Chicago: City of big stories

Looking trim, exuding cool, 81-year-old Buddy Guy dips his head to the microphone. 'They don't play this kinda blues on the radio no more,' he growls. The audience in his eponymous bar in downtown Chicago whoops in anticipation. Then this doyen of the Blues guitar, mentor and hero of Keith Richards (one of whose guitars hangs behind the bar) and Robert Plant ('Inspiring me since I was a kid,' says a note on the wall from the Led Zep frontman) launches into Love Her With a Feeling: 'The woman I love, man, she kinda big and fat...' 

Buddy is old-school and you could say the same for the city he has lived in for 60 years, since making the classic journey up the Blues Highway from Louisiana. When Buddy arrived, Chicago's unofficial poet laureate, Nelson Algren, had already written his bittersweet paean to the city, Chicago: City on the Make. Algren is a neglected literary figure these days but his muscular, ambivalent writings on Chicago merit a special exhibit in the city's new American Writers Museum and he is especially remembered for likening the city to a woman with a broken nose: 'you may well find lovelier lovelies. But never a lovely so real.' 

Well Chicago is still lovely and real but, as I discover on this midsummer visit, the city has also undergone some pretty dazzling rhinoplasty in recent years. My first view of downtown, from the window of the taxi from O'Hare, has an opening credits feel - a pumped-up, rectilinear skyline the colour of tarnished coins, foregrounded by dark-bellied clouds over Lake Michigan. This is, remember, the City of the Skyscraper - the world's first steel-framed multi-storey structure having been built here in 1885. Since then, through Prohibition and America's postwar building boom to Trump's portfolio of priapic Towers (yes Chicago has one) skyscrapers of litheness and beauty have continued to make perpendicular poetry above the city. The latest venture is the the 94-storey Vista Tower which will become Chicago's third-highest building (after Willis, formerly Sears, Tower and the Donald's hotel-and-condo complex) when completed in 2020. 

Before my jetlagged visit to Buddy Guy's blues bar (catching Buddy himself, incidentally, is a bonus as he plays unannounced) I walk the few blocks north from my downtown hotel to the Chicago River and stroll its south bank. With its score of liftable steel 'bascule' bridges and post-industrial neglect the river corridor through the city was once that broken nose on a characterful face. But since the turn of the Millennium the city has invested in an ambitious programme to pedestrianise and landscape the section that wraps an arm around the city's central district (known as The Loop) with restaurants and bars, sculptures, wildlife-friendly zones, platforms for kayakers and a general air of easy living. This is the Riverwalk and as I crane my neck skyward, glancing ahead only to sidestep the joggers, I feel I have swigged, like Alice, from the bottle labelled 'Drink Me'. At one point I find myself pirouetting in amazement as the evening sun turns the Art Deco tower capping the 37-storey Carbide & Carbon Building into a bar of gold. 

The next morning, with Buddy's blues licks still ringing in my ears, I take a guided architectural tour. Less than a decade after the city's first skyscraper broke the skyline Chicago's elevated rail system, known as the 'L', was opening its first lines on riveted steel trackways some 25ft above the new sidewalks. Nowadays the system's tentacles reach far into the suburbs but the original circuit of tracks enclosing The Loop remains, providing the template for two-hour introductions to the city's built environment run by the Chicago Architecture Foundation. My guide is 'docent' (volunteer) Howard Sachs, a retired engineer who says he's been riding the L 'since my mom was holding me in her arms'. Howard is miked up against the rackety-tack of the trains while our group of eight (mostly out-of-towners with a couple of Chicagoans) wear earpieces so as not to lose his commentary as we jump on and off trains and use various stations' platforms as viewing galleries. 

We check off Willis Tower, the city's tallest; the Jewelers' Building, capped with tower and cupola that during the Prohibition era housed a speakeasy named the Stratosphere Lounge; and a triangular building with medieval-style arrowslit windows. 'A federal jail. The top is the recreational area - some of the prisoners are waving to us,' says Howard. Tiny figures do indeed peer down but there are no arm movements - they're probably drowning rather than waving. Then, at Clinton Station - beyond the Chicago River in the West Loop neighbourhood - Howard dips a toe in the socioeconomics of the city. 

'When I was this young fellah's age,' he says, pointing to a teenager in our group, 'I didn't come out here. This was Chicago's Skid Row. Now all these warehouses and crummy buildings have been converted into apartments.' He gestures at the utilitarian brick blocks beyond the platforms, grit-blasted to pinkness and accessorised with balconies. It's that old yuppie story - appropriately enough for a city that, besides inventing the skyscraper (not to mention the ferris wheel, the chocolate brownie and the deep-pan pizza), defined the phenomenon of the young urban professional. The Y-word first appeared in Chicago magazine in 1980, in an essay that could have been written yesterday: 'Real-estate prices have skyrocketed. Lofts and townhouses are being rehabilitated ... to accommodate the rising tide of 'Yuppies'...' 

This roll of gentrification is the warp and weft of any dynamic city but it feels particularly marked in Chicago, where distinct neighbourhoods bump up against each other and guard their cultures jealously. The Near North Side, reckoned Nelson Algren, is 'almost as different as the Near Northwest Side, just over the bridge, in manners, mores, vocations and habits of speech, as Bronzeville is from Rogers Park.' And the same could be said today about the Wicker Park and Humboldt Park neighbourhoods lying to the northwest of downtown - once the stomping grounds of, respectively, Algren himself and Chicago's pre-eminent writer, Saul Bellow. To get a taste of neighbourhood Chicago, beyond the gilded cage of The Loop, I jump on the Blue Line of the L and head towards these borderlands where history and economics collide. 

