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.”

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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.

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.

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 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.

“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.”