How to Pack for a Winter Getaway in Chicago

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.

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.


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.


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


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?

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.

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