Chicago November Outfits & Packing

Chicago in November is cold, gray, and windy. But the city is beautiful this month, and the holiday season is starting. You just need the right clothes.

This guide was written by Caroline, our Chicago local. She was born and raised there and still lives in this wonderful city.

These are the travel guides we strongly recommend:

Here is what you will find below:

• November Weather Overview (temperatures, wind, rain, snow, daylight)
• The Layer System that works in this city
• What to Wear | Outfits | Packing List
• Outfit Ideas for Each Activity (boat tour, parade, Christmas markets, dinner)
• What NOT to Pack
• Local Tips most visitors never hear 💡

The short answer: I highly recommend bringing a warm water-resistant coat with a hood, thin layers you can add and remove. Also, waterproof shoes, and a hat, scarf and gloves. The wind is the real challenge in Chicago, not the temps. More details below.

Weather Overview

Chicago in November weather is cool and crisp, with average high temperatures between 43°F (6°C) and 56°F (13°C). With an average rainfall of 10 days this month, you can expect the weather to be wet, cloudy, and windy. However, it’s a great time for checking out the holiday lights.

Average Temperature

Chicago in November begins with an average high of 56°F at the beginning of the month and a 43°F average at the end. While the beginning of the month still feels reminiscent of fall, the cooler temperatures at the end of the month are a sure sign winter is underway.

In the mornings, you’ll find chilly temperatures in the low 40s. I often need to toss on a sweater or hoodie to walk around the house to avoid a chill in the morning. Since November is a rather cloudy month, it’s the perfect time to sit by the fire and sip a hot cup of cider in the mornings or evenings. The November temps are slightly higher mid-day, staying around the high 40s.

Typical temperature progression during a day in November:

• Morning (8 AM): 44°F
• Afternoon (3 PM): 49°F
• Evening (9 PM): 46°F

During November, the weather is quite unpredictable. On some days, you’ll find crisp autumn weather. On other days, it is rainy (or snowy) and cloudy. You may even experience a few days which are a combination of sunny, cloudy, and snowy/rainy.

Because of the unpredictable weather, most Chicagoans will bring extra socks and wear water-resistant items (shoes/jackets) to help them stay warm while out and about. It’s not uncommon to see locals wearing gloves, hats, and thicker layers like flannel shirts as well during this month. 💡 More about clothing later!

On chillier and wetter days in November, I often stop in a café to grab a warm drink and sit in the heat to dry off for an hour or two. I usually seek locations with a warm fire to help keep me toasty. These stops are always a good excuse to try the fall/winter-themed drinks at the local coffee shops.

Average high temperatures in November:

• Early November: 56°F (13°C)
• Mid-November: 50°F (10°C)
• Late November: 43°F (6°C)

Rainfall

Chicago gets about 2.7″ (69 mm) of precipitation in November, spread over about 10 days with rain or snow. So roughly one out of every three days is wet. As mentioned, the weather is quite unpredictable this month. Chicagoans will carry an umbrella, thicker coat, and extra dry layers on these days.

The rain here is usually not heavy. It is more of a cold drizzle that goes on for hours. That is worse for you, because everything slowly gets damp.

How Cold Does It Really Get?

The average numbers do not tell you the whole story. Here is what a normal November in Chicago looks like:

• 12 nights drop to freezing (32°F / 0°C) or below
• 2 nights drop to 20°F (-7°C) or below
• 2 full days stay below freezing all day long
• But there are also about 6 days that reach into the 60s (over 16°C)

So you can get a warm afternoon in a light jacket and a freezing night in the same week. This is why one thick coat is not enough. You need layers.

💨 The Wind | This Is the Important Part

Most packing lists for Chicago talk about temperature. That is a mistake. The wind is what makes you cold here.

The average wind speed in November is about 11 mph (18 kph), and November is one of the windiest months of the whole year in Chicago. That does not sound dramatic. But in the city it feels much stronger.

Why the wind feels so bad downtown:

• Lake Michigan is huge and flat. Nothing stops the wind before it hits the city.
• The tall buildings push the wind down into the streets. Some corners in the Loop are like a tunnel.
• The open plazas (Millennium Park, Daley Plaza, the lakefront path) have no protection at all.

