What to Wear in Chicago in Winter

Tourism in Chicago sees a pretty big dip in the months of January, February, and even into March (with the exception of St. Patrick’s Day weekend) and it’s not surprising – Chicago is cold in the winter. Really cold. Most tourists would rather head south to warmer climates for the winter than spend their time shivering in Chicago. But for those who do visit in winter, it is possible to enjoy a visit to Chicago, see the city’s best sites and attractions, and not contract hypothermia. It’s all about dressing for the weather and packing appropriately. Here’s what you need to know.


The average temperatures in Chicago in December range from 24-37 degrees and in January,  it just gets colder from there, dropping down to an average of 18-32 degrees throughout the month. The important thing to remember though, is that those are averages; it can often be slightly warmer or much, much colder thanks to the “wind chill factor” which can take a temperature of 18 degrees and make it feel like 2, or even into the negative double-digit numbers.  Officially, January is the coldest month and average temps begin to rise in February and March. But it seems that every year around the last week of January or first week of February, the city experiences a cold snap during which temperatures plummet into the negatives (with the wind chill factor) for at least a few days.

The important thing to remember though, is that if you don’t want to, you really don’t have to spend much time outdoors. Other than walking on the famed Magnificent Mile or ice-skating at Millennium Park, many of the activities you’ll want to do in Chicago in winter take place indoors. Restaurants, museums, shops, and attractions like the the Willis Tower Skydeck are all indoors and heated, and Chicago’s public transportation like the el and buses are toasty warm as well. If you do need to get dressed up for a night out and don’t want to layer up, you can always take a cab door to door and not have to worry about bundling for the weather or walking through snow.

Chicago style

Despite the cold, many Chicagoans manage to look good while they stay warm by dressing appropriately in cold-weather gear. On negative temperature days, a winter coat that kept you warm in Seattle, or San Francisco or Washington, DC, isn’t going to cut it. You’ll need a coat that is made of heavy duty wool with an insulated lining, or one stuffed with down, that hits close to the knees (seeing people in calf or ankle length down coats is not uncommon). You’d be surprised how cold the tops of your thighs can get in a shorter coat. For both men and women, good boots are a must. On a day when the sidewalks are clear, you can get away with your regular shoes (even heels for women) but if it’s below 30 degrees, be prepared for some cold feet. Men generally wear leather ankle boots, while women’s boot choices range from low-heeled leather boots to fleece-lined Uggs, to rubber wellies, to over-the-knee stiletto boots, depending on the occasion.

On most winter days in Chicago, you’ll be fine with earmuffs or a hat, a scarf, and gloves or mittens. But when the wind chill really gets going and temps plunge below zero, you may need to pull out the gear normally reserved for outings to Siberia. On these days you will see people walking down the street in ski masks and giant furry hats. At the very least, make sure you can wrap your scarf around your face to cover your nose and mouth, and be sure your gloves are insulated.

As with other seasons in Chicago, layers are key in winter. You need to bundle up to brave the cold, but once inside you’ll find temperatures ranging from slightly chilled to toasty warm to sweltering hot, and will need to remove layers accordingly.


Despite the amount of winter gear you’ll need to bring, you don’t necessarily need to pack a bigger bag for a trip to Chicago. Just wear your heaviest gear – your winter coat and boots – on the plane. For a long weekend trip, I suggest ladies bring one pair of jeans and one pair of leggings or black pants, one skirt or dress and 1-2 pairs of tights, one pair of nicer boots or shoes (casual winter boots worn on plane), one dressier top with a cardigan or wrap that can be layered, 2-3 long sleeve shirts and 2-3 cardigans or sweaters for layering over them.

For men, one pair of nicer boots and one pair of loafers will do. Bring one pair of jeans and one pair of nicer pants like khakis or black pants (and a suite jacket and tie, depending on your plans), 2-3 button-up shirts, 2-3 long sleeve shirts and 2-3 sweaters for layering.

For both men and women, don’t forget a warm hat, gloves and scarf. Sunglasses are always helpful as well; the sun glinting off fresh white snow can be quite intense.

Photo by {No Ideas,Taking Break}