What A.J. Liebling identified as Chicago's "second city" complex has probably been an urban hang-up since at least 1890, when it overtook Philadelphia in population and went head-to-head, in its own mind, with New York City. Chicagoans regularly vent their insecurity in relation to City No. 1 by boasting that they have the best--and here you can fill in the blank--symphony, opera, theater, restaurants, sports teams, or political corruption. The saddest commentary on these claims is that you can live for years in New York without hearing anyone compare anything to Chicago's version. Curiously, though, there is one topic about which you seldom hear Chicago locals touting their superiority: architecture.

The reason may be that in architecture Chicago is confidently arrogant. Everyone in New York knows that Chicago has better skyscrapers. Everyone in Chicago knows, too. Civic pride is wrapped up in the majesty of the lake-front skyline and the height of its giants. The average citizen has strong feelings about the more famous buildings and may even know something about them. Having grown up in Chicago, I've often wondered how it became the great American architectural city--and why the whole topic is so much deader in New York. With an eye to figuring this out, I took a tour of downtown with a couple of architectural historians: Tim Samuelson of the Chicago Historical Society and Rolf Achilles, who teaches at the School of the Art Institute of Chicago. I'm indebted to them for much of the information in this column.

Our tour began at the Monadnock Building, a somber, chocolate-colored structure near the south end of the Loop. (The Loop is synonymous with "Chicago's downtown business district," which is traditionally defined by the elevated train that runs in an oval around it.) Architecture buffs such as Samuelson and Achilles love this building because it's an anomaly, looking both forward and back. By the time it was built, in 1891, steel-frame construction was already being used to achieve height without the chunkiness of the early tall buildings made out of stone and brick. But the firm of Burnham & Root, which designed the north section, made this 16-story skyscraper the old-fashioned way--out of masonry. This meant it needed a massive base; the exterior walls at ground level are 6 feet thick. But the Monadnock was also path breaking. Tired of being nickeled-and-dimed by Boston developers, the architects proposed an unheard-of cost cutting measure: no exterior ornament. On the north, seen here, there's not even a pediment, just a curved lip. This gives the moody hulk a sculptural shape and a sort of Egyptoid cast, which is appropriate when you consider that the principle of its construction is that of a pyramid.

The commercial skyscraper flourished in Chicago for three reasons. The first was the great fire that flattened the city in 1871--a biggest-ever event that made Chicagoans perversely proud. The fire ignited a cycle of building, demolition, and building. But even more important were the city's exponential population growth in the second half of the 19^th century and the physical situation of its central business district. With a bursting population, the city had to build. And with a downtown of just 35 blocks bounded by water on all sides, its core had nowhere to go but up. The early skyscrapers fight against their tallness, emphasizing horizontal rather than the vertical lines. Perhaps the greatest surviving example of these buildings is the Rookery Building (1885). The long ribbons of window hold the building down rather than thrusting it up into the sky. Back then, commercial tenants weren't interested in sweeping views; big windows were to compensate for the dimness of 20-watt light bulbs. The choicest real estate back then was the opulent second floor, a holdover from the pre-elevator days.

The Rookery illustrates a point Samuelson makes about the life cycle of Chicago's commercial buildings. The period of greatest jeopardy comes 20 to 30 years after they're first finished. At this point, a building is likely to be showing signs of age and to have gone out of fashion--think of how people feel about 1970s architecture today. Yet it's still too young for anyone to think it has historical value. Twenty years after being built, the Rookery Building looked dated and was less attractive to tenants than newer construction in the vicinity. But instead of demolishing it, the owners hired Frank Lloyd Wright to redesign the lobby. Wright's 1907 renovation squares off John Root's ornamental ironwork with marble sheeting.

The great visionary and intellect of Chicago's first wave was Wright's teacher Louis Sullivan, who wanted to bring what he called "vertical continuity" to the skyscraper--to make it look tall instead of squat. Sullivan is remembered for his aphorism, "Form follows function," which sounds odd in light of his lavishly ornamented buildings in Chicago, such as the Auditorium Theater (1885-89) and the Carson Pirie Scott department store (1899-1903).

But when you look closely at Sullivan's ornamentation, as in this 1890 tomb in Graceland Cemetery, you see that it is anything but decorative. Sullivan described ornament as "perfume"--something that helped to create the experience of a building. Only when you compare Sullivan's intricate ornament to the excesses of his late-Victorian contemporaries--the nonbearing columns, plaster deities, and gratuitous filigree--can you appreciate what a radical he was. The greatest act of vandalism Chicago committed against its architectural heritage was tearing down Sullivan's Chicago Stock Exchange Building in 1972, something Samuelson fought unsuccessfully to prevent. Even today, Chicago lacks a strong preservationist ethos. But if it had one, it would probably have fewer buildings worth saving. The greed that destroyed Sullivan's stock exchange and many other great buildings in Chicago was the same force that raised them in the first place, often on the sites of earlier masterpieces. In Chicago, they love to build and love to tear down. New York, which now considers every middle-aged building a landmark, creates fewer new ones.

