What to Wear in Chicago in the Winter: Chicago Outfit Ideas

Are you looking for options on what to wear in Chicago in winter? If yes, this guide can help you figure out how to dress for Chicago winter!

The Windy City is a popular metropolis in Illinois on the shores of Lake Michigan.

I am sure most of you would know Chicago for its skyline and deep-dish pizza but Chicago winter is memorable too.

The biting cold, icy winds, and occasional snowstorms make it one of the top places to enjoy winters in the Midwest.

This is why it is important to know what to wear in Chicago in the winter to stay warm while enjoying the city’s vibrant winter activities.

Keep reading my guide on What to Wear in Chicago in the Winter: Chicago Winter Outfits!

What to Wear in Chicago in Winter: Chicago Outfit Ideas

Chicago Weather in Winter

Let me start by emphasizing that winter in Chicago is no joke.

The winter season officially starts in December and runs through February, with temperatures averaging between 20°F (-6°C) and 35°F (2°C).

As the city experiences strong winds throughout the year, you will feel much colder here, especially in January.

If that wasn’t enough, snowfall is quite common in winter as is slush. So, you must pack warm layers and waterproof footwear.

Here is a short breakdown of what you can expect to find in each of the winter months:

• December: This is the start of the winter season with temperatures ranging from 25°F (-4°C) to 35°F (2°C). You can witness snowfall this month along with plenty of festive decorations that will brighten the chilly streets. Due to the Chicago winds, it might feel colder, especially near the lake.
• January: It is the coldest month in the city and the temperatures can stay as low as 20°F (-7°C). Moreover, you can expect heavy snowfall and icy winds during this month. So, if you don’t know how to dress for winter in Chicago, then it can feel brutal.
• February: This marks the slow end of the cold winters with temperatures starting to rise slightly. You can expect temperatures between 22°F (-5°C) and 35°F (2°C). Of course, you will still experience snow but days are longer so you have more time to explore without the night chill.

This is why you must learn what to wear in Chicago in the winter so, you can easily stay warm, comfortable, and stylish while exploring this iconic city.

Tips for Choosing the Right Winter Outfit

1. Layer Always: If you truly want to stay warm in Chicago winter, then don’t forget to layer your clothes. Start with a base layer that consists of thermal tops and leggings to stay warm and comfortable from the biting cold.
2. Choose the Right Fabrics: Next, add another layer of the right fabric for our Chicago winter outfit. I think wool, fleece, and down are your best friends for this weather.
3. Pack Versatile Accessories: If you want to spice up your outfit, then you can add matching scarves, gloves, and hats too.
4. Wear Quality Footwear: Most importantly, wear waterproof, insulated boots as there will be snow and slush everywhere which can be difficult to navigate with basic footwear.

What to Wear in Chicago in December

So, what to wear in Chicago in December?

There is a moderate chance of snowfall in December and the weather can feel colder due to the chilly Chicago winds.

However, December also marks the start of holiday celebrations in Chicago.

So, with holiday markets, ice-skating rinks, and twinkling lights everywhere, December is a magical time to visit, as long as you choose the right winter outfits!

Clothing Recommendations

• Outerwear: Since it is going to be quite cold in December, I suggest that you always wear a warm, insulated coat. You can choose knee-length parkas or down coats with a hood to keep warm and cozy against the chilly wind.
• Tops: Before you layer with the outerwear, make sure to wear a thermal base layer followed by a fleece or sweater. You can wear a turtleneck as well as that will not only keep you warm but looks stylish as well.
• Bottoms: For bottoms, you can go with fleece-lined leggings or thick jeans. You can also wear thermal tights inside for added warmth.
• Footwear: Since there are chances of snow, you have to waterproof boots with good traction for the slushy streets. Ankle or knee-high boots lined with faux fur are a good choice for Chicago in December.
• Accessories: Finally, don’t forget to add a scarf, and winter gloves to keep your hands and neck warm. You can also carry a crossbody bag that is weather-resistant and can hold all your winter essentials.

Chicago Outfit Ideas for December

Since December means a Christmas celebration, one of the top things to do in Chicago in winter is visiting the Christkindlmarket.

For this visit, you can wear a red sweater with black fleece-lined leggings and a cute wool coat of black or white color to explore the holiday market.

Wear waterproof boots to navigate the snowed ground and you can add a crossbody bag to keep the essentials and your shopping from the market.

Since Ice Skating at Millennium Park is a popular winter activity in Chicago, you cannot miss doing it.

To be prepared for this, I would suggest wearing a chic puffer jacket with thick jeans and waterproof gloves to keep you warm while skating.

