Not dated, but the scene looks late 1920s. The 2 mile Loop was opened in 1895-1897 so the centennial could be viewed as either 1995 or 1997. The original text at the bottom read "Rapid Transit Lines, Fast...Reliable"
More Chicago Rapid Transit Company posters from the 1920s (the above was the only one which featured the railway itself) are on this webpage.
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