boot features in one boot with the North Face Women’s Yukiona Mid Boots, designed with style, functionality, warmth, and more in mind for ultimate comfort. 

These North Face boots are made with 200g of insulation, are made with waterproof materials, and have the North Face’s unique High Rebound OrthoLite® feature for the ultimate comfortable footbed for walking around the city. 

For those winter days in Chicago where the sidewalks are extra slippery, or the snow is melting and freezing at the same time (so fun 🤪) the best shoes for Chicago winter include the  North Face Women’s Yukiona Mid Boots as they have the North Face’s IcePick® which are rubber lugs at the bottom of the boot for extra grip. 

The boot comes in two, neutral color variations, which is great if you’re looking for a great Chicago winter boot that goes with your clothes, or if you’re planning a Travel Clothes Color Palette to make packing and dressing while on vacation easy!

“These boots are by far the warmest, most comfortable boots that I’ve purchased in a while. They are very sturdy and reasonable.”

Read more reviews at The North Face

❄️👢Click here to buy the North Face Women’s Yukiona Mid Boots

11. North Face Shellista IV Luxe Waterproof Boots

Made with full-grain leather, waterproof materials, a faux fur collar, and warm lining, the North Face Shellista IV Luxe Waterproof Boots are another great boot from this great brand to look into.

The great thing about these shoes is their warmth, as they have not only 1 but 2 faux fur collar linings to help prevent the cold from seeping in, while the seamless structure of the boot ensures that no water or chill can get into your boot and feet. 

Made with 200g of North Face’s special Heatseeker™ Eco Pro insulation, some of the other materials to make this snow boot are recycled materials (impressively around 85%)! 

Other than warmth, there is also comfort in the North Face Shellista IV Luxe Waterproof Boots, with the North Face’s OrthoLite® footbed, and their special molded-EVA midsole, which will also help keep the bottom of your feet warm from the cold of the ground. 

“I have been looking for a great pair of North Face boots for a long time. (My last pair lasted almost 10 years. Snow shoeing, to the lifts, kinking and shoveling out!) I definitely found the right ones. Super warm and comfortable. Seem to be built well. Only two snow storms so far here so we’ll see. My bet is on the boots.” 

Read more reviews at The North Face


❄️👢Click here to buy the North Face Shellista IV Luxe Waterproof Boots

12. Sorel Women’s Caribou Boot

When it comes to heavy-duty snow and winter slush in Chicago, the Sorel Women’s Caribou Boot has become a great contender for all-day comfort!

The Sorel Caribou Boot is quite a popular boot in the Sorel brand, and for good reason! 

As a local, I think this would be a great boot to bring to Chicago during the winter, as it is waterproof, has great insulation, and has Sorel’s unique lug design for extra great traction for slippery sidewalks. 

With virtually no openings to let in cold air, or worse, cold water/snow, the Sorel Women’s Caribou Boot makes the perfect pair whether it’s snowing or raining. They are specifically designed for heavy snow weather

The boots don’t have zippers, however, owners of the boots do not express difficulty with putting on and taking off the boot.  They are short boots but provide all the warmth, good traction, and dryness, regardless. 

“Bought bc of great reviews and classic style but when i first tried them on thought they may not provide enough warmth. I was wrong! Wore them with nice warm socks and pants that tucked into boot; walked in snow & stood in cold (20*F) for an hour—feet & toes stayed perfectly warm & dry!”

Read more reviews at Sorel.com

❄️👢Click here to buy the Sorel Women’s Caribou Boot

13. UGG Women’s Yose Fluff V2

Built with both style and functionality in mind, the Ugg Women’s Yose Fluff V2 is another great option when it comes to Ugg, AKA the warmest boot out there! 

Made for messy and slushy weather, these Ugg boots are made with Ugg’s specific rubber material (Treadlite by UGG™) which guarantees better traction, and grip on wet and dry sidewalks. 

The boots are also made to withstand very cold temperatures (as far as -32 Fahrenheit/ -35 Celcius), they’re waterproof with their special Dry Tech material, which not only ensures that your feet keep dry but also warm, with its 200g of insulation

These Ugg Women’s Yose Fluff V2 are made for heavy snow and rain, so they are well worth the investment if you’re looking for winter boots that will last you a while (I still have my heavily loved Uggs from 17 years ago in great condition…)

“I recently purchased these boots to wear on a trip to a snowy location. I was getting lots of steps in and didn’t have aching feet at the end of each day; my feet also stayed warm and dry.”

