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Chicago architecture in the Loop area. The Monadnock Building. per Wikipedia, 16-story at 66m, it is the tallest load-bearing brick or masonry building ever constructed. it also employed the first portal system of wind bracing in the US.

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The Chicago Board of Trade Building. current 44-story building is from 1930. the advent of steel frame structural system allowed completely vertical construction, per Wikipedia.

One First National Plaza / Chase Tower, completed in 1969. at 259m, it was among the tallest reinforced concrete buildings in the world at the time of completion.