Chicago is a city built on contrasts and corruption. Glimmering high-rises and crumbling neighborhoods; a beautiful lakefront built atop smoldering landfills. Crime writer Marcus Sakey strides through the city with swagger to show us the crimes and criminals that make Chicago unique. First, he plots the story of John Dillinger, a public enemy with panache. He robbed "The Man" by stealing from the banks, but he'd tip his hat to the ladies and let them keep their wallets. Marcus goes to a shooting range to fire a Tommy gun like the one Dillinger used and feels the rush that kept Dillinger going. Next, he enters the mind of America's first serial killer, H.H. Holmes, who used a hotel to capture and murder guests who came to the city for the 1893 World's Fair. Talking with a homicide detective, Marcus finds out that serial killers can often hide in plain sight - a shiver-producing thought. Finally, Marcus enmeshes himself in the notorious 1968 Democratic National Convention riots by engaging in both sides of the story - the police and the protestors' perspectives. He tries defensive baton training and talks with a policeman who was there to understand the cops perspective, then he gets maced and talks to one of the infamous Chicago Seven members to undergo what the protestors felt. There's two sides to every story and Marcus shows us both.