Why go?

Never mind New York – Chicago is America’s coolest city. More manageable than the Big Apple, with a rocking arts and music scene, world-class restaurants, and buildings to make architecture buffs go weak at the knees – not to mention 29km of beach-flecked lakefront – this is the kind of place visitors will find difficult to leave.

What to do

Chicago is a city of neighbourhoods, from the millionaires’ mansions of the leafy Gold Coast, to hipster hotspot Wicker Park, Boystown’s rainbow flags or towering skyscrapers in The Loop. The particular blend of architecture (everything from art deco skyscrapers to German chalet-style homes) is unique – drifting between the neighbourhoods, soaking up the scenes, could easily fill a weekend alone. But there’s plenty more. You need a few hours to do justice to the Art Institute of Chicago (http://artic.edu), whose masterpieces include Grant Wood’s American Gothic. Count jellyfish at the Shedd Aquarium (sheddaquarium.org), the largest in North America, then chow down on mac and cheese at the Lincoln Park farmers’ market. Stroll along the walking trails skirting 58,000-square-kilometre Lake Michigan’s turquoise shoreline, or work out your credit card in the shops of the Magnificent Mile. Anish Kapoor’s Cloud Gate is one of the city’s most iconic landmarks, but don’t miss taking the elevator 412m up the tallest building in the western hemisphere, the Willis Tower (theskydeck.com). You’ll get an unforgettable view of the city at dusk – buy a City Pass (citypass.com/chicago) and skip the painfully long line.

Where to stay

In the polished Gold Coast, the historic Ambassador East re-opened as Ian Schrager’s Public (00 1 888 506 3471, publichotels.com) in 2011. It pairs sleek contemporary design with Chicago legend – the original Pump Room restaurant was frequented by the likes of Frank Sinatra and Audrey Hepburn, as the framed snaps adorning the entrance walls attest. Its surprisingly affordable rooms are bright and minimal, yet exude warmth. Food is by Jean-Georges Vongerichten and the cocktail bar is heaving at weekends when Chicago’s stars come out to play. Landmark hotel The Drake (00 1 312 787 2200, thedrakehotel.com), off the Magnificent Mile, has also seen its fair share – Marilyn Monroe and Joe DiMaggio’s carved initials are still visible on the bar’s wooden countertop.

Where to eat and drink

There’s only one way to come to Chicago – not hungry, but ravenous. The city may be famous for deep dish pizza, and frankly it would be wrong to miss out on a classic Chicago hot dog (George’s, in Bucktown since 1948, is hard to beat). But there’s much more here than ‘junk’ food: highflyer restaurants like Alinea (00 1 312 867 0110, alinearestaurant.com) or Blackbird (00 1 312 715 0708, blackbirdrestaurant.com) attract serious gourmets. Wicker Park’s not-so-secret speakeasy, The Violet Hour (00 1 773 252 1500, theviolethour.com) recalls the city’s Prohibition days, but for the cutting edge of cool, head to Ada St (00 1 773 697 7069, adastreetchicago.com). The low light, high atmosphere ‘drink restaurant’ does seriously good cocktails – order the bourbon-based Fistful of Dollars – and top-notch plates. Try Boystown’s Bar Pastoral (00 1 773 472 4781, pastoralartisan.com) for American cheese platters and terrines, with local wines by the glass, or embrace the American brunch obsession at Bucktown’s always-buzzing Mindy's Hot Chocolate (00 1 773 489 1747, hotchocolatechicago.com). It’s so-called for a reason.

Time running out?

Join a Chicago Food Planet (chicagofoodplanet.com) tour to hit a number of local culinary favourites in a few hours. The Bucktown and Wicker Park walk takes in George’s, Hot Chocolate (both above), as well as Piece pizzeria and microbrewery.

Travel Information

Travel Information

Currency is the US dollar. Chicago is six hours behind GMT and is an eight and a half hour flight from London.

Getting There

United Airlines (united.com) flies direct to Chicago O’Hare airport from London Heathrow several times a day.

British Airways (ba.com) also operates direct flights to Chicago twice a day.

Resources

Choose Chicago (choosechicago.com) is an excellent resource for planning your trip, and can even arrange free neighbourhood walking tours.