A local from Chicago told a visitor on a travel forum that late November days are often in the 40s and low 50s, with nights between 20°F and 35°F, and that the wind will make it feel much colder than that. A 45°F day with strong wind feels like 32°F.

What this means for your clothes: Your outer layer must block wind. A thick wool coat that lets wind through will not keep you warm. A thinner jacket that blocks wind will.

💡 Local trick: The wind is worst in open areas, in narrow streets between tall buildings, and anywhere close to the lake. If you are walking a long distance downtown, pick a street one or two blocks away from the lakefront. It really makes a difference.

ESSENTIAL: Windproof Jackets on Amazon

Snow

Yes, it can snow in Chicago in November. This surprises many visitors.

The average snowfall for the month is about 1.8 inches (about 4 cm), on about 2 days. Some years there is no snow at all in November. Other years there is a lot. In one November, a single storm dropped more than 11 inches at O’Hare Airport.

Good to know: November snow in the city usually does not stay on the ground. It turns into gray slush within hours. So you do not need heavy snow boots. You need shoes that keep water out.

Gray Skies and Short Days

This is something most articles do not tell you. November is the cloudiest month of the year in Chicago. The sun only shines about 38% of the daylight hours.

The days are also short:

• November 1: about 10 hours and 20 minutes of daylight
• End of November: about 9 hours and 25 minutes

It gets dark around 4:30 PM at the end of the month. That means you will be outside in the dark and cold in the late afternoon, not just in the evening. Plan your outdoor activities for the middle of the day.

Two more things because of the gray weather:

• Dark colors look flat in photos this month. If you want good pictures, bring one bright piece (a red scarf, a mustard hat, a camel coat).
• The morning humidity is around 80%. Damp cold feels colder than dry cold. Wool works, cotton does not.

⚠️ Early November vs. Late November

This is a big difference and you should pack for the right half of the month.

Early November (1–10): Highs around 55°F. It still feels like fall. A medium jacket, a sweater and jeans are usually enough during the day. You might not need gloves.

Mid November (11–20): Highs around 50°F. This is the change-over period. Some days feel like fall, others feel like winter. Pack for both.

Late November (21–30): Highs around 42°F, nights near or below freezing. This is winter. You need a proper warm coat, a hat, gloves and a scarf. This is also when the holiday markets and light events start, and those are outdoor events.

⚠️ Be honest with yourself about November in Chicago: This month is a gamble. There have been Novembers with a week of 70°F days in a row. There have also been Novembers where the first half was the coldest in almost 150 years. Nobody can tell you in advance which one you will get. Check the forecast 3 days before you fly and pack for the colder option.

The Layer System That Works in Chicago

Forget the idea of one big warm coat. It does not work here, because you go in and out all day long. The trains, museums, restaurants and shops are heated very strongly. You will sweat inside and then freeze outside.

Use three layers instead:

1. Base layer (against your skin): A thin thermal top, long johns, or a long-sleeve merino shirt. This is the layer most visitors skip, and it is the one that makes the biggest difference. A traveler asked on a forum if jeans are warm enough for late November in Chicago. The best answer from a local: jeans work fine if you wear thin long johns underneath.

2. Mid layer (the warm one): A wool or fleece sweater, a cardigan, or a hoodie. This is the layer you take off inside.

3. Outer layer (the shield): A coat or jacket that blocks wind and water. This layer does not need to be very thick. It needs to be windproof.

SHOP NOW: Thermal Base Layers on Amazon

💡 One visitor on a forum asked whether to bring a pea coat or a technical shell. A user answered: put a windbreaker over a hoodie and another warm layer, and you are fine even in the wind. This is how locals dress. Thin layers beat one bulky coat, every time.

What to Wear | Outfits | Packing List

As November is cold and wet in Chicago, pack water-resistant winter or rain boots. Wear layers, like sweaters, long Johns, long-sleeve t-shirts, and extra socks so that you can stay warm and dry during your visit.

If possible, select a hotel or Airbnb with a washer/dryer to always have at least 1-2 warm/dry layers.

