Credit: Paul John Higgins

As the clock struck five on a recent Friday, patrons began to bounce through the doors at the Bar Louie in Dearborn Station. First two, then five, then a boisterous group ten strong and looking barely legal. Laughter erupted from a quartet of African-American women in business casual. Two young Latinos worked laptops at a two-top by the bar, where a lone white guy in a painter’s cap nursed a Corona and watched the Blackhawks game flash across a bank of TVs. A couple of cops in yellow vests stomped in to shake off the cold. “Sweet Child o’ Mine” squealed from the PA; somewhere a bartender dimmed the lights. Welcome to the new South Loop: Prosperous. Multiethnic. Clean. A far cry from the days when South State Street was known as “Satan’s Mile.”

The area now known as the South Loop—bounded approximately by Congress Parkway to the north, Cermak to the south, Lake Shore Drive to the east, and the Chicago River to the west—first rates in Chicago history as the site of the Fort Dearborn Massacre, an early and bloody skirmish in the War of 1812. That August, by order of General William Hull, stinging from the British capture of Mackinac Island, the commander of the garrison at the mouth of the Chicago River evacuated a party of about a hundred soldiers, women, and children and led them south along the lakeshore toward the relative safety of Fort Wayne. They didn’t make it. Somewhere around what’s now 18th Street the party was ambushed by the British-allied Potawatomi Indians. At least half the evacuees were killed on the beach; the rest were captured and sold into slavery, though they were soon ransomed by the British. Fort Dearborn itself was torched, and for the next four years the little settlement by the lake remained essentially abandoned.

Once the war was over, however, Fort Dearborn was rebuilt, and in the ensuing years settlers flocked to the Great Lakes frontier. At the end of the Civil War the area was one of the growing city’s busiest neighborhoods. Some of the first residents were Irish and German immigrants working on the Illinois & Michigan Canal, who settled inland, along the south branch of the river. But it was the arrival of the iron horse that sealed the South Loop’s destiny. The Chicago and Indiana Western Railroad’s Dearborn Station opened at Dearborn and Polk in 1885 and was followed quickly by the Grand Central (1890), Central (1893), and LaSalle stations (1903). The concentration of passenger and freight terminals established Chicago as the rail hub for the nation. By 1900 the South Loop rail yards stretched from State to Clinton, and freight depots and warehouses serving the needs of industries from lumber to printing set up shop in the area.

The Great Chicago Fire, in 1871, was good to the South Loop, sparing it for the most part and even driving businesses south of Harrison while the devastated Loop was rebuilt. More European immigrants streamed in, seeking jobs in the rail yards. Apartments and hotels sprang up to house visitors to the 1893 World’s Columbian Exposition. And the city’s wealthiest burghers—among them Marshall Field, Philip Armour, and George Pullman—built grand mansions along the eastern arteries of Calumet and Prairie avenues. A few still stand in the Prairie Avenue Historic District, most notably the Glessner House at 1800 S. Prairie, built for manufacturing magnate John Jacob Glessner in architect H. H. Richardson’s signature Romanesque style. Its thick, fortresslike granite walls protected the inhabitants from the gritty street life that, by the turn of the century, was creeping in from the west.

Prosperity begets opportunity, and a few blocks from the city’s most elite addresses, establishments of a different sort of notoriety were thriving. Though another, less famous fire in 1874 destroyed a large swath of the shantytown west of Wabash, the area was quickly rebuilt, like its neighbors north of Harrison, in brick and stone. At the turn of the century the cathouses and dives on State Street earned it the “Satan’s Mile” moniker; Chicago’s most infamous vice district, the Levee, ran from 18th to 22nd. Pimps, pushers, and prostitutes thronged in and out of opium dens and gambling parlors, while strains of ragtime tinkled from saloons like the Bucket of Blood, at 19th and Federal. The names of brothels promised exotic adventures: the Paris, the Shanghai. Others spoke the language of libertines, like the Why Not, on Armour, between 21st and 22nd. A few blocks north, morphine-addicted girls turned tricks for 25 cents a toss on Bed Bug Row.

Most notorious of all was the luxurious Everleigh Club, explored in Karen Abbott’s recent best-selling history, Sin in the Second City. It occupied a graystone mansion at 2131-2133 S. Dearborn. Outside, writes Abbott, “blind men cranked hurdy-gurdies, spinning tangled reams of melody. The air reeked of sweat and blood and swine entrails, drifting up from the Union Stock Yards just a few blocks southwest. Mickey Finn hawked his eponymous ‘special’ at his Dearborn Street bar.”

Inside, sisters Minna and Ada Everleigh presided over a house of 30 couture-clad “butterflies.” At a time when the average dinner ran 50 cents, a meal at the club’s opulent Pullman Buffet set you back $50. Boudoirs were outfitted with mirrored ceilings and marble bedsteads, parlors with gold spittoons.

