'Water Tower Plaza, please,' I ask as I shuffle into the cab seat. 'Where?' 'The Water Tower?' No recognition at all. I get out my guide and point to the map. 'Oh, OK. You're French, right?' 'No, English.' He nods at me indulgently, as if I've misunderstood his remark. Two minutes into the ride his curiosity gets the better of him.

'Vous habitez en Chicago?' 'Non, j'habite en Londres.' 'Oh well, you'll speak English then.' 'I am English.' He smiles in the rear-view mirror, and says nothing more. Even when I pay him at the destination he seems surprised that I can understand his summing-up of the fare.

I suppose I couldn't blame him. Chicago cab drivers are maybe not as used to hearing British accents as their counterparts in New York, to which the trail blazed by weekend trippers has become well worn. But that could soon change. Even before September's scars were left on Manhattan, I had heard veterans of two or three transatlantic quick breaks express a desire for somewhere new to explore in four or five days. Miami, Boston and Montreal were all in the frame. But the place that comes closest to NY, in mood, food, surroundings and culture, is Chicago.

There's the same bustle on the streets of cabs, shoppers, office workers and gawping out-of-towners - who number thousands when a big convention is in town. There are surprises, too, like the seaside atmosphere of Lake Michigan's waterfront - amusements on Navy Pier and roller-blading youths on the paths that skirt a network of huge parks.

And, literally, there's a monumental feel to the place. It was here, not New York, that the skyscraper was born (along with the zip, the Ferris wheel and the Mickey Finn, as it happens) and Chicago is proud of it. Look up as you walk around and you can see why - there are thrusting towers of Art Deco, postmodern glass, brooding Mies van der Rohe slabs and gothic creations that include one with a turret to tie your airship to. For high, read highest - Chicago boasts the tallest building in the United States, the 110-storey Sears Tower, though the 100-storey John Hancock Center is an equally popular place from which to survey the sprawl.

The city also played home to America's most celebrated architect, Frank Lloyd Wright, and his coveted Prairie homes dot the suburb of Oak Park.

Clusters of brick and mortar, though, are only as interesting as the people who breathe life into them. And few places on Earth have been as great a melting pot as Chicago.

The immigrants who turned a fur traders' outpost into a giant rail and canal crossroads came from all over: Italians and Irish, as you'd expect, but Germans and Scandinavians as well, the second biggest urban Polish population after Warsaw, and African-Americans who drifted up from the Mississippi Delta in tens of thousands.

That last group brought their songs with them, and Chicago transformed them into sounds that reverberate today: jazz, cut by the likes of Louis Armstrong and Jelly Roll Morton, and electric blues, shaped by Muddy Waters and Howlin' Wolf. Today, devotees of these musical giants take to the stage nightly in blues bars and jazz clubs to spread the word - with annual festivals that turn the city into one big party.

This summer promises to be more tuneful than ever, with the Music Everywhere event. It kicks off on 30 May with the Chicago Blues Festival, and puts on showcases for gospel music (June), country (end of June), Latin (August), jazz (end of August), Celtic (they get everywhere, don't they? September) and world music (end of September).

The instinct to work hard and play hard led to an enduring but less welcome image. When prohibition began in 1920, thirsty locals enthusiastically embraced speakeasies run by Al Capone and his fellow gangsters, and Chicago became a byword for crime. It's only in recent decades that this reputation has been shaken off.

Walk the wide, clean streets today and you feel a world away from the gritty past that earned the nickname City of Big Shoulders. Now Chicago workers are as likely to be brokers as meat packers, there is smooth as well as rough, high-brow and earthy, and the joy of the place is you can happily swing between. Drink in packed neighbourhood bars and feel the crunch of discarded peanut shells under your feet; or sip a cocktail as you lounge with the hip crowd. Munch your takeaway beef sandwich from the deli; or savour Asian-American fusion cooking at myriad new restaurants springing up citywide. See Hollywood stars tread the boards at the Steppenwolf theatre; or watch sporting heroes play out their dramas on the field.

If you want to experience the American city in full, it's all there. Like they told me one morning over coffee: 'New York with a smile.'

If you only do five things...

