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  • Cityscape Skyscrapers and speakeasies
  • City life Lakes, lunching and lounging

Confident cloud-poking architecture, world-class shopping and a vibrant foodie scene make the Windy City trip-worthy.

The combination of glossy steel masterpieces and sprawling shoreline is simply seductive. A typical day will have you spinning the racks at the finest boutiques on the Magnificent Mile (a ritzy stretch of Michigan Avenue), cruising along the shores of Lake Michigan and tucking into gastronomic dish at a Michelin-starred restaurant in the chichi Gold Coast neighbourhood. Somehow Illinois’ biggest, brashest city manages to be cosmopolitan without being overwhelming. Rumour has it that some of the culinary world’s best and brightest use Chicago as their test kitchen before launching on a larger scale. Chef side-projects and specialty spin-offs of all flavours are the order du jour, such as Graham Eliot’s gourmet sandwich shop, Grant Achatz’s molecular gastronomic masterpieces at Alinea and TV personality Rick Bayless' streetfood-inspired Xoco. From all of the Michelin love annually bestowed on Chicago’s foodie illuminati, it seems their experiments are paying off.

Do go/Don’t go

The winter months of December to February are tourist-deterringly chilly, so if you can face the cold and just want to bounce from cosy bar to restaurant, make the most of the quiet. In summer (around July and August), the temperature is more cooperative, allowing for trips to the beach, breezy bike rides and sunshine strolls around the city. Unless you can really hold your Guinness, get out of Dodge on 17 March, when the St Patrick’s Day Parade snakes drunkenly through the city.

Getting thereView map

  • Planes Catch a direct flight from New York City to Chicago O’Hare International Airport (ORD) or Chicago Midway Airport (MDW) on most commercial domestic and international carriers such as Southwest, United or American Airlines. Both airports are about 25 minutes by car from downtown Chicago. You can take the Blue Line subway from O’Hare or the Orange Line from Midway into downtown.
  • Trains Chicago Union Station, on the corner Canal and Jackson streets, has Amtrak service which includes routes to and from Los Angeles, Seattle and New Orleans.
  • Automobiles You can easily hire a car from the airport but it’s not necessary; with the daily bumper to bumper traffic it’s much easier to get around by taxi.
  • Taxis You can easily flag metered taxis on the street; ask if they accept credit cards as not all do. You can hire a limo or car through Metropolitan Limousine (+1 800 437 1700 ; metropolitanlimo.com).