💡 In November, it’s best to bring as many extra layers as possible.

In early November, I typically wear a sweater, jacket, jeans, and boots or sneakers (depending on the day’s activities).

As the month continues, I transition into thicker layers to stay warm (like other Chicagoans). If the weather happens to be warmer and sunny, I may skip the jacket and simply wear a thicker sweater.

Morning/Evening

During a visit to Chicago in November, you’ll want to bring clothes for fall/winter weather. A thick jacket is necessary for the chilly mornings and evenings. A water-resistant windbreaker is a great option to have on hand, as Chicago is known for being particularly windy during this month.

ESSENTIAL: Windbreaker on Amazon

💡 As the mornings are generally in the 40s in November, you’ll want to wear long Johns, a long-sleeved t-shirt, and thick fleece-lined pants/sweatshirts. Remember to bring a thick coat with you, which has a hood to help keep the wind off your face.

As a child, I often was ill-prepared with shoes during winter due to the unpredictable weather. Once, I wore flip-flops in November, and my parents had to purchase socks and shoes to keep my feet warm while exploring the city. After that, we could not visit the city in the winter without a proper sock/shoe check before leaving the house.

Daytime

During the daytime, the weather in Chicago is slightly warmer. However, you will still likely need a few layers to stay warm. If you plan to visit indoor attractions, ensure you wear easy-to-remove layers, as most museums and similar activities keep the temperature toasty.

If possible, carry a backpack with you to hold your extra layers while you’re indoors. A backpack is also great for storing additional dry layers on rainy/snowy days. Remember to remove damp layers as soon as possible to avoid catching a chill.

Sneakers and Boots

Sneakers offer the most comfort and versatility in November. I highly recommend the water-resistant ones for Chicago during this month:

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A comfortable pair of sneakers is essential if you plan on visiting various attractions during the day. Whereas, smart dress sneakers will be suitable for going out in the evening.

Two warnings about shoes in Chicago:

⚠️ Do not bring suede. The city puts salt on the sidewalks as soon as it gets icy, and that can start in November. Salt leaves white stains on suede and leather and it is very hard to remove. If you must bring leather shoes, spray them with a water and stain protector before you travel.

⚠️ Check the sole. Smooth soles are dangerous on wet sidewalks and slush. You want a rubber sole with real grip.

💡 If you do get white salt marks on your shoes, mix a little white vinegar with water and wipe them gently with a cloth. Let them dry on their own. This is a standard Chicago trick and it works.

Socks (Do Not Skip This)

Cold feet ruin a day faster than anything else. Bring more socks than you think you need.

• Choose merino wool or another warm moisture-wicking material
• Avoid cotton socks. They hold water and then your feet get cold
• Pack one extra pair per day in your bag if you are out all day
• For outdoor evening events, wear two pairs

The advice locals give about the Christmas markets is very simple: double up your socks and wear your warmest coat. You will be standing still outdoors for a long time, and standing still is much colder than walking.

Sweater Tips

As the weather gets chilly in November, sweaters become an essential item of clothing in Chicago. A warm knit sweater, cardigan or cozy hoodie is perfect for cooler days, and can occasionally be worn without a jacket on sunny days in the city in early November.

SHOP NOW | Amazon: Trendy Fall Sweater

However, you will need to layer up with a sweater under your jacket when the temperatures turn cold in the evening. If you find the weather colder than expected, having a good sweater to wear under jackets will provide an extra layer of warmth.

💡 Two thin sweaters are more useful than one thick one. You can wear them together on the cold days and separately on the mild days.

Warm Medium Jacket

You’ll want to bring along a warm fall coat or jacket. This could be a bomber, pea-coat, stylish trench, puffer coat, etc. As it can rain sporadically during this month, we recommend this jacket:

Color: We like to wear dark, solid colors for coats as they are easy to dress up and down and do not show dirt from the subway.

The weather in Chicago during November can be cold, especially toward the end of the month at nighttime, and rain is expected throughout the month. So it is essential to pack a jacket that is warm enough.

Another option:

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A puffer jacket or a warm parka coat that is water-resistant and windproof is ideal for the variable November weather in Chicago.

