ChicagoUnited States of America

Chicago is the Windy City that loves the Blues, where gangsters like Al Capone ran rings round the Feds, and where the skyscrapers rose as the stock markets fell. A jangling metropolis, with a thicket of classy, glassy towers shooting skywards from the shores of Lake Michigan. All that is part of the draw to this, the third biggest city in the United States. But Chicago can surprise too.

While it has one of the busiest skylines of any American city – with four of the tallest buildings in the US – Chicago had the sense to build its streets wide. So its hundred high-rises don't leave you claustrophobic, unlike some other cities that reached for skies. And Chicago's love of wide open spaces can be seen when you scale its biggest skyscraper, the Willis Tower. Look east from one of its glass balconies, and you'll see the long green-and-gold strip of the Lakefront, with its parks and museums, beaches and piers.

'Chicago's Lawn' is what Chicagoans call it, and it's where they go to play. Lincoln Park is 13 kilometres of sandy beaches and park greenery, just a step or two from the city's central district, the Loop. Here you'll find the Lincoln Park Zoo, the oldest in the country, and Lincoln Park Conservatory, home to giant palms, rare orchids and some peace from Chicago's bustle. The Chicago History Museum is here too, and will set you straight on the Windy City's often blustery past.

The Navy Pier divides northern Lincoln Park from the southern stretch of Grant Park (and its radically different Millennium Park). The Pier takes you out into Lake Michigan, and a chance to mess about on the water – or to look back at Chicago's dramatic skyline from its Ferris wheel. You'll also see a line of white-pillared and glass-fronted museums stretching along the Grant Park area: the Art Institute Of Chicago, the Field Natural History Museum, the Museum of Science and Technology, and the Shedd Aquarium. They all do what they say on their entrance signs – educating and inspiring with some of the finest collections, and the most immersive exhibits, to be found anywhere in the world.

Culture and science may rule the Lakefront area, but commerce and shopping are kings in the busy streets of the central Loop – especially the Magnificent Mile. This luxury shopping street is packed with malls, restaurants and stunning architecture – and plenty of opportunities to exercise your credit card.

A more graceful architectural walk can be had in Oak Park, a western suburb where Frank Lloyd Wright lived and worked. Widely seen as America's best architect, he left the area with a treasure trove of buildings – including the Unity Temple, seen as the world's first truly modern building. Visit the Frank Lloyd Wright Home and Museum to get an in-depth guide. Oak Park also does literature – it is home to Chicago-born Ernest Hemingway, and the Ernest Hemingway Museum And House tells the remarkable story of America's foremost storyteller.

But how about rounding your Chicago stay by fusing all four at a game of baseball at Wrigley Field. After all, this iconic stadium is where the Windy City's most vital living history is played out every season.