City Break: 48 hours in the life of Chicago

Chicago, the musical? A ticket to Chicago the city is possibly easier to get, and probably even more fun. For this week's prescription for the perfect weekend break, Simon Calder spends 48 hours in America's greatest city.

Why go now?

Because today the lights on State Street are switched on, adding to Chicago's claim to be the best place on earth to do your Christmas shopping. Because until mid-December, transatlantic airlines are almost giving away flights to the United States. And because Chicago possesses the critical mass of energy and culture that New York thinks it has.

Beam down

The new Air India flight from Heathrow to Chicago seems custom-made for the weekender. The 747 flies out at noon on Friday and returns overnight on Sunday. Through discount agents such as Welcome Travel (0171-439 3627), you can get the flight forpounds 253 including a multitude of taxes; and, if you decide to stay longer, you can change your return date without penalty.

In response, the other airlines are cutting their fares for travel within the next month; American Airlines from Gatwick, Heathrow, Manchester and Glasgow; and British Airways and United from Heathrow.

Get your bearings

O'Hare is the world's busiest airport (ignore any representations to the contrary by Heathrow). You will probably arrive at Terminal 5, which has a tourist information centre of sorts. It also has the worst-value bureau de change I have ever encountered: pounds 1 coins are changed at the rate of pounds 1 for $1.

The journey into the centre is most adroitly achieved by the CTA subway train, a bargain at $1.50 to anywhere in the city. The catch is that first you must find the station. Take the airport shuttle train to Terminal 2, negotiate a series of escalators and moving walkways, and about 10 minutes later you will reach the station.

Here, your problems are only just beginning. Either ask the attendant for a token, or solve your transportation problems for the next two days by feeding $13.50 (change machines are available) into the Transit Card machines. This will give you enough for 10 single journeys, and allow you to take transfers on buses for 30 cents each.

Do your best to persuade the attendant to give you the CTA map, which will be a trusty companion all weekend - and is the only map you need. Sit back and enjoy the 40-minute ride into town.

Once there, orientation is easy. Almost all streets run north-south or east-west, with few difficult diagonals. The main north-south roads are Michigan Avenue and State Street. The latter slices through the Loop, a rectangle covering about a square mile, defined by the elevated subway lines. (This sounds convoluted, but makes perfect sense when you see a map, honest.) Being inside or outside the Loop is an important concept to the average Chicagoan.

You will, if you follow this plan approximately, spend most of your time within or close to the Loop. Before you head significantly south of it, take local advice on safety.

Check in

Being a sensible traveller, you will have booked in advance. The McCormick convention centre has just been expanded to become the biggest in the world, which means that Chicago is often booked out with delegates. The demand for rooms means the prices quoted here can fluctuate significantly. Mid-range: Days Inn, Lincoln Park (001 773 525 7010) charges around $70 (pounds 45) including breakfast. Luxury: the Inter-Continental on North Michigan Avenue (001 312 944 8895) has winter weekend specials for as little as $89 (pounds 57) including tax.

Take a ride

The best way to get an instant understanding of the astonishing scale of Chicago is to take that Loop in full. Orange Line trains loop around it clockwise, Brown Line trains anticlockwise. On a terrain that is as flat as an untopped pizza, Chicago has created its own landscape, one that is best viewed 30ft up from a swaying train.

Take a hike

If you alight at Adams, you will be a block away from the Chicago Architecture Foundation. This commendable organisation, located on the ground floor of the Railway Exchange building at the corner of Michigan and Jackson, runs a daily tour at 10am. For $10, you spend two hours in the company of a well-informed guide who will trace the history of a city built upon unadulterated exaggeration.

Lunch on the run

At eight blocks to the mile (north-south; 12 to the mile east-west), it's a two-mile hike up Michigan Avenue to Water Tower Place. Worth the walk, though, for an unparalleled series of shops.

When you get to Water Tower Place, you find even more. Indeed, the glass elevator to the seventh floor is an excellent appetiser for your lunch. Many other cities have thought of food courts, but Foodlife - on the mezzanine floor - is different. Where else can you pile up your plate with antipasti, salad or hot dishes for $4.95 per pound?

