Best Winter Boots For Chicago – 2022 Choices For Fashion And Function

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After researching the best winter boots for Chicago, here is what we found:

Winter boot shopping usually needs a trade-off between comfort, durability, and style. A pair of winter boots are typically ugly and hard to wear because of the details that keep your feet warm and dry. But, you can discover high-performance winter boots while also looking nice.

With that in mind, we put our cold feet in various pairs to determine the best winter boots for Chicago.

But, first, let’s take a closer look at the weather in Chicago winter.

How Cold is Chicago in the Winter?

As you know, “winter” doesn’t mean late December to late March if you’re familiar with Chicago. Certainly not! There are two types of winter in Chicago: snowy and cold, and the good news is that they rarely co-occur.

You’ll hear a lot about wind chill, high winter winds, and cold temperatures. Chicago winter can drop below zero degrees Fahrenheit on rare occasions. But its temperature rating usually hovers between zero and twenty degrees Fahrenheit. The average snowfall each year is about 37 inches (949 mm).

Here Are the Best Women’s Winter Boots for Chicago

Warmer boots are the perfect pair of winter boots and coats for the Chicago winter. It should give warmth and protection from the cold, depending on the type of boot. It can also be beautiful and stylish.

SOREL Caribou

Sorel’s Caribou is a classic winter boot that never goes out of style. It’s classic, fashionable, and toasty. It has a 9-millimeter felt liner, strong leather upper, and wraparound rubber lower. It is a terrific mix for everyday tasks like shoveling snow and running errands around town.

This boot is distinctly informal and feels cumbersome and sloppy to walk in. It could be unsuitable for long distances, snowshoeing, or winter walks.


  • Waterproof Boot
  • Comfortable to carry
  • Good grip
  • Keeps warm


  • Not breathable

Columbia Minx Mid II Omni Heat

The Columbia Minx Mid II Omni Heat is an excellent choice for fashion and comfort. These boots come in a variety of fantastic colors. They will go great with your winter travel attire while keeping your feet toasty warm. These boots are 100% waterproof woven polyester and have a rubber sole to dry your feet. The boots also have a reinforced bootie overlay and a contoured PU footbed. It has excellent traction and 200 grams of insulation to keep your feet toasty.

The Columbia winter boots have thermal reflective Omni heat technology. It keeps your feet dry while also keeping them warm. The thermal reflective Omni heat technology reflects body heat. It reduces the need for cumbersome layers and allows these boots to stay light.


  • Waterproof
  • Provides good warmth
  • Comfortable
  • Medium ankle height


  • Lacks Ankle Support

Sorel Joan of Arctic

Look no further than Sorel Joan of Arctic. Aside from having the perfect name ever, it will keep you warm in sub-zero weather. It allows you to be fashionable enough to wear about town.

It has waterproof leather, a suede upper felt inner boot, and a handcrafted rubber shell. It will keep your feet warm even in -25°F weather. Don’t let the hefty price tag dissuade you. These high-quality boots will carry you through several inches of snow.


  • Stylish
  • 100 percent waterproof
  • Come in a variety of colors


  • Expensive
  • Hard to find online

Columbia Women’s Ice Maiden II Insulated Snow Boot

The Columbia Ice Maiden II is a trendy, feminine, and fashionable snow boot. They are ideal for your winter wonderland experiences.

The Ice Maiden snow boots have waterproof leather and textile upper. It also has 200g of insulation to keep your feet toasty on chilly travel days. They also have a traction-enhancing sole that keeps you upright on snowy surfaces. These boots lack the thermal reflective Omni heat technology, making them lighter.

The Ice Maiden boots are slightly less expensive than the Minx Mids. It is another attractive, lightweight Columbia alternative.


  • Lightweight
  • Waterproof
  • Inexpensive


  • Wobbly sole

Kamik Momentum Winter Boots

The Kamik Boots fit securely around your feet and calves. It can prevent rogue snow from funneling into the top. Also, you don’t need to tie them. They’re simple to put on and take off, even with gloves on or freezing fingers. The moisture-wicking insulation keeps sweat to a minimum. The waterproof nylon outer and gripping sole protect your feet from cold conditions. Also, the pricing is reasonable.


  • Thinsulate Insulation
  • Seamless Construction
  • Rubber Sole


  • Not very fashionable

Here Are the Best Men’s Winter Boots for Chicago

The best winter boots for Chicago combine design, usefulness, comfort, and warmth. It provides the ideal addition to your winter wardrobe.

Timberland Premium Waterproof Boots

We’re big admirers of Timberlands, as you may have observed. The Timberland Premium Waterproof Boots have watertight seams and a leather upper. There’s also a padded ankle for increased comfort and support. It also has insulation to prevent your toes from cold climates.


