What to Wear in Chicago During Winter

By Judith K. Tingley; Updated August 11, 2017

The best outfits to bring when you weather a winter visit to Chicago

What to Wear in Chicago During Winter

Why pick Chicago for a winter break? Because Chicago isn't just cold, it's a super-cool city in any season. With the right clothing you're ready for anything.

Chicago: city of the big chill

As recently as 2015, Chicago tied a 140-year-old record for cold weather with an average February temperature of 14.6 degrees F. The average minimum temperature during January is 14 degrees F, and that's not even counting the wind chill factor or the snow. January's average snowfall of 11 inches doesn't sound bad until you consider how Chicago winds whiz along, taking the snow with them until it settles into huge, filthy, impenetrable hillocks all over town.

Winter is coming! Be prepared.

Smart travelers plan ahead. They know to buy cold-weather clothing in mid-to-late winter, especially expensive winter coats; they're discounted drastically as people begin to "think spring." Get an insulated down, or heavy wool, coat. The down coat will be light but bulky, while the heavy wool coat might become burdensome after a while. Fortunately, longer coats remain stylish, so go with calf-length or even longer; it'll cover the calves. Boots are a must. Buy heavy-duty, not thin leather fashion boots with no insulation; those allow toes to freeze and become numb. Instead, pick wider boots lined top-to-bottom with fleece. Try to find a pair that looks good with both skirts and jeans. If they're not already waterproof, waterproof them. Leave enough room for wool socks or leggings. Bring along a hat that covers your head and your ears, preferably a knitted wool ski cap with holes for eyes, ears, and nose. If this seems unfashionable or too bank-robberish, a regular knitted wool cap will do. Earmuffs are acceptable, but just barely. And don't forget mittens; they're warmer than gloves.

Never underestimate the usefulness of layering. When the weather turns warm, simply peel off a few layers. While planning, though, always leave enough room for all the layers to fit if they have to. Underneath the coat layer thermal underwear, tops, a sweater, leggings, perhaps a midi-skirt or wool trousers for women and definitely wool trousers for the men. And don't forget – scarves keep the neck warm.

How to pack it all into carry-on luggage

Want to save time and expense by taking bulky items using only TSA-approved carry-on luggage? Just board the plane wearing as much of it as you can. That's right. Waddle through the screening process like the Michelin man. Once on the plane, top layers can be removed for comfort's sake. Naturally, there's a limit; not every piece of clothing can be worn. But, each bulky item worn leaves more space for packing such things as underwear, sundry personal items and clothing made of wicking fabric that keeps moisture out and warmth in. Bear in mind that cotton and flannel are not wicking fabrics; once wet they stay wet and transfer the wetness to the wearer. Brrr! The most space-saving method of packing clothing also helps reduce wrinkling: Just roll it up and fit it tightly together.

More ways to stay warm

Eating healthy fats stimulates metabolism, which creates a feeling of warmth. Use that stimulated metabolism to warm up with some exercise, and there are plenty of opportunities for that in Chicago. Go ice-skating in Millennium Park. Begin a Michigan Avenue walk by exploring the not-to-be-missed Art Institute of Chicago, stopping along the way for a break and snack at Water Tower Place. Finally, stroll along the Chicago Lakefront Path, preferably with someone you love. What could be warmer than that?

About the Author

Judith K. Tingley