Cultural afternoon

Conventional wisdom has it that the best gallery in Chicago is the handsome old Art Institute. But the new Museum of Contemporary Art has a couple of advantages. One is that it is only 200 yards from your table at Foodlife. The other is that the building and collection celebrate space and assertion in a manner shared by the city itself.

From the outside, it looks wantonly grubby. Inside, the sharp angles and wide windows provide a startling venue for a challenging collection. Between now and 25 January, the fuzzy frontier between art and film is explored - highly appropriate in the most cinegenic of cities, whose latest cameo is in My Best Friend's Wedding. The museum opens 10am-6pm at weekends, from 11am on other days except on Monday, when it is closed.

Window shopping

From today, the windows of Marshall Fields department store in State Street become hilariously festive, arresting passers-by who then trigger massive, good-natured congestion in Chicago's main street. You can happily venture inside because of the general rule that prices in the United States are the same as in Britain - except that theirs are in dollars, as opposed to ours in pounds.

An aperitif

Nearby, the Berghof at 17 West Adams Street is a German bierkeller which also manages to be the archetypally American bar, complete with attentive service, good beer (local brews are rapidly gaining ascendance from the mass-produced fizz from up the highway in Milwaukee) and staff who expect their tips to be as handsome as they are.

Demure dinner

Pizzeria Uno (29 East Ohio Street) is, it says, the original source of the Chicago deep-dish pizza. Many say it is still the greatest. Mine was the size of a small Midwestern town, and so tasty that I had the remains boxed up and munched them on the plane home. You may, however, need to queue for as long as an hour.

Sunday morning: go to church

Westminster Abbey? Notre Dame? You can see bits of both at the skyscraper- Gothic Chicago Tribune tower on Michigan Avenue. This cathedral to journalism is decorated by pilfered masonry from celebrated and newsworthy structures around the world, from the Parthenon to the Berlin Wall. Inside, inspirational motifs evangelise about newspapers.

Bracing brunch

The only place in town for real Chicagoans is Lou Mitchell's, the archetypal diner hidden around the back of Union Station at Jackson and Jefferson. You will be given a doughnut when you arrive, then treated to a mountain of French toast, million-egg omelettes and endless coffee, in chrome and cheerful surroundings.

A walk in the park

The icing on the cake

The 100-year-old public library at Randolph and Michigan has been brilliantly transformed into a people's palace. The Chicago Cultural Centre opens at noon on Sundays, until 5pm, and allows you to roam around four floors heavy with civic pride. The Dome Memorial Hall at the top shows that intricacy and sensitivity offer as strong an architectural suit as sheer scale, while the Corner Bakery on the ground floor is the place to fill any remaining gaps in your appetite.

Red channel

Hazards facing today's traveller on the railways of South America, as advised by the Thomas Cook Overseas Timetable.

The provinces of Argentina continue to bicker on about passenger trains, but their reluctance to pay for them is keeping the system very small. The gap in service on the southern main line remains, where it crosses La Pampa, but the long-expected service from Buenos Aires north to Tucuman, which has been stopped by Tucuman's unwillingness to contribute any cash, may finally be starting. Tucuman has subcontracted service to an operator that thinks it may be able to make some money by offering a level of service found on few trains.

The trains themselves, old but refurbished, are fairly sumptuous, and your ticket includes the services of hostesses and private security guards. Presumably the clientele is expected to consist largely of rich, libidinous men, but, if they can make it pay, perhaps it will lead the way to unexpected pleasures on trains everywhere.

We, and many others, have been predicting the end of rail service in Ecuador for at least five years, but the system staggers on, still calling itself the State Railway, though the government has washed its hands of the operation. Yet again it has produced a schedule of train services. We include it as "advertised", but would warn that a traveller who was there only seven days after the new timings were introduced found that both the railcars (they have only two) were out of service.

The Ferrocarril Arica-La Paz has been sold to the Cruz Blanca Investment Co, whose policy is not to open passenger services. The last of the routes offering rail service up into the Andes has thus been closed to passengers.

Thomas Cook Overseas Timetable, pounds 8.40