"This was a very respectable hotel early on. But by 1900, it had taken on a very unsavory character. In the basement, there were illegal gambling games going on. Upstairs, it has become a brothel. And it continued as a brothel through the 1920s," said Rich Lindberg, author and historian.
It was a very popular brothel, said Lindberg, an authority on this unseemly side of Chicago history.
"It was a place where men came to consort with prostitutes, to wager. There was likely a dope den at one time," said Lindberg. "In the heyday of the 1910s, 1920s, Michigan Ave., State St. [there] were a lot of hotels that catered to high-class vice, high-class bordellos."
It was a place to visit, but you didn't want to get caught there. So the mobsters had a system.
"Usually a clerk on the first floor would ring a bell, and the patrons would make a fast escape," Lindberg said.
Deep below the hotel was a series of secret tunnels, an elaborate 25-mile system. Today, you can still see bricked-up traces of one of the numerous gangster getaways.
"To gain protection from raids, they would come down here and they would escape," said Lindberg.
Nowhere was Chicago's underworld underground more evident than at the legendary Green Mill Lounge on the North Side.
"Well, it was a real fancy joint years ago," said Dave Jemilo, Green Mill owner.
And it was also the favorite hangout of Chicago's most infamous mobster.
"This booth here is where Al Capone used to sit. It was his favorite booth because he could see the front door and the side door without his back being to either one. So that's why he would always sit here," said Jemilo.
He could also see a trap door behind the bar. It led to the epicenter of a thriving bootleg and smuggling operation. There were miles of underground tunnels, running to the nearby Aragon Ballroom as well as the Uptown and Riviera theaters. It was a massive complex of both tunnels and private rooms, top-secret rooms where the parties were said to be out of control.
"Up here you get the liquor in a coffee cup or something. Down there, you know, anything goes! These guys wanna have stuff that you can't even do now. And you have parties down there and you got raided or something, you don't come up the trap door to get out, you go through the tunnels, and you could be on the street walking with your girl on your arm, and the coppers says 'Hey were you in the Green Mill?' 'No I was at the Riviera Theater seeing a movie with my girl. Leave us alone,'" said Jemilo.