Biking in Winter Is Way Easier Than You Think

A cycling advocate from Chicago Bike Winter tells us what to wear to stay warm and explains why biking is sometimes less arduous than taking the L.

The one thing nicer than being the only cyclist coasting down the snow-calmed city streets on a winter day may be encountering another winter biker. It might take the form of a nod and a balaclava-bound smile or a quick stoplight chat about Lakefront Trail conditions, but there’s a definite camaraderie that arises in Chicago’s bike lanes during the coldest months of the year.

If Chicago Bike Winter had its way, these encounters would be far more common. Founded in 1999, the collective aims to make the snowy season friendlier and more bikeable with group rides, guides for beginners, and even occasional crafting sessions to make fleece balaclavas (like a ski mask that leaves the eye area open) and neck gaiters (like a turtleneck sweater missing everything but the neck). It can seem hard even for enthusiastic fair-weather cyclists to keep going once temperatures reach freezing, but Bike Winter’s volunteers try to make it as easy and cozy as possible.

One of those advocates is Kevin Conway, a longtime member who often helps organize Bike Winter events (see below for a couple of upcoming meet-ups). By day, this self-described “transportation pragmatist” is an attorney who works downtown and lives in Wicker Park, and he’s been facing Chicago’s winters atop two wheels for close to three decades simply because “it’s quicker, it’s easier, it’s more fun,” he says. “You know, I’m not doing it to save the barn swallow.”

I myself have ridden through the past five or so winters, but I’ve also been known to make rookie mistakes like immobilizing my hands in three pairs of drugstore gloves rather than invest in one good pair or wearing jeans when snow’s in the forecast. For reliable advice on dressing for winter biking conditions, I turned to Conway and rounded up some gear ideal for staying warm and dry.


Look at the thermometer, then add 15.

Conway says one of the biggest surprises for new winter cyclists is how warm they actually get: “If it’s 20 degrees out, once you’re riding, it feels like it’s 35. ... So all those people who are saying ‘Oh, I don’t know how you can ride a bike’ are the same people who are standing on an L platform ... in one place, and it feels brutally cold.” If it’s in the 20s or warmer, trade in the big parka or puffy jacket for a lightly lined, water-resistant shell (1). Your helmet will also help keep in warmth, so you’ll just need to protect the periphery of your head with a thin hat that covers the ears (2) and a scarf—or, ideally, a neck warmer you can pull up over your chin (3). (You might still experience a moment of brain freeze, but it will disappear sooner than you think.)

Good gear doesn’t necessarily mean cycling-specific gear.

“The clothes that are available have evolved” in the decades he’s been riding, Conway says, but little of his arsenal consists of clothes marketed toward cyclists. “There are so many outdoor activities that stuff that I’ll wear snowmobiling may also be stuff I can bike in—or stuff that I’ll wear cross-country skiing.” At big sporting-goods or outdoor-supply stores such as REI, make sure to wander between departments with an eye toward anything that looks warm and windproof.

Spend your money on your hands and feet. 

On a bike, your arms and legs are moving, but your fingers and toes generally aren’t. It’s easy to protect the rest of your body with gear from your closet, thrift shops, and surplus stores for cheap, but you may want to invest in ultrawarm gloves and boots. Conway likes to wear boots made with Gore-Tex and two layers of gloves: one pair of thin liners and one heavy-duty outer layer. Try snowmobiling or ski gloves (4), cycling-specific lobster gloves that group the fingers together two by two for warmth, or even bar mitts, which are warm shells that slip over your handlebars and let your hands shift and brake freely inside them. (If you wear them with thin liners, they’re also good for impressing your friends, says Conway: “You pull your hands out of them and people will go, ‘Those are all the gloves you have?!’”)

Mix high-tech and classic fabrics.

If it’s wet out, you might consider slipping on some waterproof rain pants; for long rides, a moisture-wicking base layer (5) is ideal. But wool works great for socks, liner gloves, and headwear, and silk long underwear keeps you snug under street clothes. (Conway admitted he was wearing a set at his office when we spoke.) For women, a regular pair of tights will add warmth without bulk under pants, and fleece-lined tights (6) keep legs surprisingly toasty if you’re wearing a skirt. Just stay away from cotton, as it’ll soak up sweat and make for a clammy ride.

Winter cycling equals regular cycling, plus a little extra maintenance and caution. 

“It is much easier than people think it is,” Conway says. “I would say that maybe 90% of people I’ve supported in their efforts have come back to me and said, ‘You know what? You were right, it wasn’t that hard.’” His routine doesn’t change much throughout the year—for instance, he rides the same bikes year-round, with standard 32mm tires that strike a balance between stability and speed. You’ll want to wipe off and grease your chain more often than usual and give the whole bike an occasional rinse to keep salt from corroding the parts. As for safety, common sense should do most of the work: steer clear of ice as well as spilled piles of salt, exercise your right to take the lane if plows have pushed snow into your way, and be willing to step off and walk for a moment to get around dangerous conditions such as metal-grate bridges.

How to Get Involved

For beginners: The 2014 Winter Bike Swap will take over Jaks Tap (901 W. Jackson Blvd.) on Saturday, February 15, from 11 a.m. to 4 p.m. Admission is $5. 

For more experienced riders: A group ride to Three Floyds Brewing and Flossmoor Station Brewing Company (with the option to return by Metra) is scheduled for Saturday, January 11. RSVP online to attend.