Chicago THE CITY THAT KISSED THE SKY
With its gorgeous architectural bones, great shopping, food and nightlife, plus a rousing dose of local pride, the ‘Windy City’ should be every traveller’s American dream.
Asurvey last year by Condé Nast Traveler confirmed what any patriotic Midwesterner could have told you: the favourite city break of Americans is Chicago. Yes, Chicago; the blue-collared city most tourists to the US ignore for more glitzy destinations, like New York and San Francisco. In 2016, more than 52 million Americans visited. What do they know that the rest of us don’t? I hopped on a new budget, long-haul flight with Norwegian from London to Chicago to find out.
My plan was to experience the city as americans do: a little sightseeing, neighbourhood food, perhaps some nightlife.
The rest of the world knows America’s third city for Al Capone, prohibition and speakeasies. Illinois remains uptight about booze. Even if you’re pushing 60, don’t leave your hotel without ID.
Simultaneously we see Chicago as the Windy City, “[Sinatra’s] Kind of Town”, perhaps as the start of Route 66.
The American mother road began at the junction of Jackson Boulevard and Michigan Avenue. Since they shifted it a few blocks south, only Lou Mitchell’s diner at 565 West Jackson remains as athrowback in neon.
For Americans though, Chicago’s Americana is architectural. Chicago is to the skyscraper what Los Angeles is to film or Nashville is to country music — you get them elsewhere, but nothing beats the original.
The Loop — Chicago’s downtown — jostles with a century’s worth of spires and towers. To walk around is not just to shop at Bloomingdale’s or experience the cinematic thrill of elevated trains rumbling above roads. It’s to feel the upward thrust of American cities, their modernity and futuristic excitement.
Chicago has all the pizzazz of Manhattan but none of the attitude, or litter. No one snarls when you stop to gawp.
AMERICA’S BEST SKYLINE
Start at Michigan Avenue Bridge for prime wow factor. Or for the most exhilarating skyline in the States go up the city’s tallest building, Willis Tower.
The escalator takes a minute to ascend 413m (your ears pop), then the edge over oblivion on the glass floor of the highest viewing platform in the western hemisphere.
What you don’t see is the creativity,” said my guide, Ronnie. We were on a Chicago Architecture Foundation tour boat, cruising along the Chicago River through a canyon of skyscrapers: art deco spires, modernist boxes and sleek glass-skinned arcs. “You don’t see the deep foundations that got those buildings to stand up.”
PARIS OF THE PRAIRIES
The thing is, Chicago, on the shores of Lake Michigan, should be a swamp; one theory explains its name as the native American word for wild onions. As impressive as its existence is that Chicagoans erected the world’s first skyscraper just 14 years after the first Chicago burnt down in 1871. They haven’t stopped since.
If chutzpah is one reason why Americans admire Chicago, another is that this is a city that clearly enjoys its river. After 1871 it aspired to be a Paris of the prairies. Last year it came good, opening the mile-long Riverwalk promenade. Lined with waterside café-bars, it’s the Seine with skyscrapers.
The other big sight is the Art Institute; it’s huge in size (300 000 exhibits — including Joseph Mozier’s Pocahontas) and status, having the largest collection of French impressionists outside the Louvre.
SCRIBES AND MUSOS
I went to the new American Writers Museum. Local boys Ernest Hemingway and Raymond Chandler were there, also Mark Twain and JFK and Martin Luther King Jr. Reading their quotes, I began to understand what made this city, perhaps America itself, tick: a dogged belief in freedom; a determination to kick against authority.
You hear it in Chicago blues. Singers like Muddy Waters and Howlin’ Wolf invented its electrified style when they arrived in the ’50s, fleeing southern oppression. Without it there’d be no Rolling Stones. I wanted to experience it raw on a Saturday night.
First, though, dinner. It’s a mystery why Chicago brags about being the home of deep-dish pizza. It’s a sloppy quiche best served with a defibrillator. Just don’t. Not when eating well is so easy here.
Some great options include central RPM Steak; glamorous Maple & Ash in Gold Coast, Chicagos’s smartest neighbourhood with the most central of its 26 beaches; and the melt-in-the-mouth Italian beef sandwich at Jay’s Beef in Wicker Park, a Chicagoan Brooklyn of brewpubs and hipster shops.
“Best beef sandwich in America said USA Today,” Uber driver Rich told me en route.
Chicago has all the pizzazz of Manhattan but none of the attitude, or litter
HOLD THE KETCHUP
For fine-dining local-style there’s The Duck Inn, where, in a former Bridgeport tavern, Michelin-starred chef Kevin Hickey served me a down-home, five-course tasting menu that tried, but failed, to conceal its virtuosity. Dishes included Chicago hot dog (strictly no tomato sauce) cooked in duck fat, burrata with fennel, and signature rotisserie duck.
Buddy Guy’s Legends is Chicago’s famous, touristfriendly blues bar. But Rosa’s Lounge was the real deal; a scruffy, genial, Northwest Side dive that was to the slick bar-blues industry what the savannah is to a zoo. What hit me, though — far more than the potent Old Fashioneds poured by owner Tony — was the intimacy.
Barrel-chested in a zoot suit, Willie Buck, who has been performing since 1953, dropped the mic and walked through the audience growling Hoochie Coochie Man. Chicago recently named a street after him.
“Everybody got the blues whether they know it or not. Blues is truth,” he said.
IDEALS BROUGHT TO LIFE
Next day, accompanied by one of the city’s volunteer greeters, I visited the city’s arty bits in Millennium
Park: Sir Anish Kapoor’s mirrored Cloud Gate sculpture — known as “The Bean” — and Jaume Plensa’s Crown Fountain, a glass-brick monolith spewing water. What impressed me most though was the Jay Pritzker Pavilion, Frank Gehry’s outdoor concert venue.
Time Out was mocked when its 2017 City Life Index, an assessment of the world’s most liveable cities, ranked Chicago number one. Yet piece the city together — its good looks, shopping, food (at reasonable prices), nightlife, friendliness and local pride — and you have a destination of American ideals. No wonder Americans love it. For foreigners, it’s a jackpot.
I’d go back in heartbeat. It wasn’t even windy.