The airline started operations on September 15, 1978, initially operating to a number of small cities in eastern and central Montana. Big Sky took over Exec Express II d/b/a Lone Star Airlines/Aspen Express routes in October 1998, following their bankruptcy. On December 21, 2006, a press release announced that Big Sky would become a Delta Connection carrier. The airline declared bankruptcy on December 20, 2007 and announced that it would more than likely cease operations within 60 to 90 days. This was due to the loss of the Delta contract, unusually bad weather, disappointing revenue and record-high fuel prices. Big Sky's final scheduled flights arrived in Billings on the morning of March 8, 2008.