In 1909, Daniel Burnham, internationally famous architect and planner, was the principal author of the Plan of Chicago, which made recommendations on how the city could grow and improve the quality of life for its residents in an orderly fashion. “…The time has come [for Chicago and other world cities] to bring order out of the chaos incident to rapid growth” (Burnham and Bennett 1909, 188). Many of Burnham’s suggested solutions were carried out in some form or another, some very directly and others incidentally. For example, his boulevard and parks recommendations resulted in Michigan Avenue becoming a great boulevard, the double decking of Wacker Drive and the construction of Grant Park. Eighteen pages of the 164 page Plan were devoted to Chapter V, “Transportation: A Freight Center: Grouping of Passenger Stations: A Loop System.” The purpose of this paper is to examine and evaluate those freight and passenger transportation components contained in Chapter V of the plan. To put the Plan in proper perspective, Chicago was one of the fastest-growing urban areas in the world during the 19th century. Its population grew from approximately 100 people in 1812 to 1.7 million in 1900. This is even more remarkable considering the Great Chicago Fire of 1871 destroyed more than 17,000 structures. The rapid growth resulted in congestion, chaos, poverty and air and water pollution (Young 1998). Burnham envisioned a city of organized beauty and efficiency similar to the “White City” he helped create as a part of the Columbian Exposition in Chicago in 1893, celebrating the anniversary of the discovery of America (Smith 2006). The freight and passenger transportation recommendations in the Plan addressed such issues as freight congestion, consolidation of railroad passenger facilities, creation of freight loops, and elimination of rail grade crossings. Some of these recommendations resulted in immediate action plans. Others, like the consolidation of all intercity passenger trains, did not occur until 1971, when Amtrak consolidated all passenger service in Union Station. Some issues, like rail freight congestion, are still present in the region today. While the freight and passenger transportation components of the Plan have mixed results, one can argue that the Chicago region’s transportation system has benefited from the visionary planning by Burnham in the Plan of Chicago.