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| Chicago prohibition-style: a city still married to the mob | Chicago prohibition-style: a city still married to the mob |
| (about 2 months later) | |
| As “South Side”, our moustachioed, fedora-toting guide, points out the bullet holes that pockmark the cornerstone on the north wall of the grand, gothic Holy Name Cathedral, a dishevelled middle-aged man in a red anorak is tapping at the door of our tour bus. | As “South Side”, our moustachioed, fedora-toting guide, points out the bullet holes that pockmark the cornerstone on the north wall of the grand, gothic Holy Name Cathedral, a dishevelled middle-aged man in a red anorak is tapping at the door of our tour bus. |
| “The bullet holes you can see in the stone come from a hit in 1926, on Earl “Hymie” Weiss, a member of the O’Banion gang – Al Capone’s main rivals, ” says the guide while the man in red still taps away, getting more insistent and animated. | “The bullet holes you can see in the stone come from a hit in 1926, on Earl “Hymie” Weiss, a member of the O’Banion gang – Al Capone’s main rivals, ” says the guide while the man in red still taps away, getting more insistent and animated. |
| Related: Chicago's music and street food will feed your soul | Related: Chicago's music and street food will feed your soul |
| Eventually, South Side yields and asks him, through the glass, what he wants. I assume the anorak man is a tourist asking if he can join the bus tour at this late stage. “I’m related to Spike O’Donnell,” he beams, looking as if he’s three beers into an afternoon of leisure. “He was my great grand-uncle.” | Eventually, South Side yields and asks him, through the glass, what he wants. I assume the anorak man is a tourist asking if he can join the bus tour at this late stage. “I’m related to Spike O’Donnell,” he beams, looking as if he’s three beers into an afternoon of leisure. “He was my great grand-uncle.” |
| “Yeah, OK buddy,” says South Side with a look of practised, conciliatory incredulity; then turns back to face us. “Everyone in Chicago’s got a story. Everyone’s related to a mobster.” | “Yeah, OK buddy,” says South Side with a look of practised, conciliatory incredulity; then turns back to face us. “Everyone in Chicago’s got a story. Everyone’s related to a mobster.” |
| This city has an odd relationship with its gangster past. For some it is a mark of sin, for others a battle scar to flash with pride. And despite many attempts – most famously and bitterly by former mayor Richard M Daley – for the city to dissociate itself from the prohibition era, it remains a fascinating period in US history. | This city has an odd relationship with its gangster past. For some it is a mark of sin, for others a battle scar to flash with pride. And despite many attempts – most famously and bitterly by former mayor Richard M Daley – for the city to dissociate itself from the prohibition era, it remains a fascinating period in US history. |
| I’ve never agreed with Daley’s view. Capone was a man who drove around in an armoured green Cadillac and built soup kitchens for the poor while ordering the murders of judges; who forced the singer Fats Waller, at gunpoint, to play for three days straight at his birthday party, but then made him rich beyond his wildest dreams. A nice wiseguy, he wasn’t. But an interesting guy? No question. | I’ve never agreed with Daley’s view. Capone was a man who drove around in an armoured green Cadillac and built soup kitchens for the poor while ordering the murders of judges; who forced the singer Fats Waller, at gunpoint, to play for three days straight at his birthday party, but then made him rich beyond his wildest dreams. A nice wiseguy, he wasn’t. But an interesting guy? No question. |
| The Chicago History Museum, in the Lincoln Park neighbourhood, has a section on Gangland Chicago among its many exhibitions, as well as organised pub crawls and discussions with experts on the era. I marvel at the ingenuity of devices to hide booze, such as a row of fake cigars hiding test tubes or a walking stick with a handle that cloaks a small beaker. | The Chicago History Museum, in the Lincoln Park neighbourhood, has a section on Gangland Chicago among its many exhibitions, as well as organised pub crawls and discussions with experts on the era. I marvel at the ingenuity of devices to hide booze, such as a row of fake cigars hiding test tubes or a walking stick with a handle that cloaks a small beaker. |
| Related: Top 10 live music venues in Chicago | Related: Top 10 live music venues in Chicago |
