To find the events that helped shape the darker side of the city, RedEye turned to Marcus Sakey, host of the new Travel Channel show "Hidden City." Sakey broke down some of the locations he visited in the premiere of the show, as well as three more spots with plenty of history.
The deets: Dillinger, a notorious bank robber and prison escapee, famously met his end outside the Biograph Theater in Lincoln Park when FBI agents shot him three times. Dillinger was taken to nearby Alexian Brothers, where he was declared dead.
Sakey's take: Sakey was intrigued by the image Dillinger played up – one of a cool Robin Hood making his way in the Great Depression – while he led a life of crime. Dillinger "really enjoyed being viewed as a suave gangster."
Location: 2433 N. Lincoln Ave. in Lincoln Park
Sound familiar? Johnny Depp portrayed Dillinger in the 2009 movie "Public Enemies," part of which was shot in Chicago.
The deets: During the Democratic National Convention in 1968, protesters and Chicago cops clashed in Grant Park. Chicago police officers were accused of starting a riot near the Conrad Hilton, where protesters and journalists were beaten. A grand jury would indict on riot charges eight demonstrators, seven of whom were tried together, hence the "Chicago 7" moniker.
Sakey's take: On the show, Sakey talks to both a cop escorting a police captain at the time of the riots and a member of the Chicago 7 who was thrown through the window of the Hilton in question. He was surprised to learn neither had decided the truth might lie somewhere between their two extremes. "These are both really smart guys, and it's been  years, time enough that you'd think any pride issues might have faded," Sakey said.
Location: Grant Park in The Loop
Sound familiar? The 2007 film "Chicago 10: Speak Your Peace," whose stars included Liev Schreiber, Mark Ruffalo and Nick Nolte, told the story of the protesters' trial through an animated re-enactment.
The deets: One of the earliest American serial killers, Holmes found his victims among the guests staying at his Englewood hotel during the World's Fair Columbian Exposition in Chicago. He killed at least 27 people in grisly and terrifying ways – but could be responsible for hundreds more deaths.
Sakey's take: Holmes' creepy murder rooms affected even the unflappable Sakey, who said Holmes "wanted to sit outside and turn a dial" to kill his victims. "There was something so unapproachable about that, that give me shivers."
Location: The corner of South Wallace and West 63rd streets in Englewood
Sound familiar? Leonardo DiCaprio is set to play Holmes in the film adaptation of the book "The Devil In The White City."
The deets: The Feds broke into the infamous El Rukn gang in the mid-1980s in Chicago, discovering leader Jeff Fort was working – from prison – to take money from the Libyan government to commit terrorism. Fort was eventually convicted and sentenced to another 80 years in prison.
Sakey's take: Sakey said the gang's brazenness fascinated him so much that he initially wanted to include the story on the show. "I get caught up on the details," he said, exclaiming, "Really, the Libyan government?"
Location: El Rukn temple, 3947 S. Drexel Blvd. in Oakland
Sound familiar? The El Rukn street gang was the feature of an episode of "The FBI Files" TV show.
ST. VALENTINE'S DAY MASSACRE
The deets: Men pretending to be cops lined up six members of George "Bugs" Moran's gang in a Lincoln Park garage and gunned them down. The prime suspect in the crime, which never was be solved, would become Al Capone, who allegedly wanted to elbow out the competition.
Sakey's take: Sakey can't condone the glamorization of murderers and thieves like Capone, but he can understand it. "Al Capone looms large. We're conditioned to be attracted to that, the strong and charismatic figure. The bystander who got killed [by Capone's men], we don't even know who he or she was," he said
Location: 2122 N. Clark St.
Sound familiar? Rumor has it that a prequel is in development for "The Untouchables," which will star Gerard Butler in the Sean Connery role and feature a fictionalized account of the massacre.
The deets: Leader of the Almighty Vice Lord Nation, one of the oldest and biggest Chicago gangs, Willie Lloyd had gone to prison for his involvement in murder and gun violations. Lloyd was shot and paralyzed in 2003, but by then said he had renounced the gang lifestyle.
Sakey's take: Violence, murder, shootings – they're disturbing, Sakey said, but make the city what it is. "Chicago is a gang town," he said. "It's a town where gang violence is very much a part of life."
Location: Garfield Park on the West Side
Sound familiar? A 2008 documentary, "Vice Lords: Lords of the Holy City," featured Lloyd's story.
email@example.com | @gcgarvey