{2024} The Ultimate Guide to Packing for Chicago in October

Wondering what to pack for a trip to Chicago in October? Your favorite packing expert has rounded up yer favorite fall finds for a trip to the Windy City in the coziest time of year.

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Packing for a trip to Chicago this October?

Hailing from just 'down the road' (well, I-65, which is actually the world's worst road), in Indianapolis, I've been taking a yearly Fall trip to Chicago ever since I was a kid. 


A lovely chill in the air, few crowds, changing leaves, and still with everything open and available, you can't beat October in Chicago. It's the perfect time to explore a great city. I wouldn't advocate a January trip, unless you are significantly heartier than your author. Summer in Chicago is lovely, but, unsurprisingly, you can expect significant crowds and some sweaty days walking up The Magnificent Mile.


We're getting ready for our trip in a few weeks, so I thought I'd round up some of my best tips for packing for a trip to Chicago in the lovely, windy, chilly October.

Looking for fun things to do? Check out my recommendations of Fun Things to Do in Chicago for Couples

FAQs: What to Wear in Chicago in October

FAQ: It is cold in Chicago in October?

For me, I'd say the weather in Chicago in October is perfect. You'll definitely want a heavier coat, as the average temperature in Chicago in October is 62/50.

FAQ: Should I bring my winter coat to Chicago in October?

The is a bracing breeze off of Lake Michigan that can take the unprepared by surprise! If you're planning on morning and evening outings by the Lake, you'll definitely want a coat, though it's not quite Canada Goose season.

October in Chicago: Rules to Dress By

Paint it black

You'll never go wrong wearing black in Chicago, even as early in the season as October.

Casual caps

Not unlike another of my favorite cities, San Francisco, you're always 'on trend' in a baseball cap in Chicago. I actually bought one at the J Crew on Michigan Ave last visit because I had forgotten mine. No logos or slogans, please.

Layers...but not too many

You'll definitely want to wear in layers for October in Chicago, but with all the walking you'll be doing as a tourist, I'd caution against too many layers. I've spent many an afternoon in the Windy City praying for a bit of wind, or grabbing a perfume sample to freshen up before dinner when I really shouldn't have worn that many sweaters. It's likely not as cold as you're thinking it might be.

A cashmere scarf ​

One of the staples of Chicago style is, and always has been, a cashmere scarf. If you're spending time in the Gold Coast, maybe you'll add one to your wardrobe. 

Lakeside chic

You can never go wrong with boat shoes in nautical Chicago! Though, you're never supposed to wear them with socks and your feet might get chilly in October! Maybe save the top sides for your summer wardrobe.

Midwestern Casual

As you're here, you're obviously doing your homework and planning your Chicago packing list in advance! But don't stress too much about encountering dress codes during your time in Chicago. We Midwesterners are a casual group.
That said, it's a good idea to bring one pair of non-sneaker shoes and one pair of non-denim pants, if you're going to be dining at any very high-end restaurants.

{2024} The Ultimate Guide to Packing for Chicago in October {2024}

Alright, let's dive right in! Here are the items you'll need in Chicago this October!

Your most comfortable walking shoes

As with most city trips, comfortable walking shoes are a must. While you can certainly snag a cab anytime you like, I'm a huge fan of walking up and down Michigan Avenue on my own - all the way from Bloomingdales down to the Art Institute of Chicago (gasp!)


To account for Chicago weather, I would generally recommend bringing as many as needed out of these three categories of shoes, for your trip to Chicago in October:


1. Sneakers
A good pair of sneakers will serve you well all day for indoor and outdoor activities. While you will see tourists doing their tourist thing, don't bring the sneakers you wear to mow the lawn, if you want to look like a local. I'd stick with a lower profile sneaker (solid white sneakers are also fine).


2. A pair of boots (Knee-high boots or booties/ankle boots)
For days of walking and shopping, the shoe that'll take you all the way to dinner is the reliable boot or bootie. Black or brown, you can't go wrong. I wouldn't pack rain boots for exploring Chicago. They aren't chic and they're incredibly difficult to walk in. Just make sure you have one pair of boots/booties that won't get trashed if it rains.


