What to Pack for Chicago in the Fall

Last updated on August 15th, 2024 at 07:51 pm

Are you wondering how to pack for fall in Chicago? Autumn is a great time to visit Chicago when the summer heat finally dissipates and the trees turn to bright reds and oranges. Whether you are in town for one of Chicago’s fall festivals, a weekend escape before winter, or taking advantage of the low season prices, Chicago is a great place to visit in the fall. But how are you supposed to pack for a city that is known for volatile weather?

It gets crazy cold in Chicago. Am I the only one who pictures city-goers in trench coats, collars pulled up to their noses, bracing themselves as the fierce and famous Chicago wind freezes them to the bone? Luckily, most of the fall in Chicago is pleasant, and cooler temperatures don’t typically set in until November.

Weather in Chicago

The beginning of fall in Chicago is pleasant, with highs around 74°F and lows around 62 °F. October gets chillier still with 62°F as the average high and 50°F as the average low. As winter approaches, November brings highs in the 50s and lows around 39°F. 

September is likely the safest fall month to travel to Chicago, as it is usually warm and humid. However, if you are willing to risk visiting in November you can nab deals on the start of off-season pricing.

Snow is uncommon during this time of year, but happens occasionally in November. Rain is common in the fall, although it is not the wettest of the seasons in Chicago.

Since autumn is such a transitional period, it can be hard to predict the weather and it is best to plan for the cold leading up to your trip and then double-check the forecast before you pack.

Read More: 13 Reasons Chicago Should Be Your Next Weekend Trip

My Experience Visiting Chicago in the Fall

When I found out I would be visiting in November for the first time, I was racking my brain trying to figure out what to pack for Chicago. 

We were only going to be there for the weekend, so I wanted to pack as lightly as possible to avoid checking a bag. This added another element of difficulty. Luckily, I’ve done the work for you – if you are planning a trip to Chicago in the fall, this is the perfect packing guide for you.

The first day of my visit was beautiful – just a slight chill in the air, sunshine, and blue skies with the occasional fluffy cloud. The leaves were still on the trees, unlike in Colorado where the first snow had already torn them off their branches.

The second day, however, was the opposite. It poured rain for most of the morning, drizzled for the rest of the day, and a low fog lingered over the city.

When I recently visited Chicago in September it was gorgeous, with just a little rain and the occasional fierce wind. I primarily wore jeans, a light jacket, and sneakers.

So now that you know how unpredictable Chicago can be, what should you pack for fall in Chicago?

What to Pack for Chicago

This should go without saying but check the weather before you go. If you are visiting in early fall, you likely will not need everything on this list.

Packing List for Chicago – Cold Weather

Packable Down Jacket

I recommend bringing a packable down jacket. This one is warm and it shrinks down when you roll it up so it packs really well! If it is very cold and rainy, layer a down jacket under a longer, waterproof jacket with a hood like this one (paid link). This is what I did for my visit in November and I was warm and dry, even when the weather turned. 

Hats, Scarves, and Gloves

I wore all of these in early November, so if it is later in the season, it might be even colder. Scarves are one of my favorite accessories because they keep you warm but are also cute (paid link)!

Boots

Boots are my favorite cold-weather attire. My leather riding boots kept my feet warm and comfortable on the soggy Chicago streets. Just make sure you bring a pair that is already broken in since you will be primarily exploring the city via trains and walking. If you have a pair of boots with decent tread that is also a good idea.

Read More: Plan the perfect weekend trip to NYC during the Holidays

Warm Socks

These Smart Wool socks will keep your feet so warm when slogging through those city puddles (paid link).

Fleece Leggings or Base Layer

My best advice for you when traveling to cold destinations is to wear fleece leggings or a base layer. Wear these merino wool base layer leggings under your jeans or try out these fleece leggings. They make such a difference! If it is really cold, a base layer top is also great to pack (paid links).

