What to Wear to Chicago in the Fall

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Seasonal Guide: The 10 pieces you need to pack for a trip to Chicago in the fall

Outfits for Travel Packing Guides

We hope you enjoy this seasonal packing guide. To stay on-trend, each of our packing guides at Outfits for Travel is developed at the beginning of each season and updated throughout the year to ensure you can buy each item. We hope you love the guides as much as we do! Big hugs, much love! xo, OFT

What to Wear to Chicago in the Fall

Our goal in creating this Chicago packing list is to help you decide what to pack for Chicago in the fall. To best achieve this, we have created a 10-piece travel wardrobe. This Chicago packing list for fall is full of fantastic seasonal trends – think soft shearling, embroidered elements and lace-up styles. All of which combine to make amazing looks for sauntering down The Chicago Riverwalk, shopping the Magnificent Mile or doing some Museum-hopping!

Chicago Fall Weather

Average high temperatures for Chicago in the fall are wide-ranging and can fall from anywhere to the mid-40s to low-70s, dependent on which month you arrive. Fall low average temperatures in Chicago range from the low-30s to low-50s. With this in mind, be sure to check the weather before you go and adjust your packing as necessary.

It is generally a good idea to pack a substantial jacket or coat like the shearling style we recommend in our guide as it does get cool at night, even in the early months of fall. A stylish sweater dress is a good packing choice for nice dinners out in the city. Bonus, you can layer your dress over pants for a fashion-forward daytime look. And definitely pack a comfortable pair of sneakers if you plan on doing any exploring in the city. Below we have included a detailed monthly list of the the average high and low temperatures for Chicago in the fall.

This average weather list was adapted from a Chicago Weather and When to Go article on Tripadvisor.

Below we feature 10 pieces to help you create comfortable, on-trend travel outfits for a fall vacation to Chicago.

WHAT TO WEAR TO CHICAGO IN THE FALL

CHICAGO PACKING GUIDE

THE 10 PIECES YOU NEED TO PACK FOR A TRIP TO CHICAGO IN THE FALL

Shearling Jacket | Wool Pants | Embroidered Bag | Crocodile Boots | Flannel Shirt | Sweater Dress | Cozy Scarf | Lace-Up Pants | Stylish Trainers | Denim Blouse

When selecting what to wear to Chicago in the fall, your travel wardrobe should focus on comfort, warmth and style. It is a beautiful city with fantastic museums and outdoor places. The fall is a wonderful time to visit Chicago with cooler temperatures. So whether you are Chicago packing outfits for September, October or November, refer to our Chicago packing list with stylish pieces that will work great for your travels!