On November 27, 2007, Hawaiian Airlines signed a MOU (Memorandum of Understanding) with Airbus for 24 long-range jets priced at $4.4 billion. The order included six Airbus A330-200s with a further six purchase rights and six Airbus A350-800s with a further six purchase rights - plans to fly to Paris and London were discussed. Deliveries for the A330s began in 2010 while the first A350 was to be delivered in 2017.
Inter-Island Airways (Hawaiian: Hui Mokulele Piliʻāina), the forerunner of the airline which is now known as Hawaiian Airlines, was incorporated on January 30, 1929. Inter-Island Airways, a subsidiary of Inter-Island Steam Navigation Company, began operations on October 6, 1929, with a Bellanca CH-300 Pacemaker, providing short sightseeing flights over Oʻahu. Scheduled service began a month later on November 11 using Sikorsky S-38s with a flight from Honolulu to Hilo, via intermediary stops on Molokaʻi and Maui.
On August 30, 2012, Hawaiian filed an application with the U.S. Department of Transportation for a nonstop route between Kona and Tokyo-Haneda. This would fill a void that Japan Airlines left when it ceased service to Kona nearly two years earlier. However, the US Department of Transportation rejected the airline's application to begin service.
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.
During the 1980s, Hawaiian also embarked on the development and construction of Kapalua Airport on west side of Maui. Opened in 1987, the airport was designed with a 3,000-foot runway, which constrained its ability to handle large aircraft. As a result, when the airport first opened, Hawaiian Airlines was the only inter-island carrier with aircraft capable of serving the airport. With its de Havilland Canada DHC-7 Dash 7 turboprops, Hawaiian had a distinct competitive advantage in the Maui market.
On February 16, 2010, Hawaiian Airlines sought approval from the U.S. Department of Transportation to begin nonstop flights from its hub at Honolulu to Tokyo-Haneda sometime in 2010. The airline was one of 5 US carriers — the others being Delta, Continental, United, and American — seeking approval to serve Haneda as part of the U.S.-Japan OpenSkies agreement. Approval was granted from USDOT to begin nonstop service to Haneda, Japan. The flight began service on November 18, 2010. In addition, the airline is planning to establish a codeshare agreement with All Nippon Airways. On January 12, 2011, Hawaiian Airlines began nonstop service to Seoul-Incheon, South Korea. On July 12, 2011, Hawaiian added Osaka, Japan to its network.
In February 2018, Hawaiian was rumored to be canceling its order for six A330-800s and replacing them with 787-9s. It was reported that Boeing priced the aircraft at less than $115 million, and possibly less than $100 million, each; the production cost of a 787-9 is between $80 million and $90 million. Boeing Capital also released Hawaiian from three 767-300ER leases in advance; these aircraft were to be transferred to United Airlines. Initially, Hawaiian refuted it cancelled its A330-800 order, but did not dismiss a new deal with Boeing. However, on March 6, 2018, Hawaiian Airlines confirmed the cancellation of the A330-800 order and the signing of a Letter of Intent with Boeing to purchase ten 787-9 aircraft, with options for an additional ten planes; the deal was finalized at the Farnborough Air Show in July 2018.