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Packing for the Unknown: Chicago

What do you pack when you’re spending a week in a city you’ve never been to (airport layovers don’t count) and you don’t really have an itinerary? And it’s supposed to be hot and muggy? And it’s Chicago? Oh, and you only travel with carry-ons?

Not a whole lot, as it turns out. Growing up “that girl” who brought full liter-sized bottles of shampoo and conditioner for a long weekend and enough outfit changes to be eligible to host a televised awards show, it’s been a difficult process for me to learn how I pack lightly. I’ve been lucky enough to have traveled quite a bit in my twenty-something years, and with those experiences, and the ridiculous overhead luggage bin allowances, I’ve learned to rein in my “need” for frivolous outfits and toiletries.

One of the main reasons that I had to make sure I was in control of my wardrobe for the week was that I had to save room for Mel’s “Welcome to America” presents: a pair of San Francisco Giants socks, an American flag shirt, and the map frame I’d made, as well as the surprise cookies I’d made for her and Zach. I’ll have to post the yummy variation of my 1, 2, 3 Creme de Menthe Cookies I made for them, and the adorable container I crafted and packed the cookies in for safe keeping, later.


Had to make sure I could fit these little treats in my luggage!

For this weeklong trip, I packed pretty lightly when it came to clothes and accessories. I wore my bulkiest shoes (wedges) and brought my denim jacket and pashmina shawl for the plane ride. The weather was going to be a bit unpredictable, hot and muggy, but with possible rain and thunderstorms. I figured I should bring some close-toed shoes, so I brought my Toms for walking and some cute flats for going out. I also packed my comfy and broken in Rainbows for hanging out and for showering at the hostel. I realize that four pairs of shoes sounds like a lot, but three of those pairs are easily packable and very lightweight. I could have done without the Toms, as it didn’t rain at all.

When it came to outfit time, I chose three lightweight dresses, three pairs of shorts, a skirt, and one pair of ankle jeans. I chose three tanks, one short-sleeved shirt, and one long-sleeved shirt (for the trip back to chilly San Francisco) that could be mixed and matched with all of the bottoms I’d brought. A bikini, undergarments, and two pairs of pajamas later, I was set for clothing! I ended up doing a fabulous job packing, as I wore everything except for one pair of shorts and one dress.

As far as toiletries go, TSA has pretty much regulated what I bring these days. Mini shampoo and conditioner, mini face wash, dual purpose tinted moisturizer, itty bitty hairspray, roll-on perfume, etc. I tend to wear minimal makeup, so I luck out with not having to lug a huge cosmetics case in my bag. I also brought a book, A Moveable Feast: Life-Changing Food Adventures Around the World, which is a compilation of essays written by chefs and foodies, both newbies and famed. I highly recommend you check it out!

I consider this to be one of my best packed trips to date. My bag was light and I didn’t have to sacrifice style to have a carry-on suitcase. It was nice having extra room (from Mel and Zach’s presents) in my carry-on suitcase for the little bit of shopping I did on State Street. I’ll be posting some of my travel adventures from Chicago and Peoria soon, so be sure to check back for some awesome recommendations!

About In Natalie's Shoes

I’m a twenty-something food fanatic. By day, I’m working for a non-profit, by night I’m dreaming of becoming a domestic goddess, creating adorable crafts to gift and engineering delicious home cooked meals for the fabulous dinner parties I’ll one day throw. I love to travel, locally, regionally… heck, even internationally, I don’t discriminate too much when it comes to a new destination. I am a little obsessed with taking photos of the food I eat, whether I make it or pay to eat it. It is my firm belief that a girl can never have enough purses or too many shoes. I plan to fill this lovely little blog with my adventures in food, travel, and craftiness. I hope you enjoy!

2 responses »

  1. Pingback: Heavenly Hostel « In Natalie's Shoes

  2. Pingback: Packing for the Unknown: Coachella | In Natalie's Shoes

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