Chicago: A city of layers

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

After a windswept photo, I climb aboard a scarlet chopperfor a jaunt through the skies with Chicago Helicopter Experience. While theWindy City’s steely skyline is impressive from any angle, there are few bettervantage 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 WillisTower, hometo vertiginous glass-viewing platform SkyDeck. The city’stallest building, it soars like a gleaming king on a board of intricate chesspieces. Styles range from art deco (333 North Michigan) and modernist (the JohnHancock Building, or ‘Big John’) to the Spanish colonial revival of the WrigleyBuilding, its Seville-inspired clock tower telling time by the teal-colouredChicago River. From the air, doll-sized walkers, joggers, cyclists androllerbladers dot the wide paths around Lake Michigan, while others laze onbeaches and grass.

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

And it hasn’t let itself go. Maggie Daley Park opened in2015, replacing an underground parking lot with tennis courts, an outdoorclimbing wall and picnic spots next to Millennium Park’s 25 acres. Spanning thetwo parks is Frank Gehry’s BP Pedestrian Bridge, a sinuous squiggle of brushedstainless steel.

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

LUXE APPEAL

The luxury travel market is taking notice. BespokeExperiences, which works with travel agents to tailor exclusive tours, recentlyadded Chicago to its portfolio.

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

There are endless opportunities to splurge. Clients can takea champagne helicopter tour, shop for Louis Vuitton luggage on MichiganAvenue’s ‘Magnificent Mile’, or linger over nine impeccable courses atthree-Michelin- starred Grace restaurant.

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

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

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

My guide, retired businessman David Dresden, takes me toWicker Park, oneof Chicago’s oldest neighbourhoods and currently thehippest. We pass former furniture factories that are now record stores, phorestaurants and vintage emporiums, before ascending to The 606, a 2.7-mile-longelevated park on a former

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

WEIRD AND WONDERFUL

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

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

Margaret is planning to launch a luxury tour with spatreatments, 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 ArchitectureFoundation. The guides are volunteer staff members who know the buildings brickby brick (or steel rod). I lean back to gaze up at the eclectic parade ofbeauties.

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

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

Now the city twinkles with 35 Michelin stars. One-starredGreenRiver is tuckedon the 18th floor of a medical building. Not exactlyprepossessing – until I stepout to views that swoosh towards LakeMichigan. The encyclopedic cocktail menu was designed by the same team as NewYork’s Dead Rabbit, regularly rated the world’s best bar. Dishes includericotta cavatelli pasta with short rib and morels, self-sauced by a runnypoached egg. I can’t resist trying a Michelin-starred cheeseburger, rare, juicyand almost truffle-like in its richness.

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

Eden, in edgy West Lake, draws crowds keen to taste (andInstagram) 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. Inlieu 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 theblues star. “Mr Guy’s on stage right now if you wanna catch him,” drawls thedoorman.

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

There’s more music the following evening at Frank Gehry’sJay Pritzker Pavilion, where the city hosts free summer concerts. The GrantPark Orchestra fills the stage, bows and vocal chords poised. Then the symphonysoars from under the honeycombed roof, brimmed with steel ribbons. The noteshit my skin like shards of ice. Goosebumps. Visitors can pay foraseat in the stands or simply laze on the grass with a picnic – unwrappinganother gift from this big-hearted city.