What To Wear in Chicago in the Fall: Chicago Outfit Ideas

If you are looking for suggestions on what to wear in Chicago in the fall, then you have come to the right place!

Fall in Chicago is quite amazing with the autumn colors and plenty of outdoor activities and festivals to enjoy.

However, fall weather in the Windy City can be unpredictable as it can fluctuate between warm and sunny to cool and breezy in a short span.

In this guide, I’ll not only share with you what to expect from fall weather but also what to wear in Chicago in September, October, and November.

Ready to get started?

Well, then keep reading my guide on What to Wear in Chicago in the Fall for the Best Chicago Outfit Ideas!

What To Wear in Chicago in the Fall: Chicago Outfit Ideas

Chicago Weather in the Fall

Fall in Chicago is truly magical!

With golden leaves, crisp air, and plenty of activities to enjoy, this is indeed a great time to visit Chicago.

So, what to expect in terms of weather in Chicago during the fall season?

Well, the city sees a gradual drop in temperature and it becomes even more windy, making it colder than usual. Here’s a month-by-month overview of what to expect during your fall vacation in Chicago:

• September: This is the best month for anyone who doesn’t like the cold and wants to enjoy the autumn vibe as well. The weather is mild and pleasant, with temperatures ranging from 60°F to 75°F (16°C-24°C). You will still get summer feels at the start of the month while the end of September feels cooler, especially in the evening.
• October: If you want cool yet comfortable weather to visit Chicago, then October is perfect for you! The temperature averages 50°F to 65°F (10°C-18°C) and the fall foliage is at its peak.
• November: This is the month when the city gets chilly, with temperatures ranging between 45°F-55°F (7°C-13°C) and 30°F or lower (0°C-4°C). Plus, rainfall can occur with the chance of first frost.

Don’t worry, if you know how to dress for fall in Chicago, then you can enjoy your trip without being crippled by the cold.

Tips for Choosing the Right Fall Outfit

• Layer Smartly: Of course, layers will be your best friend when you are choosing your Chicago fall outfits. This will help you to add or remove the layers when the temperature fluctuates.
• Stay Comfortable: Whether you are planning to stroll around Millennium Park or through the Art Institute, make sure to wear comfy outfits for fall.
• Adopt Fall Colors: Trust me, this is the best time to fall colors in your wardrobe. Burgundy, olive, navy, etc. are a few options that go amazingly with the fall foliage in Chicago.
• Stay Ready for Rain: Don’t forget to keep a compact umbrella and wear waterproof shoes so that you are always prepared for unexpected showers.

What to Wear in Chicago in September

Let’s get started with what you can wear in Chicago in September.

The temperature is still on the higher side, compared to the winters, with the maximum at 70°F-75°F (21°C-24°C) and the lowest at 55°F-60°F (13°C-16°C).

Plus, there are chances of occasional showers and cooler evenings.

Since September is a mixture of warm and cool breezes, you have plenty of Chicago fall outfits to choose from.

Clothing Recommendations

• Tops: Since the weather is still mild and pleasant, you can make the most of your lightweight blouses and cotton shirts. If you feel cold, then long-sleeved tops work well too.
• Bottoms: For bottomwear, I find denim jeans and shorts a great choice for September. Add a midi skirt and you have one of the perfect date outfits for fall.
• Outerwear: The evenings can be a bit cooler, which is why I recommend adding a light jacket or cardigan as a layer to your outfit.
• Shoes: To stay comfortable in the fall, the best options for footwear would be ankle boots, sneakers, or ballet flats.
• Accessories: To complete the look for your chic outfits for fall, you can wear scarves and sunglasses for flair and functionality.

Chicago Outfit Ideas for September

You can also head to the famous Riot Fest, a punk rock music festival, which is one of the best things to do in Chicago in the Fall.

For this event, you can wear a graphic tee with ripped jeans and a faux leather jacket along with some combat boots. Trust me, this is one of the top cool outfits for fall.

If you want to enjoy the autumn colors in the parks of Chicago in fall, then you can wear a long-sleeved blouse with black jeans and pair it with boots.

Add a scarf to accessorize while keeping your neck warm in the evenings.

What to Wear in Chicago in October

Are you looking for October outfits to wear in Chicago?