Read more reviews at Ugg.com

❄️👢Click here to buy the UGG Women’s Yose Fluff V2

14. Women’s Intrepid Insulated Tall Snow Boots

Hunter shoes are very well known for their rain boots, but did you know they also have a few great snow boot options, that are not only warm and functional but considered some of the best stylish winter boots?

Made with recycled nylon on the outside, and lined with extra warm fleece (think of the warm welly socks you’d pair with the rain boots!), plus made with their special Ortholite footbed and waterproof materials, and you’ve got yourself a great snow boot to walk all around Chicago!

Something unique about the Women’s Intrepid Insulated Tall Snow Boots is that it also has an elastic drawstring on the top of the boot, which helps with retaining more body heat in your feet. 

All in all, these shoes are designed to withstand temperatures as low as -4 Fahrenheit/ -20 Celcius.

While these boots are great because of all that I mentioned, I also really love that the colors they come in are neutral, so you can pair them easily with your limited wardrobe, which helps streamline the packing process a bit more. 

Another popular version of this boot is the Hunter Intrepid Nebula Knee High Boot, which is the same as this one, but the color is a cool black/iridescent color that is pretty cool if you’re into something a bit different! 

“Absolutely love wearing mine. Perfect for the snow and on very cold days.”

Read more reviews at HunterBoots.com

❄️👢Click here to buy the Women’s Intrepid Insulated Tall Snow Boots

15. Columbia Women’s Bugaboot™ Celsius Plus Boot

Chockful of winter-ready features, the Columbia Women’s Bugaboot™ Celcius Plus Boot makes for one of the best options when shopping for the best Chicago winter boots!

Built with a leather outer exterior that makes for a great waterproof shoe, Columbia’s Omni-Heat™ lining helps keep your feet warm as it retains body heat, perfect for long-distance walking. 

At 400g of insulation, this is one of the warmest boots on the list today! Plus, the materials are breathable, ensuring even more comfort. 

Additionally, the Columbia Women’s Bugaboot™ Celcius Plus Boot has both TechLite™ and Techlite+™ which provides this boot with extra comfort as you walk through the city. 

To top it all off, the boot is also built with Columbia’s Omni-Grip™ to help sturdy traction whether you’re trudging through snow and slush, rain, or dry and sub-zero conditions.

Uniquely, this boot comes with thermal-reflective gold lining not only for extra warmth but reflection in the dark. It’s a great boot and one of the best to pack for your trip to Chicago in the winter!

“I bought these bugsboots to replace bugsboots that I’ve had and loved since 2007- yes, that long! Love the style, love the durability and love the warmth.” 

Read more reviews on Columbia.com

❄️👢Click here to buy the Columbia Women’s Bugaboot™ Celsius Plus Boot

16. UGG Ashton Addie Waterproof Boot

Enjoy pure comfort and protection from wet conditions with the Ugg Ashton Addie Waterproof, made with style in mind without sacrificing warmth! 

Perfect for long walks around Chicago, this boot is built with Ugg’s special UGGplush™ – which is their ultra-warm and comfortable wool blend and microfiber lining. 

The rubber exterior is perfect for heavy-duty wet conditions, and made to be durable for years to come! 

Built with a little bit of a heel, these boots are definitely a bit more stylish, but unlike other similar boots, the Ugg Ashton Addie Waterproof Boot is definitely made with quality materials. 

The boot is short and has laces, and when you purchase these boots, they come with an extra set of laces, which is great as many other brands don’t offer this! 


“ Daughter lives in Ohio and she picked out these cute boots. Fit her perfect and keep her warm out in the cold Ohio snow. Love that they have half sizes and they come with black shoe laces for shoe lace style versatility.”

Read more reviews at Ugg.com

❄️👢Click here to buy the UGG Ashton Addie Waterproof Boot

17. Sorel Women’s Joan of Arctic Boot

When it comes to finding one of the best Chicago winter boots for women, you can’t go wrong with the Sorel Women’s Joan of Artic Boot.

Enjoy a bit of style and functionality with the waterproof suede, sturdy rubber sole, and seamless structure to help retain heat and keep water out, plus other great features! 

For those looking for tall boots, these Sorel winter boots are perfect and are specifically designed for heavy snow days. 

The Sorel Women’s Joan of Artic Boot comes in various neutral colors, which again, I personally love as they help make outfit picking easy while you’re packing and deciding what to wear while you’re traveling! 

“I bought them two years ago. They still look awesome. They are warm, and comfortable, keep the high snow out, and look great.”

Read more reviews on Sorel.com

❄️👢Click here to buy the Sorel Women’s Joan of Arctic Boot

18. The North Face Sierra Luxe Waterproof Boot with Faux Shearling Trim

For the ultimate lightweight boot that seriously serves warmth, comfort, and waterproof materials like any other winter boot, you must consider the North Face Sierra Luxe Waterproof Boot with Faux Shearling Trim. 

