| 1905 | James Kennedy of Inter-Island Steam Navigation Company merged with Wilder Steamship Co. to become the largest fleet of steamers serving Hawaii. |
| 1928 | Stanley C. Kennedy, a Silver Star Navy pilot, convinced the board of directors of Inter-Island Steam Navigation of the importance of air service to the Territory and formed Inter-Island Airways. |
| 1929 | October a Bellanca monoplane offered sightseeing service for $5 per person. The original Bellanca has been restored in Oregon. |
| 1929 |  On November 11, Inter-Island Airways, Ltd. launched. FIRST scheduled air service in Hawaii. First scheduled flight from Honolulu to Hilo with stops on Molokai and Maui took three hours, 15 minutes. Airline began at the time of the Great Depression. |
| 1929 |  Fleet consisted of two, 8-passenger Sikorsky S-38 amphibian airplanes. |
| 1930 | 10,367 passengers carried. |
| 1934 | FIRST Interisland airmail service contract went to Inter-Island Airways. |
| 1935 |  Added 16-passenger Sikorsky S-43s. |
| 1935 | 13,000 passengers carried. |
| 1938 | 28,000 passengers carried. |
| 1941 | Name changed to Hawaiian Airlines to pave the way for trans-Pacific operations. Wings logo adopted. |
| 1941 |  Three new, 24-passenger DC-3s were flown in formation from Oakland, CA to Honolulu in 13 hours and 54 minutes--the then longest over-water flight ever made by a DC-3. |
| 1941 | December 7th, HA DC-3 #9 with 24 passengers had its cockpit straffed by Japanese fire at Pearl Harbor. The cockpit was on fire; a stray bullet hit the cockpit fire extinguisher putting out the fire. No one was hurt and this event made Ripley's "Believe It Or Not". |
| 1942 | HA became the FIRST scheduled air cargo service and has U.S. Cargo service certificate #1. |
| 1943 | FIRST stewardess hired. |
| 1943 | 108,000 passengers carried. |
| 1950 | The National Safety Council presented HA with a 20-year award; the first airline in history to win this award. |
| 1952 |  FIRST pressurized, air-conditioned cabin service with 44-passenger Convair 340s costing $520,000 each. |
| 1955 | Five DC-3s converted windows to larger "Viewmaster" windows. |
| 1955 | I'iwi bird became part of HA logo. |
| 1958 |  Long-range, four-engine DC-6s were added. |
| 1959 | 498,861 passengers carried. |
| 1966 |  Hawaii's FIRST interisland jet service with 99-passenger DC-9-10s. |
| 1966 | Logo changed to a Jetbird to symbolize change over to jet service. |
| 1973 | Pualani (flower of the sky) and new unified livery introduced. |
| 1975 |  130-passenger DC-9-50s added to fleet. |
| 1977 | 3,000,000 plus passengers. |
| 1979 | FIRST all-female crew to operate a certified U.S. scheduled flight. |
| 1983 | Frequent Flyer program began as Travel Plus. |
| 1984 |  Worldwide charter service with DC-8s and scheduled service to the South Pacific. |
| 1985 |  Widebody L-1011 aircraft added to fleet. |
| 1985 | HA launches scheduled service between West Coast and Hawaii. |
| 1986 | Frequent flyer program renamed Gold Plus. |
| 1994 |  Widebody DC-10s replaced the L-1011 fleet. |
| 1996 | HA Web site activated. |
| 1998 | E-ticketing launched. |
| 1999 | Frequent flyer program renamed HawaiianMiles. |
| 2001 |  Boeing 717s replaced the DC-9 fleet. |
| 2001 | Pualani symbol and livery updated for introduction of new fleet. |
| 2002 |  Boeing 767s replaced all DC-10s making Hawaiian Airlines' fleet among the youngest in the industry. |
| 2003 | "Hele On" Self Check-In at airports launched. |
| 2003 | "Hele On" Web Check-In launched. |