Chic
Burgundy and Suede Boots
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.
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.
December in Chicago is when the city's legendary winter begins in earnest — 36°F highs on mild days, 22°F lows on cold ones, and the Lake Michigan wind turning the Magnificent Mile and Riverwalk into wind tunnels where proper layering is not a preference but a safety consideration. Chicago's urban sleek winter aesthetic is built entirely around functional performance: down coats, waterproof boots, and the serious accessories — hat, gloves, face covering — that the wind chill makes necessary. The Magnificent Mile is Chicago's most iconic winter shopping destination, but its wide, lake-exposed sidewalks are the city's most challenging cold-weather outdoor environment. Wind channeling between the towers creates wind speeds substantially higher than the open lakefront forecast, driving apparent temperatures well below the actual reading. A down coat rated to 0°F or below is not excessive for Magnificent Mile December visiting — it's appropriate. Chicago's elevated CTA 'L' train platforms are fully exposed to wind and weather — the train itself is warm, but platform waits in 20°F wind at 20 feet above street level are genuinely cold. The indoor connection at underground stations provides some relief, but the system is primarily above-grade on the Loop. Layering that handles outdoor platform waits and warm train interiors requires pieces that can be managed efficiently. December in Chicago brings the city's most beautiful holiday moment — the Millennium Park Christmas tree, the Christkindlmarket along the Riverwalk, and the city lights reflecting on the frozen L track. It's worth experiencing for visitors who dress for it; those who underpack spend their time retreating indoors rather than enjoying it.
Curated Looks
Business Casual
Camel Over Knee-High
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
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
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
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.
Packing List
What to Pack for Chicago in December →
Other Months in Chicago
Frequently Asked Questions
What should I wear in Chicago in December?+
Wear serious winter gear in Chicago in December — temperatures range from 22°F to 36°F with Lake Michigan wind that creates dangerous wind chills on the Magnificent Mile and Riverwalk. A down coat rated to 0°F, thermal base layers, waterproof insulated boots with grip, and full accessories including hat, gloves, and a face covering for extreme wind are the practical requirements. This is real winter — do not underdress.
Is December a good time to visit Chicago?+
December in Chicago offers the Christkindlmarket, Millennium Park holiday lights, and the city's most beautiful festive atmosphere — but only for visitors prepared for the cold. Wind chills on the Magnificent Mile can be genuinely dangerous in inadequate outerwear. The city is fully operational and the holiday experience is spectacular for those dressed for it; those who underpack are miserable within an hour outdoors.
What shoes are best for Chicago in December?+
Waterproof insulated boots with excellent traction are essential for Chicago in December. Snow, slush, and ice on Chicago's sidewalks — plus the significant distance walking the city requires — demand footwear that is simultaneously warm, waterproof, and grippy. Fashion boots without insulation or grip become cold and slippery within the first hour of a Chicago December day outdoors.
How cold does it get in Chicago in December?+
Chicago averages a high of 36°F and a low of 22°F in December, but wind chills on the lakefront and Magnificent Mile can drive apparent temperatures to -5°F or below on cold front days. About 11 days see precipitation — rain, snow, or sleet. January is even colder, averaging a high of only 32°F. Chicago's winter is serious and requires proper preparation.
What should I pack for Chicago in December?+
Pack a down coat rated to 0°F or below, thermal base layers, warm mid-layers, waterproof insulated boots with traction, and full accessories including hat, gloves, and wind-resistant scarf or face covering. Chicago's wind chill makes every exposed surface relevant in cold front conditions. The city's urban sleek aesthetic means quality outerwear in dark neutrals looks locally appropriate while providing real performance protection.