a winter weekend in chicago: what to pack (part one)

Hello lovies! I recently had the opportunity to travel to travel and have returned from a 4-day weekend trip to none other than Chicago, Illinois. I’m so excited to share all the details with you, like what I packed, where I stayed, and what I did in the Windy City.

My trip to Chicago was rather last minute and a tight squeeze into my schedule, but I made it work! I hopped aboard a Southwest flight early Saturday morning and departed on Tuesday afternoon. 

It was about 21F when I landed, but I was rather warm, and the cool air felt nice. In fact, the cool 20 degree weather the entire time I was there felt rather nice but my toes and fingers would have begged to differ. 

There was snow on the ground and it snowed twice while present. I cannot tell you how weird it was to be in snow, let alone in 20F temperatures. The coldest weather I’ve been in has been like 40F. 

(Can you guess where I’m from? Winter is chilly (40-6F); summer is hell (100-120F).)

Despite not sticking to my itinerary, I ended up having a good time. This is my weekend in Illinois!

Psst! Check out part two, a winter weekend in chicago: 4-day itinerary!


what i packed

As I live in (did you guess?!) ArizonaI don’t own winter clothes or shoes*. Sure, I have a few hoodies and pairs of jeans, but, for a place that’s hot 10/12 months of the year, there’s no need to bundle up. Also, I never go up North, so, that’s that. 

*I’ve come to realise I own several winter coats but they’re in storage…in New York.

I had to do my best to think about what people wear in the snow and then go from there. Obviously, television and social media were no help. Although, if you can manage to survive the snow in a thin pair of jeans and a cropped sweater, I applaud you greatly. A power I must learn.

I headed to H&M for some stuff. I previously bought a coat from there for when I was moving to NYC and it was so warm but I came home and left it in storage. Because it’s not logical for me to fly from Phoenix to New York to Chicago just for a coat, I bought one – again – from H&M.

boots made for stomping

Next, I grabbed some boots! Now, I know these aren’t really winter boots, but I didn’t want to buy winter boots and then watch them collect dust, so I grabbed a pair of more fashionable boots. I got these in black, size 8 (EUR 39). My toes did get super cold, but the 2″ platforms kept me off the ground and out of water, snow, and ice.


touchscreen gloves

I packed fuzzy gloves that were gifted to me years ago. As they’re gifted (and don’t have any tags on them), I don’t have an exact link, but I did find some great gloves with great reviews to link for you all. And, honestly? I wish I had purchased these. My gloves fell apart and did nothing to keep my hands warm.

Trendoux Winter Gloves, $9.34 – $10.19 USD (available in different colors!)

mini bottle set

And the last thing I grabbed for this trip that I wanted to share, that is not clothing related, is this travel bottle pack. I usually travel with my full sized bottles as I’m usually gone a week+, but as it was only the weekend, I opted for these mini ones. They’re nice and don’t spill, as well as can hold enough for the weekend. They’re also TSA approved for carry ons!

Beveetio Travel Bottles 15 pack, $13.99 USD (available in different colors!)

The flight went well. There were two babies and a doggy on my flight, but I had no idea until we had landed and, when waited for a gate to open up, they had all gotten antsy. (Same here!)

Nevertheless, that’s what I packed for Chicago! Next time I go somewhere snowy I have two lessons I’ve learned: get better gloves (aka the ones linked above) and thicker socks!

Check out part two, a winter weekend in chicago: 4-day itinerary!

Until next time!

Hi, I’m Jade Madison!

jade Madison | lifestyle + personal blogger

When I am blogging, I work to bring you quality lifestyle and personal content, as well as printables to make your life easier.


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this post is categorized as: blog > travel > illinois

published 28 jan 2022

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