The first person to attempt flying to Hawaii spent nine days drifting across the Pacific on a makeshift sail stitched from his airplane’s wing fabric. The most recent chapter ended with a 95-year-old airline absorbed into a Seattle-based corporate parent. In between, the story of how humans learned to fly 2,400 miles of open ocean to reach these islands transformed Hawaii from an exclusive steamship destination into a place that welcomes ten million visitors a year.

This is the complete history — from the military aviators who nearly died trying, through the golden age of the Pan Am Clippers, to the jet revolution that changed everything.

The First Attempt That Nearly Killed Its Crew (1925)

On August 31, 1925, Commander John Rodgers — Naval Aviator Number 3, one of the most experienced pilots in America — departed San Pablo Bay, San Francisco in a PN-9 No. 1 flying boat with a four-man crew, attempting the first flight from the mainland to Hawaii.

Two aircraft launched. The sister plane, PN-9 No. 3, suffered engine failure five hours in and was recovered safely. Rodgers pressed on, covering over 1,200 miles without major difficulty. Then things went wrong. Higher-than-expected fuel consumption and weaker tailwinds meant the aircraft needed to refuel from a Navy ship stationed along the route. Navigation errors — from the ship’s crew providing erroneous position data — caused Rodgers to miss the refueling point entirely.

On September 1, the PN-9 No. 1 ran out of fuel and splashed down in the open Pacific.

What happened next is one of the great survival stories in aviation history. The crew tore fabric from the flying boat’s lower wings and fashioned makeshift sails, using the airplane’s ailerons and rudder for steering. They sailed the crippled aircraft approximately 450 miles across open ocean toward Hawaii. Nine days later, on September 10, lookouts aboard the submarine USS R-4 spotted the battered flying boat roughly 10 miles off Nawiliwili Bay, Kauai.

Rodgers had failed to fly to Hawaii. But he had set a new non-stop seaplane distance record of 1,992 miles, and Honolulu’s airport — dedicated on March 21, 1927 — was named John Rodgers Airport in his honor. Today it is called Daniel K. Inouye International Airport.

The Deadly Race for a Pineapple Fortune (1927)

Charles Lindbergh crossed the Atlantic on May 20, 1927, and within days, James D. Dole — the Hawaii pineapple magnate — announced a prize: $25,000 for first place and $10,000 for second in a race from Oakland, California to Honolulu. The Dole Air Derby would cover roughly the same distance as Lindbergh’s flight, but entirely over open water with no emergency landing options.

Thirty-three pilots entered. Fourteen were selected for starting positions. After pre-race accidents and inspections, only eight aircraft actually took off on August 16, 1927.

Two pilots had already died before the race began — one flew into a fog-hidden cliff, another was killed during a test flight. Of the eight starters, only two finished. Arthur Goebel won in 26 hours and 17 minutes in his Travel Air monoplane Woolaroc. Martin Jensen took second in the Aloha, two hours behind.

Three aircraft vanished over the Pacific and were never found. Among the lost was 22-year-old Mildred Doran, a schoolteacher from Michigan and the only woman in the race. She had refused to stay behind when her plane returned with engine trouble, insisting on a second departure. Neither she nor her crew were ever seen again. A third plane, the Dallas Spirit, disappeared while searching for survivors.

Ten people died. The Dole Air Derby proved that the Pacific crossing was possible — but the cost was staggering. It would be another eight years before anyone found a reliable way to fly to Hawaii.

Pan Am and the Clipper Ships of the Sky (1935-1941)

Pan American Airways solved the problem with flying boats — massive, multi-engine aircraft that could land on water, eliminating the need for island runways that did not yet exist.

On April 16, 1935, a stripped-down Sikorsky S-42 named the Pan American Clipper departed Alameda, California on a survey flight to Hawaii. The aircraft, designed for the shorter Atlantic crossing, barely had the range — its passenger cabin had been gutted and filled with auxiliary fuel tanks. Captain Edwin Musick brought it to Pearl Harbor in just under 18 hours. Navigator on board: Fred Noonan, who would disappear with Amelia Earhart two years later.

Three weeks earlier, Amelia Earhart had made her own mark on Hawaiian aviation. On January 11, 1935, she departed Wheeler Field, Oahu in a red Lockheed Vega and flew solo to Oakland in 18 hours and 15 minutes — becoming the first person, man or woman, to fly solo from Hawaii to North America. Ten previous pilots had died attempting the same route. Hawaiian sugar plantation promoters had offered $10,000 for the flight; when they got cold feet and told her to ship her plane home instead, she told them she intended to fly with or without their support.

Pan Am introduced the Martin M-130 flying boats for regular service — only three were ever built. The China Clipper, Philippine Clipper, and Hawaii Clipper were four-engine behemoths purpose-built for the Pacific. On October 21, 1936, the Hawaii Clipper carried the first paying airline passengers across the Pacific: seven people out of more than 1,000 applicants. One-way fare to Manila was $278 — roughly $6,000 in today’s dollars. A new car cost $600.

The Hawaii Clipper itself would vanish without a trace on July 28, 1938, on the Guam-to-Manila leg of a transpacific crossing. Fifteen people — nine crew and six passengers — were lost. The aircraft was never found.

Born in the Water, Built for the Islands (1929-1941)

While Pan Am was conquering the Pacific, a different kind of aviation was taking shape within the islands themselves.

