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A black and white photograph showing detailed stonework around arched windows with carved busts between each column.
The facade of Chicago’s Garrick Theater, designed by Adler & Sullivan in 1892 and demolished in 1961.
Richard Nickel/Historic American Buildings Survey, Library of Congress

Chicago’s 10 most senseless demolitions, mapped

From groundbreaking early skyscrapers to sprawling rail terminals

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The facade of Chicago’s Garrick Theater, designed by Adler & Sullivan in 1892 and demolished in 1961.
| Richard Nickel/Historic American Buildings Survey, Library of Congress

For a city that prides itself on its architectural legacy, Chicago has a mixed track record when it comes to saving its significant buildings. The city’s historic preservation movement didn’t always exist. It took the work of dedicated pioneers like photographer Richard Nickel to document what was being torn down and shock the public and city officials into taking action. “Great architecture has only two natural enemies,” said Nickel. “Water and stupid men.”

From its humble roots as a riverfront trading post to an industrial boomtown, Chicago’s been in a constant state of change. One downside to the city’s reinvention has been at the expense of the significant early skyscrapers, ornate theaters, gilded mansions, and grand rail halls lost along the way.

It might seem inconceivable to discard works from the firms of architectural icons Louis Sullivan, Dankmar Adler, or Daniel Burnham, but that wasn’t always the case. Even today, debates continue over what can and should be saved—especially when certain styles, like 1980s postmodernism displayed by buildings like the threatened Thompson Center, fall out of fashion.

With the benefit of 20/20 hindsight, it can be frustrating to see what has been so callously discarded. A loss is even more painful if the replacement is a building of lesser value or—in the case of the Old Chicago Mercantile Exchange—nothing at all. There are lessons to be learned to avoid past mistakes.

Here’s a look back at ten regrettable or controversial demolitions in Chicago. Did we leave out a notable building that you miss? Let us know in the comments below.

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1. Chicago Stock Exchange Building

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30 North LaSalle, 30 N LaSalle St
Chicago, IL 60602

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.

2. Garrick Theater

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64 W Randolph St
Chicago, IL 60601

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.

3. Cable Building

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242 S Wabash Ave
Chicago, IL 60604

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.

Richard Nickel/Historic American Buildings Survey, Library of Congress

4. Republic Building

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209 S State St
Chicago, IL 60604

The Republic Building—not to be confused with the surviving Old Republic Building at 307 N. Michigan Avenue—stood at the southeast corner of State and Adams from 1905 until 1961. Another Chicago School beauty, the 19-story commercial structure was also designed by Holabird & Roche and is considered by the Encyclopedia Britannica to be “one of their best 20th-century buildings.” Unlike some other older Loop buildings from the same era, the Republic Building was in “perfect shape” at the time of its demolition, Ward Miller of Preservation Chicago tells Curbed. The modernist Home Federal Building now stands in its place.

Richard Nickel/Historic American Buildings Survey, Library of Congress

5. Old Chicago Mercantile Exchange

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130 N Franklin St
Chicago, IL 60606

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.

6. Chicago and North Western Terminal 

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500 W Madison St
Chicago, IL 60661

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.

Detroit Publishing Company photograph collection, Library of Congress

7. Illinois Central Station

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121 E Roosevelt Rd
Chicago, IL 60605

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.

8. Comiskey Park

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324 W 35th St
Chicago, IL 60616

Wrigley Field is considered hallowed ground for its age and retro appeal, but similar qualities weren’t enough to save the original Comiskey Park. Built in 1910 by architect Zachary Taylor Davis (who also designed Wrigley), old Comiskey was the oldest ballpark in Major League Baseball when it was torn down in 1991, and a new stadium opened next door. The recent renovations at Wrigley prove that an older ballpark can offer modern amenities but still retain most of its historic architecture and charm. 

Men standing in lines at ticket booths for the National League’s Chicago Cubs and American League’s Chicago White Sox City Series games at Comiskey Park, Chicago, Illinois, 1914. Getty Images

9. Prentice Women’s Hospital

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333 E Superior St
Chicago, IL 60611

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.

10. Meigs Field

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Northerly Island
Chicago, IL 60605

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.

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1. Chicago Stock Exchange Building

30 North LaSalle, 30 N LaSalle St, Chicago, IL 60602

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.

30 North LaSalle, 30 N LaSalle St
Chicago, IL 60602

2. Garrick Theater

64 W Randolph St, Chicago, IL 60601

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.

64 W Randolph St
Chicago, IL 60601

3. Cable Building

242 S Wabash Ave, Chicago, IL 60604
Richard Nickel/Historic American Buildings Survey, Library of Congress

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.

242 S Wabash Ave
Chicago, IL 60604

4. Republic Building

209 S State St, Chicago, IL 60604
Richard Nickel/Historic American Buildings Survey, Library of Congress

The Republic Building—not to be confused with the surviving Old Republic Building at 307 N. Michigan Avenue—stood at the southeast corner of State and Adams from 1905 until 1961. Another Chicago School beauty, the 19-story commercial structure was also designed by Holabird & Roche and is considered by the Encyclopedia Britannica to be “one of their best 20th-century buildings.” Unlike some other older Loop buildings from the same era, the Republic Building was in “perfect shape” at the time of its demolition, Ward Miller of Preservation Chicago tells Curbed. The modernist Home Federal Building now stands in its place.

209 S State St
Chicago, IL 60604

5. Old Chicago Mercantile Exchange

130 N Franklin St, Chicago, IL 60606

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.

130 N Franklin St
Chicago, IL 60606

6. Chicago and North Western Terminal 

500 W Madison St, Chicago, IL 60661
Detroit Publishing Company photograph collection, Library of Congress

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.

500 W Madison St
Chicago, IL 60661

7. Illinois Central Station

121 E Roosevelt Rd, Chicago, IL 60605

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.

121 E Roosevelt Rd
Chicago, IL 60605

8. Comiskey Park

324 W 35th St, Chicago, IL 60616
Men standing in lines at ticket booths for the National League’s Chicago Cubs and American League’s Chicago White Sox City Series games at Comiskey Park, Chicago, Illinois, 1914. Getty Images

Wrigley Field is considered hallowed ground for its age and retro appeal, but similar qualities weren’t enough to save the original Comiskey Park. Built in 1910 by architect Zachary Taylor Davis (who also designed Wrigley), old Comiskey was the oldest ballpark in Major League Baseball when it was torn down in 1991, and a new stadium opened next door. The recent renovations at Wrigley prove that an older ballpark can offer modern amenities but still retain most of its historic architecture and charm. 

324 W 35th St
Chicago, IL 60616

9. Prentice Women’s Hospital

333 E Superior St, Chicago, IL 60611

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.

333 E Superior St
Chicago, IL 60611

10. Meigs Field

Northerly Island, Chicago, IL 60605

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.

Northerly Island
Chicago, IL 60605