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The Magnificent Mile: What the Street Replaced
Tour Companion

The Magnificent Mile: What the Street Replaced

May 25, 2026
8 min read

The Magnificent Mile is the most efficient act of urban subtraction in American history. A walker standing at the south bridgehead of the DuSable Bridge today reads North Michigan Avenue as one of the most iconic commercial boulevards in the United States. Limestone and terra cotta on both sides. Two clock towers anchoring the south end. A Gothic stone tower with embedded fragments of other buildings in its base. A water tower of yellow stone three blocks north, set in a small plaza with its own light fixtures and benches. Hotels, flagship retail, a postwar supertall a third of the way up. The street has a name. It has a brand. It feels old.

It is not old. Almost everything visible from the bridgehead today was built between 1920 and 1929. Before 1920 this street was called Pine Street, and most Chicagoans had no reason to walk it. The transformation took roughly fifteen years. It is the most concentrated act of urban subtraction in American history, in the sense that the entire previous character of the street was systematically replaced. One nineteenth-century building survived, by accident and then by deliberate preservation. Everything else was cleared.

The street before the bridge

The Encyclopedia of Chicago records that Pine Street in 1886 was a mixed corridor of factories and warehouses near the river and fine residences (mansions and rowhouses) farther north. The river end of the street was service. The northern end was residential. Neither read as commercial. Daniel Burnham's 1909 Plan of Chicago, co-authored with Edward H. Bennett, included among its many prescriptions a major double-deck boulevard connection between the existing Michigan Avenue south of the river and Pine Street north of it. The plan called for a new bridge at the river crossing. The plan's argument was that the city's commercial spine needed to be doubled.

Burnham died in 1912. Bennett carried the plan into execution. The Michigan Avenue Bridge opened to traffic on May 14, 1920, at four in the afternoon, with Mayor William Hale Thompson cutting the ribbon. The Chicago History Museum holds the photographs and the program. The bridge replaced an older Rush Street drawbridge. Pine Street was widened and rebranded the North Michigan Avenue extension. Bennett designed the bridge's four bridgehouses, which still stand at the corners of the bridge, each with sculptural reliefs commemorating moments in Chicago's history.

The bridge was not the building. The bridge was the permission. Once the bridge connected the south-of-river commercial spine to the north-of-river residential district, the property values on Pine Street were guaranteed to rise. The land north of the river had spent thirty years waiting for an event that would not come. The event came.

The decade

The first building was the Drake Hotel, which Marshall and Fox had finished at the north end of the street on December 31, 1920, eight months after the bridge opened. The Drake's design predated the bridge: the architect Benjamin Howard Marshall had been working on the plans for two years. The hotel anchored the north end of what would become the Magnificent Mile.

The Wrigley Building came next. William Wrigley Jr., the chewing-gum manufacturer, commissioned Charles Beersman of Graham, Anderson, Probst and White to design a corporate headquarters on the most visible corner at the south end of the new street, directly across from the bridge. The south tower opened in September 1921. The north tower in May 1924. The building was Chicago's first air-conditioned office building. Its cream-colored terra cotta sheath, floodlit at night, became a postcard image of the new boulevard. The Chicago Architecture Center records the Wrigley as the first major commercial structure built north of the river.

The Allerton Hotel followed at 701 North Michigan, designed by Murgatroyd and Ogden of New York with Fugard and Knapp of Chicago, opened March 31, 1924. The Tribune Tower opened in 1925, the product of an international competition launched by Colonel Robert R. McCormick of the Chicago Tribune in 1922. The Skyscraper Museum's count of the competition entries is 263, from 23 countries. John Mead Howells and Raymond Hood won with a Gothic Revival design that included embedded fragments of other historic buildings (the Great Wall, Notre Dame, the Parthenon, and others) in its lower exterior walls. Eliel Saarinen's second-place entry, a stepped tower of unadorned stone, became one of the most influential lost competitions in twentieth-century architectural history. Walter Gropius and Adolf Meyer submitted a modernist entry that placed twenty-third.

The Palmolive Building, designed by Holabird and Root, opened at 919 North Michigan Avenue in April 1929. A thirty-seven-story Art Deco tower with a rotating Lindbergh Beacon on its roof from 1930. The decade closed with the stock market crash of October 1929. The Mile had its first six landmark buildings. The rest of the street, the warehouses and the mansions, was being cleared.

The water tower

There is exactly one major building on the Mile that predates the bridge. The Chicago Water Tower at the corner of Michigan and Chicago Avenue is yellow Joliet limestone, designed by William W. Boyington in 1869, three blocks north of the bridge in what was then a relatively undeveloped part of the original Pine Street. The tower housed a standpipe that regulated water pressure for the city's new water-supply system. Across the river to the southeast was a matching pumping station that drew water through Chesbrough's 1867 two-mile lake tunnel from the offshore crib.

The Great Chicago Fire of October 8 to 10, 1871, burned everything around the water tower. The tower itself survived. Wikipedia's careful phrasing is exact: the Chicago Water Tower was the only major public structure in the burnt zone to survive the fire. Not the only building (several smaller residential and commercial structures survived as well), but the only major public structure. The myth that it was the sole survivor of any kind is exactly that, a myth.

Oscar Wilde, on his 1882 American lecture tour, called the water tower "a castellated monstrosity." Chicagoans, undeterred, kept it. By 1924 the city had officially designated it a landmark. When the Magnificent Mile's developers cleared the rest of Pine Street, the water tower stayed. It is the only building on the modern boulevard that the new street's developers chose to build around rather than over.

The water tower is the subtraction device made visible. Standing in the small plaza at its base today, surrounded by the buildings of the Mile, the visitor can read the layered history at a glance. The tower is 1869. The plaza around it is twentieth-century. The boulevard that the plaza interrupts is 1920s and onward. The water tower is the visible record of what stood here before the Mile. It is also the proof that the Mile was a deliberate replacement, not an organic development.

The name

There was one more piece of the construction. The boulevard did not call itself the Magnificent Mile in 1920 or in 1929 or in 1939. It got the name in April 1947, when the Chicago real estate developer Arthur Rubloff, through the Greater North Michigan Avenue Association, launched a rebranding campaign. Rubloff, born in Duluth, Minnesota, on June 25, 1902, had founded Arthur Rubloff and Company in 1930. He had spent the postwar years acquiring properties along North Michigan Avenue. The Magnificent Mile was his coinage. The association adopted it. The papers printed it. By the 1950s the name was the street.

The naming act is the closing piece of the subtraction. The street's previous identity (Pine Street, service corridor, warehouse district, mansion row) had not just been physically replaced. It had been linguistically replaced as well. The name "Pine Street" disappeared from common usage. The Magnificent Mile became the only name most people knew.

What subtraction makes visible

The Magnificent Mile is the city's most efficient transformation case study. In roughly fifteen years (1920 to about 1935 with the addition of the Palmolive and a few smaller landmarks), and then again in another wave through the 1950s and 1960s as the John Hancock Center went up at 875 North Michigan (Bruce Graham and Fazlur Khan of SOM, 1969, the first use of the exterior diagonalized tube structural system and the world's first mixed-use supertall tower), the street was rebuilt almost completely. The 1869 water tower is the only major nineteenth-century structure left standing on the corridor.

Walking the Mile teaches a discipline of urban reading that the rest of Chicago does not always teach. The other walks (the Loop, the river, Oak Park, the lakefront) are about reading what was built. The Magnificent Mile is about reading what was unbuilt, what was cleared, and what one stubborn old building can keep visible against the deliberate erasure of an entire street. The water tower is the lens. Everything else is what replaced what it once stood among.

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