Hawaiian Airlines began to expand its footprint throughout the 1980s, as the result of intense competition on inter-island routes created by the entrance of Mid Pacific Air into the market. In 1985, the company began its first foray outside the inter-island market through charter services to the South Pacific and then throughout the rest of the Pacific using Douglas DC-8 aircraft. Despite the early successes of this new business, Hawaiian was forced to curtail its charter services when the Federal Government banned all DC-8 and B707 aircraft without hush kits from operating within the US. Hawaiian did, however, manage to gain a short exemption for its South Pacific services.
ʻOhana by Hawaiian is a regional subsidiary carrier of Hawaiian Airlines. The service is operated using three ATR 42 turboprop airplanes owned by Hawaiian and operated under contract by Empire Airlines. The new service was slated to begin in summer 2013 initially flying to Molokaʻi and Lānaʻi, however the airline was unable to begin during that period due to Federal Aviation Administration delays in certifying ʻOhana's operation. ʻOhana by Hawaiian is fully integrated into the Hawaiian Airlines network.
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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. In December 2012 it was announced that Empire Airlines would operate the aircraft on behalf of Hawaiian. A fourth ATR 42 aircraft was acquired in June 2018.
Soon after, in early 1985, the company received the first two of its leased Lockheed L-1011 aircraft. One aircraft was used to launch Hawaiian's first scheduled operation out of Hawaiʻi, daily Honolulu-Los Angeles services. This new service put Hawaiian in direct competition with the major US air carriers for the first time in its history. Throughout 1985 and 1986, Hawaiian Airlines added additional L-1011s to its fleet and used them to open up services to other West Coast gateway cities such as San Francisco, Seattle, Portland, Las Vegas, and Anchorage, which placed Hawaiian in further competition against the major US airlines.
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). 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. In December 2010, Hawaiian ordered an additional six A330-200 aircraft, bringing the fleet total to 15. Further lease agreements were signed with Air Lease Corporation (one aircraft), and three aircraft each from Hong Kong Aviation Capital, and Jackson Square Aviation, bringing the A330-200 fleet to 22. In July 2015, Hawaiian announced the lease of an A330-200 from Air Lease Corporation. The purchase of another A330-200 was announced in December 2016.
On January 5, 2015, Hawaiian refiled its previously rejected application with the U.S. Department of Transportation (DOT) for the Kona-Haneda route with service, if approved, to begin in June. The request was prompted by a DOT decision in December 2014 to review the public interest in Delta Air Lines' Seattle-Tokyo route after Delta reduced the frequency of those flights from daily to seasonal. On March 31, DOT again denied the request, opting instead to allow Delta to continue operating the route, with American Airlines taking over if Delta's planned service continued to fail.
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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.