  • Durable construction 
  • Good shock-absorption
  • Gripstick rubber sole


  • Sole tend to hold rocks and mud

Columbia Bugaboot II Winter Boots

The Columbia Bugaboot III Winter Boots is full of technology for winter. The new liner, according to Columbia, is 40% warmer than the old one while remaining just as breathable. Indeed, we found these boots to be warm. It has 400 grams of synthetic insulation that keeps our toes toasty even in the dead of winter.


  • Excellent warmth feature.
  • Comfortable
  • Great traction


  • Flat footbed

Men’s Avenue Duck Boot

Many of the boots on this list are more on the casual or performance side of the spectrum. But Men’s Avenue Duck Boot is a standout. Bean’s Bean Boot series achieves a beautiful balance between the two. Its waterproof rubber design protects you against snow and other precipitation. The leather upper provides comfort while also giving the footwear a sophisticated appearance. You have a luxurious-feeling winter boot that can still hold its own.


  • Excellent Warmth 
  • Good blend of casual and performance


  • Expensive

Sorel Caribou Boots

There aren’t many things more classic than this. Sorel’s Caribou has been around for a long time. And, we enjoy the combination of comfort and performance. The Sorel Caribou Boot is a classic winter boot. Sorel’s signature boot is famous for a reason. It has a hermetically sealed toe and a waterproof design. This tractioned boot is perfect for heavy snow—and has a snow cuff to handle any powdery drifts you meet. It can endure temperatures as low as minus 40 degrees Fahrenheit.


  • Timeless looks
  • Cozy interior
  • Comfortable Boots


  • Classically heavy

The North Face Chilkat 400 II

During the last 2-3 years, this was almost the most excellent boot in everything. The North Face Chilkat 400 II remains a winter favorite and one of the best winter boots.

Its most prominent feature, though, is that it is waterproof. It is entirely waterproof and has a long-term water-resistance capability. You may walk for ten minutes in frigid, ice water and feel no difference in your feet. Its sole flaw is its sizing, which is frequently smaller than intended.


  • Perfect waterproof feature
  • Excellent Warmth 
  • Good blend of casual and performance


  • Unexpected Sizing

How to Choose the Best Winter Boots for Chicago?

When shopping for the warmest winter boots to keep your feet warm, there are a few factors to consider: 


Warmth is the first thing to consider. It is essential because you will be dealing with low and even extremely low temperatures. They use insulation to achieve this. Insulation comes in a variety of forms and materials. This insulation is inside of the boots in various weights. 

The inner insulation in winter boots varies from 200 to 400g. Naturally, the lighter a boot or shoe is, the better. But, in the winter, warm boots take precedence over lightness.


It is a must if you’re walking in not-so-cold wet conditions. Snow melts throughout the day and freezes at night in this type of environment. Also, you may need to cross streams on thin ice or walk in the water, or you may need to walk in slush or mud. 

In this scenario, your boots must be well-designed to be waterproof. Wetting inside is inconvenient in regular seasons, but it can be dangerous in the winter. 

There are two methods for making winter footwear waterproof. First, we need a suitable, breathable membrane. Second, the height of the boot and the tongue’s form. It is significant since wetting issues are generally more prevalent in the winter.


Walking in snowy and icy conditions is more dangerous than walking on dry ground. When walking on ice, it’s easy to slip and fall. You wouldn’t tumble if you just walked on snow (significantly deeper snow). But if your boot doesn’t have adequate traction, you’d at least go more slowly. 

As a result, well-designed soles with a rough surface can provide good traction. At the same time, the sole must be sufficiently firm to allow for the most comfortable walking on snow and ice.


It is an important trait during the winter weather. But, you can remedy it with gaiters, unlike waterproofing. Yet, snow can enter from above if you walk through deeper snow without gaiters. Two things can aid in this situation. 

The first is, once again, the height of the boot: the higher the boot, the deeper the snow you may walk on. The second is to wrap your upper leg around your leg. The tighter the wrapping, the less snow will get through. But, the winter boots must not be too high or too tight, affecting comfort.

Frequently Asked Questions

What shoes should I wear in Chicago winter?

Expect to spend any time outside during the Chicago winter. So, wear a thick, waterproof pair of boots that can withstand deep snow, ice, and the cold.

What is the coldest month of the year in Chicago?

From December 2 to March 9, the cold season lasts 3.2 months, with an average daily high temperature below 43°F.

January is the coldest month in Chicago. It has an average low of 22°F and a high of 33°F.

Why is Chicago so cold?

Chicago is the largest city in Illinois and lies on the banks of Lake Michigan in the American Midwest. Despite its location at a middle latitude, the city is frigid in the winter. It is because the North American landmass cools rapidly. So, polar air outbreaks and temperature variations are common. It is due to the distance from the sea and the exposure to various types of air masses.


Winter in Chicago is no joke. So, the best winter boots for Chicago are essential cold-weather clothing.

Worry no more! We’ve got you covered for everything winter throws at you. This article will save you from spending thousands of hours researching. So, you can spend more time doing what you love outside and less time indoors thinking of spring.

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