A subway had been planned since the late 1930s to reach downtown in a more direct way than the portion of the Logan Square branch where Chicago was located.

A commercial building built by the CRT across the street from the station survives as of 2023[update], however, and has a low profile that marks where the "L" once passed above it.

The Metropolitan West Side Elevated Railroad Company was granted a 50-year franchise by the Chicago City Council on April 7, 1892,[1] and began securing right of way shortly thereafter.

[8] The Metropolitan's tracks on the Logan Square branch were finished by the middle of October 1894, and were powered on in April 1895 for test and inspection runs.

[17] Chicago petitioned the Public Works Administration (PWA) for construction funds for a subway on State Street in 1937.

[19] Harold L. Ickes, the administrator of the PWA and a longtime Chicagoan, vetoed the streetcar tunnel plan and insisted instead on a second subway that would go under Dearborn Street and Milwaukee Avenue, which would provide a more direct route from Logan Square to downtown.

[19] Although this idea engendered considerable local opposition, especially from mayor Edward Joseph Kelly, Ickes's influence in the federal government led to the Dearborn plan being adopted in 1938.

[20] Damen Tower, serving the Humboldt Park branch divergence, was rebuilt with the expectation that it also would switch trains between the subway and the elevated, in the same manner as the State Street subway supplementing the earlier elevated North Side main line,[21] and as late as 1949 commuters were promised such a setup that would have preserved the old Logan Square trackage.

[23] Despite this incomplete state, and complaints from riders no longer given a direct trip to the Near West Side,[24][25] the new subway had over 60 percent higher ridership than the old Logan Square branch by the end of the year.

[27] Wooden parts from the old stations on the Connector, including Chicago, were removed to reduce fire hazards, as were the lowest flights of stairs to deter trespassing.

[27] The portion of the Connector north of Kinzie Street, including where Division, Chicago, and Grand stations stood, was demolished in 1964 and the right of way sold to adjacent landowners.

It had a corniced and dentiled front bay containing dual doors specifically marked "Entrance" and "Exit" and prolific use of terra cotta.

[36] As part of an overhaul of streetcar service by operator Chicago Surface Lines on September 14, 1924, these two lines were consolidated to one and the downtown route was discontinued, although streetcars bound for downtown from Halsted Street turned onto Chicago rather than Madison Street as part of the same plan.

[37] "One-man cars", without a separate conductor, entered service on June 24, 1950; after the station was abandoned, streetcars were replaced by trolleybuses on May 11, 1952.