Valens was one of the five acts billed for the Winter Dance Party tour, performing with Buddy Holly, "The Big Bopper" J. P. Richardson, Dion and the Belmonts, and Frankie Sardo beginning on January 23, 1959, in Milwaukee, Wisconsin. The tour was plagued by subzero temperatures and numerous logistical problems. The unheated tour buses twice broke down in freezing weather, with Valens and Richardson experiencing flu-like symptoms throughout the tour. After the bus stalled in Duluth, Minnesota on January 31, conditions were so bad that Holly's drummer, Carl Bunch, was hospitalized for severe frostbite sustained on the bus. To fill in for Bunch, Holly, Valens, and Dion all took turns drumming for one another.
After the February 2, 1959, performance in Clear Lake, Iowa (which ended around midnight), Holly, Richardson, and Valens flew out of the Mason City airport in a small plane that Holly had chartered.[20] Valens was on the plane since he won a coin toss with Holly's backup guitarist Tommy Allsup. Bob Hale, a disc jockey with Mason City's KRIB-AM, was emceeing the concert that night and flipped the coin in the ballroom's side-stage room shortly before the musicians departed for the airport. Valens is apocryphally said to have remarked, "That's the first time I've ever won anything in my life." Holly's bassist, Waylon Jennings, voluntarily gave up his seat on the plane to J.P. Richardson, who was ill with the flu.
At around 12:55 a.m. on February 3, 1959, the four-passenger Beechcraft Bonanza, (N3794N), departed for Fargo, North Dakota, and crashed a few minutes after takeoff. The cause was apparently loss of control by the pilot Roger Peterson, who was not qualified for the deteriorating weather. The crash killed all four men instantly upon impact. As with Holly, Richardson and Peterson, Valens suffered massive fatal head injuries along with blunt-force trauma to the chest. At the age of 17, Valens was the youngest to die in the crash.
The tragedy inspired singer Don McLean to write his 1971 hit "American Pie", immortalizing February 3 as "The Day the Music Died". Valens was buried at San Fernando Mission Cemetery in Mission Hills, Los Angeles, California.