What to Wear in Chicago in January

Let me warn you, January is the coldest month in Chicago.

You can expect lots of strong winds, snowfall, and icy sidewalks.

Don’t worry, I have covered below how to dress for winter in Chicago, especially in January.

Clothing Recommendations

• Outerwear: Of course, you cannot go anywhere without a heavyweight down jacket with a fur-lined or fleece-lined hood in Chicago in January. Try for a water-resistant coat that can handle both snow and sleet.
• Tops: Your base layer should be a thermal shirt. On top of that, you can add a fleece-lined hoodie or a chunky knit hat
• Bottoms: Wear insulated snow pants or wool trousers to keep your legs warm. If you are going for a casual outing, then fleece-lined leggings can work great too.
• Footwear: This should be a no-brainer but if you are going to be walking around a lot in the Chicago snow, then snow boots with thick soles are a must. Check for footwear with shearling or faux-fur linings to keep your feet cozy.
• Accessories: Style your winter outfits further while keeping warm with earmuffs, a thermal hat, and a scarf. If you feel particularly cold, then wear double-layer gloves—knit on the outside and fleece on the inside. Also, you can use a sturdy tote with a waterproof exterior for carrying extra layers and a thermos.

Chicago Outfit Ideas for January

Are you planning to watch the famous Chicago Polar Plunge? If yes, then make sure to layer up for this chilly, festive event.

You can wear black fleece-lined leggings with a bright red oversized sweater for a pop of color. Layer it under a navy waterproof parka with a faux fur hood.

For footwear, insulated snow boots are perfect. You can accessorize your outfit with a cream-colored knit beanie with a pom-pom, a matching scarf, and waterproof black gloves.

Complete the look with polarized sunglasses to shield your eyes from lake glare.

If you are planning to visit the indoor museums in Chicago in January, then you can wear a cozy cream turtleneck sweater layered under a camel wool coat with black skinny jeans.

Pair it with a black leather ankle boot and accessorize with a burgundy scarf, neutral knit beanie, and matching gloves.

You can also carry a crossbody bag for essentials.

What to Wear in Chicago in February

Still confused about what to wear in Chicago in the winter, especially in February?

Since February signals the end of winter, it can be slightly warmer than January but it is still quite frosty outside.

And the tours in Chicago are starting to resume.

The weather is still cold but there are longer daylight hours so you can explore more of the city.

Clothing Recommendations

• Outerwear: Stick with a long, insulated coat. A wool-blend overcoat can work for milder days when layered well.
• Tops: Thermal tops under stylish sweaters or lightweight knitwear are perfect. Consider adding a blazer for a polished, professional look.
• Bottoms: High-rise jeans or tailored trousers paired with thermal tights are ideal. For extra warmth, try corduroy pants.
• Footwear: Sturdy ankle boots or insulated sneakers are great for drier days. On snowier days, stick to snow boots.
• Accessories: A stylish beanie, oversized scarf, and lined gloves are winter essentials. Sunglasses are also useful for snowy glare on sunny days.
• Handbag: Opt for a structured handbag or crossbody bag made from durable material to brave the winter elements.

Chicago Outfit Ideas for February

One of the perfect date outfits for Valentine’s Day in Chicago is a red sweater dress with black fleece-lined tights and a black wool coat for warmth.

Wear heeled ankle boots with this outfit and accessorize it with gold hoop earrings, and a pink or blush scarf.

Add a neutral beret and leather gloves for a romantic, cozy look which will be perfect for a romantic date out.

You can visit 360 Chicago for amazing panoramic winter views of the city.

For this attraction, you can dress up in a cream knit sweater with black fleece-lined leggings and brown ankle boots.

Wear a charcoal wool coat on top of it to stay warm and cozy along with a burgundy scarf, grey beanie, and black gloves.

What To Wear In Chicago In Winter Packing List

If you will be traveling, either by plane or by car to Chicago, here are some tips on how to pack lightly.

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday. It is made of lightweight aluminum and so easy to use.

I never leave home on a trip without my Bobble filtration bottle. The 18.5-ounce size is perfect for when exploring.

And the replacement carbon filter ensures fresh clean water whenever you fill the Bobble.

Then this collapsible silicone foldable water bottle would work well for you as well.

This foldable water-resistant backpack would be great.

Not all beaches are created equally and these quick dry slip-on Aqua shoes will come in handy for pebbly Chicago beaches. (Not in winter!!!)

These men’s quick dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in a lot of lens colors and frame designs and are extremely affordable too.

If you are fond of aviator-style sunglasses these polarized aviators may interest you.

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Read my suggestions on the best things to do in Chicago.