Ultracity: the luxury travel guide to Chicago

There’s a moment, on my helicopter flight above Chicago, when it all falls into place. We’re flying north, following the route of Lake Shore Drive. To the right, the blue haze of Lake Michigan; to the left, the thicket of skyscrapers that forms one of the world’s great skylines. As we turn back near the beautiful obelisk of the John Hancock Center, the jumble of buildings opens up to reveal the deep canyon of North Michigan Ave, aka the Magnificent Mile. The jolt the chopper receives could be turbulence – or it could be all that urban energy pulsing upwards. It’s as if the true Chicago has suddenly revealed itself.

America’s ‘Second City’ (it’s actually the third largest after New York and LA) is on an upward swoosh of high-spec development, from new restaurants and hotels to the redevelopment of some of its old industrial buildings. Newly opened and forthcoming hotels include Nobu Chicago and the city’s first Viceroy, while the 94-storey Vista Tower, a condo and hotel complex, will become Chicago’s third-highest building when topped out in 2020. The regeneration is most notable in the Riverwalk promenade by the Chicago River, dwarfed by an architectural massif that wrenches one’s neck in a permanent crick of amazement.

Did ever a place take more care of the face it shows to the world? The city that’s credited with inventing the skyscraper over 130 years ago has been flexing its big shoulders ever since. In 2015 it confirmed its place in the vanguard of urban design with the first Chicago Architecture Biennial (CAB). Starting in autumn 2017 and continuing until this month, the CAB’s second ‘edition’, featured 100 companies, artists and architects from 20 countries on a mission to ‘make new history’ with their designs and concepts for urban living. The event is going from strength to strength; the style influencers are coming home.

But you can bet that however cool they are, they’ll do that tourist thing and take a stroll in Millennium Park, where they’ll be drawn to Anish Kapoor’s reflective sculpture Cloud Gate. Nicknamed The Bean, it traps the stupendous urban fabric in its silver skin and gives it a fish-eye bend. I spend a good half hour watching people interact with it, and most can’t get enough of their own reflections. Because, like the city itself – like all the best cities – it makes us feel good about ourselves.

Where to stay, where to eat and what to do during a luxury holiday to Chicago

The hotels
Kimpton Gray is part of the city’s latest generation of hotels, having opened in 2016. It exists partly in order to conserve the building that contains it: the former Midwest headquarters of the New York Life Insurance Co, which dates from 1893. Designed by William Le Baron Jenney, who built the city’s first skyscraper (in 1884), it has a lobby and staircase of grey marble, the original bank of elevators with evocative signage and a stylish Untouchables vibe. Rooms from around £123 per night.

Housed in a classic Mies van der Rohe-designed building overlooking the Chicago River, the Langham offers great location and floor-to-ceiling windows, plus plenty of original art on the walls: from £440 per night.

The Peninsula, just off the Magnificent Mile, is the billet of choice for Hollywood A-listers: Art Deco style, impeccable service, great spa: rooms from £330 per night.

The lunch stop
The 18th-floor Green River in Near North Side is a Michelin-starred restaurant with a rooftop terrace and views of Lake Michigan. It does a seriously good cheeseburger and great cocktails including the Tommy Gun: Kappa Chilean Pisco, pineapple, lime, garam masala and aromatic bitters.

The dinner venues
In a crowded, talented field, two restaurants stand out – and were first and second in the Chicago Tribune’s top dining spots for 2017. In pole position is Alinea in Lincoln Park, where chef Grant Achatz boasts three Michelin stars thanks to his ‘multi-sensory’ fine dining with ‘experimental moments’ (one dish comprises ‘lobster, curry, Earl Grey and grapefruit’). Tasting menus from £135.

Then there’s Grace in the West Loop, where chef Curtis Duffy, formerly of Alinea, also maintains three Michelin stars with tasting menus (the ‘Fauna’ includes Alaskan king crab with sudachi – a Japanese citrus fruit – cucumber and lemon mint) from £180.

Two exciting new kids on the block that are hoping to challenge the hegemony of such established high-end eateries have their roots in the sustainable and local food movement: Proxi in the West Loop is the brainchild of chef Andrew Zimmerman, who has maintained a one-Michelin-star rating at Sepia, just around the corner, for the past six years. The decor is canteen-chic; the menu inspired by street food that Zimmerman has fused in unexpected combinations – such as ‘tempura elotes’. “Elotes are grilled Mexican street corn,” he tells me. “Putting those two together didn’t seem like a huge leap to me, although it’s probably a bigger leap than a Japanese or Mexican chef would have made.”

In a similar vein, Eden, in the up-and-coming West Lake district, sources ingredients from its own greenhouse and urban garden. Try grilled baby octopus and curried lentil brik.

The bars
The Signature Lounge on the 96th floor of the John Hancock Center is a little touristy, but the views, especially at sunset, are superb: an Old Fashioned costs £13.50.

Buddy Guy’s Legends in the South Loop – admission varies depending on act and day of the week – is the city’s premier blues venue. If you’re lucky, the great man himself will take to the stage (usually unannounced).

Green Mill Cocktail Lounge is an intimate, atmospheric former Capone hangout in Uptown that dispenses cool jazz seven nights a week. Cover charge (amount depending on act) on door; no food.

The place to be seen
Maple & Ash in the ritzy Gold Coast neighbourhood, opened in late 2015, labels itself “an innovative take on the traditional steakhouse”. This puts it up against two of Chicago’s most stylish hangouts: RPM Steak (an Obama haunt) and Chicago Cut. The Maple & Ash clientele are well-heeled; the decor darkly glamorous. The ‘I don’t give a f*@k’ menu is £115.

The places to see
The Art Institute of Chicago – one of the world’s great art galleries, home to Grant Wood’s American Gothic and Edward Hopper’s Nighthawks. Noble Art Tours offers private tours: a one-hour tour is £195 for up to six people. 

The Cultural Center at E Washington St and S Michigan Ave – a tessellated monument to learning, with the world’s largest stained-glass dome.

Try a guided tour with the Chicago Architecture Foundation, or see it from above with Chicago Helicopter Experience. It offers 15-minute private tours (just you and the pilot) for £195.

The places to shop
The ‘Magnificent Mile’, aka North Michigan Ave north of the river has flagship stores such as Apple, Ermenegildo Zegna, Giorgio Armani, Burberry, Cartier and Tiffany.

The celebrity haunt Ikram at 15 Huron St in River North brings high-end fashion labels (Alexander McQueen, Givenchy, Kenzo) under one roof. Nearby at 212 W Chicago Ave the effortlessly stylish boutique Blake counts Dries Van Noten among its avant garde designers.

For bespoke hats head for Optimo at 51 W Jackson Blvd in The Loop.

Getting there
The author flew with Aer Lingus from the UK via Dublin, conveniently ‘preclearing’ US Immigration in Dublin Airport: from £229 each way; £1,099 in Business Class.

For more information on what to see and do in the city visit choosechicago.com