How to Pack for a Winter Getaway in Chicago

The following packing list for Chicago in winter was submitted by JJ Berman. See all packing list posts here.

Every time I mention going to Chicago for the holidays, I get shocked looks and questions on why would I want to go to a place so cold. It’s true Chicago winters are rough, but not as bad when you come prepared.

As a Chicago native, I go home during the winter because there’s something special about the city when it’s covered in snow. While Chicago’s summer festival season is not to be missed, Chicago does have a lot of wonderful romantic holiday fun in the winter. You can drink mulled wine out of a boot mug at the Christkindlmarket, ice skate in Millennium Park, and watch the lighting festival on the Magnificent Mile.

Usually you can catch me defrosting at one of Chicago’s iconic establishments like the Green Mill for jazz or wandering the Art Institute of Chicago. I also love heading to Second City for some improv comedy; however, I do recommend booking ahead of time during the holiday season. Who doesn’t like to warm themselves by laughing really hard with a beer in hand?

Chicago is a city of neighborhoods, so I try to get to as many as I can each trip. My favorites are Pilsen with Instagram worthy street art and Bridgeport for great beer. If I could tell visitors one thing, it would be to get off the Mag Mile and head to the different neighborhoods.

Each time I visit I usually stay for a week and pack a carry-­on worth of essentials. Here is a list of things I pack to brave the cold and explore the hidden gems throughout the city. Think practical as most Chicagoans do, function is key.

Clothing

Selecting key pieces that are functional, flattering, and easy to layer is the key to enjoying your time in Chicago. Anything to keep warm and forget the cold, so you can concentrate on enjoying the city.

1 pair of dark jeans – for day to night adventures, comfortable enough to walk around in all day

1 pair of black pants – either denim or wool to dress up or down

2 pairs of thick stockings

1 skirt – I typically bring a black wool skirt

1 long sleeved dress – I usually bring a shirt dress with me that can be layered underneath a sweater if needed

1 button down denim shirt

1 flannel shirt – for a pop of color and to stay warm

4 T­shirts – for layering

2 sweaters – I typically leave a cardigan in my bag to put on when cold and bring another crewneck sweater for a more polished look

7 pairs of underwear – so I don’t have to do any washing

4 bras

7 pairs of socks – quick dry wool socks work best for keeping your toes warm and dry of course! My preferred brands are Teko and SmartWool, but any thick hiking socks will do.

1 scarf – a solid color scarf makes matching easier

1 winter hat – I prefer American Apparel’s cuffed beanie because it is thick enough to keep my ears toasty and can be easily stuffed into my day bag

1 pair of gloves

1 full length coat – North Face’s full length coats are a Chicago favorite since most are lightweight and block the wind

cozy pajamas

Shoes

The great thing about going to Chicago is that much of the style is practical. I always see so many people wear gym shoes wherever they happen to go. The great thing about that is I get to bring comfy and functional shoes, while fitting in.

1 pair rubber soled boots – Chicago weather is erratic, even in the winter. What most visitors don’t know is that the worse part of the winter is “black ice.” When snow melts, mixes with the soot on the ground, and freezes again you get black colored ice that blends in. I have skidded and fallen enough times to learn my lesson. I bring L.L. Bean’s shearling-­lined boots, which keep my feet toasty and match with most outfits. They are also perfect for dive bars.

1 pair of leather boots – I always bring a pair of boots for going out to nicer restaurants and parties. I make sure the bottoms are ribbed or in someway provide traction as to not embarrass myself by slipping.

Toiletries

Bring your favorite moisturizing creams along because no one likes chapped and flakey skin. Plus, it’s just uncomfortable and can be easily avoided.

2 in 1 shampoo and conditioner

Moisturizing soap – I bring a travel size of Dove for both face and body.

Dry Shampoo – will help you refresh after wearing a hat all day long

Heavy Duty Moisturizer – I bring Weleda’s Skin Food everywhere I go to prevent cracked hands.

Argan oil – helps moisturize your skin and control fly-aways

Toothbrush and toothpaste

Tinted lip balm with sun protection – I bring Fresh’s Sugar Lip Treatment SPF to protect my lips from the cold and sun at the same time. Also, you’ll never know who you’ll meet.

Makeup essentials and makeup removing wipes

Deodorant – Sometimes museums or restaurants have the heat turned up too high for all the layers you have on, so a little deodorant doesn’t hurt.

Extras

I always keep a few extra items in my travel purse while walking around downtown. I’m usually running between the Art Institute of Chicago and meeting friends for dinner in the Fulton Market neighborhood.

Umbrella – just in case there’s sleet. While not typical, getting caught outside in icy rain is not fun by any means.

Bottle opener – Chicagoans like their beer, so why not be prepared?

Phone and phone charger – It might be useful to download an app for public transportation i.e. the “L,” which is what we call the subway since it is on an elevated rail. Even for a Chicagoan like myself, they are useful when the trail goes underground and you don’t have any reception.

Book or Kindle – the perfect companion for longer train rides and eating solo.

Travel documents and a debit card – Most major banks are located downtown. I have never had any issues finding an ATM close by.

Camera – Chicago is known for its architecture and I’m reminded every time I walk around downtown. There is always some building or detail that surprises me. For times when I want to zoom in close to the top, I’m glad I bring my camera around.

This list was created to provide you with the essentials to keep you comfy during Chicago’s unruly winter so you can really enjoy all the city has to offer. Just remember to leave a little extra room for a boot mug from the Christkindlmarket and a Chicago flag hat or scarf.

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About the author: JJ Berman is a Chicago native. She is a freelance writer and the creator of the travel food blog, Urbane Nomad. She lives for eating, dinner parties, and well made cappuccinos. When she is not blogging, you can find her planning her next adventure. Catch her everyday adventures at theurbanenomad on Instagram.