Chicago in the Fall is one of the best times to visit. Not only is fall fashion my favorite, but the city itself is gorgeous. Changing of the leaves are beautiful and the temperatures, muah, perfect! Here is what you should pack for Chicago in the fall.
I love the colder temperatures because I love sweaters and layers. The style to me is better. Then again, I live in the desert where summers are dreadful.
It’s nice to travel to a colder place where beanies, scarves and cozy sweaters are acceptable and necessary. Average temperatures in Chicago in October are high 62 degrees and low 50 degrees Fahrenheit.
Though my trip was limited to a long weekend, we still managed to do a ton of great things. We mainly explored the Loop and briefly ventured into Andersonville. More of that in this post.
I highly recommend a Fall trip to Chicago. And when you go, make sure to pack these cute and cozy essentials.
Most everything on this list is the exact items I brought with me. Some items I couldn’t find online anywhere, so I gave you a similar alternative.
Table of Contents
Is Chicago Safe to Visit?
The question on every visitor’s mind is, “Is Chicago Safe?”. And the answer. . .
When you’re visiting Chicago: avoid the South Side, pay attention to your surroundings, don’t wander back alleys late at night, don’t talk smack about their sports teams.
How to Pack for Cold Weather in a Carry On
3 Words: Get Packing Cubes!
Ever since my luggage got lost, I’m hesitant to check a bag unless I absolutely need to. Even then, I’m fighting it. So of course, I packed for a weekend trip in just a carry-on. The only downside to off-season travel is packing tends to be more challenging. Goodbye thin, easy to roll, summer dresses, hello bulky sweaters, that take up an entire corner of your carry-on.
Here’s how to pack for cold weather in a carry-on like a boss:
Step 1: Get a variety of packing cubes: a small one for undies and socks, big ones for outfits, an extra one for dirty clothes, shoes, etc.
Step 2: Using the largest packing cube – stack your daily outfits on top of each other and roll. If not, roll your garments separately and place them in the packing cube.
Step 3: Place your folded twice sweaters on top of your clothes. Wear your thickest jacket on the plane if needed.
Step 4: Sit, Zip, Breathe
Bonus Step: Make sure to check-in to your flight asap. The sooner you board the more likely you are to have space in the overhead bin for your luggage.
Now, here’s what to pack for Chicago in Fall.
This is what I wore on the flight to Chicago. It’s super comfy and kept me warm the entire time. Plus, nothing wrong with showing a little skin.
A nice and toasty orange turtleneck is perfect for Fall. I’m pretty sure this shade was invented for fall. Just throwing it out there.
If you’ve read any of my other packing guides, which I hope you have, then you know stripes are easily my favorite look. This shirt is one of the top favs.
Between the stripes and beanie, I was beginning to feel like Where’s Waldo’s cousin. You know, the one that wears yellow instead of red?
The overall theme: Jeans.
What else are you supposed to wear? Or, am I just jeans kinda gal? If you are too them check these good-looking bottoms out.
I wear these black jeans so much someone needs to ban me for a month or so. Maybe then will my wardrobe game get better.
I love the contrast between dark jeans and colorful tops. I wore these with my striped tee and yellow down vest.
Because you need a light pair too, especially with black and white tops. Duh!
This maxi dress was debuted towards the end of summer on my Instagram, which by the way you should follow me. I’m always sharing my latest adventures and more!
I wasn’t kidding when I said it’s my new favorite dress. I’ve worn it at least a dozen times since. The sleeves are mid-length too, which kept me plenty warm most of the day
And yes, it comes with not one but two pockets!!
I always carry one or two extra pieces with me just in case there’s a spill or I suddenly lose interest in my other options. Only if space allows for it, which in this case, it did. Sadly, I never got around to wearing it but did try it on. It fits amazing.
Jackets & Sweaters
This jacket will keep you warm ANYWHERE! Promise.
It’s actually my second one. The first one got stolen from Buca Di Beppo. I hope the person who took it loves it as much as I did.
I mostly wore this on the plane and inside if I got cold. The dark green shade is so pretty for fall. Looks great in outdoor pictures.
This is my go-to fall jacket. The neutral tones and deep pockets on both sides scream practical, goes with every fall outfit.
What I love most is that it’s thin so it’s easy to layer and it rolls nicely for packing.
Sadly, this raincoat isn’t the exact one I have, because I bought mine years ago.
Raincoats don’t serve much use in Las Vegas, but I had to have it. I knew one day it would come in use and so far it has many times.
So this one is a light pink look-a-like.
The weather in Chicago in October has its rainy days. When I was there, two of the days had rain. Fortunately, the heaviest rainfall was on the day we left.
I wouldn’t recommend bringing a ton of waterproof stuff. A raincoat will do. That is, of course, if the forecast predicts rain. Check the weather forecast the week leading up to your trip.
Shoes to Keep Your Feet Warm
Boots, boots, boots galore. I think Boots are starting to become my favorite.
Of course, I love heels so some of these give you height, look sexy, go with everything (neutral colors woohoo). The heel is wide enough so you don’t trip on those street cracks.
Some of the streets in Chicago are in desperate need of a facelift.
These are my go-to boots for a night out on the town. I don’t prefer to spend a ton on ever day shoes because they get so beat up. These are comfy and affordable.
Every day walking around the city boots. I will be real with you an say they aren’t the best at keeping your toesies warm, so wear thick socks if you get easily cold feet. I think that speaks for most women.
Honestly, these boots have the tallest heel but are so comfy. I think when it comes to heels, the key to comfy happy self, is to get a shoe with a front heel. That way your foot is a little flatter.
Cold Weather Accessories
A scarf is a no-brainer. It’s amazing what a difference a scarf makes. This one comes in all different colors!
Beanies are the best way to stay warm. Plus, the ones with the pom poms on top are just too cute.
I’m growing fond of hats. This one especially.
I love a sleek watch. Plus, I hate digging for my phone to check the time.
Fall Travel Essentials
This is a must if you plan on being out all day. I generally don’t return to the hotel till before dinner, so having a proper day bag is essential. Did I mention this one has cool safety features in it?
My boyfriend and his Italian ways got me hooked on this super moisturizing lip balm. A must for windy days outside.
My nose, hands, and lips get so dry in the colder months. Maybe it’s because my showers get hotter. Either way, they crack and hurt; therefore, lotion and chapstick are crucial!
Not going to lie, I was so busy having fun around Chicago that I barely took any photos. Sorry, I don’t have more photos to show you with various outfits on. Hopefully, you found this post useful in helping you pack for Chicago.
Psst. . . Looking for more fashion guides? Check out these posts:
Do you carry on your luggage or check more? Share your story in the comments below!
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