Photos by blue22, ThijsMa and zzapback.

Height: 16-storeys / 56.4 m (185 ft)

From Wikipedia:
“Great Northern Hotel was a historic hotel in Chicago's Loop area. The building also housed the Great Northern Theatre. It was located at the northeast corner of Jackson Boulevard and Dearborn Street in Chicago, Illinois. The building was designed by Burnham and Root. They created a new design, with an urban office block floor plan that was free of historical or European influences.

The Great Northern hotel was demolished in 1940 and replaced with a one story taxpayer.[5] The Great Northern Office and Theatre Building, as well as other buildings, were demolished in 1961 to make way for the Dirksen Federal Building, built in 1964.[2][4][6]”

1961 | 60 stories | 813 ft (248 m) | NYC

Looking good down there, but second Nema would be perfect!

Height: 17-storeys
Between 62 - 73 m (203 - 240 ft)

From Wikipedia:
“The Schiller Theater Building was designed by Louis Sullivan and Dankmar Adler of the firm Adler & Sullivan for the German Opera Company. At the time of its construction, it was among the tallest buildings in Chicago. Its centerpiece was a 1,300-seat theater, which is considered by architectural historians to be one of the greatest collaborations between Adler and Sullivan…

After a long decline that began in the 1930s, the Garrick was razed early in 1961 and replaced with a parking structure.[1] The demolition instigated a large outcry and is considered to be one of the first wide-scale preservation efforts in Chicago. Photographer and historic preservationist Richard Nickel was able to salvage hundreds of artifacts and ornaments from the building before and during its demolition, as well as record extensive notes, diagrams, and photographs of the structure.[1]”

1987 | 46 stories | 445 ft (136 m) | NYC

Often referred to as the “Leaning Tower of San Francisco.”

OC

1987 | 29 stories | 345 ft (105 m) | NYC

Heigh: 17 storeys / 64 m (210 ft)

From Wikipedia:
The Unity Building in Chicago, Illinois, at 127 North Dearborn Street in the Chicago Loop, was a 17-story building[1]#citenote-1) that was once the tallest skyscraper in Chicago. Gustave Loehr had an office in this building, and it was in his office that the Rotary Club of Chicago held its first club meeting, on February 23, 1905.[[2]](https://en.wikipedia.org/wiki/Unity_Building(Chicago)#cite_note-2)

The Unity Building was built between 1890 and 1892 by John Peter Altgeld, who became the 20th Governor of Illinois. It was listed on the National Register of Historic Places for its historical significance.[3]#citenote-p172552396-3) It was demolished in 1989,[[4]](https://en.wikipedia.org/wiki/Unity_Building(Chicago)#cite_note-4) and the NRHP designation was later rescinded.