Made with both waterproof and water-repellent materials throughout the boot, the boot is made with 100g of insulation and is designed with the North Face’s Waterproof DryVent™ for a dry yet breathable boot

Though warm winters are not common in the middle of January, if you visit in December, or March/April, these winter boots will be more than enough to keep your feet warm and dry.

The material of this boot is like a jacket, which makes it easy to slip on and off, and has a warm fleece lining to ensure proper insulation. 

Built for slushy and wet conditions, the hardware on this boot is rust-proof, while the insole is made with the North Face’s OrthoLite®, for maximum foot comfort. 

The boot is also made with the North Face’s Surface Control™, which makes it built with durable materials for multiple uses for years to come. 

Each boot weighs about 14oz, and it comes in two colors: tan and black.

“I hate a heavy snow boot when its already hard to navigate snow and ice. I cannot believe how lightweight they are. Still keep my feet warm and are really comfortable. Easy to get on and off.”

Read more reviews at The North Face

❄️👢Click here to buy the The North Face Sierra Luxe Waterproof Boot with Faux Shearling Trim

19. Royal Canadian Cambridge Waterproof Boot with Genuine Shearling Trim

Made with waterproof leather that is both warm and breathable, has a stylish faux fur collar lining, and a zipper for perfect slip on and off, the Royal Canadian Cambridge Waterproof Boot with Genuine Shearling Trim is a great winter boot!

Designed with thermal insulation merino wool, and memory foam for long-distance sightseeing all around Chicago, the boot is made specifically to withstand climates down to -22 Fahrenheit/ -25 Celcius.

Made in Canada, the Royal Canadian Cambridge Waterproof Boot with Genuine Shearling Trim is a great option to look into for your trip to wintery Chicago. 
The boot reaches around mid-calf, and comes in various colors to match your own travel capsule wardrobe!

“They just looked beautiful first of all. I tried them and n and they were definitely true to size, but also so comfortable!! Cozy is a better word even. They have almost a rocking effect which makes walking even easier. The side zipper has always been a deal maker or breaker for wk and it has everything. Beauty, comfort, and functional 100%. Love them.”

Read more reviews at Royal Canadian

❄️👢Click here to buy the Royal Canadian Cambridge Waterproof Boot with Genuine Shearling Trim

20. Timberland Women’s White Ledge Mid-Insulated Waterproof Hiking Boot

Built with 200g of insulation, waterproof and insulation materials, these Timberland Women’s White Ledge Mid-Insulated Waterproof Hiking Boot is another great boot to brave the brisk Chicago cold weather.

Made with Timberland’s special PrimaLoft™ insulation, and their TimberDry™ waterproof membrane you can ensure that you will not only explore Chicago in style, but true comfort, dryness, and for a long while. 

The Timberland Women’s White Ledge Mid-Insulated Waterproof Hiking Boot is tall and comes in two colors: black and tan. 

“Got these right before we got hit with a cold front of negative 24 with wind and these kept my feet warm” 

Read more reviews on Amazon

❄️👢Click here to buy the Timberland Women’s White Ledge Mid-Insulated Waterproof Hiking Boot

21. Baffin Chloe Boot

Keep your feet warm and toasty with the best of insulation technology with the Baffin Chloe Boot by the Canadian brand – Baffin.

A Canadian-made shoe is one of the best options for the best women’s boots for Chicago winter, for more than one reason. 

The first is the B-Tek™ Dry Waterproof Base and incredible insulation level, which is removable with the multi-layers inside the boot for a customized feel. 

The boot is also equipped with great breathability features including its PolyWool polyester wool blend, and its Hydromax™ layering for moisture-wicking properties

The shoe is easy to slip on and slip off with the pull loop, and the base of the winter boot has a cold-resistant Arctic™ Rubber shell and it’s special Polar Rubber® outsole for great grip as you walk through slippery and slick conditions. 

With all these cold-weather functionalities, style is not sacrificed with different color options, the faux-fur collar and laces. 

Not bad for these Baffin Chloe Boots that can withstand down to -7.6 Fahrenheit/-22 Celcius weather!

“These boots are amazingly comfortable and warm and they feel very solid in icy conditions.”

Read more reviews at Baffin.com

❄️👢Click here to buy the Baffin Chloe Boot

A Local’s Guide to the Best Chicago Winter Boots Q&A

What kind of boots to wear in Chicago in Winter?

When picking out boots to wear in Chicago, there are a few things to keep in mind.

First, warmth rating, if they are waterproof, grip/ outer rubber sole for good grip in slippery conditions, and interior lining. 

