Staying Warm Strategies for Frigid Chicago Days

Des Plaines River Trail at Beck Lake, January 1, 2018

Des Plaines River Trail at Beck Lake, January 1, 2018

Temperatures in Chicago have not climbed above the teens since Christmas Day. Yet, this was the week that Chris and I decided we must positively bike to work regularly. Honestly, it's been some time since we've biked daily in this weather, so --although we've developed a number of strategies over our many cumulative years of biking -- there was quite a bit of trial and error involved.

This is still a work in progress, and not all of our efforts were 100% successful, but this is what has worked so far.

#1 Rule I live by for cold-weather cycling:

You will not succeed in keeping extremities warm if your trunk and legs are not comfortable.


  1. Thin t-shirt. I know it's against all rules, but I use cotton. It keeps the other wool layers from scratching me.

  2. Lightweight long-sleeved merino wool crewneck. It's absolutely true that it wards off odors much more effectively than synthetics. I own two Smartwool tops and rotate them through the week before either has to be washed.

  3. Chunky wool turtleneck. I have a handful of thrift shop finds in merino wool, wool blend and cashmere.

  4. Thin packable down jacket.

  5. Waterproof-breathable outer shell. I use Outdoor Research Aspire jacket (Foray is the men's version) one size up from normal to comfortably layer over everything else. This jacket offers great protection form the elements, and has full-length pit-zips for venting when needed.


  1. Medium-weight tights. I use inexpensive generic synthetic ones. For me, contoured cycling-specific ones are too restrictive in this weather.

  2. Heavy-weight stretch-fleece tights or leggings. Again, I go for stretchiness over excessive construction.

  3. Loose-ish windproof pants over everything else.


  1. Thin merino wool balaclava.

  2. Warm fleece hat with windproof characteristics.

  3. Jacket hood or additional hat.
    NOTE: I prioritize keeping my head warm over wearing a helmet, especially since my commute does not involve going through heavy traffic or any challenging terrain. For instances where a helmet would be necessary, I'd use a thick windproof balaclava.

Outdoor Research Mt. Baker Modular Mitts. Amazing!

Outdoor Research Mt. Baker Modular Mitts. Amazing!

Wool balaclava, hat and Gator face mask.

Wool balaclava, hat and Gator face mask.

Getting ready to hand-warm frozen toes.

Getting ready to hand-warm frozen toes.

The full outfit including goggles & pogies (on bike)

The full outfit including goggles & pogies (on bike)


  • Option 1: Excellent quality gloves. For years, I have relied on my Smartwool Gore-Tex merino fleece gloves, but their age has made them inadequate for super-cold days. I have found Outdoor Research Mt. Baker Modular Mitts to be fantastically warm, though dexterity is somewhat compromised. In moderate cold, I can use the insulated glove alone, and in more extreme temperatures, I use the outer Gore-Tex mitts for super-toasty fingers.

  • Option 2: Handlebar pogies from BarMitts or 45NRTH are an excellent alternative. They attach over the handlebars, and allow you to use a thinner glove and maintain good dexterity. Chris has been using the Cobrafist pogies from 45NRTH, and they make him happy. The only drawback it that they only work on the bike. If you have to walk or be off the bike for any reason, you'll need additional hand protection.


For a long time, I used nothing special on my face, except the lower part of my balaclava, and the turtle of my turtleneck sweater, which I slide up and down over my mouth as I ride to regulate the temperature. I usually find that after I warm up a bit, I don't need to have my face consistently covered. However, pulling wool layers over my mouth and nose does force air up behind my glasses and causes them to fog up. So....

....yesterday, I tried a game-changer: a neoprene facemask, which velcroes over the lower part of the face, and has breathing holes for the nose and mouth. Like I said -- game-changer. There were a couple of drawbacks: (1) you have to deal with a little snot accumulation, as it is not easy to wipe off under the facemask (2) you can't use your teeth to pull on your gloves if you need to make a quick fist to warm up your hands, which I sometimes do (though with my new OR modular mitts it's no longer pressing) (3) the facemask limits side-to-side head movement somewhat, so using a handlebar mirror is advisable if you ride in traffic.

Chris wears goggles and swears by them, as do many others. I have not tried them yet and my eyeballs have not frozen, but it is something that's on my list.

Finally -- FEET.

Sheesh. I have not solved this problem yet. For walking, my awesome waterproof Ahnu boots with wool socks are perfectly adequate. For biking, not so much. Neither are Chris' Lake Shoes winter boots. In fact, cold feet is what caused us to cut our recent NYD expedition short. At one point, we were literally on our backs in the snow pedaling our feet in the air to encourage circulation.

For a short hop to work (< half-hour), we'll keep using what we have, but for longer adventures, we're still looking for alternatives. Stay tuned. And -- of course -- we welcome your suggestions!