| If you want a great way to hear and see the sights of the prohibition era, the Untouchables Tour is a blast. As the tour bus trundles into the city’s actual South Side, we’re regaled with tales of mobsters such as Capone, Johnny Torrio, “Diamond” Jim Colosimo (so called as he would keep a bag of diamonds on him, sinisterly playing with them while talking to associates), red anorak man’s possible ancestor Spike O’Donnell, and Dion O’Banion, head of Chicago’s biggest Irish gang. | If you want a great way to hear and see the sights of the prohibition era, the Untouchables Tour is a blast. As the tour bus trundles into the city’s actual South Side, we’re regaled with tales of mobsters such as Capone, Johnny Torrio, “Diamond” Jim Colosimo (so called as he would keep a bag of diamonds on him, sinisterly playing with them while talking to associates), red anorak man’s possible ancestor Spike O’Donnell, and Dion O’Banion, head of Chicago’s biggest Irish gang. |
| As some of the landmarks of the prohibition era are no more, the guides, South Side and Louie, make up for it by dressing up and dropping into character as hoods – complete with spats, pinstripe suits and two-tone shoes – while the sound system pipes out the rat-a-tat-tat of machine gun fire and jazz music to help us imagine the scene back in the 1920s. So, while the site of the St Valentine’s Day massacre is now a car park, in the hands of the guides we feel all the tension of the fateful 1929 day, with an account of how seven members of Bugs Moran’s gang were lined up and shot by hoods dressed as cops. | As some of the landmarks of the prohibition era are no more, the guides, South Side and Louie, make up for it by dressing up and dropping into character as hoods – complete with spats, pinstripe suits and two-tone shoes – while the sound system pipes out the rat-a-tat-tat of machine gun fire and jazz music to help us imagine the scene back in the 1920s. So, while the site of the St Valentine’s Day massacre is now a car park, in the hands of the guides we feel all the tension of the fateful 1929 day, with an account of how seven members of Bugs Moran’s gang were lined up and shot by hoods dressed as cops. |
| The next day I feel I’ve had enough blood and guts and want to hear more about what ordinary folk got up to in those boozeless, boozy times. Chicago Detours is a walking tour that its founder Amanda Scotese describes as “a history of the way people had fun in Chicago”. So, as I follow Amanda into the bowels of Chicago’s odd double- and even triple-decker street layout, along the subterranean roads under South Wacker Drive, I’m shown iPad pictures of how the buildings looked then compared to now, and told of the music that would come streaming out of them. Later we stop for drinks in the grand 437 Rush – one of the first venues to play a new-fangled type of music called jazz. | The next day I feel I’ve had enough blood and guts and want to hear more about what ordinary folk got up to in those boozeless, boozy times. Chicago Detours is a walking tour that its founder Amanda Scotese describes as “a history of the way people had fun in Chicago”. So, as I follow Amanda into the bowels of Chicago’s odd double- and even triple-decker street layout, along the subterranean roads under South Wacker Drive, I’m shown iPad pictures of how the buildings looked then compared to now, and told of the music that would come streaming out of them. Later we stop for drinks in the grand 437 Rush – one of the first venues to play a new-fangled type of music called jazz. |
| Perhaps the most absurd legacy of the Volstead Act of 1919 is its effect on Chicago’s nightlife. Speakeasies sprung up in every neighbourhood – so called as you would have to whisper the password to get in – and some still exist today, such as the Green Door Tavern on North Orleans Street, and the Green Mill in the Uptown neighbourhood. The Green Mill remains a stalwart of old-time good times, jumping till the early hours, with guests that dress the part: feather fascinators sticking out from ladies’ hats, men of all ages in homburgs and trilbys dancing the Charleston and the jitterbug, sipping whisky and gin cocktails chased down with a shot of Jeppson’s Malört, a local spirit that slips down about as smooth as granite. | Perhaps the most absurd legacy of the Volstead Act of 1919 is its effect on Chicago’s nightlife. Speakeasies sprung up in every neighbourhood – so called as you would have to whisper the password to get in – and some still exist today, such as the Green Door Tavern on North Orleans Street, and the Green Mill in the Uptown neighbourhood. The Green Mill remains a stalwart of old-time good times, jumping till the early hours, with guests that dress the part: feather fascinators sticking out from ladies’ hats, men of all ages in homburgs and trilbys dancing the Charleston and the jitterbug, sipping whisky and gin cocktails chased down with a shot of Jeppson’s Malört, a local spirit that slips down about as smooth as granite. |