Alighting at Division station I catch a no.70 bus due west on Division Street, through the heart of Wicker Park. In Algren's latter days here (he moved away in the mid-1970s) the neighbourhood was blighted by crime. Notwithstanding a crazy homeless person pushing his world in a trolley it's now hipsterishly smart, with spacious mid-century apartment buildings and eclectic bars and restaurants such as Fifolet ('Cajun & Cocktails') and Joe's Wine Cellar ('Purveyor of fine wines, cheese, and craft beer'). But as the bus speeds west the picture changes. Beneath a steel-framed structure representing the Puerto Rican flag we enter the Paseo Boricua, a half-mile-long microcosm of Puerto Rico, the Caribbean island with a semi-detached relationship to the US (it holds 'Commonwealth' status). Here the amenities are culturally specific: a branch of Alcoholicos Anonimos, a grocer's that sells the staples of Puerto Rican cooking such as malanga and calabaza, and Lilly's Records, where you can buy men's guayabera shirts and seemingly infinite manifestations of the Puerto Rican flag. 

This is Humboldt Park, the neighbourhood that takes its name from an actual park that was in turn named for the 19th-century German naturalist Alexander von Humboldt. His statue stands in the park along with that of the Viking explorer Leif Erikson - a legacy of the area's origins as a home-from-home for German and Scandinavian immigrants. In the park there's a European-style boating lake with boathouse, a beach with lifeguard tower, and a half-timbered complex of buildings that wouldn't look out of place in Bavaria. 

This turns out to be Humboldt Park's former stables which, in a process of seamless immigrant appropriation, now houses the National Museum of Puerto Rican Arts and Culture. Here I get chatting to Bianca Ortiz, the Director of Exhibitions, who shows me the current exhibition, a set of brightly coloured portraits completed in prison by the Puerto Rican activist Oscar Lopez Rivera. A hero to the Puerto Rican community, he spent 35 years in US jails for alleged terrorist links before having his sentence commuted by Barack Obama in May 2017. 'Rivera grew up in this neighbourhood,' Bianca tells me. 'It's thanks to him and his brother that the people here had access to Latino education.' 

That was a generation ago. Now, she says, the Puerto Rican identity in Humboldt Park is under renewed threat: 'I was born and raised in the island. I moved here three years ago. People say it's safer now, but it's changing too. Puerto Ricans are having to move out because they can't afford it any more.' She fears it going the same way as Wicker Park, where Latinos have already been chased out by gentrification. The museum, she says, stands 'like a rock' in the midst of this tide: 'We are trying to preserve the culture here. It is free, open door to everyone.' 

That evening I see this dynamic from the other side when I return to the West Loop, the 'Skid Row' of Howard Sachs's youth, to eat in one of Chicago's innovative new restaurants. Eden, which has its own garden and greenhouse, offers 'a fresh take on Mediterranean and American food,' having evolved from a catering business that reflects the neighbourhood's origins as Chicago's meatpacking district. 'This is, or was, an industrial corridor,' confirms chef Devon Quinn. But it's flourishing in new ways. The United Center, home of the Chicago Bulls (basketball) and the Blackhawks (hockey), is just two blocks away; the Chicago HQ of Google, which opened in a former cold storage warehouse in late 2015, lies a mile or so east. 'It's a fast up-and-coming neighbourhood. It's been really interesting, watching the changing demographic,' Devon continues as I eat a seafood stew as gutsy as Marseille itself, with a hoppy lager described (inevitably) as 'craft' on the drinks list. 

So the neighbourhoods wax and wane, in some cases turning Chicagoans into visitors to their own, racially segregated city. In Millennium Park, The Loop's green and pleasant heart, 26-year-old artist Chanel Thomas finds refuge from Chicago's notorious South Side, where she admits life can be rough and dangerous. I find her sitting on a park bench with examples of her embroidered denim jackets draped over the bench while she works on a large hanging depicting a scene from The Fresh Prince of Bel-Air, the TV sitcom with Will Smith. 'I come down here because I know nobody's going to bother me,' she says. 'I just feel sorry that a lot of people on the South Side don't come down here much. My mom don't ever come, I guess because she wasn't ever able to from a child.' 

Swarming with tourists from scores of countries, Chanel's daytime haunt is one of the most relaxed, congenial urban spaces in the world. I spend a dreamy final afternoon watching the tourists watching themselves in the silver skin of Anish Kapoor's sculpture Cloud Gate (jelly-bean-shaped, hence its popular name of The Bean), cooling my bare feet (side-by-side with lunching office workers) in the stream that runs through Lurie Garden and shimmying through the hushed halls of the world-class Art Institute (Hopper's Nighthawks, Grant Wood's American Gothic and more works of French Impressionism than you can shake a palette knife at). 

Then, as the shadows lengthen, I head for the outdoor, Frank Gehry-designed Pritzker Pavilion, buying a cold beer from a food truck on the way. In the summertime Chicago hosts a munificent programme of free cultural events that makes living in the city so beautifully easy and this evening the resident Grant Park Orchestra and Chorus is performing a contemporary Missa Latina (Latin Mass) by the Puerto Rican composer Roberto Sierra. Surrounded by those coin-coloured canyons I settle into my seat, crack open the beer. And as Hosanna in excelsis blasts through speakers hidden in Gehry's ingenious overhead latticework of steel pipes, the neighbourhoods sing back with a fanfare of sirens. 

Published in the December 2017 issue of National Geographic Traveller