Terminal is a misnomer. North Shore had a luxurious ticket office on Wabash in the Loop for passengers after February 1927. Roosevelt Road was just where trains ended and started there runs. Until 1938 many trains had actually continued on to 63rd Street. And this was during the time when North Shore ran trains with observation parlor cars and dining cars.
There is some information on chicago-l.org under the Roosevelt station:
"Roosevelt was one of the original ten stations of Chicago's first "L" line, the South Side Rapid Transit. The original station, which was a street-level facility just like all the other South Side stations outside the business district, had a brick exterior and a large bay in the center of the front elevation. The station had two side platforms with short "humpbacked" canopies.
In 1907, as part of an ordinance to allow the South Side Line to install a third track for express service, all stations north of 43rd Street, including this one, were required to replace their grade-level facilities with mezzanine-level stations, clearing the alley beneath the tracks. This required relocation of the northbound platforms between 18th and 39th Streets and raising of the structure (with grades of up to 1.44% at some stations to compensate for the change in elevation) to gain sufficient clearance for the mezzanine facilities. The mezzanine facility was a fairly simple structure, constructed of sheet metal with simple ornamentation.
The station was one of 23 Howard, Jackson Park, Englewood and Ravenswood stations closed on August 1, 1949 as part of the CTA's institution of A/B skip stop service on the North-South Route. As part of the same service revision, the "L" tracks from Wabash/Van Buren (Tower 12) to 15th and State streets were abandoned after North-South Route trains were rerouted into the State Street Subway.
Although all "L" service to Roosevelt Road ceased on August 1, 1949, the facility continued in use as the Chicago North Shore & Milwaukee's terminal until the end of their service in 1963. Normal procedure was for a combine to be held open at Congress Terminal to receive baggage and merchandise dispatch shipments until about 15 minutes before a scheduled northbound departure from Roosevelt Road, then run half a mile south to Roosevelt to couple onto the coaches. After the North Shore Line ceased operation in January 1963, the station closed and was demolished."
You will find the location of the Congress Street stub terminal here in a 1942 Loop map.
There were three through tracks at Roosevelt including the express track later used as an open air service track (a ghastly thought in a Chicago winter).
The photo was found on the internet and documents Roosevelt Road as an outdoor inspection pit when the CRT was still running through the station.