A Chicago gangster tour can help piece together the city’s unwanted past – as can visits to the Valentine’s Day Massacre site and the Green Mill.
The efforts to gloss over Chicago’s gangster past
Dressed in his snazzy fedora and wide pin-stripes, Southside tells it like it is. “You go anywhere in the world – Bolivia, West Africa, wherever – and tell a kid that you’re from Chicago. He’ll shout: ‘Al Capone’, turn his arms into a machine gun and start rat-a-tat-tatting ya.”
The City of Chicago dearly wishes that this wasn’t the case. Vaultloads of taxpayer dollars have been spent on cleaning up the city’s image and promoting it as an A-grade tourism destination. By and large, this has been emphatically successful – Chicago is an instantly enchanting, exciting place to be. It has managed to maintain and update several more savoury old traditions – electric blues bars, comedy clubs, an unparalleled collection of skyscraping architecture – whilst introducing world class public art and restaurants spread out over several distinctive, thriving neighbourhoods.
Just don’t mention the G Word. The city has zealously tried to purge its gangster past from the cityscape. Old haunts have been razed, plaques commemorating famous hang-outs are conspicuous by their absence and the Chicago History Museum devotes just one meagre panel over two floors to the city’s most infamous era.
Chicago’s Untouchable Tour
Despite these efforts, it seems as though visitors can’t get enough of the Capone shtick. The Untouchable Tour around the gangster-era sites regularly sells out for up to four departures a day, despite the fact that the visitor centres like to pretend it doesn’t exist or has long since gone out of business. In a bizarre way, this helps, admits Southside. “It just means we have to be smarter in the marketing, and customers feel like they’re in on a secret.”
Southside and his cohort ‘Johnny Rocco’ take their pimped-out, black-painted freightliner around the parts of town that aren’t on the promoted tourism trail. It’s part comedy routine – the guys are in character, passengers frequently have to duck in their seats to the pre-recorded sound of gunfire and there are regular cracks about forging money – but part handy history lesson.
Prohibition in Chicago
There’s far more to Chicago’s gangster history than just Al Capone – the Levee district to the south of the centre had a highly dubious reputation long before Capone came over from New York City in 1923.
The real story starts with Prohibition, however. The banning of the sale and production of alcohol came into force on January 16th, 1920 – ironically, the day before Capone would turn 21 and thus be legally allowed to drink. Chicago was a city with a heavy concentration of beer-loving Poles, Germans, Czechs and Irishmen, along with a large community of Italians for whom a glass of wine over dinner was second nature.
The city’s mayor had declared himself to be “as wet as the Atlantic Ocean” and it was quite clear that Chicago wasn’t about to go teetotal – it was merely a question of where the alcohol was going to come from.
Chicago’s bootleggers
The answer was the bootleggers. Several enterprising brewing and distilling operations cropped up, and many members of Big Jim Colosimo’s South Chicago vice operation thought that their boss was missing a trick by not getting in on the booze racket.
Sure enough, Colosimo was shot dead in his own café in May 1920 and his nephew, Johnny Torrio, took over the patch. He had no such qualms about going into the alcohol business, and brought over his old Brooklyn contact – Capone – as his enforcer. Capone would remain little more than a glorified heavy until an assassination attempt led Torrio to retire in 1925, leaving operations to his right-hand man. In the meantime, under Torrio’s savvy guidance, illicit speakeasies on the South Side boomed.
Of course, Torrio and Capone weren’t the only ones trying to make a fortune out of delivering alcohol to the thirsty masses. Rival loose coalitions on the north and west side of Chicago were also bootlegging, and it wasn’t long before uneasy truces were broken.
The Holy Name Cathedral
The original key man in the north was Dion O’Banion, whose cover was a rather profitable flower shop outside the Holy Name Cathedral. With all those gangster funerals taking place over the road, the commemorative wreath trade was pleasingly brisk. In November 1924, however, he was taken out inside his own store.
