Winter bicycling in Chicago: Experts who do it offer a survival guide

It’s convenient, affordable and, as a photojournalist — possible. Come winter, it also can become a test of endurance amid Chicago’s most difficult riding conditions.

I’ve often wondered what motivates the riders I encounter in the cold. So, along a 60-mile route across the city undertaken in stops and starts in December and January, I stopped to speak with a broad group of winter cyclists determined to see the season through. Couriers, commuters and enthusiasts shared their limits, their strategies and the vital gear that helps get them where they want to go.

Mile No. 4

In Mile No. 4 of my ride, I met 32-year-old courier Robert Bigelow-Rubin just before the evening shift change at Cut Cats Courier Service on Lincoln Avenue as he was gearing up for a six-hour shift making deliveries across Lake View.

Bigelow-Rubin moved to Chicago to be a courier in 2013 — that was the winter a polar vortex dropped temperatures well below zero. He said he’s made deliveries in every season, developing a system for layering.

“Space-wise and weight-wise, you can’t afford to just bring the whole closet with you on a shift,” he said. “I’ve done it long enough that I know exactly what I need.”

Wool knee socks and base layers are Bigelow-Rubin’s secret to beating the cold. Unlike cotton, the material breathes — keeping him dry and warm during deliveries.

The sun was setting when dispatch called in a delivery order. Bigelow-Rubin powered on his bike lights, mounted his KHS Flite 100 bicycle and headed east on Addison Street.

An experienced rider who knows the ins and outs of city cycling, he called out turns and lane obstructions as we navigated the North Side during rush hour.

It can be difficult being a courier in the wintertime, Bigelow-Rubin said. Snow and freezing rain. Slick conditions. Several falls a season not uncommon. But Bigelow-Rubin said he’s managed to avoid any serious accidents.

“Bike lanes virtually disappear in the snow, which push us out into the road,” he said. “You just gotta take it a bit slower.”

Somewhere along Southport Avenue, we stopped to pick up the order — Thai food. Bigelow-Rubin packed the food into the largest cycling bag I’ve ever seen. We set off again, coasting North Broadway amid radio chatter from dispatch.

Mile No. 19

Mile No. 19, inside the storefront of Uptown Bikes, I met 59-year-old Randy Fleer.

The Edgewater resident laid a backpack filled with piano equipment near the front counter and waited to pick up his winter-outfitted Trek 820. Fleer works in piano services — tuning, repairing and commuting by bike most days to jobs across the city.

On Sundays, he plays organ at his church. Handlebar-mounted mittens keep his hands warm.

Mechanic Leah Plummer wheeled out Fleer’s bicycle and showed off the repairs. He had opted for the bike shop’s winter special: trued tires, a new drive train, brake pads, cables.

Fleer pulled out his phone and showed me a map of his recent 11-mile ride to Winnetka. I began to understand the need for his bike’s winter overhaul. He’s a high-mileage commuter who puts serious wear on his equipment year-round.

“Once you go an hour and a half one way, going an hour is nothing,” Fleer said. “Once you ride in five-degree weather, 20 degrees is nothing.”

I lingered by the counter to speak with shop owner Maria Barnes, 56. A customer needed new brakes and thinks the chain is falling off; that was Barnes’ downstairs neighbor. Another — who’d known Barnes for nearly two decades — had a tear in the sidewall of a tire.

“We try to be active in the community,” Barnes said. “We try to know our neighbors.”

Mile No. 27

Across town, at West Town Bikes, a social meetup for women, trans and nonbinary cyclists was about to start. I stepped inside the backroom of the bike shop and met Kingston Smartt-Nalli, 29, who was preparing for the evening ride.

Smartt-Nalli helps lead the monthly meetup on its route through Humboldt Park. Riders tune up their bicycles in the shop and chat at stops along the way. One by one, riders trickled in. Smartt-Nalli welcomed a new member who looked unsure of whether the event was still happening.

“We’re building a community,” Smartt-Nalli said. “Even through the winter, a handful of people show up.”

Outside, he showed me the e-bike he’d built from scratch. He added 4.8-inch-wide tires and a motor to help him power through snow.

“This winter, I have this amazing bike, and I’m going to test the limits — that’s the plan,” he said.

Smartt-Nalli said his mental and physical health motivate him to ride year-round. The monthly meetups at West Town Bikes help.

“The folks that I’ve met here, I can always reach out to when I’m struggling,” he said. “We nourish each other.”

Soon, the ride kicked off. Bike lights descended down Campbell Avenue. I photographed the cyclists as they passed beneath a streetlamp and rode off into the night.

