Haunted Ledgers: The Remarkable Pasts of Chicago's Landmark Office Buildings

Office buildings don't usually get ghost stories. They get leases, renovations and, if they're lucky, a long second act.

But walk the Loop with the right history in hand and you'll find buildings with pasts as dramatic as any haunted house. Here are a few for Halloween, with fact and legend clearly labeled.

The Real Estate Board's old address

At the corner of Randolph and Dearborn stands the Delaware Building, believed to be one of the oldest surviving commercial buildings of its kind in the Loop. It went up between 1872 and 1874, while Chicago rebuilt after the Great Fire, and opened as the Bryant Block, named for its first owner, James W. Bryant.

In 1889 it took a name with a familiar ring for anyone in our business: the Real Estate Board Building, after its new tenant, the Chicago Real Estate Board.

The building is a Chicago Landmark and is listed on the National Register of Historic Places. Its next chapter is still being written. Preservation Chicago put it on its 2025 list of the city's seven most endangered buildings, citing a long-term lease on its vacant lower floors that has stalled a planned conversion of the upper floors to residences.

"Death Alley," next door

The Delaware Building's neighbor to the east is the Oriental Theatre, now the Nederlander. It stands on the site of the Iroquois Theater, where a fire broke out above the stage during a matinee on December 30, 1903. The theater had no sprinklers or fire escapes, and most of its exit doors were locked. About 602 people died, many of them children.

The alley behind the theater, where many victims fell from a balcony exit, is known as "Death Alley." According to local lore, people still report cold spots, strange lights and the shadowy figure of a woman in a tutu.

Whatever you believe, it's a sobering reminder of what every exit sign and sprinkler head in a building is really for.

The Stock Exchange's last visitor

Some buildings don't need a ghost story.

The Chicago Stock Exchange Building, designed by Adler & Sullivan, was completed in 1894. In February 1970, the city's Landmarks Commission recommended protecting it. A City Council committee voted against designation that August, a renewed recommendation in 1971 went nowhere, and demolition came in the spring of 1972.

Photographer Richard Nickel had spent years documenting Adler & Sullivan's work and rescuing ornament from doomed buildings. He was hired to photograph the Stock Exchange before it came down, and he kept going back, despite warnings that the structure was unsafe, to save what he could. On April 13, 1972, part of the building collapsed while he was inside. His body wasn't found for weeks.

Pieces of the building did survive. Its Trading Room was reconstructed in its entirety inside the Art Institute of Chicago, and its entrance arch was re-erected just outside the museum on the Columbus Drive side. If you pass that arch this Halloween, now you know its story.

When the presses went quiet

Not every office-district story ends in loss.

Printer's Row, just south of the Loop, earned its name. The Franklin Building at 720 S. Dearborn St., designed by George C. Nimmons and completed in 1916 for the Franklin Printing Company, ran presses until 1983.

Over its main entrance, a mural by Oskar Gross called "The First Impression" shows men working a Gutenberg press to print the first Gutenberg Bible. More painted tiles honor the trades behind a printed page, from the typesetter to the bookbinder.

In 1989, the building was converted into 65 condominium lofts, the last major Printer's Row building to make the switch.

That's a story worth remembering as owners weigh office-to-residential conversions today. A building with good bones and real character tends to find its next use, even when its first one is long gone.

Office buildings change names, tenants and purposes. The ones with real history tend to stick around, and that durability is a big part of their value. Own an office building with a story? Tell us about it at investment@kwcommercial.com.