Walking the Prairie Avenue Historic District is a bit like visiting a ruin. Your imagination is essential because only a few late-19th-century mansions still stand, remnants of a time when the street was the city’s most prestigious address, home to such famous millionaires as George Pullman, Philip Armour, and Marshall Field. Today the district is dominated by development, not preservation. Industrial buildings are fast being converted into loft residences, while hundreds of new town houses and condos are springing up around them.

The street’s heyday was short-lived. The first factory arrived by 1915, and after World War I many grand homes were turned into rooming houses. As the street became more commercial, most of these houses were torn down. Not much remained by the time Prairie Avenue became a city landmark district in 1979.

From 18th Street south to the McCormick Place complex at 22nd, the area’s remaining old houses are scattered along three avenues–Indiana, Prairie, and Calumet. The district is anchored by two famous buildings: the Clarke House Museum at 1827 S. Indiana and the Glessner House Museum at 1800 S. Prairie. The city’s oldest building, Clarke House dates back to 1836, the year before Chicago incorporated, but it was moved to its present site in 1977. Its backyard is Hillary Rodham Clinton Park, a block-long expanse of green that connects Clarke House with the Prairie Avenue buildings to its east. The district’s other major building–that striking stone fortress, Glessner House–was designed by noted architect H.H. Richardson in 1887. Some neighbors weren’t fans of his work. Pullman, whose mansion stood catercorner to it, at 1729 S. Prairie, was once heard wondering what great sin he’d committed to have to see the house each day.

A block east of Prairie, at 2020 S. Calumet, stands the Wheeler Mansion, an inn owned by contractor-architect Debra Seger and her husband, Scott, a real estate broker and property manager. Seger says she originally approached owner Ed Magnus about buying the Marshall Field Jr. Mansion, but he declined to sell, referring them instead to the nearby Wheeler house. “He said, ‘Lady, if you’re interested in saving a mansion, save this one!'” After buying the house in 1997, she says, “we cleaned down to the studs,” stripping 25 coats of paint off the walls and filling 40 Dumpsters with debris. “We jacked up the house,” says Seger, to put in a new foundation. The house was built for Chicago Board of Trade president Calvin Wheeler in the Second Empire style, but like many of the area’s mansions it eventually served a commercial purpose–a publishing firm bought it in 1922 and a butter-and-egg company took over in 1944. Now spectacularly restored, the inn is a designated landmark–its 11 rooms fetch between $200 and $365 a night.

Across the street from Glessner House, at 1801 S. Prairie, is Kimball House. The onetime home to the piano and organ family is now the headquarters of the U.S. Soccer Federation. It’s beautifully restored, as is its next-door neighbor, the Coleman-Ames House. A full block to the south, at 1900 S. Prairie, is the Keith House, where Woman Made Gallery occupies the first floor. Farther south, on the east side of the street, is Reid House–the city’s first steel-frame residence and the only Prairie Avenue house that has always been a private home.

South of Keith House are two old residences. No one answered the door at 2110 S. Prairie, though it appears to be occupied. A few lots away a beautiful though worn marble staircase leads to the boarded-up entryway of another elderly red-brick building. It appears to have been tuckpointed recently, but its upper windows are covered with cardboard. Grass is growing in the cracks of the marble steps.

Buildings like these certainly need some kind of assistance. Does landmark designation help? “City landmark protection is protection from the wrecking ball, essentially,” says Peter Scales, a spokesman for the city’s Department of Planning and Development. Though owners may not see direct financial benefits, Scales says, “landmark designation can add tremendous value to buildings and tremendous stability to a neighborhood.” But even a structure in a landmark district can be demolished if it’s not considered a “contributing building.”

City tax relief is available for commercial buildings, and the Wheeler Mansion was the first beneficiary of a Cook County property tax abatement program for renovators of historic buildings–taxes are cut in half for ten years. The state of Illinois also offers some tax breaks for residential and commercial restorations, says Kent Haag of the Illinois Historical Preservation Society, but it gives cash grants only to nonprofits, mostly museums.

Yet tax breaks and even cash can only do so much–and not much is left to save on Prairie Avenue. Apart from its two museums, the district’s best reminder of the past is a series of plaques set into the wrought-iron fence surrounding Hillary Rodham Clinton Park. The plaques describe some of the homes that once stood there. Each plaque provides a photo or a drawing, and some have pictures of the former residents. They tell stories about the families who lived in the homes–some are personal, others explain the social customs of the era. One plaque offers a vivid description of a lavish party where some of Chicago’s first electric lights wowed hundreds of guests.

The plaques are helpful in conjuring the long-gone world of Prairie Avenue’s gentry, but reading them can also be strange–and weirdly fitting. The experience resembles paging through a scrapbook: faded pictures are as close as we’ll ever come to the charmed lives enjoyed by a privileged few on Prairie Avenue.

Art accompanying story in printed newspaper (not available in this archive): photo/Dorothy Perry.