From 1895 to 1909 the Levee toasted itself annually at the First Ward Ball, an orgy of debauchery that by 1907 drew a crowd 20,000 strong. Cops mingled with madams, judges with thugs, politicians with grifters and prostitutes. Is it any surprise it was also a fund-raiser for the local aldermen, Bathhouse John Coughlin and Hinky Dink Kenna?

When, in 1905, rumors flew that Marshall Field Jr. had been shot at the Everleigh Club, the coroner stuck with the story that his revolver had fired accidentally while he was cleaning it at home. But change was in the wind. Progressive Era reformers took to the streets, agitating for the city to clean up the Levee. Among their leaders were preacher Ernest Bell, editor of the anthology War on the White Slave Trade: Fighting the Traffic in Young Girls. With the passage of the Mann Act in 1910, “white slavery” was the cause of the hour, fueled as much by xenophobia and racism as by concern for the well-being of young women. In the South Loop and across the country early waves of northern European immigrants had given way to an influx of Italians, Hungarians, Jews, and other “swarthy” types, not to mention the northern migration of African-Americans from the south.

In 1911 the city’s vice commission issued an exhaustive report, “The Social Evil in Chicago.” Its shocking and premonitory final recommendation: the “absolute annihilation” of the Levee. A year later, after only a few days of police raids, this mission was well on its way to accomplished.

Though illegitimate enterprises lurked on the fringes with characteristic tenacity, residential streets were slowly given over to light manufacturing and shipping concerns as proximity to the rail lines turned the area around Dearborn Station into the midwest’s largest printing district. The R.R. Donnelley, Donohue, and Franklin firms built huge printing plants at the south end of Dearborn, while type foundries, binderies, and manufacturers set up shop in lofts between Polk and Congress. Over in the Fred V. Prather-designed Transportation Building at 600 S. Dearborn, Eliot Ness stalked Al Capone from his third-floor office.

The residential streets flanking the Second Presbyterian Church at 1936 S. Michigan—where the Armours and the Glessners once worshipped in the glow of spectacular Tiffany windows—gave way to grand auto showrooms for Ford, Buick, Hudson, and Pierce-Arrow. The industrial buildings along “Motor Row,” designed by some of the city’s premier architects, drew commercial traffic ever farther south.

The Gilded Age patriarchs of Prairie Avenue passed away, and their widows and children—crowded by encroaching industry and choked by soot from the railroads—decamped for places like Lake Forest and Libertyville. Some of their homes were chopped up into boardinghouses. Others—like the three-story Pullman mansion at 1729 S. Prairie, which contained a conservatory, a theater, and a bowling alley—were razed. By 1930 this “sunny street of the sifted few” was all but abandoned. To the southwest, the Everleigh Club mansion was demolished in 1933. Bertrand Goldberg’s landmarked Hilliard Homes, two arcing and two bulbous towers in a park to make Le Corbusier proud, stand on the site today. Built in 1966 for the Chicago Housing Authority, they’re now leasing as mixed-income housing under a banner advertising “Free Heat!”

As rail transport gave way to interstate trucking, the South Loop’s fortunes declined. Following World War II, printing companies began to move to the suburbs and, in some cases, out of state, and the infrastructure that had supported Printers Row dried up. At 2120 S. Michigan, Phil and Leonard Chess turned a former auto-parts factory into the recording studio that from 1957 to ’67 produced some of the greatest R & B records of all time—but even Chess Records couldn’t keep the neighborhood humming. With the consolidation of passenger rail lines at Union Station in 1971 the area was effectively ceded to the down and out. Chess closed in 1975 (though the building was landmarked in 1990 and is now home to the Blues Heaven Foundation). Porn shops and peep shows proliferated. Single-room-occupancy hotels like the Roosevelt and the St. James, at 1234 S. Wabash, housed the very poor and transient. The neon cross of the Pacific Garden Mission, founded in 1877 and providing food, shelter, and medical care at 646 S. State since 1923, glowed in the night, promising that “Jesus Saves.”

Mapmaker Dennis McClendon moved to Printers Row in 1983. He describes the landscape, in the terms of his trade, as a “zone of discard.” Though a few printers were still in business, the warehouses and depots that once drove the economic engine were mothballed, and Dearborn Station itself was in ruins, fenced off and “just waiting for something to happen.”

But by then, something was happening.

In 1973 a group of corporate leaders, the Glessners and Pullmans of their day, put their heads together to figure out how to bring investment back to the South Loop. The result, after many years of fund-raising, political wrangling, and trips back to the drawing board, was Dearborn Park, a planned community on 51 acres of former rail yards. Bears owner George “Papa Bear” Halas had them earmarked for a new stadium until the Dearborn Park planners wrestled them away. Bisected by Roosevelt Road, the community now stretches from Dearborn Station, at Polk and Dearborn, south to 15th Street.

