What to Pack for Chicago in Winter: My Carry-On Packing List for a Long Weekend
Inside the Robie House in Chicago
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Having grown up in New Hampshire, I’m no stranger to cold weather, but even I am cowed by Chicago’s winters. The city’s lakeside location and brutal winds result in some bone-chilling temperatures. If you aren’t dressed properly, the cold will seep into your marrow.
To stave off the shivers, the key is to layer. That is, you need to layer your clothing. Now, you might be thinking: if I have to wear layers, won’t that mean having to pack a lot of clothes? And the answer is no. If you pack smartly, you can fit everything in your carry-on and personal item, which is precisely what I did for a recent four-day trip to Chicago, and if you read on, you can see everything that I brought with me.
Please note that everything in this list is in addition to my base packing list.
Tops
I packed four long-sleeve shirts and one sweatshirt. To save room in my suitcase, I wore the sweatshirt on the plane.
© Vuori
Vuori Sedona Weekender Crew
What I love about this sweatshirt is that it’s both stylish and practical: it’ll keep you warm while looking good. This particular pullover is not fleece-lined, which I prefer for layering under a thick winter coat, but if you tend to run cold and want an extra bit of warmth, Vuori sells a fleece-lined sweatshirt as well.
© Aritzia
Aritzia Isabelle Wool Cashmere Sweater
The exact sweater I packed is no longer available (I’ve had it since high school), but this wool-cashmere crew from Aritzia is about as close to the sweater I own as I can find.
American Giant Premium Slub Crew Tee Long Sleeve
I brought two of these long-sleeve tees from American Giant — in different colors, of course. Made in Los Angeles from 100% cotton, these shirts are both durable and breathable. Plus, they have a timeless look, making them a great staple piece. They are also available in a V-neck, in case that’s more up your alley.
Land’s End Cashmere Sweater
As with the Aritzia Isabelle wool cashmere sweater, this Land’s End cashmere sweater is not what I actually packed; it is the closest approximation to the red-and-white striped top that I brought with me and have owned for well over a decade. If you’d prefer a non-cashmere top, this cotton boat-neck shirt from Banana Republic is another suitable alternative.
Bottoms
As my trip to Chicago was just for a long weekend, I only brought two pairs of jeans, one of which I wore on the plane. I also brought a pair of long underwear (to wear under my jeans) for the days when I’d be walking outside a lot.
American Eagle Next Level Low-Rise Kick Bootcut Jeans
A classic cut with a slight flair: these jeans remind me of the ones I wore back in high school (which is probably why I like them so much).
© Aviator
Aviator Best Travel Jeans Relaxed Straight
If you’ve read some of my other packing lists and travel guides, you’ll know that I’m a big fan of Aviator’s jeans. Not only are they functional, featuring deep front pockets and zippered back pockets, but they’re also stylish. And if that weren’t reason enough to love them, they’re crafted here in the USA.
Psst, to save 20% off your order, use the code BOOKISHWAYFARER at checkout.
Smartwool Classic Thermal Merino Base Layer Bottom
Everyone always remembers to put on a warm coat when going outside during the winter, but people often forget to bundle up their legs. Jeans alone will not cut it; the cold air will go right through them. To keep your legs warm, long underwear is a must, and my go-to pair is this one from Smartwool. It’s made from Merino wool, which is naturally odor-resistant and temperature-regulating.
Jacket and Other Outerwear
A winter coat, scarf, hat, and mittens: all of the outerwear that came with me. I wore the jacket on the plane, as there was no way that it’d fit in my suitcase.
Fjällräven Singi Down Jacket
I love my Singi down jacket. I’ve owned it for several years, and it has held up beautifully. It keeps me warm on the coldest of winter days.
© Kiltane
Kiltane Heritage Tartan Cashmere Scarf
I prefer cashmere scarves over regular ol’ wool ones because they aren’t itchy. And when you have something wrapped around your neck, trust me, you don’t want it to be itchy.
Turtle Fur Freya Beanie
This hat is not only cute but also warm.
Alpaca Wool Mittens
The mittens I packed were actually hand-knitted by my sister, but these alpaca wool mittens from Feighner Family Farms on Etsy look similar to the ones she made me. If you’re wondering why I brought mittens instead of gloves, the answer is simple: mittens do a better job at keeping your hands warm.
Footwear
The feet often get overlooked, but it’s important to keep them happy, especially if you plan on doing a lot of walking in chilly temps.
© Hoka
Hoka Anacapa 2 Low GTX
How do you keep your feet not only warm but also comfortable? For me, the answer is my hiking shoes: Hoka Anacapa 2 Low GTX. While not as insulated as my winter boots, they keep my feet warm when paired with a thick pair of socks, and more importantly, unlike my winter boots, they are actually comfortable to walk around in for extended periods of time. Plus, they are waterproof, ensuring that my feet don’t get wet when walking around on snow-covered sidewalks. To save on suitcase room, I wore these on the plane.
© Sockwell
Sockwell Circulator Moderate Graduated Compression Socks
I wore a pair of compression socks on the plane, both to and from Chicago. Compression socks help to promote circulation, something which is important when seated for any length of time. While this is the style and compression level that works for me, I recommend consulting your doctor to find the style and compression level that works best for you.
© Bombas
Bombas Chunky Ragg Calf Socks
With a vintage look and cozy feel, these Bombas socks are great for brisk days.
Other Clothing Items and Accessories
Here are the other odds and ends that I packed.
L.L. Bean Scotch Plaid Flannel Pajamas
I am a flannel fiend. As soon as the temperature drops below freezing, I pull out my flannel pj’s (and sheets). I couldn’t bring my flannel sheets with me to Chicago, but I could bring my flannel pj’s.
© Bombas
Bombas Gripper Slipper
Personally, I’m not one to walk around barefoot in a hotel room. My solution? Bombas’ Gripper Slipper, a travel-friendly pair of slippers.
I also packed toiletries, such as shampoo and conditioner, but given that everyone has their own skincare and hair routine, I’m not going to bother listing those out.
I hope that you’ve found this packing guide helpful, and as always, if you have any questions, feel free to ask them in the comments section!
Happy travels!
-Julia
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