The 5 Cheapest Flights from Portland to Hawaii

Heed the call of Hawaii's lush mountains and black-sand beaches without breaking the bank: Check out Hopper's rundown of the 5 cheapest flights from Portland to Hawaii.

Hopper Editors - Oct. 26, 2017

When a hop across the continent to the sun, sand and sea of the Caribbean seems just a little too far, then Portland locals would do well to consider the 50th State! Lingering out in the swells of the Pacific Ocean, Hawaii, a cluster of volcanic islands, has long been a veritable paradise of palm trees and pristine beaches, while its lands are also dotted with the relics of Polynesian warriors and towering memorials to the American plight in World War II. If that's got you thinking, then be sure to check out the list below, which has been put together using Hopper's acclaimed big data research method and shows the top five cheapest flights currently running between Portland and Hawaii.

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5. Fly from Portland to Hilo for as low as $551 round trip

Starting us off at an attractive round-trip price of just $551 are these indirect connections between Portland and Hilo, a volcano-shrouded town on the Big Island. They come courtesy of United Airlines and Hawaiian Airlines and transport passengers to one of the Hawaii's most rugged, wild and metamorphic corners, where the calderas of the Hawai'i Volcanoes National Park spout lava and smoke, and the soaring tips of Mauna Kea are peppered with pearly-white observatories.

4. Fly from Portland to Kahului for as low as $474 round trip

Set in the shadow of the soaring West Maui Forest Reserve, the pretty port town of Kahului is the traveler's gateway to the legendary Kaanapali Beach, where some of the state's top all-inclusive hotels sit back from stretches of shimmering yellow sands, golf courses adorn the volcanic hills and locals still perform the ancient Black Rock cliff-diving ceremony at sunset. Expect to pay in the region of just $474 for round-trip tickets, going indirect on United Airlines or Delta Air Lines for the cheapest seats overall.

3. Fly from Portland to Kailua-Kona for as low as $427 round trip

Why not follow in the footsteps of Polynesian royalty this year by hopping aboard one of these bargain air connections with United Airlines to the picture-perfect resort town of Kailua on the Big Island's western shore? You can listen to the voices of Hawaiian kings still echoing between the swaying palms and the lapping sound of the sea still speaking of ancient legends. One thing's for sure: You won't need the money of royalty to do it — not when indirect flights into town are priced at an average of just $427 round trip!

2. Fly from Portland to Lihue for as low as $427 round trip

Ecotourists and nature lovers of Portland, listen up, because little Lihue on the eastern edge of Kauai is your gateway to sites like the gushing cataracts of the Wailua Falls, the paradisiacal reaches of Wailua River State Park, the historic Menehune Fishpond and the heartbreakingly beautiful Na Pali Coast, to name just a few. What's more, tickets into town should cost in the region of just $427 round trip this year, with indirect routes on United Airlines coming out on top.

1. Fly from Portland to Honolulu for as low as $394 round trip

While primarily famed for its happening beaches, Hawaii's state capital is also the gateway to all the other must-see sites of Oahu, like the sobering Punchbowl Cemetery and the USS Arizona Memorial for the attacks on Pearl Harbor. With such a diverse set of interests catered for here, it's hardly surprising that connections on the route between Portland and Honolulu are the most popular on this list, but the good news is they're also the cheapest, boasting a round-trip price tag of just $394 when going direct on Hawaiian Airlines.

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