On February 11, 2013, the airline announced a new venture in the turboprop interisland business, "ʻOhana by Hawaiian." Service is operated by Empire Airlines using ATR 42-500 turboprop airplanes. Service began on March 11, 2014, to Molokaʻi and Lānaʻi. The airline expanded more "ʻOhana by Hawaiian" routes between Kahului, Kailua-Kona & Hilo during the summer of 2014.
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.
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.
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.