Big, vibrant Chicago has meant many different things to many different people over the decades. To the Native Americans, it was ‘Chicagoua’ (The Land of the Wild Onions). To thousands of 19th-century immigrants who settled in what are now about 77 neighbourhoods – Chinatown, Greektown, Mexican-American Pilsen, etc – it was what poet Carl Sandburg celebrated as ‘The City of the Big Shoulders’. Prohibition-era gangsters John Dillinger and Al Capone turned it into a mobsters’ Mecca; Frank Sinatra sang that it was ‘My Kind of Town’, and, in more recent years, it served as the political launching pad for US President Obama.

Now referred to either proudly or dismissively, depending upon your viewpoint, as America’s ‘Second City’, this community of more than 2,707,000 people, in fact sometimes equals or even surpasses its much larger rival, New York City. Its skyline is at least as dazzling at that of Manhattan, particularly if viewed across the green expanse of Grant and Millennium parks or from the deck of a boat cruising the Chicago River. And, unlike Manhattan’s Central Park, a number of its parks are fringed by wide, sandy beaches as it overlooks the great inland sea of Lake Michigan.

Although Manhattan’s Broadway theatre district is unrivalled in glitz and glamour by any besides London, Chicago – the only American city with five regional Tony Award-winning theatres – has an impressive 250 professional theatres, some of them launching new plays that go on to dazzle Broadway and even London audiences.

Chief among them is the 90-year-old Goodman. Chicago’s largest and oldest not-for-profit theatre, it has been praised for taking numerous successful creative risks under the leadership of executive director Roche Schulfer while regularly attracting such star performers as Brian Dennehy and Nathan Lane.

In 2009, its play Ruined, about the plight of women in war-torn parts of Africa, won the Pulitzer Prize for drama; in 2010-2011, it launched five world premieres, four by minority playwrights; and by 2012-2013, its ticket sales had risen to $11.4 million per annum, with an average 90 per cent occupancy in its two Dearborn Street theatres. One of the high points of late 2014 will be the production of its ever-popular, ever-changing version of A Christmas Carol while simultaneously staging The Second City’s Twist Your Dickens send-up of the Christmas classic.

SOME OF AMERICA’S TOP COMEDIANS BEGAN THEIR CAREERS WITH SECOND CITY

Speaking of The Second City, this iconic Wells Street improv theatre group continues to produce side-splitting comedy turns while spawning the likes of TV and film stars Tina Fey, John Malkovich, Bill Murray, Dan Aykroyd and Steve Carrell, even as the world-renowned Blue Man Group continues to perform in its Lakeview theatre.

Other theatrical seedbeds include the acclaimed Steppenwolf, Lookingglass, Court, Shakespeare, Redmoon and Victory Gardens theatres as well as the Ford Center for the Performing Arts, situated in the glorious 1925 Oriental Theatre, and Broadway in Chicago productions. A great source of information is the League of Chicago Theatres.

Not only is Chicago a great theatre city, it’s also a great film set. Who can forget the scene in The Untouchables, which starred Kevin Costner and an Oscar-winning Sean Connery, when a pram bounces down the steps of majestic Union Station in the middle of a gun fight; Matthew Broderick as the namesake hero in Ferris Bueller’s Day Off skipping school to bum around such places as the Art Institute of Chicago; or John Belushi and Dan Aykroyd as The Blues Brothers driving their Bluesmobile through the window of the Richard J Daley Center? It was in a house in suburban North Chicago that child star Macaulay Culkin foiled the burglars in Home Alone and on the campus of the University of Chicago that Billy Crystal met Meg Ryan in When Harry Met Sally.

Partly because of this rich filmic heritage Star Wars creator George Lucas announced earlier this year that he would be setting up his Lucas Museum of Narrative Art here rather than in rival sites Los Angeles or San Francisco.

