[1] The CNW advertising and public relation staff went to work to promote the show in the early months of 1948, beginning with a series of photographs made by company photographer Don Lidikay of people in 19th century costumes posing with the locomotive Pioneer, which had pulled the first train out of Chicago in 1848.

[1] The fair was rapidly planned during the winter and spring of 1948, and originally scheduled to run between July and August of that summer.

A grand opening for the fair commenced on July 20[1] with a parade that featured such spectacles as a military marching band and a replica of a troop train, a contingent of cowboys and Native Americans, a replica of the Tom Thumb, the first American locomotive, and the spry, octogenarian widow of Casey Jones, who served as honorary Grand Master of the parade.

[3] The Santa Fe also sponsored an Indian Village where Native Americans sold handicrafts, staged dances, and explained the different types of lodging that were on display.

For the 1949 Fair, D&RGW provided a second train, with its own refurbished 2-8-0 number 268 and coaches, all lettered for the fictional "Colorado Springs and Tincup Railroad".

The companies that participated included:[10] The highlight of the Chicago Railroad Fair was the "Wheels A-Rolling" pageant.

This was a dramatic and musical presentation intended to showcase the development of transportation and the railroads across the country beginning with trails and waterways.

The pageant included a recreation of the Golden Spike ceremony at Promontory, Utah, and various historic rolling stock and replicas of equipment in operation.