With its soaring glass skyscrapers, spectacular views across Lake Michigan and its cultural scene, Chicago symbolises all that’s great about the USA.

It’s a city that melds the cosmopolitan chic of New York with the Mid-West’s legendary friendliness.

While world-class shopping, thousands of restaurants and spectacular modern architecture make it a city of the 21st century, there’s plenty about Chicago’s shady past to attract the more adventurous tourist...

From Al Capone to Bonnie and Clyde to Ma Barker, the region has always been synonymous with gangsters – a reputation bolstered by the recent hit film Public Enemies, about mobster John Dillinger and starring Johnny Depp and Christian Bale.

And if the movie piqued your interest, Chicago offers a wealth of attractions sure to delight those intrigued by the workings of organised crime.

Housed in an award-winning building sculpted to reflect the landscape’s rolling pastures, flowing streams and industrial heritage is the Indiana Visitors Center in Hammond, three miles from the city limits, which has its very own Dillinger Museum (southshorecva.com) featuring original artifacts, interactive exhibits and period newspaper clippings.

For a very reasonable entry fee (adults £2.50, children £1.20) you can learn about Dillinger’s early life, a journey illustrated by family photos and even a pair of the mobster-to-be’s baseball boots. You can even be locked-up in a replica of the tiny Indiana State Prison cell in which he spent almost nine years after a robbery in the mid-1920s. Dillinger’s release in 1933 marked the beginning of his career as America’s most famous mobster, a man portrayed as a vicious thug by the police and as a Robin Hood figure who held up the banks that had foreclosed on so many working families during the Depression.

It was also in the 1930s that the Dillinger Gang was formed, with members including Baby Face Nelson. The museum has waxworks of all the prominent members, plus displays of period weapons (including, of course, those iconic Tommy guns) and their preferred getaway car – with a top speed of 85mph – the 1933 Essex Terraplane. Most fascinating of all are the checked trousers – still bloodstained – that Dillinger wore when he was shot by members of the fledgling FBI in 1934. Housed in a glass case, they’re a grisly reminder of the day justice caught up with him, while above is his death mask.

And, although it doesn’t quite square with the museum’s logo – Crime Doesn’t Pay – you can also buy Dillinger T-shirts, keyrings and even shot glasses at the gift shop.

Even more fascinating is the Lake County Jail, the scene of the man’s most daring and celebrated escape in 1934. The prison, in Crown Point, Indiana, was actually used in the Public Enemies film.

After being arrested with his gang in Tuscon, Arizona, Dillinger was extradited to

the state to stand trial for

the murder of a policeman. Run, unusually for the time,

by female sheriff Jesse

Sarber, the jail was meant to be escape-proof and it was here that the captured gangster famously posed for the press.

On the morning of Saturday, March 3, 1934, Dillinger shoved a “gun” into the stomach of a janitor and, using him as a hostage, locked up the prison guards and made his daring escape. While nobody knows for sure, it seems the gun was made from wood and smuggled into the jail.

Today, there are regular tours (adults £3.10, children up to 11 £1.25) allowing you to see the cells, with their mechanically-operated doors, the very spot where Dillinger held up the guards and even the place where he commandeered the unfortunate sheriff’s car to make his getaway.

While Crown Point is about an hour’s drive from Chicago, there are plenty of ways of exploring the city’s darker side without the journey.

Perhaps the best way is through Untouchable Tours

(gangstertour.com), which offers daily

two-hour bus rides (£16.70pp) visiting infamous crime scenes.

Our guide was Craig “Southpaw” Alton, who, like the rest of the guides, dressed up in full gangster regalia and spoke in 1930s parlance to really set the tone.

As he explains: “Dillinger was seen as a people’s hero because he was robbing the banks that robbed the people. That explains people’s enduring fascination.”

The tour includes a look at the Tumble Inn, where Dillinger’s girlfriend, Billie Frechette, was arrested, along with the site of the St Valentine’s Day Massacre – now a parking lot – and the Biograph Theatre, where Dillinger was shot dead.

But no matter how much of a gangster fan you are, Chicago offers a host of other attractions that no visitor should miss...

Probably the first thing you’ll see in Windy City is the Willis Tower, which dominates the skyline with its distinctive forked TV antennas.

Formerly known as the Sears Tower, it stands 1,450ft high, boasts 108 storeys and is the tallest building in the US. And for a fee (adults £9.30, children up to 11 £6.25) visitors can visit the 103rd floor to take in unrivalled views of the city.

If you’ve a head for heights, you can also venture into one of the skyboxes that jut from the building’s sides and allow you to look straight down at the street below.

Also worth a look is the John Hancock Center (adults £9.30, children up to 11 £6.25) approximately a mile away offering views from its 94th floor, which is just 100ft lower than that of its rival.

Back on ground level, some of the world’s most prestigious stores, such as Bloomingdale’s, Saks Fifth Avenue and Macy’s can be found along the Magnificent Mile, which forms part of Michigan Avenue. Boasting more than 450 shops and 51 hotels, there are also close to 300 restaurants.

And food is something Chicagoans take very seriously.

While it won’t do much for your waistline, you’d be mad not to try a Chicago-style pizza offered at many eateries.

Forget the thin-crust – or even the deep-pan variety – this is more like a pie complete with a thick crust and a calorie-busting filling of chunky tomato sauce, cheese and... well, pretty much anything else that’s bad for you.

Provided you’re not too full to move, the city’s nightlife offers something for everyone. There are dozens of theatres offering everything from improvisation to Broadway-style musicals while the Symphony Center is home to the world-renowned Chicago Symphony Orchestra.

There are also a host of venues where soul, jazz, gospel and blues are played every night.

Remember, this is the city that gave us brilliant musicians as diverse as Nat King Cole, Bo Diddley, R Kelly, Patti Smith and Muddy Waters.

And the cheapest and often quickest way of getting about is on the “L”, a train line that runs throughout the city, with much of it elevated above street level.

/ Public Enemies is now out on DVD and Blu Ray.

/ American Airlines operates daily direct flights from Heathrow to Chicago O’Hare airport. A return economy flight, leaving on December 1 and returning on Dec 8, costs £323.80, including taxes. Visit americanairlines.co.uk.

/ Marriott Hotel, Magnificent Mile, Chicago. Go to marriott.co.uk. Rates vary but expect to spend at least £125pppn.

/ Chicago info: gochicago.com. Dillinger Museum is on southshorecva.com.

Currency: US dollar £1 = $1.62

Time zone: GMT -6hrs

Best time to go: Now! Shop till you drop for Christmas