That evening, the guitarist, with his band Double Trouble, joined as special guests for a concert at the Alpine Valley Musical Theater, along with Eric Clapton, Buddy Guy, Robert Cray and Vaughan’s big brother, Jimmie.
After the show, four helicopters, owned and operated by Omniflight Helicopters Inc., were reserved to fly the artists and their crews back to Chicago. One helicopter was reserved for Stevie, Jimmie and Jimmie's wife Connie. Members of Clapton’s crew, however, had already taken seats on the helicopter when the Vaughans arrived to board.
Stevie asked Jimmie and Connie for the last seat. With dense fog settling in, the helicopters began departing at 1 a.m. the pilot of Vaughan’s helicopter, banked sharply to the left about a half-mile after take off. The helicopter collided into a ski slope and everyone on board was killed instantly.