As for music, Chicago is world famous for its blues and jazz, first brought to the city in the 1920s by African Americans migrating from the South in search of work. Throughout the ensuing decades, the Chicago Blues developed, featuring such legendary names as Blind Lemon Jefferson, a blues singer and guitarist from Texas, and Big Bill Broonzy, a country blues singer, songwriter and guitarist from either Mississippi or Arkansas, depending on which source you believe.

After the Second World War, there was another influx of migrants from the South and, in the late 40s and early 50s, Chicago Blues flourished, with a rash of clubs springing up as well as record labels, such as Chess, releasing music from the likes of Muddy Waters, Willie Dixon and Howlin’ Wolf.

Today, Chicago is reputed to be the Blues Capital of the World, and the Chicago Blues Festival, staged every June – when crowds of around 500,000 attend the three-day event in Grant Park – is the largest free blues festival on the planet.

There are also countless blues clubs in the city – such as Blue Chicago, Rosa’s Lounge, Kingston Mines and B.L.U.E.S. – but the most famous is probably Buddy Guy’s Legends (www.buddyguy. com). Time your visit for January and you could well catch Guy performing; the rest of the year he might be at the bar, keeping tabs on the band on the stage that night.

The early decades of the 20th century also saw promoters bring lots of the top jazz musicians to the city, many from New Orleans, including Louis Armstrong, who joined the Creole Jazz Band in the 1920s. In the 30s and 40s, the jazz scene in New York lured many of them away, but by the 50s, Sun Ra and Herbie Hancock were making names for themselves in the city as, years later, was Ramsey Lewis.

In the 50s and 60s, jazz greats Nat King Cole, Benny Goodman and Louis Armstrong were regular performers in Chicago. Such was their impact that the city launched the Chicago Jazz Festival, which takes place every year over four days at the end of August and is one of the largest free jazz concerts in the world,

Chicago - Green Mill Jazz Club

The Green Mill Cocktail Lounge, a former haunt of Al Capone and Frank Sinatra, is famous for its variety of types of jazz

Nowadays, the famous Green Mill Cocktail Lounge, a regular haunt of Al Capone and his cronies in the 1920s as well as Frank Sinatra in the 50s, is where you can hear jazz across the board – from traditional and bebop to contemporary and improvisational. When Capone entered the club, the band would immediately stop what they were playing and switch to Rhapsody in Blue, a Capone favourite. Other clubs to check out are The Back Room and Andy’s Jazz Club.

Nor is Chicago limited to blues and jazz – the Chicago Symphony Orchestra is highly rated, as are the Lyric Opera and Joffrey Ballet, and, in the summer, Millennium Park’s stunning, stainless-steel Jay Pritzker Pavilion stages everything from classical to hip-hop, rock to folk concerts, even as the other parks are alive with numerous music festivals.

A great park and stunning architecture

The 'Bean' in Millennium Park

The ‘Bean’ in Millennium Park

Speaking of Millennium Park – this is indeed the outdoor living room of Chicago, particularly during the balmier months. Fronted by a wide, long, sandy beach – as, indeed, are a number of the other parks along Lake Michigan – it is also home to such people-pleasers as Anish Kapoor’s gigantic Cloud Gate stainless-steel sculpture (known locally as ‘The Bean’), which reflects and distorts the surrounding skyscrapers as well as the clouds above and the pedestrians below. Nearby, twin 50ft towers are adorned with huge images of the faces of local residents which periodically purse their lips and spew out water at the laughing children and adults wading in the shallow pools below.

Elsewhere, there are statues by Picasso and Calder, a whole parade of marching legs totally devoid of heads or torsos and a series of figures reminiscent of Antony Gormley’s Another Place sculptures on Crosby Beach near Liverpool. These complement the stunning architecture in the city where the skyscraper was born (the first ten-storey steel one in America, the 138ft-high Home Insurance Building, was completed in 1885), and which now has a plethora of striking buildings to admire (and not just skyscrapers) from the legendary, riverside Wrigley Building and Cadillac- Palace Theater with its stunning interiors to the glitzy, modern Trump International Hotel & Tower, also on the riverside, and the Frank Lloyd Wright Home and Studio in the Oak Park suburb.