1. Reach for the sky. Go up the Sears Tower, 233 S Wacker Drive (00 1 312 875 9447) or the John Hancock Center, 875 N Michigan Ave, to take in the view from way up high (each costs $9.50). For a more indulgent sightseeing experience, head for the Signature Room on the 95th and 96th floors of the Hancock - it has a bar if you only want to wet your whistle, and an excellent restaurant serving modern American fare if you want dinner with a view. Book ahead; south-side tables are best (00 1 312 787 9596).

2. Do an architecture tour. The Chicago Architecture Foundation does a fantastic job of spreading the word about the city's built heritage. It offers walking tours, bus tours and - particularly recommended - boat tours on the Chicago river. Book in the CAF shop at the foot of the John Hancock Center or its headquarters in the Santa Fe building, 224 S Michigan Ave (00 1 312 922 8687). For more architecture head out to Oak Park and the Frank Lloyd Wright Home and Studio, 951 Chicago Ave. Volunteers take you through the key points of his 'Prairie' style of design, and if you're keen you can also do an hour's walking tour round the surrounding streets to see several private homes he designed (00 1 708 848 1976).

3. Visit the Art Institute of Chicago, an exceptional collection of painting, sculpture and ancient artefacts from around the world. It has its share of international draws such as the Impressionists, Picassos and Chagall's giant stained-glass 'American Windows', but linger longest in the rooms filled by US artists to appreciate the breadth of home-grown talent, from Winslow Homer to Georgia O'Keeffe. Don't miss Edward Hopper's Nighthawks and Grant Wood's American Gothic. (If you've time, then head for the shore of Lake Michigan and wander down to Museum Campus for the Shedd Aquarium, Field Museum of Science and Technology and Adler Planetarium.)

4. Ride the El - you've seen it on ER, now take in the view from just above street level on a journey from downtown to the suburbs. If you've already done the trip out to Oak Park, head north to Lincoln Park for some offbeat shopping and dining. Or pick another neighbourhood to explore: Wicker Park is arty, Hyde Park holds the university, Pilsen - despite the Czech name - is Hispanic, while Little Italy and Ukrainian Village are as billed.

5. Pay your dues to the blues. From slick to rough-and-ready, dozens of clubs and bars offer live bands nightly. House of Blues, 329 N Dearborn St (00 1 312 923 2000), is a commercial temple to the genre that pulls in the tour groups. For a more intimate feel, head for Buddy Guy's Legends, 754 S Wabash Ave in South Loop, owned by the guitarist himself, or north to Kingston Mines, 2548 N Halsted St in Lincoln Park (00 1 773 472 2031).

Don't even think about...

· Mentioning Al Capone. His name conjures up the days of prohibition, Tommy guns and wild nights at the speakeasy - and that's the problem. Successive mayors have fought hard to rid the city of its image as a den of crime and corruption. However, Untouchable Gangster Tours, 10924 S Prospect Ave (00 1 773 881 1195), is keeping the mobster spirit alive with a tour of historical haunts, so you didn't buy those spats in vain.

· Asking for brown sauce on your breakfast bacon. For a start, the nearest equivalent is called steak sauce in the States, but they haven't yet discovered its magical properties within a butty. So it's ketchup or maple syrup and piling on the pounds for now.

· Taking to the lake by boat. You can get just as satisfying a grand view of the skyline from the promontory of Grant Park beside the Adler Planetarium or the end of Navy Pier. Do spend the money instead on a river tour to get close up to the buildings.

· Going out to a club without ID. While some bars are more relaxed, nightclubs - or it seems, anywhere with a bouncer - will want proof of age before you can enter. No matter how wrinkled you look.

Room for the night

Budget: Cheap options are hard to find, but Ohio House Motel may be your best bet, at 600 N LaSalle Drive (00 1 312 943 6000), a few blocks west of the Magnificent Mile in River North. It's a classic Fifties-style double-decker roadside lot, so get used to the rumble of passing trucks. Rooms cost $85 (£59) per night, suite $140 (£97).

Moderate: The Seneca (200 E Chestnut St; 00 1 312 787 8900) is right next to the John Hancock Center just off the Magnificent Mile, and offers good-sized rooms surprisingly cheaply. Rooms start at $129 (£89) per night, suites $149 (£103), but be sure to ask if there are any special deals going. Two more hot tips in this bracket are the Gold Coast Guest House (00 1 312 337 0361) and designer-trendy Hotel Allegro (00 1 312 236 0123).

