Chicago can be very cold and snowy. If you’re from a relatively warm place, visiting Chicago for the first time may need some preparation so that you can have a good experience.

You can certainly survive through Chicago winter with general sneakers & dress shoes if the weather doesn’t get too cold, but Chicago can be freezing and snowy depend on the season.

The best shoes for Chicago winter are warm boots. Boots provide warmth and protection against cold weather, and depends on the type of boots, they can be very fashionable & stylish at the same time.

Some of the boots you can consider are Chelsea boots for fashion, waterproof boots for rain and snow, tall & furry boots for extra warmth, and insulated snow boots for freezing temperature.

Before we dive into which boots are the best for you to wear in Chicago, let’s take a deeper look at the weather in Chicago winter, compare it with other seasons, and how cold it can get.

How Cold is Chicago in the Winter?

Chicago’s temperatures generally range from 10-50°. Chicago can be as warm as California during summer with above 85 degrees Fahrenheit, but it will be quite the opposite during the winter and you may be miserable depend on the tolerance you have toward cold weather. According to the Weather Channel, Chicago has ranked in the 6^th coldest major city in the USA.

If it’s an average 30 degree day, a casual walking boots can be comfortable enough. Depending on your activity, you can even wear cute Chelsea boots for style. But Chicago weather can be unpredictable. The average precipitation in Chicago compared to the entire nation look like this:

Rain:

• USA Average – 38 inches per year
• Chicago Average – 38 inches per year

Snow:

• USA Average – 28 inches per year
• Chicago Average – 35 inches per year

How much Snow does Chicago Get?

Here’s the not-so-fun part of Chicago Winter. Freezing temperature can occur once a year in Chicago, where the temperature may drop down to zero degrees Fahrenheit (gosh). But this happens, it occurs only once a year between November to April (typically December to February) for approximately 7 days. So ho much snow does Chicago get in comparison with other major cities?

• Chicago has less snow than a city like Cleveland and Buffalo
• Chicago has more snow than a city like Washington DC and New York City

You will probably need to consider a winter insulated boots for this. You also need an awesome Jacket or Coat, layers of warm clothes like sweaters, hood, mittens, etc to survive throughout this time of year if you have plans of outdoor activity.

Chicago’s winter weather is typically around 25-35 degrees on average. Below is a table showing Chicago’s winter temperature average from the past 30 years so you can see it more clearly:

Shoes to Wear in Chicago Winter

Below is a table showing the average temperature in normal Chicago Winter between November to March. You will be fine with Chelsea boots or even just a sneaker. Make sure to wear warm socks.

Month	High °F	Low °F	Rain (average)	Snow days	Snow height
November	48	32	4 days	1.8 days	1.3 inches
December	35	21	7 days	6.7 days	8.7 inches
January	31	17	5 days	8.1 days	11.5 inches
February	35	20	7 days	5.5 days	9.1 inches
March	47	29	5 days	3.8 days	5.4 inches

If the freezing temperature occurs, it may be a smart thing to start considering better boots for more protection against the cold air and snow. Here is a table showing Chicago’s not-so-fun freezing temperature. Again, this occurs once a year for around 7 days:

Shoes to Wear in Chicago Freezing temperature

There are about 7 days of freezing temperature in Chicago that occurs once a year during winter. You’re going to need a pair of much warmer boots like insulated snow boots for this climate. Below is a table showing the Chicago freezing temperature:

Month	0-10° F	20° F	30° F
November	0	3	14
December	6	13	26
January	9	17	28
February	6	13	24
March	1	5	20

Source: “1981-2010 U.S. Climate Normals” – NCAA (National Centers for Environmental Information)

Best Boots for Chicago Winter

We have covered the weather in actual numbers above, so you have an understanding of the statistics. But how cold does it get in Chicago? This depends on your point of reference and your tolerance toward cold weather.

If you’re born and raised in Chicago, or if you’re from cold places like Canada and Alaska, you may quite well enjoy Chicago Winter. Many people jog with their sneakers in snow. A normal winter day in Chicago can just be chilly without snow, and once a while even sun will peek out to give you a break.

Most of the people around me prefer cold weather than hot weather. But I can’t stand cold. I hate winter and while 50 degrees to some people may consider cool, it is freezing to me.

While people like my friends are in the fashion mode, shopping for cute boots for Chicago winter, I am in the survival mode looking for boots that offer extra warmth as the first priority. So you will have to decide what’s more important to you.

Best Overall: SOREL – Women’s Caribou Waterproof Boot for Winter

For bitter cold weather, snowy lanes and icy streets, the SOREL – Women’s Caribou Waterproof Boot is the perfect boot to keep the moisture and chill of winter away from your feet.

The boot features a warm inner lining that traps heat inside while making it safer and more comfortable to navigate icy paths with its remarkably strong grip found on the base of the thick rubber outsole.

The upper is made from high-quality, 100 percent waterproof full-grain suede leather that not only works in harmony with the rubber to keep you dry but also makes the boots more stylish.

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Best Chelsea: Asgard Women’s Ankle Rain Boots Waterproof Chelsea Boots

Keep your feet nice and dry without sacrificing your favorite style trends when you choose the Asgard Women’s Ankle Rain Boots Waterproof Chelsea Boots.

