Chic
Burgundy and Suede Boots
Flatters smaller busts
A burgundy quilted jacket and matching turtleneck over a cream maxi skirt in light snow is a considered tonal look. Brown suede knee-high boots under the skirt add the textural detail.
What to Wear in Chicago in December
In December, Chicago averages 22–36°F with about 11 rainy or snowy days and the Lake Michigan wind that transforms already-cold temperatures into genuinely dangerous wind chills on the Magnificent Mile and along the Riverwalk. Serious insulation, wind-resistant outerwear, and waterproof boots with grip are the minimum requirements — the wind corridor between skyscrapers amplifies cold dramatically, and exposed skin at -5°F wind chill loses heat quickly. This is real winter; pack accordingly.
Also packing for this trip?
Full December packing list for Chicago →
Checklist of clothes, shoes, and gear — separate from these outfit ideas.
Plan your stay
Hotels in Chicago
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Dates prefilled: Dec 1–42 guests
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What to wear
top / Long-Sleeve Top
fitted long-sleeve
bottom / Jeans
straight-leg
chinos for a slightly smarter look
footwear / Waterproof Boots
ankle boots
rubber sole for traction — keep feet dry all day
outerwear / Heavy Coat
puffer coat
insulated for sub-freezing temps
top / Sweater
crew neck
mid-layer warmth between base and outer coat
fleece zip-up if it gets colder
Consider bringing:
GlovesScarfBeanie
Based on typical December conditions in Chicago. Weather varies year to year — check the live forecast when you're within two weeks of your trip.
Chicago in December is synonymous with deep winter, presenting a beautiful but undeniably chilly experience. Average temperatures hover around 28-35°F (-2 to 2°C), frequently dipping into the teens, especially overnight. While significant snowfall is common, contributing to a picturesque landscape, you might also encounter occasional sleet or freezing rain. The "Windy City" moniker becomes particularly relevant, as strong winds off Lake Michigan amplify the cold, making the wind chill a critical factor that can drop the perceived temperature well below zero. Packing for Chicago in December demands a strategic approach to warmth. Layering is paramount: begin with thermal underwear or long-sleeved base layers, add insulating mid-layers like wool sweaters or fleece, and top it all with a heavy, insulated, and preferably waterproof or water-resistant winter coat. Don't underestimate the power of accessories; a warm hat that covers your ears, insulated waterproof gloves, and a thick scarf are non-negotiable for protection against biting winds. For footwear, sturdy, waterproof, and insulated boots with good traction are essential for navigating potentially icy or snowy sidewalks, paired with thick wool socks. Prioritize warmth and protection without sacrificing comfort to truly enjoy the city's festive atmosphere.
Curated Looks
Business Casual
Camel Over Knee-High
Flatters long-torso frames
A camel coat over dark indigo ankle jeans with black knee-high boots adds coverage in light snow. The cream leather tote keeps it office-ready.
Cute
Faux Fur and Stripes
Flatters long-torso framesFlatters smaller busts
A camel faux fur coat over a striped long-sleeve and cream wide-leg sweatpants makes light snow feel considered. Suede knee-high boots make the casual bottom half look deliberate.
Casual
The Olive Vest Stack
Flatters petite framesFlatters smaller busts
An olive puffer vest over a cream sweatshirt covers light snow with just enough layering. Dark indigo jeans and Chelsea boots keep the bottom half clean.
Cozy
Parka and Cable Knit
Flatters long-torso framesFlatters smaller busts
A black longline parka with a grey cable knit sweater for light snow — cozy layering that doesn't look shapeless. Combat boots and a grey scarf are the finishing details.
Other Months in Chicago
Frequently Asked Questions
What should I wear in Chicago in December?+
Layering is key for Chicago in December. Start with thermal base layers, add warm sweaters or fleece, and finish with a heavy, insulated, and windproof winter coat. Don't forget a warm hat, waterproof gloves, a thick scarf, and insulated, waterproof boots with good grip.
Is Chicago cold in December?+
Yes, Chicago is very cold in December. Average temperatures typically range from 28-35°F (-2 to 2°C), but strong winds from Lake Michigan frequently make the wind chill significantly lower, often feeling well below freezing. Prepare for consistently chilly conditions.
Does it rain in Chicago in December?+
While occasional freezing rain or sleet can occur, precipitation in Chicago during December is predominantly snow. Heavy rainfall is uncommon; however, waterproof outerwear and footwear are still essential to protect against any type of winter moisture.
What should I pack for Chicago in December?+
Pack a heavy, insulated, and windproof winter coat, thermal underwear, warm sweaters, and waterproof boots with traction. Include essential accessories like a warm hat, insulated gloves, a thick scarf, and plenty of wool socks to stay comfortable outdoors.
Packing tools
Decide jackets, outfits, shoes, and bag fees for Chicago in December
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Trip
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Capsule
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