By the 1920s, Chicago had clearly lost the race for urban supremacy, and the second city complex began to take over. New buildings imitated styles from New York and elsewhere. In the big bank lobbies, Sullivan's functionalism gave way to a vulgar grandiosity. One of the worst offenders was the winner of the $50,000 competition to design an office tower for the Chicago Tribune, an exercise in wedding-cake gothic chosen over a visionary design submitted by Eliel Saarinen. But even Chicago's mediocre buildings seem to have a majesty that their cousins in New York lack. Sullivan explains the reason for this in The Autobiography of an Idea, published in 1924. In New York's narrow streets, skyscrapers crowded next to each other become "mutually destructive." The buildings form canyons and are individually invisible. On Chicago's wider avenues with vistas open to every side, by contrast, skyscrapers retain "the element of loftiness, in the suggestion of slenderness and aspiration, the soaring quality as a thing rising from the earth as a unitary utterance," as Sullivan puts it. The fact that you actually see tall buildings in Chicago and don't in New York goes a way toward explaining why the one city has a thriving popular culture of architecture and the other doesn't. (This difference also explains why Chicago is a far better city for outdoor sculpture.)

No big buildings went up in the Loop for about 20 years, between the Great Depression and the early 1950s, when Chicago's next wave of architectural supremacy crested. Its guiding spirit was Ludwig Mies van der Rohe, who came to Chicago from Berlin in 1938 after the Bauhaus closed. Declaring his affinity for Chicago's earlier tradition, Mies asserted, pace Sullivan, that form is function. Since the steel frame held the building up, there was no need for bricks and stones at all. Among Mies' influential Chicago buildings were the residential towers at 860 and 880 N. Lake Shore Drive, completed in 1951.

The new office skyscrapers that rose downtown between the 1950s and the 1970s were either by Mies or influenced by Mies. For example, Skidmore, Owings & Merrill designed the Inland Steel Building (1954). This is one of my favorite modern buildings. The thin stainless steel and green glass gives it a hammered, almost hand-made look.

Mies himself designed the Federal Center, constructed over the period 1959-74. The conventional view is that these glass boxes are absolutely minimal. Samuelson sees them differently. He points up at the I-beams on the skin. Though these girders serve a function as "stiffeners," they aren't a structural necessity. Thus Samuelson argues that they constitute a "romantic" and "poetic" element in the tradition of Sullivan--the point being to give the building upward thrust.

Mies inspired Chicago's two giants, the 100-story Hancock Tower (1969) by Skidmore, Owings & Merrill, and the 110-story Sears Tower (1969-74), also by SOM, which was the tallest building in the world when completed. Chicago loves having the biggest of anything. Unfortunately, the Sears Tower lost its title in 1996, when a skyscraper by Cesar Pelli in Kuala Lumpur, Malaysia, bested it by 22 feet.

I'd make a case that the greatest Chicago architect after Mies was the recently deceased and still much underappreciated Bertrand Goldberg. Though Goldberg studied at the Bauhaus, he repudiated Miesian doctrine, answering rectangularity with roundness. Like Sullivan, Goldberg saw architecture as organic and thought his buildings through from master plan to tiny detail. Goldberg's iconic work is the Marina City Towers (1967), in which pie-shaped apartments with fabulous views of the city are laid out around a core that acts as a kind of central nervous system. From the outside, the Marina Towers look like standing corncobs. More of a communitarian than Mies, Goldberg designed Marina City not just as a pair of buildings, but as a residential neighborhood that he hoped would persuade people to live near the Loop. The original Marina City had not only boat and car parking, but also a restaurant, stores, a theater, a pool, a skating rink, and a bowling alley.

Since the 1970s, Chicago has been in a relatively fallow period for architecture, somewhat like in the 1920s. There have been some interesting additions to the Loop, such as the Kohn Pedersen Fox office building at 333 Wacker, and the State of Illinois Center designed by Helmut Jahn, as well as some catastrophes, such as the ghastly postmodern Harold Washington Library designed by Thomas Beeby, and the new Museum of Contemporary Art designed by the German architect Josef Paul Kleihues.

But for the most part, Chicago's new buildings of the past two decades have been the indifferent work of big-name, international architects who might have raised them in any of several dozen cities. Chicago has a Pelli, a Phillip Johnson, a Kevin Roche, and a Ricardo Bofill. There's nothing yet by any of the most interesting architects working today--Frank Gehry, Renzo Piano, Rem Koolhas, or Stephen Holl, though buildings by Piano and Gehry are in the works. I'm not sure that anyone is designing really novel or interesting tall buildings--as opposed to wide ones--anywhere in the world right now. But if the skyscraper rises again, I'd bet on it happening in Chicago.