Chicago brims with atmospherics – the rattling elevated trains, old school blues clubs and Tiffany glass windows – but retains an unpretentious attitude. For those who love big city energy but find New York overly intense and Los Angeles unmanageable, it hits the sweet spot.

Reach for the skies

It’s not hard to draw up a list of things to do, but it’s also a city to just hang out in. Hip neighbourhoods – whether mural-filled, Latin-flavoured Pilsen; gentrifying hipsterville Wicker Park; or dining hotspot West Loop – spread out from the centre.

A big Chicago drawcard is its look. The Chicago Architecture Foundation runs several informative walking tours that point out the classics, as well as demonstrating the evolution of styles, from decorative original skyscrapers through Mies van der Rohe’s sleek, black modernist efforts to modern-day environmentally innovative show-stoppers. It also offers architecture-centric cruises along the Chicago River.

The Tribune Tower, just north of the river, has chunks of World Heritage sites – including the Great Wall of China, the Parthenon and the Taj Mahal – built into its exterior walls. The Marquette Building in the city centre, meanwhile, has extraordinary Tiffany glass mosaics in the lobby.

The tallest skyscrapers are the Hancock Tower and Willis Tower, both of which have observation decks at the top. The Hancock Tower is lower, but offers a better panorama, while the Willis Tower’s glass-floored ‘Ledge’ has the bigger thrill factor.

It’s not all about height, though – Prairie-style architecture has strong Chicago links.

“The Frederick C Robie House, Frank Lloyd Wright’s masterpiece, has recently been restored and added to the UNESCO World Heritage List,” says Naomi Hattori, Global Development Director, Choose Chicago.

Culture quest

Not all of Chicago’s great buildings are done in local styles, though. The Art Institute – big on impressionists and modern art, with magnificent Chagall stained glass windows – is a neo-classical stunner. But it’s far from Chicago’s only big ticket cultural attraction.

The Field Museum is huge, and while most people come to see the dinosaur skeletons, the other sections – particularly those on native Americans and evolution – are well presented, with story-telling panache.

The American Writers’ Museum looks at those who have shaped American literature. There’s interaction too, with an area where visitors can use typewriters to add to stories created by other visitors.

Chicago also as a strong theatre heritage – with the likes of the Steppenwolf Theatre putting on challenging plays and Second City legendary comedy revues. The latter was the breeding ground for the likes of Dan Ackroyd, Bill Murray and Tina Fey.

Chicago is also the birthplace of the electric blues – and venerable blues clubs such as Buddy Guy’s Legends have a near-holy vibe to them.

Don’t miss…

Deep dish pizza: You either love or hate this big, gooey take on pizza. Chicagoans argue over whether Pizzeria Uno, Lou Malnati’s or Giordano’s does it best - trying to decide can be fun if you’re the former.

Millennium Park: Cloud Gate (aka the Bean) and the spitting video wall faces of Crown Fountain have become two of the world’s most famous pieces of public art. Enjoy mingling with the crowds.

Wrigley Field: This gnarled old baseball stadium has to be one of the most atmospheric places in the U.S. to watch a ball game. Behind-the-scenes tours are available for aficionados.

Logan Square: An emerging hip neighbourhood home to microbreweries, highly-rated sharing plates, restaurants, galleries and live performance venues. It’s on the blue line from the centre to the airport.

The Chicago History Museum: Telling the story of the city, including the Great Fire of 1871, the Columbian Exposition of 1893 and the notorious gangster era, this museum is at the edge of sprawling Lincoln Park.

Where to book it

America As You Like has a five-night break to the Windy City from £1720pp including return international flights with United in Premium Plus from London and five nights’ accommodation at The Conrad Chicago. The hotel is located on Michigan Avenue at the heart of the city and has smart technology in all rooms. The price is based on two people sharing