Architecture historian Robert Bruegmann observes that of the 61 Plan of Chicago illustrations (out of the total of 142 in the book), 33 are "maps, diagrams, or plans of areas of the city made for the purpose of showing the proposed changes in streets, railroads, and parks." The maps often have an aesthetic appeal approaching that of the drawings. They consist both of views of the Chicago region and of the the city itself. The latter, Bruegmann points out, were adapted from the Sanitary District Map of Chicago.

Diagram of a System of Freight Handling for Land and Water Transportation

This map illustrates how the planners hoped to keep heavy shipping, through freight, and freight sorting outside the commercial center of the city.

Diagram of General Scheme of Street Circulation and Parks in Relation to the Areas Covered by Industries and Manufacturing

One of the many maps adapted from the Sanitary District Map of Chicago. Areas covered by industries (located mostly along the branches of the Chicago River) are in red, railroad properties and lines (which take up a great deal of the downtown) are in blue.

Diagram of General Scheme of Street Circulation and Parks in Relation to the Population

One of the goals of the planners was to improve access to recreational areas for Chicago residents in as many neighborhoods as possible.