| In recent times, a host of newer restaurants and bars have sprung up taking, if not inspiration, then at least assimilation of the city’s gangster past. I’m talking about speakeasy-style bars such as Double A in the River North district, replete with a sliding wooden slat in the door to identify you as a John or a G-man, the Drawing Room in the Gold Coast, Trenchermen in Wicker Park and Scofflaw in Logan Square, which sit alongside venues with a more establishment air, like the debonair Glunz Tavern in Old Town or The Berghoff – the first place in the city to receive a liquor licence after prohibition officially ended in 1933. | In recent times, a host of newer restaurants and bars have sprung up taking, if not inspiration, then at least assimilation of the city’s gangster past. I’m talking about speakeasy-style bars such as Double A in the River North district, replete with a sliding wooden slat in the door to identify you as a John or a G-man, the Drawing Room in the Gold Coast, Trenchermen in Wicker Park and Scofflaw in Logan Square, which sit alongside venues with a more establishment air, like the debonair Glunz Tavern in Old Town or The Berghoff – the first place in the city to receive a liquor licence after prohibition officially ended in 1933. |
| To complete the homage to the Hollywood version of the era, see the white marble steps at Union Station where the famous shoot-out scene from The Untouchables (1987) was filmed; and the Blackstone hotel, where a ménage à trois between Capone, an underling and a baseball bat is said to have occurred. | To complete the homage to the Hollywood version of the era, see the white marble steps at Union Station where the famous shoot-out scene from The Untouchables (1987) was filmed; and the Blackstone hotel, where a ménage à trois between Capone, an underling and a baseball bat is said to have occurred. |
| To look the part, I visit the city’s wide choice of vintage clothing stores, such as Randolph Street market, and get a proper wisgeguy hat at Store B and Optimo – a Chicago institution whose clients include Johnny Depp, Jack White and the late, great John Lee Hooker. | To look the part, I visit the city’s wide choice of vintage clothing stores, such as Randolph Street market, and get a proper wisgeguy hat at Store B and Optimo – a Chicago institution whose clients include Johnny Depp, Jack White and the late, great John Lee Hooker. |
| The second place to get a liquor licence when the city went “wet” again was the Drake hotel. It has a beguiling view of Lake Michigan, chandeliers and dragon-headed lamp fittings, and the elegant Coq D’or bar downstairs. | The second place to get a liquor licence when the city went “wet” again was the Drake hotel. It has a beguiling view of Lake Michigan, chandeliers and dragon-headed lamp fittings, and the elegant Coq D’or bar downstairs. |
| For those after a more modern hotel with a minimalist aesthetic, there’s Public. Previously the Amabassador East, this was the playground of a different set of hatted hoodlums in the 1950s: the Rat Pack and their entourage. Frank Sinatra had his own table at the hotel’s famous restaurant – the Pump Room – just as Capone had his at just about every bar in town. And 90-odd years after the mobsters ran Chicago, they still have their fingerprints over much of what still makes the city special today. | For those after a more modern hotel with a minimalist aesthetic, there’s Public. Previously the Amabassador East, this was the playground of a different set of hatted hoodlums in the 1950s: the Rat Pack and their entourage. Frank Sinatra had his own table at the hotel’s famous restaurant – the Pump Room – just as Capone had his at just about every bar in town. And 90-odd years after the mobsters ran Chicago, they still have their fingerprints over much of what still makes the city special today. |
| How to do it | How to do it |
| The trip was organised by Choose Chicago (choosechicago.com), with accommodation at the Drake Hotel (+1 312 787 2200, thedrakehotel.com, doubles from $139) and Public (+1 312 787 3700, publichotels.com, doubles from $175).United (united.com, 0845 8444 777) flies from Heathrow to Chicago from £557 return, including taxes |
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