The old Chicago Stock Exchange Building is one of the city’s best-known cases when it comes to regrettable demolitions. Completed by legendary Chicago architects Dankmar Adler and Louis Sullivan in 1894, the 13-story office building featured detailed exterior ornamentation and a trading hall on its second floor. Despite the best efforts of local preservationists, the Chicago Stock Exchange Building was torn down in 1972. Tragically, architectural photographer Richard Nickel perished in a partial collapse while documenting the demolition work. The old Stock Exchange is gone, but the building’s entrance archway and interior trading floor were salvaged and moved to the Art Institute of Chicago.

Before Richard Nickel lost his life in the old Stock Exchange Building, the photographer helped energize Chicago’s historic preservation movement with his images of another lost Adler & Sullivan gem: the Garrick Theater. One of the tallest buildings in the city when it was completed, the Garrick stood on Randolph Street from 1892 until 1961, when it bit the dust for a parking structure. Nickel managed to salvages pieces from the building, including exterior terracotta busts. Some of those artifacts were later incorporated into the facade of Old Town’s famous Second City improv theater.

Architecture firm Holabird & Roche designed the ten-story Cable Building at the corner of Wabash and Jackson for piano manufacturer the Cable Company in 1899. The steel-frame structure had three-part bay windows and was a quintessential example of the Chicago School—a style of early skyscrapers that emerged following the Great Chicago Fire and included the aforementioned Stock Exchange. The Cable Building was demolished in 1960, despite its status as a Chicago Architectural Landmark.

The senseless demolition of so many historic Loop buildings during the so-called “urban renewal” period of 60s and 70s certainly stings. But the more recent loss of the 1927 Chicago Mercantile Exchange in 2003 is borderline inexcusable. Designed by architect Alfred S. Alschuler, the building was in good shape and essentially fully occupied when its owners abruptly decided to tear it down. At the time, Preservation Chicago feared the location would “become yet another surface parking lot for the foreseeable future, in place of this landmark-worthy structure.” Thirteen years later, the site at 130 N. Franklin is still a fenced-off lot filled with gravel and weeds. The outrage caused by the destruction of the Mercantile Exchange led the city to adopt a 90-day demolition hold for historic and architecturally significant buildings that don’t have landmark protection.

Chicago owes its rise as a major industrial powerhouse to its railroad system. But when it comes to historic stations, the city has demolished far architecturally significant rail-related buildings than it has saved. One especially poignant example is the Chicago and North Western Railway Terminal, which stood along Madison Street from 1911 to 1984. Designed by architects Frost and Granger in the Beaux Arts style, the Chicago and North Western Terminal had a detailed limestone facade and a stunning vaulted interior hall lined with shimmering green tiles. Ogilvie Transportation Center replaced the terminal, and a glass and steel high-rise was added in 1987.

Chicago lost another notable piece of its railroad legacy in 1974 when crews took down the Illinois Central Station at the southern edge of Grant Park. The Romanesque Revival structure was completed by architect Bradford L. Gilbert in 1893 to accommodate visitors traveling to the White City of the Columbian Exhibition. The Illinois Central Station went on to play a significant cultural role as a gateway to Chicago for African Americans who settled nearby neighborhoods such as Bronzeville during the Great Migration of the early 20th century. The recent multi-building redevelopment of the surrounding area borrows its Central Station name from the old rail depot, but little else remains.

Surrounded by a forest of rectangular boxes, the curving four-lobed shape of Prentice Women’s Hospital cantilevered over its base like a concrete flower in the heart of Streeterville. Penned by architect Bertrand Goldberg and completed in 1972, the Brutalist structure was one of the first buildings to use computer-aided design techniques. Despite hard-fought preservation efforts, the Chicago Landmarks Commission voted against protecting the building, and Prentice met the wrecking ball in 2014. A glassy Northwestern University biomedical research center now stands in its place.

In 2003, Chicago Mayor Richard M. Daley ordered bulldozers to tear up the runway of Meigs Field under the cover of darkness. Daley had been trying to turn the airport into a park since 1994 but acted unilaterally—some would argue illegally—to get what he wanted. While open space offers more public benefit that a commuter airport that served the privileged few, the undemocratic manner in which Meigs was demolished wasn’t one of City Hall’s finest moments. The old terminal building still stands at Northerly Island as a vestigial reminder of the long-gone airport.