Chicago: A city of layers

A guide to the birthplace of the skyscraper

Chicago oozes luxury on every level, finds Ella Buchan


I don’t need an app or the toot of a horn to know my ride has arrived. I can tell by the quickening of the air, the whoosh of wind and the rhythmic ‘thwop-thwop’ of the rotor blades.

After a windswept photo, I climb aboard a scarlet chopper for a jaunt through the skies with Chicago Helicopter Experience. While the Windy City’s steely skyline is impressive from any angle, there are few better vantage points than 1,500 feet above ground.

Other cities may have taller buildings but Chicago, birthplace of the skyscraper, still stands spires and shoulders above the rest.

The helicopter zigzags past the twin antennae of the Willis Tower, hometo vertiginous glass-viewing platform SkyDeck. The city’s tallest building, it soars like a gleaming king on a board of intricate chess pieces. Styles range from art deco (333 North Michigan) and modernist (the John Hancock Building, or ‘Big John’) to the Spanish colonial revival of the Wrigley Building, its Seville-inspired clock tower telling time by the teal-coloured Chicago River. From the air, doll-sized walkers, joggers, cyclists and rollerbladers dot the wide paths around Lake Michigan, while others laze on beaches and grass.

Chicago knows it’s gorgeous. All that architecture, water and lush green spaces has earned it the nickname ‘Urbs in Horto’, or city in a garden.

And it hasn’t let itself go. Maggie Daley Park opened in 2015, replacing an underground parking lot with tennis courts, an outdoor climbing wall and picnic spots next to Millennium Park’s 25 acres. Spanning the two parks is Frank Gehry’s BP Pedestrian Bridge, a sinuous squiggle of brushed stainless steel.

Then there’s the art. The Art Institute’s permanent collection – world-famous paintings include Grant Wood’s American Gothic, Picasso’s The Old Guitarist and Edward Hopper’s Nighthawks – is as dizzying as those buildings, which glint through the glass as I weave between floors.



The luxury travel market is taking notice. Bespoke Experiences, which works with travel agents to tailor exclusive tours, recently added Chicago to its portfolio.

New hotels include the chic Kimpton Gray, named for the original Georgia Gray marble in the lobby. Then there’s the city’s first Conrad, a classically elegant choice for business travellers. This autumn sees the Viceroy open in the glitzy Gold Coast neighbourhood, while the new Ace Hotel Chicago caters to moneyed millennials.

There are endless opportunities to splurge. Clients can take a champagne helicopter tour, shop for Louis Vuitton luggage on Michigan Avenue’s ‘Magnificent Mile’, or linger over nine impeccable courses at three-Michelin- starred Grace restaurant.

All this could easily go to a city’s head. Yet the city oozes down-to-earth, Midwest charm and generosity of spirit.

From my first strides around The Loop (central business district), face tilted upwards to gawp at the towers, I felt the entire city wrapping me in a welcoming blanket.

Chicagoans love their city so much, they want to tell you everything. Take the Chicago Greeters, locals who show visitors around for free, like a welcome gift. The scheme has been curated by Choose Chicago, the destination’s official marketing organisation.

My guide, retired businessman David Dresden, takes me to Wicker Park, oneof Chicago’s oldest neighbourhoods and currently the hippest. We pass former furniture factories that are now record stores, pho restaurants and vintage emporiums, before ascending to The 606, a 2.7-mile-long elevated park on a former

railroad. The paths are bordered by fragrant grasses and wildflowers, and dotted with sculptures. “Ah, Chicago is a great city,” sighs David.


Few are as enthusiastic about their neighbourhood as Margaret Hicks, who founded Elevated Tours. And few neighbourhoods are as strange as hers.

The comedian has a passion forthe Pedway, a subterranean networkof tunnels linking some of The Loop’s famous buildings. She guides me past a gallery of stained glass underneath Macy’s towards the Marriage Bureau, where photographer Ed waits patiently to hawk his wedding portraiture.

Margaret is planning to launch a luxury tour with spa treatments, cocktails and dinner, all without stepping outside.

“Not everyone gets it,” she admits. “But I just love it. It’s so weird.”

Less niche is a boat tour with the Chicago Architecture Foundation. The guides are volunteer staff members who know the buildings brick by brick (or steel rod). I lean back to gaze up at the eclectic parade of beauties.

Afterwards, I devour oozy burrata (cheese) with a glass of rosé at Chicago City Winery on the Riverwalk.

Food has always been a big deal in Chicago, though it has moved beyond deep-dish pizza and hot dogs splodged with mustard.

Now the city twinkles with 35 Michelin stars. One-starred GreenRiver is tuckedon the 18th floor of a medical building. Not exactly prepossessing – until I stepout to views that swoosh towards Lake Michigan. The encyclopedic cocktail menu was designed by the same team as New York’s Dead Rabbit, regularly rated the world’s best bar. Dishes include ricotta cavatelli pasta with short rib and morels, self-sauced by a runny poached egg. I can’t resist trying a Michelin-starred cheeseburger, rare, juicy and almost truffle-like in its richness.

Proxi, in the West Loop, is chef Andrew Zimmerman’s second restaurant. His first, Sepia, already has a star. With sharing plates like tempura elotes (smoked corn fritters) and crisp-fried fish collars with garlic chilli sauce, I predict another.

Eden, in edgy West Lake, draws crowds keen to taste (and Instagram) its umami doughnuts with roasted mushroom miso and raclette.

Sepia lighting and scantily-clad staff mean Maple & Ash, in Gold Coast, feels more like an exclusive nightclub than a restaurant. In lieu of an amuse-bouche, the waiter pours a citrussy aperitif, stiff with rum. We opt for the chef’s choice, and the table groans under platters of crab legs, oysters and wood-fired filet mignon.

The treats keep coming at Buddy Guy’s Legends, owned by the blues star. “Mr Guy’s on stage right now if you wanna catch him,” drawls the doorman.

And there he is, 81 years old in a green plaid shirt and still working the crowd with gravelly, melodic riffs about whiskey and wimmin’.

There’s more music the following evening at Frank Gehry’s Jay Pritzker Pavilion, where the city hosts free summer concerts. The Grant Park Orchestra fills the stage, bows and vocal chords poised. Then the symphony soars from under the honeycombed roof, brimmed with steel ribbons. The notes hit my skin like shards of ice. Goosebumps. Visitors can pay fora seat in the stands or simply laze on the grass with a picnic – unwrapping another gift from this big-hearted city.

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