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Everyone does it. Tourists do it, business travellers do it, and even the Rough Guide to Chicago, just 60 words into its large-type introduction, does it. Everyone compares Chicago to New York.

Even Chicagoans do it. There you are, mopping the last of the meat-sweats off your brow at Gibsons Steak House, and a nice elderly couple will hobble across from some table in the farthest corner of the room to let you know that there’s no place you can eat steak like this in New York.

Or you’re sitting in the Second City Comedy Club (see, right there in the title – they’re doing it again). It’s the intermission. You’ve laughed so hard, you’re asking the waitress for extra napkins to dry your seat, and some hairdo will lean across and tell you they’ve done all of the entertainment in Chicago – Oprah, Jerry and now here – and do you know, by the way, Chicago’s produced more funny people than New York ever did?

Chicago, Chicago

There’s so much to the city, it’s amazing that people compare it to America’s ‘other’ city

Background

• A marathon in Chicago

• Chicago loses its oldest restaurant

All right, Chicago, I get it: you’re not New York.

I got it as soon as I walked off the plane into O’Hare airport and, instead of standing in the world’s biggest queue, I was gliding through walkways that look as though they’ve just had the marble dust blown out of them and the bubble wrap taken off the slinky, multi-hued neon ceiling lights. I got it, too, when I realised that every taxi driver here is also an immigrant, but one who has bothered to learn English.

Let’s get the comparisons out of the way: New York has seasons. Chicago has weather. Go out when it’s chilly in NY and you’ll get cold. Go out when it’s winter and blowing in Chicago (not for nothing is it called the Windy City) and your nose’ll fall off.

New York’s got the night, Chicago has the day. If you can afford it or hustle it, get a room with a view over Lake Michigan. When day breaks over the water, light floods the avenues and it’s like optimism just walked into town.

Frank says about New York that if you can make it there, you can make it anywhere. But he was just as right when he said about Chicago: “They have the time of their life.”

New York is full. Chicago has space. The Big Apple’s little Apple store has queues so long, they’ve hired bouncers; there’s an Apple store in Chicago as big as a ballroom.

New York has districts. Chicago has neighbourhoods. Take a late-morning walk around Bucktown and see the young urban singles slouching into the popular cafe Toast, fortifying themselves for an afternoon’s boutique retail therapy.

There’s more. New York: famous diets. Chicago: farmers’ portions. New York: jazz. Chicago: blues. New York: glitzy Broadway openings. Chicago: John Malkovich. New York: white collar. Chicago: blue collar.

But the biggest distinction of all is this. New York has buildings. Chicago has architecture.

In New York, there’s not a square foot of sky that hasn’t been built on. Down on the street, you’re walking in canyons. Chicago gives you vistas, and it is true civic generosity that made this difference. In the 1920s, city ordinance laws stipulated that above 262ft (the 24th floor), all buildings have to be stepped back to just one-quarter of their footprint. So in Chicago, you can now see over the shoulder of the world’s tallest building in 1920 to the world’s tallest building in 1999.

The most enjoyable way to take it all in is on board Chicago’s First Lady river cruiser (www.cruisechicago.com), with live commentary by a volunteer from the Chicago Architecture Foundation. Sit at the back up on the top deck, stretch your legs and, for 90 minutes, the grand plans and individual whimsies of 20th-century architects glide before you.

Chicago invented the skyscraper, and it did it in the 19th century and started in stone. It continued with stone for a long time, and from the river you can see the grand aspirations behind the 1925 Tribune Tower, styled on the cathedral at Rouen – all soaring gothic, flying buttresses and ornate scrollwork.

But Chicago was growing up and the higher you go in stone, the thicker the walls at ground level have to be. The city was flattened by fire in 1871, just about the time it found itself at the intersection of the railroads heading west and a shipping route that connected the North Atlantic ports (via the newly built Erie Canal, and the Illinois & Michigan Canal) to the south and the shipping hub of New Orleans. After the fire, what had been an urge to build became a fury. The unbroken vertical lines of art deco, the neoclassical pretensions of beaux-arts masterpieces with Greek temples on top and Spanish Renaissance wedding cakes such as the Wrigley Building were still being made, but Chicago had its own ideas.