The baton passed, temporarily, to Hymie Weiss, who made it to 1926 before being mown down in a hail of machine gun fire outside the cathedral. The site of the flower stall is now a car park (something of a common theme), but according to local lore, the cathedral still bears the scars of the Weiss murder. On further investigation, there is what appears to be a bullet hole on the corner stone above the 1874 date marker – although it looks suspiciously fresh and straight.
Chicago’s lost gangster hangouts
As with other notorious sites, you either need a guide to point them out or a good book that details addresses alongside the background information. Many of the Torrio/ Capone outfit’s key hang-outs are within a block or two of the junction of South Wabash and East Cermak Street on the South Side, but none still stand.
There’s no Four Deuces Club or Metropole Hotel to see, while the Lexington Hotel has been pulled down and turned into the Lexington Park Condominiums.
The site of the Valentine’s Day Massacre
The most infamous site is on the North Side, however, near Lincoln Park. 2122 North Clark Street was the scene of the 1929 Valentine’s Day Massacre, where seven associates of the North Side gang were lined up against a wall by men in fake police uniforms and then shot.
It was the event that turned the tide of public opinion against the gangsters – up until that point, Capone and co were lauded as celebrities. Predictably, though, the site is now a scrubby patch of grass and car park outside an apartment block.
Capone’s grave and the Intercontinental Hotel
Some spots have been spared the revisionist wrecking balls, however. Capone’s surprisingly understated grave can be found at the Mount Carmel Cemetery in the nondescript western suburb of Hillside.
Meanwhile, the Intercontinental Hotel at 505 North Michigan Avenue gives a hint of the extravagance of the era. Its south tower was formerly the Medinah Athletic Club, a private gentlemen’s sporting club used pretty much exclusively by the richest members of the community (where those riches had come from wasn’t an issue).
The lavish ballrooms remain, but the swimming pool on the 14th floor is extraordinary – it’s surrounded by intricate blue and white tiling, fountains and Moorish-style arches. Back in the 1920s, this was arguably the most extravagant pool in the world, and guests can still take a dip where Capone and his cohorts would have knocked off a few laps.
Non guests should just ask at reception – you’ll be given a pamphlet on the building’s history and allowed to saunter up through the decidedly more contemporary fitness centre.
Jazz at the Green Mill
Chicago’s most extraordinary Prohibition-era relic, however, can be found in the north of the city near the Lawrence train station. The Green Mill is the cocktail lounge and jazz bar once part-owned by Capone’s chief set of muscles, Jack McGurn. Capone used to have his own favourite booth here, and the bandleader would strike up Rhapsody In Blue whenever he entered. A series of escape tunnels were built beneath the bar, and still remain – show up early and plead with fluttering eyelashes if you fancy a peek.
Turn up in the evening, however, and you’ll find yourself transported back. The doorman insists on strict silence while the band is playing, the meandering jazz is listened to in hushed reverence and eyes flit towards the extraordinary wood panelling that lines the walls.
The Green Mill has the right look, sound and taste – cocktails became the drink of choice during Prohibition as a way of masking the often rough-as-guts alcohol being produced by the bootleggers.
Remnants of Chicago’s gangster story
This darkened room may not be what Chicago does best anymore – the city is far too dynamic and exciting to have to rely on old tales of gangland hang-outs – but it shows that you can still relive the bad old days if you choose to.
The old speakeasies have just about managed to survive amongst the skyscrapers, the car parks with a sordid past still pull in the visitors and Chicago’s kids will still play gangsters rather than cowboys and Indians. The undesirable parts of Chicago’s legend remain Untouchable.
More Chicago travel
Other Chicago articles on Planet Whitley include:
- Tribune Tower – the building that stole the world.
- Kayaking along the Chicago River.
- The joy of visiting Chicago third time round.
- The best places in Chicago for Frank Lloyd-Wright architecture.
For more Chicago activity and experience ideas, head here.
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