The C&EI introduced the Whippoorwill in 1946 as a day train supplement to the express streamliners it operated in conjunction with the Louisville and Nashville Railroad (L&N). The Whippoorwill was one of the first new streamliners introduced after World War II, with completely new equipment delivered by Pullman-Standard. A C&EI advertisement in Trains magazine touted the "ultra-modern chair car accommodations" and "latest type passenger Diesel locomotives."
The train's original consist, as delivered by Pullman-Standard, included the following cars:
|#304||Baggage-coach||Turkey Run||Sold to the Shedd Aquarium and used as a fish transport. Now at the Monticello Railway Museum.|
|#460||Coach||Vigo Trail||Sold to the Illinois Central Railroad (IC) in 1961; converted to maintenance of way in 1971.|
|#461||Coach||Vincennes Trail||Sold to the IC in 1961; destroyed in a derailment involving the City of New Orleans in 1971.|
|#462||Coach||Vanderburg Trail||Sold to the IC in 1961; sold to Silcott Railroad Equipment in 1971.|
|#463||Coach||Vermillion Trail||Sold to the IC in 1961. Sold to Black Hills Central Railroad in 1971. Sold to the Oregon, Pacific and Eastern Railway (OP&E) after 1971; possibly 1972 and no later than 1975. Sold to Louisiana and Arkansas Railway (LA) in 1975 and named "Sierra Madre."|
|#505||Diner||Shakamak Inn||Sold to the IC in 1962. Conveyed to the Louisiana Arts and Sciences Center in Baton Rouge. Now at the Monticello Railway Museum.|
|#702||Parlor observation||Chicagoland||Rebuilt as a coach in 1964.|
A famous publicity photograph, which the C&EI used long after the train's discontinuance, showed a single EMD E7 locomotive (#1102), leading these seven cars which made up the train's original consist. The photograph was colorized to accentuate the train's purple and yellow color scheme. The northbound train (#4) departed Evansville at 7:00 am and arrived in Chicago's Dearborn Station at 12:20 pm. The train then returned south (as #3) at 5:30 pm, arriving in Evansville at 10:50 pm.
The C&EI discontinued the Whippoorwill in 1948 after the L&N began running a section of the Georgian to Chicago over a similar schedule. The C&EI reassigned the Whippoorwill's equipment to the Georgian and the Humming Bird until finally selling most of it to the Illinois Central in the early 1960s.
- "Orange 'n Blue: Streamliners Celebrate a Happy Birthday". Trains. December 1947.; 70
- Monticello Railway Museum. "Equipment Roster". Retrieved 2011-05-06.
- "ILLINOIS CENTRAL RAILROAD PASSENGER EQUIPMENT: Car numbers 1800 - 2599". Mississippi Railroad Information. March 10, 2010. Retrieved 2011-05-07.
- "11th victim is dead after train derails". Boca Raton News. June 11, 1972. Retrieved 2011-05-07.
- "Current Projects". Retrieved 2011-05-07.
- Schafer, Mike; Joe Welsh (2002). Streamliners: History of a Railroad Icon. Saint Paul, MN: MBI. ISBN 0-7603-1371-7. OCLC 51069308.