You want to look for winter boots that have all of these ideally.

Do people wear snow boots in Chicago?

Yes! We wear snow boots and winter boots because the winters here are no joke! 

Some of us have multiple pairs depending on how drastic the weather is outside. For slushy snow, bitter cold, etc. 

Are Timberlands good for Chicago winter?

Timberland is known for it’s well-made boots, and they actually have some promising winter boots to help you survive a Chicago winter! 

For instance, there are the Timberland Women’s White Ledge Mid-Insulated Waterproof Hiking Boots that are both waterproof and have great insulation, plus are designed for hiking – win! 

There are many great brands that make winter and snow boots, as we saw throughout the post, and I hope that you also now know what some of the important things to look for are.

Specifically looking at what the insulation rankings mean and why they matter when shopping for good winter boots with Timberland, and any other brand.

Are Doc Martens good for Chicago winter?

Doc Martens carries a few good options when it comes to winter boots, that are both waterproof, fleece-lined, have orthopedic footbeds, and of course, have that undeniable cool style that Doc Martens is known for.

Personally, I would just do my research (knowing what I know now about winter shoes) and make sure that the winter boots I’m eye-ing tick off the boxes for me. 

Knowing there are other brands that design winter boots specifically for cold and slippery weather conditions, I think I’d look at those brands first. 

Which winter boots are the warmest? 

On this list, the warmest winter boots for Chicago winter are the North Face Women’s Chilkat V 400 Waterproof Boots and the Columbia Women’s Bugaboot™ Celcius Plus Boot, which both have 400g of insulation.

What shoes do you wear in Chicago winter?

Preferably, you’ll want to wear appropriate shoes to withstand the bone-chilling cold temperatures of Chicago in the winter. 

Tennis or gym shoes will not cut it (in my opinion) especially as many come with breathable materials, which let not only cold air into the shoes, but also rain and snow, and plus, don’t have the best grip for ice and snow.

I recommend investing in a good pair of winter boots, like the ones mentioned in this post, to help make your trip to Chicago not only warm and cozy but safe. 

How to survive Chicago winter?

With appropriate clothes, shoes, gear, and other accessories! 

Make sure to invest in a good quality jacket, insulated winter boots, a great pair of gloves, hats, scarves (the holy winter trinity) plus undergarments, and warm wool socks for extra warm layers. 

The name of the game in Chicago during winter is lots of layers, so make sure to include them, plus more warm essentials when packing for your winter trip to Chicago! 

What does winter look like for Chicago?

Chicago is cold in winter, yes, but very beautiful! 

The city looks magical when it snows, and especially when the sun comes out afterward. 

To see the snow sparkle against the steel-frame buildings and of course, sights like The Bean, is quite remarkable and stunning to witness.

Sometimes as the snow is melting, it forms a glass/crystal-like coating on the tree branches, which looks amazing, and makes for a great nature photo-op!

Not to mention, the ice that forms on the surface of Lake Michigan is quite beautiful to witness, whether from Navy Pier, or the top of the viewing platorms of the Willis Tower or the John Hancock tower!

Winter boot shopping tips

When shopping for your own pair of Chicago winter boots, and you’re looking for something that will last you for future winter destinations, take a look at the brand’s warranties and return policies.

For instance, there are stores like REI that have a great return policies of up to 1 year for REI members and 90 days for non members.

Other stores like Nordstrom accepts returns on shoes even after being worn, and sometimes without a receipt, and other stores like L.L Bean which also accept returns 1 year after original purchase date.

The North Face has a good limited lifetime warranty that covers the lifetime of the product for any manufacture defects, as well as a one year warranty.

in the same vein, Columbia also has a similar 1 year warranty, as does UGG and Merrell.

In the past, I have taken in my North Face jackets (2) for them to get more fill at the store after several years of owning them, and without hesitation, I’ve gotten them filled, or received credit (amount equal to the jacket) to use on a new jacket.

So based on my experience, The North Face has a great limited warranty policy.

Just make sure to research the return policies of each store/brand to make sure that the return policies/guarantees are to your liking.

The Wrap-Up: A Local’s Guide to the Best Chicago Winter Boots

I hope this guide to the best boots for Chicago winter was helpful, and that you now feel equipped with the knowledge of the best winter boots for women, whether you visit in January or March!

As a recap, here are the best (21) Chicago winter boots (by a local):

If you’re visiting Chicago during the winter season, make sure to know what’s up, and what kind’s of activities there are to see while in Chicago for the holidays!

Which winter boots caught your attention? Let me know down below in the comments! 

To more (warm) travel moments like these, 

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