City slicker: Chicago

The Windy City, home of Barack Obama, is gearing itself up for one of the most exciting presidential elections in many years, says Kate Simon

Why visit?

The place to be this week is Chicago, home of Barack Obama, for it's likely to turn into Party Town USA. If the polls are correct, the Illinois senator will become the first African-American to be elected to the Oval Office.

This tough, industrial Midwest hub is an appropriate backdrop for the man accused by his rival John McCain of perpetrating "class warfare". The lakeside city was built on commerce, establishing itself as a mid-continental hub for the railroad network in the 1830s and growing into a booming business centre. Today's visitor comes to enjoy the fruits of that labour in the shape of the great Art Deco skyscrapers commissioned by the industrialists who built this town.

But Chicago's attractions aren't confined to its past. Frank Gehry's audacious Jay Pritzker Pavilion and Anish Kapoor's mesmeric Cloud Gate reveal a willingness to embrace the zeitgeist. And this city isn't all about work either. Chicago has a flourishing art scene, from the world-class sculptures on its streets and the fine collections in its museums and galleries to the clubs where jazz developed and house music was born.

Don't miss...

Gazing at the Art Deco architecture, such as the Jewelers Building at 35 East Wacker Drive, with its car-size lift so the rich could literally drive to the door of their jewellers. Al Capone ran a speakeasy at the top;

Millennium Park, for a turn around the ice rink in winter, to stand beneath Anish Kapoor's Cloud Gate sculpture and spot your reflection, and to see Frank Gehry's symphony in steel, the Jay Pritzker Pavilion;

Joining the outdoor-loving Chicagoans down by Lake Michigan – it looks like the sea, but it's just one hell of a pool of water;

Strolling around the open-air Frank Lloyd Wright museum, aka Oak Park;

Touring the sculptures in the Loop to see works by everyone from Miro to Moore;

Giving the credit card a workout on the Magnificent Mile;

Taking a Greeter Tour to see this town from the perspective of a local;

Catching an open-air festival in summer;

Listening to some live jazz at Buddy Guy's Legends – with luck, the great man might be performing.

What's new

Pilsen

Working-class Pilsen is the new place to be. First settled by Polish, Czech and German immigrants, it's now home to the city's working-class Mexican community and, latterly, a host of boho types. The arty crowd has been hanging out here for some years, but Pilsen is now seriously gentrifying, which isn't universally popular because of the inevitable rise in house prices. But this new cool neighbourhood is being embraced by visitors who love its cheek by jowl mix of galleries, vintage shops and authentic taquerias.

Details: gochicago.com

Trump Tower

It's no surprise that billionaire Donald Trump has bagged a prime waterfront site on North Wabash for his new hotel and residential complex. And if that wasn't enough, he's built a structure to rival its neighbours in sheer scale. When Trump International Hotel and Tower pops a 22-storey spire on its top floor later this year, it will be the city's second tallest building after the Sears Tower. Within its walls, guests enjoy spacious suites with kitchenettes, one of the classiest hang-outs in town, Rebar, and a luxurious spa.

Details: trumphotelcollection.com/chicago/.

The view

The trouble with admiring the view from the highest building in a city is that you don't get to see the very structure that you're standing at the top of. That's why locals will tell you to head for the John Hancock Observatory – to gain a great view of the Sears Tower. Of course, there's plenty more to take in too through its windows, all of which you can find out about courtesy of new multimedia tours for adults and kids narrated by Chicago resident David Schwimmer, aka Ross in the TV show 'Friends'.

Details: hancock-observatory.com

Skylark Bar

Chicago's dive bars may not be so popular with Sarah Palin since one displayed a 4ft-high gun-toting nude portrait of the ambitious hockey mom. But the vibe's somewhat different at the Skylark Bar in Pilsen, where an alternative crowd is served good beers and hearty burgers at decent prices, and can chew the fat with friends in the 1930s booths or enjoy some all-American fun on the pinball machine and jukebox.

Details: 2149 South Halsted Street, 001 312 948 5275

Mado

Drawing diners to trendy Bucktown, Mado is making a name for itself with its Med cuisine. The husband and wife team behind this recent arrival on Chicago's culinary scene puts the emphasis on flavour, rustling up local and sustainable ingredients, and have created a rustic chic atmosphere with the bare brick and chalk boards and BYOB policy. Must eat: the hanger steak.

Details: madorestaurantchicago.com

MySpa

This gritty city has its indulgent side? You'd better believe it. Check it out at mySpa, a day spa that's as easy on the eye as it is on the body. Massages, rituals, skin care and beauty treatments for men and women, teens and pre-teens, are applied by top-notch technicians according to individual needs in a vast luxurious space tucked away from the hubbub at the Fairmont Chicago.

Details: myspachicago.com

Insider's secret: Abina Manning

"My favourite place is the Velvet Lounge (above), home of free jazz and Fred Anderson," says Abina Manning, director of the Video Data Bank at the School of the Art Institute of Chicago.

"It's my idea of a jazz club – not fancy. Fred is at the door; he serves drinks and sometimes plays music with the guests, too."

Details: velvetlounge.net

How to get there

Virgin Atlantic (08705 747 747; virginatlantic.com) flies from London Heathrow to Chicago daily from £330 return.

Trump International Hotel & Tower (001 312 588 8000; trumpchicagohotel.com) offers double rooms from $525 (£320) a night.

Further information

Chicago and Illinois Tourist Office (08700 503 410; gochicago.com).