Well, then let’s see what to expect from October first.

As I mentioned before, October is slightly cooler than September and the fall foliage is at its peak right now. It’s the perfect time to enjoy cozy layers and autumnal hues.

You will notice the temperature ranges between 55°F-65°F (13°C-18°C) and 45°F-50°F (7°C-10°C). The weather is mostly cool and dry with a slight breeze and plenty of fall colors around.

Fall is the best time to eat some of the best pizza in Chicago!

Clothing Recommendations

• Tops: As October ushers the cold, I would suggest you wear long-sleeved sweaters, turtlenecks, or flannel shirts for both comfort and style.
• Bottoms: For the lower, you can wear pleated skirts with tights or corduroy pants. This will keep you warm but not mess with the aesthetics of your October outfits.
• Outerwear: Add another layer of trench coat, wool blazer, or lightweight parka for warmth and comfort.
• Shoes: To keep your feet warm, faux leather boots or sneakers work best for fall.
• Accessories: Lastly, accessorize your fall outfit with a beanie, a knit scarf, or a cross-body bag. Do keep a compact umbrella also for protection from unexpected rain.

Chicago Outfit Ideas for October

If you end up spending Halloween in Chicago, then I have the perfect outfit for you, especially if you are not into the kids’ costumes.

You can wear a black turtleneck with pumpkin or star patterns, faux leather leggings, and a long trench coat with ankle boots. Add an orange/rust scarf with a tote in tan to complete the autumn look.

For exploring the markets in Chicago in October, I would suggest you wear plaid accents in red or orange tones with a denim midi skirt paired with tights.

Wear brown moccasins and a quilted vest and accessorize the outfit with gold jewelry and a crossbody bag.

What to Wear in Chicago in November

November is the last month of fall in Chicago after which winter officially arrives in the windy city.

This is why it is also the coldest of all fall months with shorter and rainier days.

The temperature is cold with the highs being at 45°F-45°F (7°C-13°C) and 30°F-40°F (-1°C-10°C). It can get quite chilly with occasional rain and frost this month.

So, if you want to enjoy exploring Chicago in November, then layering becomes essential to stay warm.

Here are some of my recommendations if you are spending the weekend in Chicago.

Clothing Recommendations

• Tops: The best option for staying warm yet stylish in November is wearing knit sweaters and thermal tops.
• Bottoms: You can pair the tops and sweaters with thick leggings, wool pants, or dark-wash jeans.
• Outerwear: Further, add a layer of a wool coat or quilted jacket to stay warm. If you are more susceptible to cold, then you can add a puffer jacket for extra warmth.
• Shoes: In footwear, insulated sneakers and waterproof boots with thick warm socks are good choice for this month
• Accessories: Finally, don’t forget to wear gloves, knit hats, and a warm scarf to stay warm amidst the chilly, breezy weather.

Chicago Outfit Ideas for November

One of the best parts about visiting Chicago in November is that you can attend the Magnificent Mile Lights Festival!

Watch the tree-lighting parade and fireworks while wearing a sweater dress with knee-high boots and a chic wool coat over it.

Do wear a knit scarf and gloves to stay warm while enjoying the holiday-themed activities.

If you are planning to visit the Art Institute of Chicago, you can wear a chunky knit sweater with corduroy pants and a belted trench coat.

Style it up with Chelsea boots, a patterned scarf, and a tote bag to carry your essentials.

What To Wear In Chicago In Autumn Packing List

If you will be traveling, either by plane or by car to Chicago, here are some tips on how to pack lightly.

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday. It is made of lightweight aluminum and so easy to use.

I never leave home on a trip without my Bobble filtration bottle. The 18.5-ounce size is perfect for when exploring.

And the replacement carbon filter ensures fresh clean water whenever you fill the Bobble.

Then this collapsible silicone foldable water bottle would work well for you as well.

This foldable water-resistant backpack would be great.

Not all beaches are created equally and these quick dry slip-on Aqua shoes will come in handy for pebbly Chicago beaches.

These men’s quick dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in a lot of lens colors and frame designs and are extremely affordable too.

If you are fond of aviator-style sunglasses these polarized aviators may interest you.

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Read my suggestions on the best things to do in Chicago.