The Chicago and South Side Rapid Transit Railroad Company was incorporated on January 4, 1888,[4] and secured a franchise from the City of Chicago on March 26 of that year to construct an elevated railroad between Van Buren Street and 39th Street (Pershing Road).

[5] A 6-car train carrying 300 guests made the inaugural run along first section of the line—running between a station at 39th Street and the Congress Terminal downtown—on May 27, 1892,[8] and the line opened to the public ten days later.

[3] The line was gradually extended over the following months, with the route reaching Jackson Park on May 12, 1893 to provide service to the World's Columbian Exposition.

[12] When the World's Columbian Exposition closed, lack of development along the southern portion of the route led to plummeting passenger numbers.

The Chicago and South Side Rapid Transit Railroad Company went into receivership in 1895 and was sold under foreclosure in September 1896 for $4,100,100.

[19][20] Most of the rest of the route of the South Side Elevated Railroad continues in service as part of the CTA's Green Line.