In March 2003, Hawaiian Airlines filed for Chapter 11 bankruptcy protection for the second time in its history. The airline continued its normal operations, and at the time was overdue for $4.5 million worth of payments to the pilots' pension plan. Within the company, it was suggested that the plan be terminated. As of May 2005, Hawaiian Airlines had received court approval of its reorganization plan. The company emerged from bankruptcy protection on June 2, 2005, with reduced operating costs through renegotiated contracts with its union work groups; restructured aircraft leases; and investment from RC Aviation, a unit of San Diego-based Ranch Capital, which bought a majority share in parent company Hawaiian Holdings Inc in 2004.


On May 4, 2006, Hawaiian Airlines expanded service between the US mainland and Hawaiʻi in anticipation of the induction of four additional Boeing 767-300 aircraft, primarily focused on expanding non-stop service to Kahului Airport from San Diego, Seattle, and Portland. Additional flights were also added between Honolulu and the cities of Sacramento, Seattle, and Los Angeles.

On May 4, 2006, Hawaiian Airlines expanded service between the US mainland and Hawaiʻi in anticipation of the induction of four additional Boeing 767-300 aircraft, primarily focused on expanding non-stop service to Kahului Airport from San Diego, Seattle, and Portland. Additional flights were also added between Honolulu and the cities of Sacramento, Seattle, and Los Angeles.


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Hawaiian Holdings revealed on July 17, 2012, that it had signed a Letter of Intent to acquire turboprop ATR 42 aircraft with the aim of establishing a subsidiary carrier to serve routes not currently in Hawaiian's neighbor island system.[69] In December 2012 it was announced that Empire Airlines would operate the aircraft on behalf of Hawaiian.[70] A fourth ATR 42 aircraft was acquired in June 2018.[71]

Meanwhile, Hawaiian Airlines also entered the new international markets of Australia and New Zealand in 1986 with one-stop services through Pago Pago International Airport. Hawaiian also aggressively grew its international charter business and pursued military transport contracts. This led to a large growth in the company's revenues and caused its inter-island service's share of revenues to shrink to just about a third of the company's total.[22]
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