By Nik Hunder
What would it be like to ride a bicycle to all of Chicago's officially designated community areas in a single day? Dozens of hearty bike riders recently found out.
The second annual Tour de Chi, a 146-mile ride visiting all of Chicago's 77 community areas, took off from DuSable Harbor, near Randolph Street, at 6:30 a.m. It turned out to be a 15-hour (10.5-hour total travel time) bike ride.
The idea for the ride came from local bike rider Ben O'Malley, who designed and tested the route before the masses hit the course. He told Streetsblog the idea for the ride "was a product of many different little things going on at the time." Before it was an official event, Ben and his roommate had planned for such a ride to be closer to a travel vlog. But ultimately decided to turn it into a single-day ride. He successfully completed a solo attempt in April 2023.
The feedback from his solo ride was overwhelmingly positive, and even spawned a Block Club Chicago article. After that, O'Malley decided to create a similar ride for that anyone could bike in.
After a successful inaugural run last year, the 2025 ride drew more than twice as many participants. Over 45 started the journey, with 30 riders finishing the entire route.
While the ride was not a race, a group of six participants took off from the peloton after the first six miles and completed the journey shortly after 6 p.m. The remaining 24 finishing a little before 9 p.m.
The participants included a diverse mix of those seeing if they could accomplish such a feat of physical prowess, and those seeking the bounty for completing it as fast as possible. But no matter one’s speed, everyone knew it was going to be more fun to spend the many miles together as a group.
Participants lucked out with the weather. Despite recent heat and humidity, the group was fortunate to benefit from partial cloud cover, virtually no wind, and temperatures in the high 60s to mid 70s for the first six hours of the ride. But eventually the temperature went up to 87 degrees, making for an intense pedal in dry heat. The inaugural run involved much higher temperatures and no cloud cover, so this was a welcome change.
The group began the day by heading south the Lakefront Trail immediately turning the warmup pace into a brisk hustle down to the 43rd Street bridge over DuSable Lake Shore Drive. Then they headed west through Kenwood in the quiet morning, before visiting the Grand Boulevard, Fuller Park, and the New City community areas.
The ride then made its first of many cutbacks, a common feature throughout the day. The move allowed the group to reduce to total number of miles cycled by doing one side of a community area border and then quickly jogging north or south before then heading back in the direction they just came from, but in a new community area.
Between 43rd Street at Racine Avenue and 103rd Street, riders checked off Englewood, West Englewood, Hyde Park, Woodlawn, South Shore, Grand Crossing, Chatham, Burnside, Calumet Heights, South Chicago, East Side, and South Deering. By 9:15 a.m., the group arrived at Big Marsh Park, a favorite of Chicago’s cyclists for its many dirt trails, pump track, and jump lines that accommodate all levels of riders.
This also marked the first planned rest stop of the day, allowing the group to rehydrate, replenish electrolytes, and consume some nutrition with fruit, carbohydrates, and protein. Food became a big theme of the day both out of necessity and as a reward.
Getting to Big Marsh highlighted the lack of bike infrastructure on the South Side as a whole but especially in the Wild Hundreds (a nickname for Chicago neighborhoods south of 100th Street.) The group worked together to ride a multi-lane bridge over a rail yard on 103rd Street between Stony Island and Oglesby avenues. Then they headed left onto Doty Avenue to get to the bike park.
After visiting the park, they turned left on Doty again and went over a bridge that crosses the Calumet River at 130th, Street which has large entrance and exit ramps for the Bishop-Ford Freeway.
You may be wondering, given the inherent danger of a high-speed street like 103rd or 130th, why bike on it? The answer is that there are no other options that would allow participants to meet the goals of the ride. And, frustratingly, decision-makers have been dragging their feet about building a long-requested sidepath on 130th, much of which lacks sidewalks.
O'Malley said that during his solo ride in 2023, he sometimes had to pull over or ride the sidewalk to stay out of the way of fast traffic on these wide east-west roads. He was nervous about sending a group on them in 2024, but doing so didn't turn out to be problematic. He added, despite the challenges of 103rd and 130th, "a lot of credit goes to the work that has been done by Chicago [sustainable transportation] advocates current and past that have created such a solid network of roadways with bike lanes across the city" for making the rest of the ride as safe as it was.
After leaving 130th, riders passed by Pullman National Historical Park, northern portions of the Major Taylor Trail (and its easy-to-miss entrance at 95th street), Dan Ryan Woods, and Marquette Park for a quick bio break before picking up snacks at a nearby gas station.
Then it was time to head northwest to Clearing where some excited riders
enjoyed the three planes that flew only a few hundred feet above their heads on the way to Midway Airport. That thrill was followed by a zig-zag up to another highlight, themini water at McGuane Park which gave everyone the opportunity to cool off and refuel again after having ridden 83 miles.
Viktor Köves, the person behind the Chicagoans Who Bike project (read Streetsblog's interview with him) stopped by the park to do interviews, snap photos, and join the ride for a few miles, while holding a heavy camera rig.
After the much-needed break from the heat, the group passed through Chinatown and then took a route over glass-filled roads on their way to Douglas, Garfield, and Humboldt parks. Stopping at Humboldt is not part of the official route but for both years, riders detoured through the green space to buy treats. Last year people feasted on roadside barbecue, and this year the snack of choice was coconut ice cream.
After some more time in the shade, it was back to hot pavement as the group headed northwest through Austin, Belmont Cragin, and Dunning. Next, they took an unpaved section of the Des Plaines River Trail in Schiller Woods
featuring a path whose surface was a mix of dirt, gravel, and plastic drainage tiles.
The ride exited the forest at East River Road and Bryn Mawr Avenue before entering Higgins Road, a northwest-southeast diagonal with up to seven lanes. They also passed through a local bike secret, a passageway under Metra's Union Pacific Northwest tracks leading to Edison Park, the final community area of O’Malley’s solo attempt, aptly named 'The Tunnel.'
Finally, they reached the most anticipated stop, Superdawg in Norwood Park. Having completed 121 miles, riders chowed down on hot dogs, burgers, tamales, fries, and especially milkshakes. One guy got an earful for putting ketchup on his hotdog.
The departure from Superdawg was the home stretch of the ride with only 25 miles to go, a task that when phrased that way, seems easy – and the task was getting easier. The sun began to go behind buildings, cooling the asphalt off, and the ride entered shaded portions of the North Branch Trail, the 312 River Run, and North Shore Channel Trail.
At the north end of the Lakefront Trail at Ardmore Avenue, some riders burned up all that was left in the tank, pushing 20 mph at times. Others chose to remain at the same pace or slow to a cool-down pace.
After 15 hours, just before 9 p.m., the 24-person peloton crossed the finish line at North Ave Beach after traveling 146 miles at an average of 14.5 mph and visiting all 77 community areas along the way. They achieved what it appears fewer than 50 people have ever done.
Riders can start training now for the third annual Tour De Chi, expected to take place on June 27, 2026. For those who feel trying to bike 146 miles in a single day might be biting off more than you can chew, there will also likely be shorter South Side Century (100 miles) and metric century (62 miles) options.
But whatever length might be your speed, consider checking out at least part of the ride O'Malley called the "Mount Everest of Chicago adventure." It surely felt that way.
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