They Were Part of the Winter Dance Tour
The three musicians were flying around the country as part of the Winter Dance Party, a tour that involved a hectic 24-concerts-in-a-span-of-three-weeks schedule. They had already performed at several locations before reaching their final concert at the Surf Ballroom in Clear Lake, Iowa.
At this point in the tour, Holly was tired of the freezing, uncomfortable tour busses, so he decided to charter a plane instead. The two other passenger seats beside him were originally reserved for his bandmates, Waylon Jennings and Tommy Allsup.