In fact, the readers of one American magazine voted Chicago as having the ‘best skyline in the US’ and, certainly, it would be difficult to argue with that, whether you view it from either of the city’s rival ‘viewing decks’, from ground level with a Chicago Greeter, or from the water on a Chicago River cruise.

The four protruding glass ‘Ledges’ of the 1,353ft-high Willis Tower’s Skydeck let you peer down to the river through the glass floor, whereas the new attraction in the John Hancock Building’s 1,000ft-high 360 CHICAGO is the glass-fronted TILT!, which tips visitors 30 degrees over the Magnificent Mile shopping area and the Historic Water Tower.

But perhaps the best way to see some of the sheer variety of Chicago’s skyscrapers is from a Chicago Architecture Foundation River Cruise on board Chicago’s First Lady Cruises, where one of their hugely-informative guides relates tales of the Great Fire of 1871 (in which many of the city’s buildings were destroyed) and structures so large that staff used roller-skates to get round. Alternatively, check out the Chicago Greeters, a group of enthusiastic volunteers who, in a list of 40 special-interest tours, offer free Art & Architecture outings that explore the city’s rich and varied history.

A choice of 40 some Chicago Museums

There are many more treats inside when the day is rainy or cloudy or the late autumn or winter weather rolls in bringing frigid temperatures, ice and snow. The city has more than 40 museums, ranging from The Field, home of Sue, the world’s largest and most-complete Tyrannosaurus Rex, and the Museum of Contemporary Art, where a September-opening exhibition will spotlight the life and work of charismatic performer David Bowie, to specialised ones focusing on such things as the city’s Chinese, African-American and Ukrainian heritage. The Chicago History Museum puts local things in perspective but the best-known of them all is the majestic Art Institute of Chicago, its outside guarded by two large bronze lions and its inside showcasing everything from one of the world’s largest collections of Impressionist and Post- Impressionist paintings outside Paris to some of the best-known works by such American artists as Grant Wood (American Gothic) and Edward Hopper (Nighthawks).

Nor are families travelling with children forgotten. In addition to Brookfield Zoo, the Chicago Children’s Museum and the various attractions – mini-golf courses, a Ferris wheel, summer fireworks – along the city’s most visited attraction, Navy Pier, there’s the Shedd Aquarium, the Adler Planetarium and, for older children (and their parents), the Museum of Science and Industry.

Chicago Shopping

Those who consider shopping and sport other types of art forms are also in for a treat. The stretch of Michigan Avenue known as ‘The Magnificent Mile’ is lined with such famous department stores as Saks Fifth Avenue and Bloomingdales, designer shops and three vertical indoor malls; nearby Oak Street is known for its chic boutiques; and, across the Chicago River on State Street, within the area circled by the elevated railway and thus known as the Loop, there’s Macy’s, one of the world’s largest department stores. The numerous neighbourhoods also have their commercial charmers and the city is ringed by discount outlet malls.

Chicago Sports & Outdoors

If you have always been fascinated by America’s addiction to baseball, the place to head for is Wrigley Field. America’s second-oldest ballpark and the home of the Chicago Cubs, it is celebrating its centenary this year with a series of special events. There’s more baseball in US Cellular Field, home of the city’s other baseball team, the White Sox, plus American football (NFL), represented by the Chicago Bears at Soldier Field, and Major League Soccer, led by the Chicago Fire team in Toyota Park.

If you, too, want to display your athletic skills, why not enjoy a game of volleyball at one of the lakeside  beaches, take a guided Segway or bike tour, or make use of the city’s bike-share scheme, Divvy Bike, and explore Chicago on your own – there are some 4,000 bikes at 400 stations around the city.