CHICAGO — Forty-two stories above ground, Jon Gottlieb traced his bicycle route. From his vantage point by the pool, on his building’s roof, he could see the stop sign where he turns right, the road he hates crossing, the park he rides through and the tunnel that leads to the Lakefront Trail bike path.

Gottlieb, 75, rode this route at least five times a week through the 13 years since he moved into the Lincoln Park building, the tail end of a five-decade commitment to cycling. For half a century, the retired railroad services manager tracked his mileage on bicycles and compiled it in a spreadsheet. Mark Mattei, who serviced Gottlieb’s bikes for 36 years, said it was clear that Gottlieb was honest about his mileage.

In 2020, he passed 100,000 miles on his bike. In 2023, he hit 110,000. La

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