What to Pack for Chicago in the Fall

Last updated on February 7th, 2024 at 11:34 pm

We’ve all heard about how cold it gets in Chicago. I pictured 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. 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.

Weather in Chicago

The beginning of fall in Chicago is not terribly cold, 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 still warm and humid.

Snow is uncommon during this time of year, but does happen 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 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

The first day 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 absolutely 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 your trip?

What to Pack for Chicago

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

Packing List for Chicago – Cold Weather

Layers

I brought only long sleeves for my trip in November, a warm down jacket, and a longer jacket with a hood to wear over it (paid link). The first day I was fine with just the down jacket, but the second day I wore both. If you have a single warm jacket that has a hood, that would probably also work. However, if the sun comes out and you’re walking around it can get warm.

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

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

Smart Wool Socks

These socks will keep your feet so much warmer when you are slogging through those city puddles (paid link).

Fleece Leggings

These are one of my favorite travel accessories. Wear these leggings under your jeans and they make such a difference (paid link).

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 one for Chicago because it is small enough to fit under the seat. 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).

How to pack in a Carry On

This can be tricky the colder your destination and I absolutely had this problem in Chicago. This was in the early days of travel, so I was still using my old college backpack as a carry-on. My life would have been so much easier if I had invested in a decent travel backpack earlier, see above for my options.

Usually if I am bringing two jackets, which I often do because I’m always cold, I will try and pack the larger one and plan to wear or carry the other through the airport. I limit myself to one pair of jeans for a weekend and often I will wear my fleece leggings on the plane because they are so comfy.

I try to limit myself to two pairs of shoes as well, usually one a little dressier and one more casual, so 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, hat, gloves, a scarf or two, and toiletries. Toiletries should also be limited, as most AirBnBs or hotels will provide these things.

I always find room in my backpack for my extra light weight noise cancelling headphones – they make the plane ride so much better (paid link).

What to do in Chicago with bad weather:

It happens so often when I’m traveling that the weather turns nasty and all the activities we planned to do that day are ruined. 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 and the Field Museum are popular museums and if you are planning to visit both of these attractions, you can save time and money with the Chicago City Pass.
• The Shedd Aquarium is another option for avoiding the outdoors and one of the more impressive aquariums I have visited.
• Attractions including the Skydeck, 360 Chicago, or the Signature Lounge 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.

These tips helped me make the best of my short weekend despite the weather.

Tell me your best packing tips for Chicago below!

Planning a trip to Chicago? Check out my weekend itinerary.

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