I’m three years a city cyclist with no intentions to retire my ’70s Schwinn road bike anytime soon. It’s convenient, affordable and as a photojournalist — possible. Come winter, it can also 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, and if they feel the same sense of community in passing. Along a 60-mile route across the city undertaken in stops and starts in December and early January, I stopped to speak with a broad-ranging group of Midwestern winter cyclists determined to see the season through.
Couriers, commuters and enthusiasts shared their limits, their strategies for the road and the vital gear that helps get them where they want to go.
Along mile 4 I met 32-year-old courier Robert Bigelow-Rubin just before evening shift change at Cut Cats Courier Service on Lincoln Avenue.
Bigelow-Rubin was gearing up for a six-hour shift of deliveries across Chicago’s Lake View neighborhood.
The route was nothing new for Bigelow- Rubin and neither was the mid-December night ride. He moved to Chicago to be a courier in 2013 — the winter a polar vortex dipped temperatures well below zero. He told me he’s made deliveries in every season, developing his own system for layering along the way.
“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 outlasting the cold. Unlike cotton, the material breathes — keeping him both 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 down Addison Street.
I tailed behind while Bigelow-Rubin was in full command of our route. 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 rush hour.
It can be a difficult job being a Chicago courier in the wintertime, Bigelow-Rubin said. Snow and freezing rain makes for slick conditions. Several falls a season are not uncommon, but Bigelow-Rubin said he’s managed to avoid any serious accidents thus far.
“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.
It was mile 19 and 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 the organ at his local church. Handlebar mounted mittens keep his hands warm during the ride.
Mechanic Leah Plummer wheeled out Fleer’s bicycle and showcased the repairs. He 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 north suburban 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 a few more minutes by the counter to speak to 56-year-old shop owner Maria Barnes.
A customer needed new brakes and thinks their chain is falling off; that was Maria’s downstairs neighbor. Another had a tear in the sidewall of their tire; they’ve known Maria nearly two decades.
It was evidence of the relationships the bike shop has fostered on Chicago’s North Side for years.
“We try to be active in the community,” Barnes said. “We try to know our neighbors.”
Across town, it was mile 27. At West Town Bikes, a social meetup for women, trans and non-binary cyclists was about to get underway. I stepped into the backroom of the bike shop and met 29-year-old Kingston Smartt-Nalli who was preparing for the evening ride.
Smartt-Nalli helps lead the monthly meetup on its route through Chicago’s Humboldt Park neighborhood. Riders chat at stops along the way and tune up their bicycles in the workshop before hand.
One by one riders trickled in. Smartt-Nalli welcomed into the warmth a new member who looked unsure if 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 built from scratch. He’s added 4.8-inch-wide tires to the frame 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 are what motivate him to ride year-round. The monthly meetups at West Town Bikes help, too.
“The folks that I’ve met here I can always reach out to when I’m struggling,” he said. “We nourish each other.”
A few blocks south, the event soon kicked off. As bike lights descended down Campbell Avenue, the group’s conversation drifted back toward me. I photographed the cyclists as they passed beneath a street lamp and rode off into the night.
Monday morning and mile 30 I stopped at a busy intersection along North Milwaukee Avenue as cyclists navigated steady rain and rush hour traffic. To my right was 40-year-old Logan Square resident Melanie MacKay atop the largest bike of the intersection — three wheels and a front cargo compartment with holiday lights strung about its exterior. Inside that compartment sat two small bike helmets.
MacKay was on her way to her job in the Loop, having just biked her children to school before hand.
“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 Midwestern-born cyclist wasn’t expecting to bike in the rain that morning but three wheels keep her riding through most weather conditions. On Chicago’s 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.
I pulled up to a bike rack inside a Kostner Avenue shopping plaza along mile 36.
Moments later, nearby resident Luis Gomez walked out of the West Humboldt Park Aldi store with a bouquet of flowers for his partner and snacks for the ride home.
It wasn’t a typical grocery haul for the 31-year-old. 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 a group effort that takes several layers of clothing, two drawstring bags and an oversized 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 suburban 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 38.
A familiar looking bike exited the end ramp. It was Smartt-Nalli heading my direction.
He asked where I was headed and offered to ride with me along the way. We coasted east down the trail and talked about bike repairs, jobs and ways I could volunteer at West Town Bikes on the weekends.
At Maplewood Avenue we parted ways. I turned east and he turned west, each seeking refuge from the cold.
I approached mile 50 a few days into the new year. On a foggy afternoon in Chicago’s Bronzeville neighborhood, I entered Small Shop Cycles & Service in the 4200 block of South Cottage Grove Avenue.
Inside, I met 39-year-old shop owner Chris Willard, who was working on a bike near the store’s front entryway.
Willard, who grew up in nearby Hyde Park, has been educating and riding bikes on Chicago’s South Side for close to two decades. He spent nine years teaching at Woodlawn-based Blackstone Bikes, a youth-focused bike mentorship program, before opening Small Shop in 2016. It’s one of only a few bike shops on Chicago’s South Side, and the only shop 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. “I know it’s a bike shop, but it’s the same principle,” Fields said.
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 of Willard and the company of his animals di lui in the shop.
“This gentleman is good — he’s done it before,” Fields said. “They do good work here.”
Lou Foglia is a freelance photojournalist based in Chicago.