These boots look like simple everyday leather ankle boots but come with the water-resistant properties you need from rain boots.

Lightweight and comfortable, the footwear features EVA foam insoles that offer plenty of support with a roomy toe area to prevent pinching with durable traction to keep you stable on your feet in wet conditions.

With the elastic goring on both sides working with the pull tab at the heel, it is simple to step into and out of the boots in seconds.

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Best Combat: Dr. Martens Vegan 1460 Smooth Black Combat Boot

Give your outfits a bold, powerful new update when you pair your favorite looks with the classic Dr. Martens Vegan 1460 Smooth Black Combat Boot.

These boots feature the traditional combat boot look while also being durable enough to withstand the elements by providing abrasion resistance and slip resistance in wet or icy conditions.

The boots feature two-tone synthetic uppers with stylish Goodyear welt stitching along the base of the shoe to give them plenty of style.

A pull tab in the back makes it easy to put on and take off the boots.

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Best Men: Timberland Men’s White Ledge Mid Waterproof Ankle Boot

Whether you’re trudging through wet city streets or hiking through thick, wet trails, the Timberland Men’s White Ledge Mid Waterproof Ankle Boot can keep your feet cool and comfortable wherever the day takes you.

These 100 percent leather hiking boots rest securely around the ankle, allowing you to move more easily than you might otherwise be able to in boots with higher shafts.

The footwear is made from premium full-grain leather that is totally waterproof with seam seals that go the extra mile to keep water out.

The rustproof laces also won’t succumb to damage and will offer you the convenience of their swift lacing mechanism for years to come.

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Best Leather: Dr. Martens – 2976 Leather Chelsea Boot for Men and Women

Enjoy the durability and resilience that you have come to know and rely on from the Dr. Martens’ brand with the stylish appeal of a Chelsea boot by choosing the Dr. Martens – 2976 Leather Chelsea Boot.

These boots are fashioned with high-quality leather uppers and finished with stylish Goodyear welt stitching along the base.

The high-quality, heavy-traction rubber outsole makes them durable and slip-resistant. The ankle-high boots feature tabs in the back to pull on to facilitate simpler on and off.

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Best for Waterproof: Columbia Women’s Newton Ridge Plus Waterproof Hiking Boot

Conquer your favorite trails in wet weather conditions in the Columbia Women’s Newton Ridge Plus Waterproof Hiking Boot.

These high quality boots feature a waterproof quality that keeps out moisture to keep your feet nice and dry.

The durable, yet ultra-lightweight midsole provides high levels of cushioning and support without weighing you down and causing your feet to become fatigued prematurely.

Because of the advanced traction of the rubber sole, you can enjoy peace of mind with the slip-free movement even on wet, rough terrain.

The lace-up closure offers a more secure and stable fit.

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Best Duck Boots: Sperry Top-Sider Women’s Saltwater Boots

No matter if you are strolling on a wet sidewalk with light moisture or trekking through a few inches of snow on the ground, you can trust the Sperry Top-Sider Women’s Saltwater Boots to keep your feet dry and cozy.

The boots feature a high-quality, moisture-impenetrable lower half fashioned out of high-quality rubber, ensuring dryness all day long.

The uppers are crafted out of suede leather with matching leather shoelaces that offer a more stylish look.

The boot openings measure approximately 6.75 inches around to allow you to easily slip your feet inside.

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Best Calf Boots: Columbia Women’s Minx Iii Mid Calf Boot

The Columbia Women’s Minx Iii Mid Calf Boot brings you a blend of high fashion and the comfort you love from a brand you trust all in one high-quality boot.

This tall snow boot features a quilted exterior along its upper foot and shaft, which extends approximately 10 inches from the arch.

The elastic lacing system secures the shoe to the foot and calf in a way that cuts down on the time needed to lace up traditional boots.

Thanks to the Omni-Grip, non-marking traction rubber outsole, you can take stabler, more secure steps on any wet terrain.

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Best vs Rain: HUNTER Women’s Original Short Rain Boot

Get the classic appeal of rain boots that you love both in terms of style and performance with this HUNTER Women’s Original Short Rain Boot.

These rain boots feature a rubber outsole with ample traction, which makes it easy to walk with security and stability upon wet, slippery ground.

Inside of the boot is multi-layer sponge cushioning that makes each step you take more comfortable while delivering just the right amount of support.

The rain boots come in your choice of colors, allowing you to customize your ensembles and express your personality even on rainy days.

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Best Insulated Snow Boots: Columbia Women’s Ice Maiden II Insulated Snow Boot

No matter what kind of weather winter throws your way, you’ll be ready to handle it in the warm and stylish Columbia Women’s Ice Maiden II Insulated Snow Boot.

These 100 percent leather and textile boots feature a tall shaft rising around nine inches from the arch, offering coverage not just over your feet but also your ankles.

The Techlite technology promises a lightweight midsole to give you long-lasting support and comfort without weighing your feet down and causing premature foot fatigue.

The footwear is made from waterproof leather with 200 grams of insulation to ensure warmth and dryness.

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