In February 2018, Hawaiian was rumored to be canceling its order for six A330-800s and replacing them with 787-9s.[82] 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.[83] 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;[84] the deal was finalized at the Farnborough Air Show in July 2018.[85]
Hawaiian Airlines started HawaiianMiles, their frequent-flyer program, in 1983. Miles accumulated in the program allow members to redeem tickets, upgrade service class or obtain free or discounted car rentals, hotel stays, merchandise, or other products and services through partners. The most active members, based on the amount and price of travel booked, are designated Pualani Gold (fly 30 Segments or fly 20,000 Flight Miles) and Pualani Platinum (fly 60 Segments or fly 40,000 Flight Miles), with privileges such as separate check-in, Premier Club Lounge access in Honolulu, Hilo, Kona, Kahului, and Līhuʻe, priority upgrade and standby processing, or complimentary upgrades.[90] Travel award redemption from the HawaiianMiles program account for 5% of total revenue passengers.

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.
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