Built by imaginative and energetic Minnesotan, A.B. Stickney, the Chicago Great Western Railway began in 1885 as a 110-mile pike from St. Paul to the Iowa state line and the Minnesota & Northwestern Railroad. Instead of selling the short line to another railroad, as Stickney had done with previous roads that he constructed, he retained ownership and quickly extended the tracks to Chicago and Kansas City. By connecting these important gateways the railroad became a respectable carrier.

In 1887, the M&NW was acquired by another Stickney road, the more appropriately titled Chicago, St. Paul, & Kansas City Railroad, which was acquired in 1892 by yet another Stickney road, the Chicago Great Western Railway. Because the three lines radiated out from Oelwein, Iowa, Stickney logically chose this location to construct the system shops. At the time when the Oelwein shops were opened in 1899, they were the largest and best-equipped shops in the U.S. The final extension of the CGW was completed in 1903 as tracks were extended to Omaha.

Initially, the CGW relied heavily on rate cutting and efficient operations to compete with other railroads. Although its reputation as a rate cutter ended when Stickney retired in 1908, the railroad remained dedicated to flexible and innovative practices. Among the pioneering efforts for which the CGW is remembered are its early use of internal combustion equipment, extremely long freight trains, piggyback service, and welded rail. The railroad had little choice considering the competition from powerful neighbors, rubber-tired vehicles, and government subsidized aviation.

The CGW was never financially strong, but managed to survive two receiverships and an episode of horrible mismanagement during the first few decades of this century.

The CGW enjoyed relative economic prosperity during the post World War II boom that funded badly needed modernization of the physical plant. Unfortunately, profits were ephemeral for the railroad as the constantly rising costs of labor and material sent the CGW into the red during the 1960's.

Proposed mergers would also change the position of the railroad with other carriers. As a result, management believed that bankruptcy would ultimately result if the railroad did not merge with another carrier. The CGW found a mate in the Chicago & North Western Railway and officially merged on July 1, 1968. The C&NW subsequently abandoned most of the CGW.