11 Non-Bulky Essentials I Always Pack for Winter Trips, as a Travel Writer from Chicago

published Jan 30, 2023
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Cold weather travel can be tricky because it feels like you need to bring about 50 pounds worth of extra things just to keep yourself warm. Also, if you’re coming from a warmer place, it may be hard for you to gauge exactly how cold it’ll be at that ski resort or on the streets of Toronto. Luckily for you, I tested out these products in Chicago’s recent winter storm, which was the most intense cold weather of my life. Plenty of the items were chosen specifically to go easy on your luggage, so you can still get away with bringing just a carry-on. Here are 11 items I recommend adding to your winter travel packing list. 

1. Vacuum Storage Bags

Compression cubes wouldn’t last five seconds in the ring with these vacuum storage bags. Using a vacuum, you can suck all the extra air and volume out of your clothes, fitting nearly five times (at least it seems that way to me) more stuff in your luggage. Because even if you pack light, winter clothes are just bulkier. Plus, the handy travel pump keeps you from needing a vacuum at your hotel to re-pack. 

2. Winter Leggings

These Alo leggings are the absolute truth. When the wind was raging so hard during Chicago’s polar vortex that the weather channel said it felt like -43 degrees Fahrenheit, these leggings kept me warm as I walked the three excruciating blocks from my best friend’s apartment to mine. But they’re also my favorite for any cold day — not too hot and perfectly warm on the chilliest of days. Plus, they’re high-waisted and stay up very well. 

3. Roku Stick for Snow Days 

I know, I know. You didn’t come on vacation to stay inside and watch TV. Unfortunately, sometimes snowstorms or painfully low temperatures keep you cooped in your hotel. If rewatching “Law & Order: Special Victims Unit” isn’t your thing, you can plug a Roku Stick into your hotel TV and instantly have access to all your favorite streaming platforms. 

4. A Bigger Carry-On 

I try to never pack more than a carry-on, but winter travel, with all its sweaters and coats, can sometimes make that hard. I love the Away Bigger Carry-On because it’s still small but has little extra room. Maybe the best feature is your ability to add a USB charger to the suitcase so you don’t get stranded with your battery at 3 percent. Plus, it rolls effortlessly on snowy and icy sidewalks that might leave other suitcases constantly getting stuck. 

5. A Light Jacket That’s Easy to Pack

While you need a super-warm coat if you’re traveling somewhere cold, some days might be warmer than you expect and you’ll be wishing you had brought something lighter. This light jacket from Aritzia is ideal for winter packing because the pocket converts into a compression packing tube, making it super easy to throw in a suitcase or even clip to your backpack. 

6. An Electric Hand Warmer

Cold hands are one of the most uncomfortable things you can experience while traveling in the winter, especially when you have to walk around a lot. And those single-use hand warmers, while effective, aren’t super sustainable or easy to pack. This rechargeable hand warmer easily keeps your fingers from getting frostbite without having a bunch of ripped-open plastic packets everywhere.  

7. An Oven of a Winter Coat

When I first moved to Chicago from Denver, I immediately realized I’d need a new coat. I bought this Fjallraven Nuuk Parka and it hasn’t let me down since. It has plenty of pockets — I often store my wallet, a book, reusable grocery bags, and lots of other stuff there — and it feels like a comforting fireplace when you zip it up.

8. A Tumbler for Hot Drinks

Hot drinks keep you warm whether you’re hanging out at the ski resort or walking the streets of a cute town while the snow falls. This classic from Hydro Flask keeps your drinks warm and is easy to stash in a backpack. 

9. A Waterproof Backpack

Snow can be deceptive, falling down in soft flakes, keeping you from knowing exactly how soaked your clothes and bags are getting. And if you’re carrying around paper or electronics, you really want to make sure they stay dry. That’s why Yeti’s Panga Backpack, designed for water sports like fishing and boating, is a great investment to protect your valuables. 

10. Wool Socks

Grab a few pairs of wool socks to keep your toes warm and dry on snowy days. These ones from Amazon are a great price and get the job done. 

11. A Stylish Pair of Snow Boots

Snow boots are necessary for cold weather travel, but they can often feel so… bleh and unstylish, leading you to load up your suitcase with more pairs of shoes. These Adiroam Hiker boots from Ugg are suited for -26 degrees Fahrenheit, but they’re also stylish enough to go with dresses and unique streetwear looks, keeping the amount of shoes you need to pack to a minimum.