Looking for what to wear in Winter in Chicago? This is the guide for you!
Visiting Chicago in winter can be a magical experience, with snow-dusted landmarks and festive lights illuminating the city.
However, to fully enjoy your trip, it’s crucial to pack wisely for the biting cold and swirling winds.
Chicago is known for unpredictable weather which can entail freezing winter weeks. The weather changes so frequently that planning what to wear when packing your bags can be confusing!
As an experienced visitor, I can assure you that the right clothing and gear not only keep you warm but also allow you to explore the city comfortably.
From layered outfits to essential accessories, this guide will help first-time visitors navigate the chilly weather while making the most of their Chicago adventure!
17 Things To Pack For Winter in Chicago
Essentials
1. Winter Jacket
A winter jacket is probably the most self-explanatory item you would plan to pack when visiting Chicago in the winter.
Many long winter jackets come equipped with windproof and waterproof features adding another layer of security against the unpredictable weather!
This added length also allows for easier layering underneath, ensuring you stay comfortable while exploring the city’s outdoor attractions.
2. Packable Puffer Jacket
A packable puffer jacket is your friendly alternative to a long, winter jacket. I love these because they are easily collapsible into your suitcase or backpack.
This is super ideal if you are traveling from a warm climate and are not planning to wear a long winter jacket on the airplane!
However, they’re typically not as warm as a long winter jacket and would likely require layering to remain warm enough. They’re also not always waterproof, so if it starts snowing a ton, you may get drenched.
Tip: If you’re planning on a puffer, I recommend pairing it with a rain shell because this is waterproof and will ensure you stay dry in case it snows!
3. Comfortable Boots
Depending on what month you visit Chicago (or what winter is like in that particular year), there may be lots and lots of ice.
I highly recommend prioritizing packing comfortable boots with great tread in favor of fashion boots. Or perhaps you can combine the two!
I can’t tell you the number of times I almost face-planted… this is a must.
Tip: Make sure they are water proof.
4. Comfortable walking shoes
If there’s no snow on the ground, you might be most comfortable in some walking sneakers. My favorite way to spend long city exploration days is by walking.
Bringing your most comfortable pair of walking shoes is essential. (And ideal if they convert into a pair of nice shoes for evening restaurants or nightlife!)
5. Gloves
I struggle with excyma on my hands, and venturing outside in the winter, even if only for a few minutes, requires that my hands are covered.
Exposure to frigid temperatures without proper hand protection can lead to discomfort and numbness, making it difficult to fully enjoy your urban adventure.
Opt for waterproof or insulated options to ensure your hands stay warm and dry, especially during snowfalls or while engaging in outdoor activities.
These thermal gloves are touchscreen friendly.
Clothing
6. Fleece-lined Leggings or Tights
Let’s begin at the base of a solid winter outfit- fleece-lined leggings. These have been a savior more times than I can remember!
If you’re looking for fancy or want to convert your outfit from day to night, I recommend fleece-lined tights. This allows you to pair your tights with a fun dress or skirt while staying warm.
The best part of tights and leggings is they are super packable and can easily fit in a carry-on bag (even a personal item with the right packing list).
7. Jeans
I always recommend packing one pair of jeans. Jeans are practical, go with everything, and are thick enough to keep you warm! Dress them up or down- you know the drill.
8. Long sleeve t-shirts
With all of the warm clothing, you’re bound to get hot when bopping in and out of shops, restaurants, or museums in Chicago.
Consider wearing breathable, long-sleeve shirts so you can easily remove your winter jacket and be comfortable inside.
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9. Layered Tshirts
Layered T-shirts are an essential addition to your winter packing list for Chicago.
The city’s ever-changing temperatures, especially when moving between the brisk outdoor air and warmly heated indoor spaces, make layering crucial for comfort.
A lightweight T-shirt allows you to adjust easily: by wearing it under a warmer jacket, you can stay warm outdoors, while shedding a layer indoors helps prevent overheating.
10. Cozy Sweater
A cozy sweater is an essential item for any Chicago packing list in the winter. As a first-time visitor, you’ll quickly notice that Chicago’s cold winds can be biting, especially along the lakefront.
Opt for a medium-weight knit that can be layered under your winter coat or over long-sleeve shirts, giving you flexibility as you transition between temperatures indoors and outdoors.
Besides practicality, a stylish sweater can effortlessly elevate your look whether you’re enjoying a day at Millennium Park or having dinner at a cozy restaurant.
11. Skirt or Dress
A skirt or dress is a chic addition to your Chicago winter packing list, easily paired with fleece-lined leggings to keep you warm while maintaining style. This combination allows for flexibility as you transition from daytime explorations to a night out in the city.
A layered look can be both fashionable and functional, ensuring you’re comfortable despite the dropping temperatures.
Whether you’re visiting unique boutiques or enjoying dinner at a trendy restaurant, a skirt or dress gives you the versatility to adapt your outfit while embracing the vibrant Chicago atmosphere.
❄️Chicago Winter Planning
Helpful Extras
12. Hat
Including a winter hat, ear muffs, or a headband in your Chicago winter packing list is essential for staying comfortable amid the city’s chilly climate.
The biting wind, particularly near the lakefront, can quickly chill exposed skin, making it crucial to cover your head and ears.
Ear muffs and headbands are excellent alternatives, offering warmth without the bulk of a hat, perfect for those who may want to keep their hairstyle intact.
13. Scarf
The city’s biting winds can make temperatures feel much colder than they are, and a scarf serves as a crucial barrier against the chill.
Not only does it provide warmth around your neck, but it also adds a layer of style to any outfit.
Whether you’re strolling along the Magnificent Mile or enjoying a walk by the lakefront, a scarf keeps you comfortable and complements the city’s fashionable vibe.
Bonus Packing Essentials
14. Sunscreen
While winter temperatures in Chicago may be low, the sun can still be surprisingly strong.
A broad-spectrum SPF on your face and any other exposed areas will help ensure you stay safe while enjoying the best things to do in winter in Chicago.
15. Backpack
Long days of city exploring require having the essentials with you… and this is best with a large purse or backpack.
I like carrying a collapsible backpack because these roll back into my suitcase so nicely, and can also serve as a personal item or souvenir bag if you end up returning with more than what you packed.
(Or if you’re me, I struggle to pack my bag when leaving the same way as when I arrived!)
16. Ice Skates
If you are planning to ice skate in Millennium or Grant Park and own your own ice skates, you may want to save money on rentals if you already own a pair!
I don’t recommend making an extra purchase for this because they might not even fit in your bag, but it’s something to consider if you have the space.
17. Hiking Boots
If you plan to take any winter day trips from Chicago during your visit, packing comfortable walking shoes or hiking boots with great tread will allow you to experience winter wonders like Starved Rock State Park or Indiana Dunes.
These are some of the best places to hike near Chicago!
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Conclusion
In summary, packing wisely for a winter trip to Chicago is essential for a comfortable and enjoyable experience!
Focus on versatile clothing such as fleece-lined leggings, long-sleeve shirts, and a reliable pair of jeans, while also including helpful extras like a hat and a lightweight scarf.
Don’t forget sunscreen to protect your skin against the sun’s rays, even in colder weather, and a collapsible backpack for your daily essentials.
Equip yourself with the right gear, and you’ll be ready to explore all that the Windy City has to offer. Happy travels!