Expensive: The new Peninsula Chicago hotel is in prime position on N Michigan Ave (108 E Superior St; 00 1 312 337 2888) and it's very posh, with uniformed revolving-door spinners to prove it. It has a fine panelled bar, a choice of swish restaurants and a spa where you can try any number of Oriental treatments before taking a dip in the pool high above the streets. Rooms are as luxurious as you'd expect, and even come with a TV screen to watch in the bath. Single rooms cost from $325 (£224) per night, suites start at $375 (£258).

Where to eat

Fast and filling: Chicagoans favour the 'Italian beef' sandwich as a snack on the hoof. Many cafes and lunch bars do them, but the most celebrated is Mr Beef at 666 N Orleans St (by W Huron St, in the Near North area), whose praises are sung by the Tonight show host Jay Leno. A sandwich plus soft drink will set you back about $5 (£3.50).

Good: The city's most enduring contribution to the world's menu is the pizza pie. Based on a pastry crust, the high-sided pizza is crammed with filling - and is thus more, er, filling. Do not underestimate this food. Anything larger than an individual one - and that includes the next up on the menu, small - is enough to feed an army. There are many restaurants to choose from, but try Pizzeria Uno, 29 E Ohio St (on the corner of N Wabash Ave, in Near North). Food and drink will cost $15-$20 (£10-£14) if you don't overdo it. If you do overdo it, skip the next meal and have a lie-down.

Totally sinful: Chicago has a celebrity chef, with his own cookbooks and TV shows to prove it. Charlie Trotter's is his eponymous restaurant, at the Wyndham Chicago Hotel, 816 W Armitage Ave, Old Town/Lincoln Park. Expect fine cuisine, fine wines and no hope of a bill less than $100 each. You'll need to book three months ahead if you want a weekend table, a mere six weeks ahead for a weekday meal (00 1 773 248 6228).

Objects of desire

· The exchange rate doesn't throw up the bargains it once did, but if you're determined to go home with bags full of new staples, head for North Michigan Avenue - or the Magnificent Mile as the signposts proclaim - where you'll find all the big-name US chains. If you're after something more exclusive, head for E Oak St at the Mile's northernmost tip.

· For more individual clothes and mementoes, head instead for the neighbourhoods. Lincoln Park boasts W Armitage Ave's eclectic mix of stores. Find the cowboy or cowgirl inside at Out of the West, 1000 W Armitage, selling frontier knick-knacks , clothes, blankets and shot glasses with desert cacti sculpted at the bottom. And after a hard day on the range relax in an Archipelago Botanicals rice milk bath from Soapstone at number 819. Over in Wicker Park, meanwhile, head for the funky boutiques of N Milwaukee Ave; accessories and shoes from Softcore at number 1420, fashions from Una Mae's Freak Boutique next door at 1422. In Wrigleyville, look for Hit the Road, 3758 N Southport Ave, which sells all kinds of Route 66 memorabilia and other road-trip kitsch.

· Your younger relatives won't forgive you if you return home without gifts bearing the names of Chicago's top sports teams. Choose from basketball vests (Bulls), baseball caps (Cubs or White Sox), ice hockey jerseys (Blackhawks) and American football shirts (Bears), plus more besides, at Sportsmart, on the corner of N La Salle St and W Ontario St. While you're in town, tickets for games are worth trying to come by too. The Bulls and Blackhawks play at United Center Arena (info 00 1 312 455 7000). The Cubs' home is Wrigley Field (00 1 773 404 2827). The Sox play at Comiskey Park (00 1 312 674 1000). The Bears can be seen at Soldier Field (00 1 847 615 2327). And don't forget one of the country's biggest college football teams, the Northwestern Wildcats, who play in Evanston, 14 miles north.

· Whatever your cultural fix - opera, classical music, drama - there are top-notch performers to provide, not least the Steppenwolf Theatre Company. Co-founders John Malkovich and Gary Sinise have led starry casts in challenging productions, and tickets for the company's modern home in Lincoln Park are prized possessions (1650 N Halsted St; 00 1 312 335 1650). Equally starry but less intense is the Second City comedy club in Old Town (1616 N Wells St; 00 1 312 337 3992) whose alumni include Bill Murray, Dan Aykroyd and John Belushi.

