Chicago: My kind of town

Sunday Times
Published: 27th July 2003

The sassy, amoral, very female musical Chicago changed my mind with the gaiety of its lyrics: “Let’s go to hell in a fast car”; “He ran into my knife... he ran into my knife 10 times”; “There’s men everywhere, booze everywhere, jazz everywhere, joy everywhere”. So I went for a long weekend to get a bit of the razzle-dazzle for myself.

The Hotel Allegro, in the theatre district, was the right choice. It is inside “the Loop”, the inner core of Chicago, where a circle of elevated train lines provides the occasional atmospheric shudder. Roxie Hart and Velma Kelly, the merry murderesses of the musical, would have loved the Allegro’s stage set of a lobby, with its oversize mirrors, dark corners splendid with red velvet sofas, and rock and jazz pounding from the loudspeakers.

The bedrooms are just as theatrical, with salmon walls, golden bed covers and curtains drawn back as if a show were about to start. Chicago is an 8-hour flight from London, with a six-hour time difference, but the hotel and the city felt so vibrant on the sunny day I arrived that it was easy to recover.

Feeding the exuberant fantasy is Chicago’s position, on the edge of a lake that thinks it’s an ocean. In winter the waves on Lake Michigan can whisk up into a frenzy, but during my visit there were sailing boats and soaring seagulls. The expanse of water pours light through the wide avenues, and together with the Chicago River this gives the city an almost Venetian sense of spectacle.

Then there are the preposterously theatrical skyscrapers, each vying for attention as if they were showgirls themselves. The curved green glass of one glorious building, 333 West Wacker Drive, designed to follow the bend of the river, reflects the buildings opposite, providing a show within a show. Equally iconoclastic are the Marina City towers, which were inspired by corncobs — and, no doubt, by the joie de vivre of the city.

The planner of Chicago, Daniel Burnham, told his builders: “Make no little plans, they don’t have the magic to stir men’s blood.” And, as one of those original architects said: “If people are going to take the trouble to look up, I’m going to make it worth their while.”

On the excellent architectural tour along the snaking river (00 1-312 527 1977), the skyscrapers seem to leap out beside the water as your boat approaches. Meanwhile, the guide speaks in excited tones of buildings where walls fade away and vanish, of diamond shapes in steel, of buildings like waterfalls.

There is innocence and boldness, too, at the Art Institute of Chicago, with Warhol’s huge portrait of Mao, Chagall’s blue-jewelled stained-glass American Windows and Renoir’s Acrobats at the Circus Fernando. The last-named depicts the daughters of a Montmartre circus owner taking a bow after their act, and the institute’s first owner, Mrs Potter Palmer, loved it so much she kept it with her at all times, even when travelling abroad.

This is a rich museum in every sense, packed with Van Goghs, Monets and Picassos. In Toulouse-Lautrec’s At the Moulin Rouge, theatrical types loll and glimmer in the half-light. They look as though they’re about to commit a killing or two, like Velma and Roxie.

The other place to see a good show in Chicago is the shops. Michigan Avenue is nicknamed the Magnificent Mile, and rightly so. It has an efficient, inclusive grandeur that saves it from pretentiousness, making New York’s Fifth Avenue look tacky by comparison.

The avenue is wide, the trees lush and the shops uncrowded, from Tiffany, Bulgari and Armani to Victoria’s Secret. The great American department stores are here, too — Neiman Marcus, Saks, Bloomingdale’s — all displaying their wares, putting on great performances, shimmying till their garters break. With the pound strong against the dollar, the prices are excellent.

Despite all that jazz, Chicago’s prevailing air of dignity gives it a particular charm. Its wealth grew from meatpacking, grain, lumber, steel and the railroad. It was the city of the blue-collar worker — though now it is foremost a financial centre, and America’s second great metropolis.

The city also has a reputation as a haunt of gangsters, where Al Capone ran riot during Prohibition. It still has some remnants of that rule- breaking era. Capone used to sit facing the door at the Green Mill club (4802 North Broadway, 773 878 5552; £4.50), keen to keep an eye on who came in. Today, the club is no tourist extravaganza, no American Moulin Rouge. It is serious and uneasy, and a vague air of intrigue still pervades its dimly lit booths. The Green Mill hosts regular experimental jazz and blues bands.

Chicago abounds with good music clubs, and even in the streets there is syncopation. Trumpets played as I strolled through Wrigley Plaza (only in America could a romantic square be named after chewing gum), and the fading sunlight smudged the top of tall buildings all around.

But the show you really must not miss is the city itself, seen in miniature from the top of a skyscraper. The best views are from the Sears Tower Skydeck (233 South Wacker Drive, 312 875 9696) and the observatory of the John Hancock Center (875 North Michigan Avenue, 312 751 3681); while the Ferris wheel at Navy Pier (600 East Grand Avenue, 312 595 7437) is fun after dark, when lights fill the city streets like poured gold.

As for food, the world is your menu. Don’t miss dinner at a “chophouse”, for huge fillet, ribeye and porterhouse steaks. And go to Pizzeria Uno (29 East Ohio Street, 312 321 1000), where pizzas are more like pies — oozing with melted cheese and everything else you can think of — and the waitresses are so good-humoured, they make you feel you’re the only person in the world they’ve ever really liked.

If you have time, wander around neighbourhood Chicago — it may help you understand why New Yorkers who relocate to Chicago are said never to want to return. Take in the Shedd Aquarium, where dolphins perform against the backdrop of Lake Michigan; visit the Adler Planetarium; and hire a bike from North Pier and ride beside the lake. Then drive to Oak Park and see Ernest Hemingway’s birthplace, or visit trendy Wicker Park, with its galleries and boutiques.

I am told Chicago can be cold in the winter, and far too windy, of course. But on a bright day in early summer, when mirror-fronted buildings bounce against each other and people smile from cars, its good nature and lust for life are hard to beat. As for razzle-dazzle, the whole city is just full of it, from the shimmering skyscrapers to the musicians playing on street corners in the dying light. 

Need to Know

Sally Emerson was a guest of Thomas Cook Signature. 

Getting there: American Airlines (0845 778 9789, flies to Chicago from Heathrow, Glasgow and Manchester — from £300 to £700, depending on date. British Airways (0870 850 9850, and United Airlines (0845 844 4777, fly from Heathrow; BMI (0870 607 0555, flies from Manchester. Aer Lingus (0818 365000, flies from Dublin and Shannon; from €511.

Where to stay: the four-star, art-deco Hotel Allegro (171 West Randolph Street, 00 800 5467 8660; doubles from £119) is luxurious and fun. Also inside the Loop is the Hotel Burnham (1 West Washington Street, 00 1 312 782 1111; doubles from £131), built in the 1890s and furnished accordingly.

Tour operators: Thomas Cook Signature (0870 443 4446, has four nights at the Allegro from £811pp, including BA flights from Heathrow. Direct departures are also available from Manchester; from £20pp extra. Or try Travel 4 Less (0871 222 3423,, Kuoni (01306 742888, or Travelocity (0870 111 7060,

In Ireland, American Holidays (01 673 3800, has two nights at the three-star Holiday Inn from €539pp, including flights from Dublin.

Best guidebook: Chicago (Rough Guides £9.99).

Links: informative tourist-board site.