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Famous son Ernest Hemingway dubbed Chicago 'the city of the big shoulders'. And it doesn't take long for anyone to figure out why. Chicago has always been the city that distilled the raw (and probably bootlegged) spirit of Middle America: blue collar, hard working, meat-loving, no-messing, can-do... While New York and LA spent a century busily buffing their laminate egos, America's second city buffed automobiles, packed meat, bagged grain; and invented the big American brand, suburbia and the skyscraper for afters. Basically got on with the business of making America what it is today. In fact, Chicago is what you think about when you think of the USA, even if you don't know it. From Wrigleys to Walgreens, Jerry Springer to Oprah, Playboy magazine to Sears catalogues; many of this young nation's icons grew up against the soaring skyline of the windy city.

Chicago is brash, boastful and pretty big for its steel-toed boots, yes; but it's exactly this bullheaded dynamism that made Chicago - and America - great. Submit for evidence the fact that when 1871's Great Fire (caused by a cow knocking over an oil lamp) wiped out much of the founders' city, Chicago simply rebuilt in steel, creating a scraper city a full decade before New York - or indeed the rest of the world - caught on. With scant break for restorative big Mac, the big-shouldered Chicagoans ploughed the resultant rubble into Lake Michigan, transforming the spur of land reclaimed from Mother Nature into a vast memorial park. A few short years later, Chicago's engineers tackled the old-man might of the Chicago River, reversing its water flow to produce navigable waterways which stretched from Lake Michigan to the Mississippi, facilitating trade between the wild Western frontiers, the south and the established cities of the eastern seaboard.

Chicago's tourist department is pretty keen to play down this gangster history, 'selling up' the city's architecture, food and musical heritage. But decades-old bloodstains don't wash whiter than white, and signifiers of Chicago's sullied past still decorate the city's corridors of power. This, after all, is Jerry Springer's city - the ultimate slick politico turned titan of media sleaze. It's also the city that made a fast buck off the back of many a sordid dream (see the Playboy empire); and the city that pioneered back-room dealing and iron-fisted control.

The testosterone-charged texture of the Capone era lived on, in politicians such as mayor Richard R Daley, who held the city in his concrete grip from the Fifties until his death in 1976. Notorious in his distaste for left-wing flimflammery, Daley is best remembered for his brutal treatment of anti-war protestors at the 1968 convention. In true mobster tradition, his son Richard M Daley now holds the reigns. To experience the real Chicago, you need to make like a real red-blooded, cigar-smoking man. Breathe deep of the atmosphere in smoke-fogged speakeasies that are unchanged since the dark, gangland days of the prohibition; joints scented of resinous timber and the threat of violence, peopled by with complexions like a deep pan pizza you forgot to throw out. The Green Mile - with its uneasy atmosphere, feebly lit booths, mid-century elegance and experimental blues - has an impeccable pedigree. This is where Capone - the most notorious alumnus of Chicago's ruthless and brazen 30s criminal syndicates - hung out, slugging hooch and eyeballing punks foolhardy enough to enter. It's still heady stuff, although these days lighter jazz and classic rock and roll get a look-in too.

To indulge in so much professional bloodletting, a man needs to steel himself with a massacre on a plate, and in this department Chicagoans excel. Put simply, they love meat, and the average Chicagoan meal entails a lifetime's cholesterol intake in one mouthful. The city's tastes are writ particularly large in 'Check Please', a local TV show on Channel 11, which allows Chicagoans to play restaurant critic, denouncing establishments whose portion sizes are lacking. The popular Gibson's, a leather-clad old-time steakhouse with a solid and traditional feel, is typical of the more robust Chicago restaurants in offering diners a plate of glistening cuts of red flesh from which to chose their meal (www.gibsonssteakhouse.com). Equally, a Chicago deep pan pizza - a mammoth pie stuffed with molten mozzarella - has more in common with a sidewalk slab than anything ever tossed in Italy. The debate as to the 'best', 'ultimate' and 'original' of this bizarre gustatory breed rages on, with the juxtaposed Pizzerias Uno and Due frequently receiving plaudits, although rival Giordano's chain justifiably vies for credit (unos.com, North Wabash Avenue, Chicago, IL 60611-271 (312) 266-8999. Giordano's, 310 West Randolph Street, 312 735 7774).

But the tourist department does have one thing right. If you want to truly appreciate what Chicago has done for today's world, you should forget your swelling stomach for a minute and look up. It's a city as well attired as the sharp-suited gangsters who used to prowl in its far-cast shadows. Chicago, home to Sears Tower, which at 1,450ft is the tallest building in North America, is a showcase for modern architecture and its architects have inspired international architecture movements and styles. The post-Great Fire planner of Chicago, Daniel Burnham, famously said to builders: “Make no little plans… they don't have the magic to stir men's blood...” And his big thinking certainly bore fruit - scrapers rip up into the crisp blue Chicagoan skies, like so many salutes to priapism: the Chicago tribune tower, with its art deco ledges from which financiers threw themselves on black Tuesday; the curved green glass of 333 Wacker Drive, designed to follow the bend of the river; and the iconoclastic Marina City Towers (inspired by a corncobs) have defined the day dress of the modern cities, from Sydney to Shanghai.

Watch Chicago's mirror-fronted buildings bouncing off each other in the dying light of day, as musicians playing on street corners welcome the long night, their trumpets in infectious, toe-tapping syncopation. Perhaps follow the rhythm to an blues bar such as Buddy Guy's legends in the South Loop, where you'll see a flash of the electric-guitar magic that inspired Hendrix and Clapton; or seek out some sliced and spliced dance beats in the city that invented house (named after a long-defunct club on the West Side). Or visit Rush Street's 'Viagra Triangle' of bars, named for the hopeful sods who head down there for the promise of picking up young totty. But be sure to top it all off with a Chicago dog - dog barely visible under a gooey mound of chopped onions, tomatoes, peppers, sweet pickle and gherkins.

Chicago grew up as the main connection between east and west, between the wheels of commerce and the nascent consumer culture, between Middle America and big-city attitudes, a crucible of modern innovation. This is the city where the American dream finds its most undiluted expression; and I'll join the boys in raising a neat whisky to that….

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