Construction on the development wasn’t complete until the mid-90s, but the first residents moved into town homes and high-rises and terraced mid-rise buildings in 1979. (Lois Wille tells the whole fascinating story in her 1997 history At Home in the Loop: How Clout and Community Built Chicago’s Dearborn Park—essential reading for any urban-planning geek.) In perhaps unwitting homage to the Glessner mansion, Dearborn Park faces inward, its homes opening onto green culs de sac and sheltered patios while the uninterrupted exterior wall offers protection from the street—and confounds anyone trying to drive from State to Clark.

Early Dearborn Park residents embraced the idea of a small-town lifestyle in the shadow of the Sears Tower. Still, Wille points out, the community was missing a lot of the amenities of small-town life. “No odd neighborhood characters sat on porch stoops or roamed around,” she writes. “People had different skin colors but they dressed and talked and acted alike and held similar jobs. There were no little Ma-and-Pa storefronts tucked among the residences. . . . In Dearborn Park no one even dared paint a door or window trim a different color; that would violate a townhouse association rule.”

But while Dearborn Park probably deserved some criticism, it was undeniably successful, and it’s widely credited with sparking further South Loop development. Over on the other side of Dearborn Station, artists and other edge dwellers were starting to colonize Printers Row, attracted as ever by cheap rents, big windows, and freight elevators. Architect Wil Hasbrouck and his wife, Marilyn, were among the first commercial tenants, setting up his firm and her acclaimed Prairie Avenue Bookshop in the Donohue Building. The Transportation Building, once so beset by vandals and scavengers that it was considered a public health hazard, was rehabbed in 1981, the same year chef Michael Foley opened his Printer’s Row Restaurant in the Pontiac Building. In 1982 Ulrich and Ellen Sandmeyer opened Sandmeyer’s Bookstore up the street from the Hasbroucks, and in 1984 the first Printers Row Book Fair was staged along the strip.

In 1977 Columbia College purchased the first of the more than a dozen South Loop buildings it now owns. The first high-rise south of Roosevelt went up at 1212 S. Michigan in 1982. And two years later, on the river to the northwest, Bertrand Goldberg went ahead with his long-planned River City complex, though his original grand scheme for a subsidized development of 6,000 apartments accommodating tenants of all incomes ran afoul of the Dearborn Park planners and was scotched by the city. By the time the first building (containing 446 units) of his scaled-back project hit the market, the South Loop was already experiencing a rental glut. The rest of River City was never built.

In the early 80s the neighborhood struggled to define itself, with what’s now the South Loop Planning Board making a push to rename it Burnham Park, believing that “South Loop” bore the indelible stigma of the slums. It didn’t work. South Loop residents, wrote Dennis McClendon, in a 1985 letter to the Reader, “are proud to be ‘urban pioneers’ and object to a suburban-style name. . . . ‘Taylor Homes North,’ or ‘Bubbly Creek Meadows’ would be just as appropriate.”

Further changes you can see for yourself, from the gleaming new high-rises that tower over Prairie Avenue to the townhomes of Central Station, from the $350,000 condos of Motor Row to the University Center “superdorm” at State and Congress. There’s a Target and a Whole Foods and a shiny new Central District police station at 17th and State. None of this happened in a vacuum; the transformation of the South Loop into a high-density residential and commercial area by 2020 is a cornerstone of the city’s sweeping Central Area Plan.

But with change comes conflict. The pace and scale of development has sparked angry protests. The neighborhood’s magnet elementary school is embroiled in controversy. Parking is a bitch. And while many argue that because so much of the land was abandoned or industrial the South Loop doesn’t fit gentrification’s typical model of residential displacement, the face of the neighborhood is far more affluent than it was even ten years ago.

“The real issue in the South Loop right now is not race, ” says Columbia College historian Dominic Pacyga, who grew up in Back of the Yards. “The real issue is social class.”

In the mid-90s the Chicago Coalition for the Homeless led a campaign for affordable housing in the South Loop, urging the city to preserve existing housing for the very poor and to enforce affordability requirements for new projects receiving tax increment financing funding. During the 1996 Democratic Convention one homeless man, Ron Lonas, dressed up like a tree and dogged beautification-obsessed Mayor Daley at every turn, carrying a sign asking “If I dress like a tree, will you care about me?”

But though the city supported construction of two new SROs on South Wabash, affordable options are pretty meager. The Roosevelt is now full of market-rate apartments, many housing Columbia students; there’s a Jewel where the St. James used to be. The Pacific Garden Mission, forced out by the expansion of the Jones College Prep magnet high school, relocated to a spiffy new facility at 14th and Canal last year. And the city’s last “cage hotel”—the optimistically named New Ritz at 1001 S. State—closed last summer.

“Now the South Loop isn’t someplace that only pioneering or crazy urbanophiles would want to live,” observes Dennis McClendon. “It’s just another neighborhood that kids being transferred in from the San Francisco office or the Charlotte office consider as a convenient place to live.”   v