29, Rogers Park
Commute: Six miles to 20 miles round-trip, "depending on where I'm going."
Can't-live-without gear: Leggings and tops with fleece under the fabric; a long, heavy coat; Bern helmet with a liner.
Craziest weather you've ridden through: "I would say a few years ago when I was working for Apple, I had to commute one morning to work in the spring and a crazy storm came in and almost blew me off my bike."
Why you do it: "I bike because it's freedom from constraint of transit and driving. ... Also, to see time stand still when the snow does fall."
27, Palmer Square
Commute: "I keep bees in gardens all over the city. Now that it's winter I don't visit them as often, but when I do, I take whichever roads are the least congested, most likely to be plowed or salted."
Can't-live-without gear: Thin wool layers, wool glove liners, a wool buff that can be worn as a hat or a balaclava.
Craziest weather you've ridden through: "I always like riding in thunderstorms. I like riding when it's snowing as long as I have a hat with a good brim."
Why you do it: "I don't have a choice, and I hate public transit. Even if I'm inside and I'm looking outside and it's going to be cold and awful, as soon as I get down there and I get down on my bike, it always makes me feel good once I get there."
34, Logan Square
Commute: Two miles to get to West Town Bikes in Humboldt Park, where he manages the bike shop Ciclo Urbano.
Can't-live-without gear: Chunky, puncture-resistant tires; layers; windproof vest; ski goggles.
Craziest weather: "I did ride during the super extreme blizzard of 2011, and that was pretty amazing. It was my first time seeing thunder and lightning during a snowstorm, very low visibility, but that was still kind of fun."
Why you do it: "This time [of] year with snow and cold is not as bad actually as the fall. ... If you have a bike that's set up well, it can actually be a lot of fun. As long as you have all of your skin covered, then you're like a space man riding on the moon or something like that; you don't really feel the cold."
Commute: "It's an 8-mile trip [south to Navy Pier]. I don't use the lakefront path so much in the winter because parts of it aren't plowed, like the Oak Street curve, so that's off-limits. The major streets are plowed pretty quickly."
Can't-live-without gear: Face mask, mittens, Gore-Tex shoes that clip into the pedals.
Craziest weather you've ridden through: "This spring there were a couple of really bad rainstorms. It was one of those times when the weather changed suddenly and I was super duper under-dressed."
Why you do it: "I really like riding my bike because it clears my head. I think it's good to get a little exercise every day. I find driving really stressful in the city, especially when the weather is bad."