Heading into the 1990s, Hawaiian Airlines faced financial difficulties, racking up millions of dollars in losses throughout the previous three years. Due to the airline's increasingly unprofitable operations, it filed for Chapter 11 bankruptcy protection in September 1993. During this time, the company reduced many of its costs: reorganizing its debt, wrestling concessions from employees, cutting overcapacity, and streamlining its fleet by disposing many of the planes it had added to its fleet just a few years earlier.[24]
Honolulu to Sydney Manila to Honolulu Seattle to Maui Honolulu to Maui Sydney to Honolulu Honolulu to Manila Los Angeles to Honolulu Seattle to Honolulu Honolulu to Las Vegas Honolulu to Los Angeles Maui to Honolulu Las Vegas to Honolulu Maui to Las Vegas Phoenix to Honolulu San Diego to Honolulu Honolulu to Seattle Honolulu to San Francisco Honolulu to Phoenix Honolulu to San Diego San Francisco to Honolulu
On October 27, 2008, Hawaiian announced that prior to the arrival of its new A330s, it would lease two additional Airbus A330-200 aircraft, beginning in 2011, at the same time extending the leases of two Boeing 767-300ER aircraft to 2011 (to be withdrawn from service coincident with the delivery of the A330s).[73] Two weeks later, the airline announced the lease of an additional A330-200 for delivery in the second quarter of 2010, along with negotiating for delivery of one aircraft from the earlier lease agreement to be moved up to the same quarter.[74] In December 2010, Hawaiian ordered an additional six A330-200 aircraft, bringing the fleet total to 15.[75] Further lease agreements were signed with Air Lease Corporation (one aircraft),[76] and three aircraft each from Hong Kong Aviation Capital,[77] and Jackson Square Aviation[78], bringing the A330-200 fleet to 22. In July 2015, Hawaiian announced the lease of an A330-200 from Air Lease Corporation.[79] The purchase of another A330-200 was announced in December 2016.[63]
On August 30, 2012, Hawaiian filed an application with the U.S. Department of Transportation for a nonstop route between Kona and Tokyo-Haneda.[41] This would fill a void that Japan Airlines left when it ceased service to Kona nearly two years earlier.[41] However, the US Department of Transportation rejected the airline's application to begin service.[42] 

On August 30, 2012, Hawaiian filed an application with the U.S. Department of Transportation for a nonstop route between Kona and Tokyo-Haneda.[41] This would fill a void that Japan Airlines left when it ceased service to Kona nearly two years earlier.[41] However, the US Department of Transportation rejected the airline's application to begin service.[42]
In October 2015, Hawaiian Airlines announced that they will be upgrading their business class seats from the standard cradle seats to a 180-degree lie-flat seats on their A330 fleet in a 2-2-2 configuration. The new seats will be installed starting the second quarter of 2016. In addition to the new business class seats upgrade, the airline will add 28 additional Extra Comfort seating.[101]
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