Mile No. 30

Monday morning and mile No. 30, I stopped at a busy intersection along North Milwaukee Avenue as cyclists navigated through steady rain and rush-hour traffic. To my right was Melanie MacKay, 40, a Logan Square resident, on the largest bike of the intersection — three wheels and a front cargo compartment with holiday lights strung about its exterior. Inside that compartment were two small bike helmets. MacKay was on her way to her job in the Loop, having just biked her children to school.

“I like having them in the front so they can see,” she said. “It’s my car, really — I don’t have a car.”

The Midwest-born cyclist wasn’t expecting to bike in the rain that morning, but three wheels keep her riding through most weather conditions. On the coldest days, she wears snow goggles. The windchill reminds her of snowboarding trips she took to Colorado growing up.

“I love the freedom of a bicycle,” she said. “I love fresh air. When the winter gets cold, I put on my snowboarding gear, and I feel like I’m on the mountain again.”

I was photographing MacKay when a cyclist called out my name from the bike lane to our right. It was Bigelow-Rubin heading to the Loop on a morning round of deliveries.

Mile No. 36

I pulled up to a bike rack inside a Kostner Avenue shopping plaza along mile No. 36.

Moments later, Luis Gomez, 31, walked out of the West Humboldt Park Aldi store with a bouquet of flowers for his partner and a snack for the ride home. It wasn’t a typical grocery haul for Gomez. On weekends, Gomez and his partner bike up Kostner Avenue to the Cermak Produce store in the 4400 block of West Armitage Avenue to get the bulk of what they need. It’s an effort that takes several layers of clothing, two drawstring bags and an oversize backpack intended for art supplies. Still, Gomez said he prefers the trek to driving.

“I get to see what’s around me,” Gomez said. “When I’m in the car, I’m just focused on the car in front of me.”

He’s biked as far south as Jackson Park and as far north as Wilmette. It’s impressive ground to cover for a recent transplant to the city. Gomez, who moved from San Francisco in 2020, said he makes sure to survey new neighborhoods along the way.

“In a way, I feel like I’ve gotten to see parts of Chicago that I don’t think I’ve heard my friends talk about,” Gomez said. “It’s given me more to appreciate.”

Heading home, I approached the west end of The 606 / Bloomingdale Trail along mile No. 38.

A familiar looking bike exited the end ramp. It was Smartt-Nalli heading my way. He asked where I was headed and offered to ride with me. We coasted east along the trail, talking about bike repairs, jobs and ways I could volunteer at West Town Bikes on weekends.

At Maplewood Avenue we parted ways. I turned east, and he turned west, each seeking refuge from the cold.

Mile No. 50

I approached mile No. 50 on a foggy afternoon in Bronzeville and entered Small Shop Cycles & Service in the 4200 block of South Cottage Grove Avenue.

Inside, I met shop owner Chris Willard, 39, who was working on a bike near the store’s front entryway.

Willard, who grew up nearby in Hyde Park, has been riding bikes on the South Side for close to two decades. He spent nine years teaching at Blackstone Bikes, a youth-focused bike mentorship program, before opening Small Shop in 2016. It’s one of only a few bike shops on the South Side and the only one in Bronzeville.

Willard, a year-round cyclist, said he’s excited to have seen an increase in biking activity, community rides and bike share stations on the city’s South Side over the years.

“The more bikes you see, the better it will be for everyone,” Willard said. “That makes more people aware that cyclists are out here and overall leads to a safer ride for everyone.”

I asked Willard what neighborhood he lived in and he hesitated — Rogers Park. It’s a recent move that’s put a 16-mile ride between home and work. Commuting by bike isn’t realistic for the full-time shop owner, so he’s been driving instead.

Still, Willard said he’s exploring his new neighborhood this winter with what’s most comfortable — his bicycle.

“The first time I biked around Rogers Park was the first time I got a sense of the neighborhood,” Willard said. “A car is just a bubble and makes it really easy to disengage with the neighborhood — the bike gives that ability to me.”

Just then, one of Small Shop’s regular customers entered with a niche repair. Dwayne Fields, 70, pointed to his medical walker and laughed, saying, “I know it’s a bike shop, but it’s the same principle.”

Fields doesn’t ride a bike, but, when the right brake cable snapped on the Hyde Park resident’s walker a few days before, he sought out a temporary fix nearby. Seated near the store’s front counter, Fields enjoyed the attention of Small Shop’s resident orange tabby cat Gourd.

The break is a recurring issue for Fields, who said his walker moves too fast, forcing him to continuously engage the brakes. But Fields said he enjoys the work Willard does and the company of his animals in the shop.

“This gentleman is good — he’s done it before,” Fields said. “They do good work here.”