It’s October, and you know what that means: 

it’s time for the leaves to change colors, the weather to get crisp, and the Halloween season to kick off.

But what do you wear in Chicago? 

How do you stay warm while still looking stylish?

And how on earth do you avoid looking like a pumpkin when the days get shorter and shorter?

If you’re planning a trip to Chicago this fall, you may be wondering what kind of clothing to pack for your visit.

We’re here to help! Here are some tips on how to dress in Chicago this October.

Chicago Weather in October

October is the month of Halloween and fall foliage. 

Temperatures are perfect for outdoor activities and the weather is usually pretty mild to cold.

The weather in Chicago in October is similar to the weather in September, but with a slightly higher chance of rain and cold wind. 

The average high temperature is 68°F, while the average low temperature is 44°F. 

October can be a bit more humid than other months due to the amount of moisture in the air from all the rain that falls during this month.

The average rainfall for October is 2.4 inches, with about two-thirds of that coming over just four days: October 6th through 8th.

What to Wear at Your Daytime Activities in Chicago?

It’s a question that can be answered with a single word: layers.

That’s right, layers.

The weather in Chicago has a reputation for being unpredictable, and while it may be true that Chicago can get cold in the winter months, it’s also true that fall is one of the best seasons to visit.

Fall in Chicago can bring some chilly temperatures at times, so be sure to pack your warmest clothes as well as your lightest ones.

You see, Chicago is known as the “Windy City” for a reason—you wil get some serious gusts here. 

And while that might be great news if you’re a fan of roller coasters or snowboarding, it isn’t so great if you’re just trying to get from point A to point B without getting blown over by the wind.

So what should you do when you find yourself walking down Michigan Avenue or strolling through Millennium Park and feeling like the wind is trying to pick you up and carry you away? 

Layer up! 

You’ll want at least two sweatshirts on top of each other, plus at least one coat (or more!). And don’t forget your scarf!

Our Chicago fashion packing guide for fall includes:

  • Sunglasses are a must-have for those who want to protect their eyes from sun damage. We recommend bringing a pair with UV protection.
  • Comfortable, closed-toe walking shoes are essential when exploring Chicago on foot. A good pair of sneakers will do just fine! If you’re going for style points instead of comfort, we would recommend bringing a pair of sandals or slides instead.
  • Shorts, pants, or comfortable joggers are perfect for those who want to stay cool but not too cold. Jeans or khakis can also be worn instead if desired!

What to Wear During Your Nighttime Activities in Chicago?

Chicago is home to many of the country’s best restaurants, bars and clubs. The city is known for its nightlife, so it’s no surprise that there are many great places to visit after dark. 

It can be difficult to know what to wear during your nighttime activities in Chicago. While you might not want to dress too casually, you also don’t want to overdo it with your outfit.

In general, men should dress in a way that makes them feel comfortable and confident. 

Women should dress in a way that makes them feel attractive and confident. 

You want to look nice but not too nice so that you don’t stand out as being out of place at your destination.

If you’re going out for dinner or drinks, then jeans are fine for both men and women. 

You can also wear khaki pants or dress trousers if you prefer. 

For women, a nice blouse with slacks or a skirt works well for most restaurants and bars in Chicago. 

Men should avoid t-shirts with logos or words on them unless they’re going somewhere like Wrigley Field where everyone else is wearing one.

On weekends when there are fewer people out at night, then wearing something fancier may be acceptable such as a suit jacket.

Additional Things You Should Pack For Your Holiday in Chicago:

Chicago is a great city for sports fans and visitors alike. 

Whether you’re going to the Cubs game or just want to check out some of the best museums in the world, Chicago has something for everyone. 

Here are some additional things to pack for your holiday in Chicago:

Sneakers. Sneakers are a must for a trip to Chicago. Whether you are exploring the city or going for a jog, sneakers will be your best friend. 

The streets can be very slippery when it rains and you never know what kind of terrain you might encounter on your travels.

Winter Boots. If you plan on visiting Chicago during the winter months, then it is essential that you pack some good quality winter boots. 

The snow can get pretty deep in some areas and the sidewalks can be icy during the colder months of the year. 

I highly recommend investing in a pair of waterproof winter boots that have good grip on them as well.

Parka. Chicago winters can get pretty cold at times so make sure you pack at least one warm jacket with you when you travel there during the winter months! 

You do not want to freeze while exploring around this busy city so make sure you have everything covered with this essential item!


A beanie is another must-have item if you plan on visiting Chicago during the colder months of the year! 

It gets really cold there sometimes so make sure that your head stays warm by wearing.

Additional Things You Should Pack For Your Holiday in Chicago:

  • Scarf.
  • Baseball Cap.
  • Gloves.
  • Rain Jacket / Windbreaker.

Final Verdict

Each of the four seasons are special to Chicago, and there is a fashionable way to enjoy it’s legendary weather. So no matter what you wear, it is going to be cold. The best thing you can do is dress in layers and make sure you have a few extra pairs of socks, of course.