UPTOWN — John Dillinger is considered one of America's most prolific bank robbers.
During the Great Depression, the Indiana native looted two dozen vaults and escaped from jail twice. He was eventually shot to death by police outside the Biograph Theater, 2433 N. Lincoln Ave., in 1934. But not before spending time in one of his favorite Chicago 'hoods — Uptown.
"He had hung out here and had a lot of hideouts," said Gene Tenner, a history buff who plans trips with Bike Uptown. "He shot pool and got his fingerprints erased."
On Oct. 5, Bike Uptown will sponsor a police-escorted John Dillinger bike tour. The free ride starts at Uptown Bikes, 4653 N. Broadway, and guides riders to nine of the gangster's favorite haunts.
"It gives you a sense of: He was alive and here and doing things," Tenner said. "It just adds to the sense of Uptown history."
Tenner first got the idea for the tour while visiting his son, whose office is near the Green Mill, 4802 N. Broadway. Dillinger allegedly had plastic surgery performed by a doctor who worked above the famed jazz club.
Dillinger "figured he'd better change his identity, so he did, and that didn't work," Tenner said. "He almost died during the surgery. He tried to change his fingerprints, and that didn't work, and a month later, he was shot."
Tenner swung by the Uptown library and began researching Dillinger, whom he described as a "charismatic guy."
The bank robber shot billiards on Sheridan, dated a woman (one of several) who worked on Wilson Avenue, and went for pints at a tavern on Broadway, Tenner said.
"He was a charmer. He had multiple girlfriends at the same time. He obviously has this Robin Hood aura around him. When he died, there were lines going out the mortuary."
Tenner, who has conducted architecture bike rides in the past, plans to lead cyclists to several of Dillinger's favorite spots and highlight the history at each.
Most have changed over time. Dillinger's favorite billiard bar is now an Ace Hardware at 3921 N. Sheridan Road, and the sandwich shop where Dillinger made silly faces at a girlfriend has become a park.
Still, Tenner said, the ride is "a nice way to get out and learn some history about your neighborhood."
The tour concludes at Buena Circle Park with a free brunch courtesy of Michael's Pizza, 4091 N. Broadway, according to Sarah Brune, associate director of the Uptown Chamber of Commerce.
The John Dillinger bike tour starts — rain or shine — at 10 a.m. Oct. 5 at Uptown Bikes, 4653 N. Broadway.