Inter-Island Airways was incorporated on January 30, 1929. Founded by Stanley C. Kennedy, a World War I Navy pilot who ran the Inter-Island Steam Navigation Company, the airline started with two Sikorsky S-38 amphibian flying boats — eight-seat aircraft that could land on water or grass — named HAWAII and MAUI.

The first sightseeing flights launched on October 6, 1929, giving nervous islanders their first taste of air travel. Scheduled service began on November 11, 1929 — Honolulu to Hilo via Maui. The flight that had taken a full day by steamship could now be done in hours.

By 1936, after seven years without a single accident, the traditionally boat-minded islanders finally embraced air travel. The company upgraded to 16-passenger Sikorsky S-43s. On October 1, 1941, Inter-Island Airways changed its name to Hawaiian Airlines — barely two months before Pearl Harbor.

War, Grounding, and Recovery (1941-1959)

The attack on Pearl Harbor on December 7, 1941 shut down civilian aviation in Hawaii instantly. All airports were seized by the military. Oahu was placed under martial law. Hawaiian Airlines’ three DC-3s were permitted to fly only during daylight, only to specific islands, and only with military permission — carrying engineers, medicines, and munitions.

By 1944, Oahu alone had 15 military airfields. The islands had been transformed into the most heavily defended air base in the Pacific. But when the war ended, something unexpected happened: hundreds of thousands of American servicemen who had experienced Hawaii during the war wanted to come back as tourists.

The Matson steamship lines resumed service, but the future belonged to aviation. In 1950, Pan American completed the first commercial nonstop flight from Tokyo to Honolulu. The propeller era was reaching its peak — and about to be obliterated.

The Jet Revolution and the Year Everything Changed (1959)

Two events in 1959 transformed Hawaii forever, and they happened almost simultaneously.

On August 21, Hawaii became the 50th state. Weeks later, on September 24, Pan American inaugurated Boeing 707 jet service to the islands. The jets cut travel time roughly in half compared to propeller aircraft. A journey that once took five days by Matson steamship could now be done in five hours.

The numbers tell the story of what happened next:

• 1910: roughly 5,000 visitors (steamship era)
• 1959: 243,000 visitors (statehood and jets)
• 1967: one million visitors
• 1970: 1.8 million
• 2019: 10.4 million (all-time record, $17.7 billion in spending)

Hawaiian Airlines added its first jets in 1966 — Douglas DC-9-10s with 85 seats that cut inter-island travel time to 20-30 minutes. The DC-9 fleet would eventually number 38 aircraft and serve for decades before being replaced by Boeing 717s.

Before 1959, there were three major hotels in Waikiki. After statehood, rooms quadrupled. More than 2,000 rooms were added in 1960 alone. Tourism replaced sugar and pineapple combined as Hawaii’s largest civilian income source. The man-made beach at Waikiki suddenly needed to accommodate millions instead of thousands.

Southwest Shakes Up the Market (2019)

For decades, Hawaiian Airlines and its smaller competitor Aloha Airlines dominated inter-island flying. Aloha went bankrupt in 2008 after a devastating fare war with go! Airlines, which had launched inter-island tickets as low as one dollar. Hawaiian survived and thrived as the dominant carrier.

Then, on March 17, 2019, Southwest Airlines flew its first Oakland-to-Honolulu service with an introductory fare of $49 each way — when competitors were typically charging $250 or more. Within three months, Southwest had launched inter-island service at fares as low as $29. Hawaiian responded with its own discount fares, and the competitive landscape was permanently altered.

Southwest flew 7,511 flights to and from Hawaii in its first year of service. The era of cheap Hawaii flights had arrived.

The End of an Era and a New Beginning (2024-2026)

On December 3, 2023, Alaska Airlines announced its acquisition of Hawaiian Airlines for $1.9 billion. The deal closed September 18, 2024. Hawaiian’s final flight under its own call sign — HA866 from Pago Pago — landed on October 29, 2025, ending 95 years of independent operation.

The merger has been complicated. Routes to Boston, Seoul, and Fukuoka were cut. Over 300 employees lost their jobs. The booking system transition has been painful. But the Hawaiian brand survives on planes flying Hawaii routes, inter-island service continues unchanged, and the combined airline has the fleet — including Boeing 787 Dreamliners — to open new international routes that Hawaiian could never have afforded alone.

From Commander Rodgers sailing his crippled flying boat across the Pacific in 1925 to a merged Alaska-Hawaiian operation flying Dreamliners to Tokyo in 2026, the history of flights to Hawaii is a century-long story of ambition outrunning technology — and technology eventually catching up.

Explore the Full Story

This article is the hub of our Flying to Hawaii series. Each piece goes deeper:

• What Happened to Hawaiian Airlines — The Alaska merger explained for travelers
• The History of Tourism in Hawaii — From Captain Cook to ten million visitors a year
• The White Ships Era — How Matson Navigation created Hawaiian tourism before the planes came
• Duke Kahanamoku and the Beach Boys — How surfing built Hawaii’s brand
• Every Airline That Flies to Hawaii in 2026 — All 20 airlines compared, with points and deals
• Is Waikiki Beach Man-Made? — The extraordinary engineering behind the beach

Planning Your Flight to Hawaii

Ready to make the crossing yourself? Explore our hotel guides by island:

• Oahu Hotels — including Waikiki’s historic and modern properties
• Maui Hotels — luxury resorts on the Valley Isle
• Kauai Hotels — romantic stays on the Garden Isle
• Big Island Hotels — from Volcano House to beachfront resorts