Brian, your pic looks to be 1939-1950-ish? This one is early '60s from about the same spot! IIRC (vaguely) Dad took this pic from the Capitol coming into town in the early AM. This pic got me scratching my head over how we were at a different level from the coach yard below. Then I remembered:
Chicago was a large hub for passenger trains. Six stations. This pic taken of a page in a Santa Fe timetable.