Behaving badly

· Clubs are springing up all the time - converted factories in city-centre fringe areas, or temples to dance in trendy/arty places such as Bucktown. One hedonistic cluster worth heading for west of Old Town includes the go-gotastic Crobar (1543 N Kingsbury St), rope-swinging Circus (901 W Weed St) and trippy Zentra (923 W Weed St). They're not open every day, so check out web listings for times and cover charges.

· For drinks, Encore serves lip-smacking cocktails underneath the trendy Hotel Allegro (171 W Randolph St) in the Loop. If you'd rather just prop up the bar with a beer, try Pippin's in Near North (806 N Rush St), where you get free peanuts to nibble on (and you can drop the shells on the floor without being told off), or the Old Town Ale House at 219 W North Ave - which is a short hop from the Second City comedy club.

· Sports fans can release energy in the amusement arcade at the ESPN Zone in River North (43 E Ohio St), before watching a game over a meal or a beer. A more regular sports bar is Kincade's in Lincoln Park (950 W Armitage Ave), which has banks of screens on every wall and good beer.

What the tourist board doesn't say

· Know your North, South, East and West when it comes to street names, otherwise your taxi driver will get lost. Instinctive guesses are no good to you, since all points are west of the lake. It's also crucial to memorise or commit to paper the street number of the restaurant/bar you're aiming for - and of your hotel for the return journey - because it holds the key to which block the building's in. Numbers 200 and 1000 can be a very long way apart.

· When riding the El, think in colour. Stations can have the same name but be miles apart because they're on the same street but served by different lines. For instance, the blue line's Damen station lands you in the hip suburbs of Wicker Park and Bucktown, the brown line's Damen is a few miles north, in Ravenswood (where kind people put you on the right bus to go south again...).

· Discover the seamier side of American life at first hand in the audience of The Jerry Springer Show, which is filmed in Chicago (ticket reservations 00 1 312 321 5365). Or, for a better behaved spectacle, you could see The Oprah Winfrey Show being recorded instead (00 1 312 591 9222).

Getting there

The flight time to Chicago is roughly eight-and-a-half hours.

United Airlines (08458 444777) has three flights daily from Heathrow (starting at £258) and one from Manchester.

British Airways (0845 7733377) has two flights daily from Heathrow. American Airlines (08457 789789) has three.

BMI British Midland (0870 6070555) flies daily from Manchester.

Getting around

· The El, subway and buses will take you most places you want to go. All are operated by the Chicago Transit Authority, and have a flat fare of $1.50 (£1) per trip. For 30c (20p) more at the time of paying, you can get a transfer ticket that allows two more rides within two hours. Better still, take the worry out of it all and buy a Transit Card from the machines at El stations, which you can load with credit for multiple journeys. It gives you a $1 bonus for each $10 (£7) spent; up to seven people can use the same card (so it's great for families); and you can reload it with more cash if you need. Turnstiles at stations even calculate how much fare you have left to spend.

· A quick way to get to the University of Chicago campus is the Metra Electric train. The most convenient station is near the junction of N Michigan Ave/E Randolph St, and it's $1.95 (£1.35) single to 53rd St or 59th St depending on which corner of Hyde Park you are headed for.

· Taxis are plentiful and cheap - best of all, they don't just serve the haunts of well-to-do visitors. I found cabs quickly late at night, in the neighbourhoods and in the rain.

Get out of town

· Get your kicks on Route 66 - or the Interstate 55, as you will now find it on the maps. Hire a car and head across Illinois, taking in Abraham Lincoln's birthplace at Springfield and other diverting towns along the way (including one intriguingly called Normal). St Louis is the next biggest town, but those with musical odysseys to pursue can go all the way to California.

· Forget autumn in New England, the Great River Road along the Mississippi river, which separates Illinois from Iowa and Missouri, is the hot tip for leaf-peepers. It's a three-hour drive west of Chicago.

Further information

Pick up the free Chicago Reader (out Thursdays) from newsstands. It has exhaustive reviews and listings.

Other great web sites detailing what's on are www.metromix.com, www.ci.chi.il.us and www.newcitychicago.com.

Reading: My American Century, by Studs Terkel, is a testament to the working life of the city. For a fictional delve into the dark side of Chicago's past, read the crime novels of Nelson Algren.