Load-bearing stone walls were superseded by steel frames, which enabled architects to build higher. Steel frames also meant that thick walls weren’t necessary, and more space could be given to glass windows. With more glass and less stone, there was less room for elaborate ornamentation. The soaring skyscraper was invented.

But the buildings were still clad in stone and justifying themselves with historical references. When German émigré Mies van der Rohe arrived, he wanted to simplify things further and put the steel supports on the outside, cladding the whole in glass, altering the skyscape of Chicago and every other city.

Other movements in architecture all slide past on your river cruise. Gasp as you were meant to at the 1960s brutalist style, or see how buildings were given a new role during another city population explosion in the 1980s: the giant multistorey cold-storage building had windows punched through its sides, but only after waiting 17 months for it to defrost.

Visible from just about anywhere in Chicago is the 1970s Sears Tower (the world’s tallest building until the late 1990s, when the weaselly builders of Kuala Lumpur’s Petronas Towers added an extra-long radio mast). From the Skydeck, 103 storeys above the city, reached by an elevator that takes less than a minute to get to the top (and, yes, it does make your ears pop), you can see all of the city.

You can admire its wide avenues, given warmth and friendliness with trees and well-maintained flowerbeds. You can see Lake Michigan stretching to the horizon and the 20-mile Lakeshore Path, where you can run or cycle with the water on one side and some of the world’s most important architecture on the other. Up here you can see the shopping district of the Magnificent Mile, which has every kind of store you’d hope for – including, until recently, Marshall Field’s, the world’s first department store, sadly rebranded as Macy’s in 2006. Over there is Wrigley Field, home to the baseball team with the world’s longest losing streak and the world’s most loyal fans.

You can see the Navy Pier with the Ferris Wheel on the end, and its wide, clean boardwalks and pseudo-authentic eateries – all of which is shocking not because of how tacky it is, but because of how tacky it isn’t.

Somewhere down there is where rollerskates, the zipper, the railroad sleeping car and McDonald’s were all invented, and where you blew your mind (and your wallet) with the NoMI sushi restaurant.

You can see one of the world’s largest free zoos, the Museum of Contemporary Brunch (sorry, I mean the Museum of Contemporary Art, with its wonderfully airy restaurant to have brunch), and the lovely Art Institute of Chicago, where you walk down wide corridors going, “Oh, they’ve got that... and that... and that.”

It’s all spread out there, far and wide, laid out generously and pleasantly, with as much space as you want. Yes, ma’am, it is all bigger in the Midwest, and Chicago really is like no other city you know.

Chris West travelled as a guest of Virgin Atlantic and the Park Hyatt Hotel

Getting there: fly from Heathrow with Virgin Atlantic (0870 574 7747, www.virginatlantic.com), American Airlines (020 7365 0777, www.americanairlines.co.uk), British Airways (0870 850 9850, www.ba.com) or United Airlines (0845 844 4777, www.unitedairlines. co.uk). American and BMI (0870 607 0555, www.flybmi.com) also fly from Manchester. Fares start from £400.

Where to stay: the elegant Park Hyatt (00 1-312 335 1234, parkchicago.hyatt.com) has double rooms from £275. The Raffaello (888 560 4977, www.chicagoraffaello.com) was refurbished in 2006 and has rooms from £112. Budget travellers should try the Best Western River North (312 467 0800, www.rivernorth hotel.com); from £91.

Where to eat: Park Hyatt’s NoMI (312 239 4030, www.nomirestaurant.com) offers sushi (from £11) and Mediterranean-inspired food (mains from £20). Gibsons Steak House (312 266 8999, www.gibsonssteakhouse.com) has steaks from about £15. A great cops’ favourite is Portillo’s Hot Dogs, with numerous locations (312 587 8910, www.portillos.com); £2.50 for a dog and a Coke. Toast is at 2046 North Damen Avenue (773 772 5600). The Bluebird (1749 North Damen Avenue; 773 486 2473) is one of Chicago’s friendliest bars, with good food and bar staff.

Tour operators: Complete North America (0845 263 7100, www.completenorthamerica. com) has a week in the boutique Hotel Monaco from £1,098pp, including flights from London and all taxes. Alternatively, try North America Travel Service (020 7499 7299, www.north americatravelservice.com).

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