How long should it be? Get a coat that covers your bottom. The wind in Chicago comes from below and from the side, not only from the front. A short jacket leaves your lower back cold all day.

Does it need a hood? Yes. An umbrella is often useless here (more about that later), so a hood is your rain protection.

A Chicago local said it well on a travel newsletter: when the wind picks up in this city, a puffer jacket is a life saver. A light packable puffer is also easy to put in your suitcase.

Hat, Gloves and Scarf

Many visitors leave these at home in November because “it is not winter yet”. Then they buy a hat on Michigan Avenue on day two for three times the price.

Hat (beanie): You lose a lot of heat through your head, and the wind hits your ears directly. Bring one that covers your ears completely.

Scarf: This is the most useful small item you can pack. It closes the gap at your neck where the wind gets in. You can also pull it over your face at the lakefront. And it is the easiest way to add color to a dark winter outfit for photos.

Gloves: Get touchscreen gloves. You will take photos constantly in Chicago, and normal gloves mean you take them off every two minutes.

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💡 For early November, thin gloves are enough. For late November, get lined ones.

What To Wear List /Packing List

• Waterproof thick jacket (easiest way to stay dry in the rain)
• Windbreaker (to help you stay warm on windy days)
• Waterproof boots/shoes (to help avoid soggy feet while in the city)
• Multiple pairs of thick socks (best if they are quick-dry)
• Medium to thick sweaters/jackets (for cooler morning temps + layering)
• Thermal layers
• Jeans/fleece-lined pants
• Long-sleeve t-shirts (for layering)
• Sweater dresses (for special occasions, get-togethers, dinners)
• Hats/gloves
• Backpack/larger bag (for storing extra dry layers)

Extra Items I Would Add

• Beanie that covers your ears (a normal hat is not enough in the wind)
• Scarf (closes the gap at your neck, and adds color to photos)
• Touchscreen gloves
• Crossbody bag for markets and events (you need your hands free)
• Hand and toe warmers for outdoor events
• Lip balm and hand cream (the wind dries your skin very fast here)
• Portable charger (cold weather drains your phone battery quickly)
• Water and stain protector spray, if you bring leather shoes
• A packing cube or plastic bag for wet clothes
• Small windproof umbrella (optional, see below)

Outfit Ideas for Each Activity

The right outfit depends a lot on what you are doing. Standing still outdoors is completely different from walking around downtown. Here are my suggestions.

1. A Day Downtown (Loop, Michigan Avenue, The Bean)

You are walking a lot and going in and out of shops and buildings.

• Long-sleeve top or thin thermal
• Sweater
• Windproof coat with hood
• Jeans or fleece-lined pants
• Water-resistant sneakers
• Scarf and light gloves
• A backpack for the layers you take off inside

Good to know: Millennium Park and the area around The Bean are very open and very windy. Keep your hat on there even if you were warm five minutes earlier.

2. Architecture River Cruise or Any Boat Tour

This is the outfit mistake I see most often. It is much colder on the water. There is nothing blocking the wind, you are sitting still, and the boat is moving. Plan for 10 to 15°F colder than the city.

• Thermal base layer, top and bottom
• Sweater or fleece
• Your warmest windproof coat
• Hat that covers the ears (a hood alone blows off)
• Scarf
• Warm gloves
• Two pairs of socks

💡 Most boats have an indoor level. If you get too cold on the open deck, go inside for a while. Nobody will mind.

3. Thanksgiving Parade or Any Outdoor Event

You will be standing still on cold concrete for two hours or more. This is the coldest thing you can do in Chicago in November.

• Everything from the boat outfit above
• Plus hand and toe warmers (the small disposable ones)
• Plus thick or double socks
• Plus a thermos with a hot drink if you have one

Good to know: The cold comes up from the ground when you stand still. Thick soles help a lot. Thin sneakers do not.

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4. Christmas Markets and Light Events (Late November)

The Christkindlmarket opens on the Friday before Thanksgiving. ZooLights at Lincoln Park Zoo and the Magnificent Mile Lights Festival also start in the second half of the month. All of these are outdoor evening events, when it is coldest and darkest.