3. Loafers
Though you may not want to wear them for a big tourism day, or in the event of very cold weather, loafers are great for less heavy walking days in Chicago, and for evening events and a nicer restaurant. Don't you dare wear loafers that aren't broken in. Just don't do it.

The perfect purse for Fall in Chicago

While your instinct might be to bring your largest, most expensive tote back to haul around all of your possessions in October, I would fight that impulse.


You want the purse you bring to Chicago to be lightweight, hands-free, and to close fully. A leather crossbody bag is my go-to. And if it rains, you can tuck it under your jacket to keep it dry.


Feeling fancy?
Feel free to bring your designer bag!
Just make sure it zips.
​Pickpocket experts also recommend against a hand-held bag, because it's just too easy to snatch. I never want tourists in any city I discuss to be too paranoid, but you do want to be smart. Not to mention, how can you shop when your hands are tied up with your existing purse the whole time? Super annoying.

The right pants

As far as packing pants for your time in Chicago, I'd include a couple:


First, obviously a good pair of nice dark jeans. That's likely what you'll wear the most. They're the right weight for the temperatures you can expect in Chicago in October, even if you encounter a surprise hot day, and they're welcome basically everywhere in the city.


In addition the pair of jeans, I'd also bring some joggers and probably at least one pair of black leggings.

Medium-weight tops

Under your light jacket you'll want a few long sleeve, medium-weight or even light-weight tops for day-to-day wear in Chicago.


I'd stick with cotton, as a merino wool sweater under your jacket might be a bit too heavy for a full day of walking. If you have your heart set on a cashmere sweater, I'd say leave the jacket at home and layer with a button-up Oxford shirt for a tourist day, or save the sweater for dinner.

Versitile accessories

Pack the athleisure

As with most large American cities, the athleisure craze has definitely taken hold in Chicago. That said, I'd stick to darker colors for October. You definitely do not want anything midriff revealing, as you'll have a cold tummy. And if you are leaning into athleisure for your daytime activities in Chicago, I would make it a bit elevated, if you'll be shopping at high-end stores.

A Light-ish Jacket

One of the most important items you'll pack for your trip to Chicago in October is your light jacket. Not only will it keep (or NOT keep) you comfortable during your time exploring the Windy City, but it'll also be the only thing most people will see of your outfit during your trip! 


A trench coat or quilted jacket are the best options, in my opinion. As we discussed earlier, it won't be cold enough for a winter coat, and you'll just end up sweating. A jacket that will keep the wind away, but that you can easily carry if you want to take it off, will meet all of your needs.


It's not London, so I wouldn't worry too much about an actually waterproof jacket unless you're looking at a very dire forecast. I would pack a small, foldable travel umbrella, which I recommend when visiting any city.

Day-to-Night Dresses

I would include a simple dress or two in my Chicago suitcase. I generally wear an easy dress for at least one dinner during my visit. There will be days that are warm enough to wear a dress during the day, but I would be sure to include leggings/tights in your suitcase if you're planning to wear dresses much during your stay. That breeze off the Lake can be chilly, even in the heart of Downtown Chicago!

October in Chicago Packing List
​{Long Weekend}

• Jacket
• Scarf
• Small, foldable umbrella
• Crossbody bag
• Sneakers
• Boots/booties/ankle boots
• (optional) Loafers
• 2 light weight tops
• 1 sweater
• Pair of jeans
• Pair of travel pants
• Pair of leggings
• Dress
• Socks/underwear
• Cosmetics & hair products

Thanks for stopping by!

I so appreciate you coming by the blog to help you plan your time in Chicago! I hope you have a wonderful time. And while you're planning your trip, why not check out my other (excellent) Chicago travel guides:

• A Weekend in Chicago
• {Hotel Review} The Viceroy Hotel, Chicago
• {Hotel Review} The Drake Hotel, Chicago
• 8+ Great Midwestern Road Trips

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