Packing List for Chicago  – All Seasons

Umbrella

Get a travel umbrella that is light and easy to carry. It’s always good to have even if you may not use it. I like this one because it’s small enough to keep in my purse (paid link). When I visited in September, even though it wasn’t cold it still rained on and off one of the days.

Sunglasses

Sometimes the sun decides to peak through those clouds even when it is chilly, sunglasses are always a good idea (paid link).

Cross-body bag

In a big city like Chicago, you should always be aware of theft. I feel safer carrying a cross-body bag so that if someone tries to grab it, hopefully, it will be more difficult (paid link). They are also usually smaller and lighter, which I prefer when I am adventuring all over a city.

Travel Backpack

Investing in a good travel backpack will make your life so much easier. Do it sooner rather than later unlike I did. I have two backpacks from Osprey that I like, depending on the length of the trip and the type of plane ticket booked.

I used this backpack for Chicago because it is small enough to fit under the seat as a personal item. The 55 L backpack is too large to fit under the seat but works well as a carry-on and comes with this handy detachable day pack for when you reach your destination (paid links).

Travel Entertainment

I always bring some form of entertainment for the plane, even when I am packing light. You never know when you might get stuck or delayed and need something to do. When packing light, I leave my big noise-canceling headphones at home and bring my Airpods for the plane. I love to travel with a Kindle because that gives me access to more books without taking up all of the space in my bag (paid links). 

How to Pack in a Personal Item or Carry-On

Do you ever score a cheap flight only to panic that you have to pay as much or more than the flight to bring a carry-on? It is possible to pack everything you need for a weekend trip in a personal item-sized backpack (I have done it many times), but it is difficult. This can be especially tricky when packing for colder destinations. 

Regardless, here are some tips for packing in a personal item (or if you are lucky, a carry-on).

If you need to bring more than one jacket, which is sometimes necessary for unpredictable weather, I recommend wearing one on the plane or carrying it through the airport. As annoying as this sounds, two jackets can easily take up most of a personal item. Plus, they make good blankets/pillows on the plane. 

Try to limit yourself to one pair of jeans for a weekend. Often I will wear my bulky clothes on the plane, usually jeans, so you might be able to squeeze in another pair. 

Also, try to minimize the number of shoes you bring. When I pack in a small backpack I usually bring two pairs, a dressier pair and a casual pair. Again I will try and wear the bulkier ones on the plane.

Hopefully, that leaves some room in your backpack for a couple of shirts to mix up your look, another pair of shoes, socks, underwear, a beanie, gloves, a scarf or two, and toiletries. I try to make sure all the clothing I bring goes well together so I can mix and match the same pieces. 

Toiletries should also be limited, as most AirBnBs or hotels will provide these things or you can always buy anything you couldn’t fit once you get there. 

What to do in Chicago with Bad Weather

No matter how well you plan, you can’t control the weather. Sometimes, you are going to have to change your plans because of bad weather. Of course, I always recommend trying to brave the cold/wind/rain as much as possible, because you only get so much time, right? But often it is better to squeeze in some of those indoor activities while the weather beats on outside. Here are some tips to optimize Chicago attractions to avoid adventuring in the cold.

Chicago has so many museums and this is the perfect time to discover them. The most recent time I visited Chicago, we went to the Driehaus Museum, a 19th-century restored mansion, which I highly recommend.

The Art Institute, Field Museum, and the Shedd Aquarium are popular indoor activities in Chicago. If you are planning to visit these attractions, you can save time and money with the Chicago City Pass, which saves you 48% at the top five Chicago attractions!

Attractions including the Skydeck or 360 Chicago may be less enjoyable in the fog. Plan to visit these attractions when it’s sunny if you can so you have good visibility.

Plan to make stops for coffee, tea, drinks, or donuts when it’s cold or rainy. We spent some of our weekend warming up at Argo Tea.

Take the train whenever you can to avoid the weather.

I hope these tips help you to pack for fall in Chicago so you can get the most out of your trip!

Tell me your best packing tips for autumn in Chicago below!

Planning a weekend trip to Chicago? Check out this perfect weekend itinerary!

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