What I Packed: 5 Wintery Days in Chicago
A 5-day work trip to Chicago in mid-November in, you guessed it, one backpack. Cold weather travel makes it tricky to stick to one bag but I managed to pull it off. Read on for my full packing list, what I overpacked, and my most valuable piece (MVP)!
Travel Specifications
LOCATION
Chicago, IL
TIME AWAY FROM HOME
5 days, 4 nights
TIME OF YEAR
Mid November
LAUNDRY
No laundry needed this trip
WEATHER
Cold—coldest day was a high of 25 F degrees and a low of 16. Some snow one day.
PACKING REQUIREMENTS
Two days of conference attire
Host 3-hour marketing workshop
Layers to stay warm while exploring the city
Be able to go to the gym
What I Packed
Travel Gear
DAY BAG
My day bag is the Joshuvela Baja Backpack (use coupon code "THANKS10" to get $10 off) to carry all my gear. It's sturdy as hell, looks great, and is produced ethically in San Francisco. My favorite feature is that it can be carried as a tote bag to look dressy for client meetings, or slung over my shoulders for ergonomic walking without making me look like a college student.
TRAVEL POUCHES
My travel bags are from the Spacepak System:
Flight 001: clothes, toiletries, liquids/makeup
Amazon (exact styles not available): clothes in dots or stripes, toiletries, undies, makeup
BACKPACK
My backpack is the Everyday Backpack 30L from Peak Design. I did tons of research before purchasing because I intend this to be my one and forever bag. I’ve traveled with this bag on 6+ trips and I’m thrilled.
Wardrobe & Accessories
CLOTHES + SHOES
4 Tops:
Long and lean travel shirt—Athleta (I wear this every time I travel)
Short-sleeved mock neck top—Madewell
Striped silk blouse—Everlane
T-shirt—Everlane
1 Graham Longline Plaid Blazer—Anthropologie (I like this one too)
5 Bottoms:
Black jeans—Everlane
Blue jeans—Everlane
Black slacks—Everlane
Brooklyn ankle pants—Athleta (I wear these every time I travel)
Gym shorts—Athleta
Leggings—Athleta (for warmth and pajamas)
3 Shoes
ACCESSORIES
Yarn hat—Madewell
Scarf
Black leather gloves—Nordstrom Rack
TOILETRIES
Makeup (tinted moisturizer with SPF, brows, mascara, eyeliner, cheek tint, lipstick)
Shampoo (I didn’t bring a brush but wish I did since my hair is getting longer and I don’t use conditioner)
In Two Minds face wash, toner and moisturizer—Aesop
Deodorant—Native
Toothbrush and Bite toothpaste bits
Coconut oil for removing makeup
Between hosting/attending a conference in Chicago and leading a 3-hour workshop, I was in the spotlight a lot. I needed to be comfortable moving around on stage and and not wear the same thing I’ve worn to the other cities—New York, San Francisco, and Boston so far. London is next!
LAYERING UP
It snowed…in November…
Luckily, I was prepared and could make unhelpful quips like “there’s no such thing as bad weather, just inappropriate clothing.”
With the biting cold, no one felt much like taking their hand out of their pocket to snap a photo so pics are limited and mostly indoors.
What I Overpacked
WHITE SWEATER TUNIC
I only ended up wearing the white sweater tunic once on day 1 of the conference. While I love how it looked and it kept me warm, I think I could have lived without it since it takes up a lot of space in my backpack. Instead, I should have packed more under shirts to layer underneath my dress shirts to keep them from getting sweaty during multiple wears.
Most Valuable Pieces
Anthropologie grey duster coat—I wore this almost every day (same as my Boston trip!). It’s the perfect balance between casual and professional and kept me warm indoors and out.
Canada Goose Winter Coat—yes I realize it’s expensive and not kind to animals, but this thing is WARM. I almost packed a lighter coat since it’s only November after all but that would have been a critical error. ❄️
It was another great work trip. Very few packing regrets—just wish I could have stayed longer since Chicago is a great town!
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