Should you be honeymooning in Chicago, there is a once-clandestine side to the “Windy City” which shouldn’t be missed: the “speakeasies,” the once hidden watering holes which flourished during Prohibition.

With the repeal of Prohibition in 1933, the legalization of alcohol brought to a close yet another chapter in the city’s nefarious history.

Speakeasies were no longer necessary … yet in modern-day Chicago the sexy mystique of these once clandestine hangouts lingers, attracting people in search of food, drink and wicked nostalgia – into their storied establishments.

Among some of today’s favorites:
The Violet Hour – Knock softly on the graffiti-splashed “hidden” door and you’ll be ushered into the dark, muted world of a 1920s speakeasy. This is the “real deal” with hard wood floors, velvet curtains, shimmering chandeliers and high backed blue velvet chairs around low tables which promise total anonymity. The draw here: unusual drinks, especially the lavender martini.

Green Mill Cocktail Lounge – “The Mill” started out in what was once Lake View (now Uptown) in1907 as Pop Morse’s Roadhouse before its name and morphing into one of Prohibition’s most frequented speakeasies. It became a favorite haunt of Alfonse “Scarface” Capone when fellow gangster Jack “Machine Gun” McGurn acquired 25 percent of the club.
Capone’s favorite perch - a booth across from the side door at the end of the bar – which allowed him a clear view of whoever entered – welcomes today’s patrons. Joe E. Lewis, Billie Holiday, Sophie Tucker and even Frank Sinatra were just a few of the regulars “back in the day.”

Capone and McGurn are immortalized in photos behind the bar. There’s live music daily and martinis are at the top of the list of cocktails.

John Barleycorn Memorial Pub – During Prohibition “Barleycorns” was boarded up to appear vacant to the authorities while bootleg booze flowed freely inside. The back room was used to front a Chinese laundry where bootleggers would stash their “goods.”
The notorious John Dillinger, a frequent patron known for frequently “buying the house a round,” was gunned down in the street just two blocks away.
Today, this Lincoln Park institution dishes up tasty pub grub and is known for its beer garden.

Green Door Tavern – Opened in 1921, it was allegedly one of the first speakeasies to operate in the downtown area and as such, it attracted a host of Chicago gangsters during Prohibition. Nowadays it’s a popular after work watering hole with memorabilia galore, good burgers and beer.

Burwood Tap – One of the first taverns in Chicago to obtain a legal liquor license in 1933 this former “soda shop” (i.e. speakeasy) is located in the city’s trendy Lincoln Park. These days it’s touted as an “upscale bar with down-to-earth personality” and caters to a hip sports crowd with seven flat screen TVs, pool table and designer drinks.