• Full winter outfit, as for the parade
• Double socks
• Boots, not thin sneakers
• A crossbody bag or small backpack (you need your hands free for food and drinks)

Good to know: The heated tents at Christkindlmarket sound like a good escape, but they fill up completely. Visitors regularly describe the market as extremely crowded, with one long slow line through the whole area. Plan to stand outside in the cold, and dress for that. Going on a weekday morning is much more relaxed than a Saturday afternoon.

5. Museum Day (Field Museum, Art Institute, Museum of Science and Industry)

The museums are very warm inside and you will be there for hours.

• Wear a t-shirt or thin top as your base, not a thick thermal
• Sweater and coat that both come off easily
• Bring a backpack, because carrying a heavy coat all day is annoying

💡 Most museums have a coat check. Use it. It usually costs a few dollars and it is worth it.

6. Dinner or Going Out in the Evening

Chicago is a casual city. You do not need to dress up for most restaurants. But the evening is the coldest part of the day, and you will walk between the restaurant, the bar and your hotel.

• Sweater dress with warm tights, or nice jeans with a knit top
• Ankle boots with a grippy sole
• A coat that looks good over the outfit (this is where a wool coat works, if you have a windproof layer under it)
• A scarf you can leave on inside if the restaurant is cold near the door

💡 If you plan a rooftop bar, bring one more layer than you think. Rooftops in November are very cold, even with heaters.

What NOT to Pack for Chicago in November

This part is just as useful as the packing list.

❌ A normal umbrella. The wind here will destroy it, and you will see broken umbrellas in the trash all over downtown. A coat with a hood is better. If you really want one, get a small windproof one.

❌ Suede shoes or boots. Road salt and slush will ruin them. See the shoe section above.

❌ Cotton socks and cotton base layers. Cotton holds moisture. Once it is damp, it makes you colder, not warmer.

❌ One giant winter parka and nothing else. You will be too hot on the train and in every museum. Layers work better.

❌ Shoes with smooth soles. Wet leaves, slush and early ice are all present in November.

❌ Too many “nice” outfits. Nobody sees your clothes. Everyone is wearing a coat.

How Many Outfits Do You Need?

You do not need a new outfit every day. You are wearing a coat over everything anyway. Here is what actually works for a typical trip:

For 3 days:

• 1 coat
• 2 sweaters
• 3 base layer tops
• 2 pairs of pants
• 5 pairs of socks
• 1 pair of walking shoes + 1 pair for the evening

For 5 days:

• 1 coat + 1 lighter jacket
• 3 sweaters
• 5 base layer tops
• 2-3 pairs of pants
• 8 pairs of socks
• 1 pair of walking shoes + 1 pair for the evening

💡 The rule is simple: repeat your pants and your coat, change your top layers. Pack more socks and fewer outfits.

Local Tips for Staying Warm

Use the Pedway

This is my favorite tip and almost no visitor knows it. Under the Loop there is a system of underground walkways called the Pedway. It connects train stations, office buildings, shops and food courts.

On a cold and windy day you can walk a long way downtown without going outside. It takes a little practice to find your way, and you will get lost the first time. But on a really unpleasant November day it is worth it.

The Indoor Heat Is Real

Trains, buses, museums, restaurants and shops in Chicago are heated very strongly. A visitor once asked a local how much you take off indoors in late November. The answer: jeans and a sweater are comfortable inside.

So build your outfit that way. Your indoor outfit is jeans plus a sweater. Everything else is what you add for outside.

Plan Warm Breaks Into Your Day

Do not try to stay outside for five hours. Locals do not do that either. Plan a café, a museum, a shop or a food hall every 60 to 90 minutes. Your day will be much more enjoyable.

Check the Wind, Not Just the Temperature

Before you go out, look at the “feels like” number in your weather app instead of the actual temperature. On a windy day in Chicago the difference is often 10 to 15°F. That number tells you what to wear.

💡 The most important thing: If you only remember one sentence from this article, make it this one. In Chicago in November, block the wind and keep your feet dry. Everything else is a detail.