Flying from PDX to OGG

Question

I don't know about this topic but I would like your feedback anyway. Since Alaska took over Hawaiian, Hawaiian no longer has my favorite flight, Nonstop PDX to OGG at leaving at 10:00 a.m. Now, there is a 7 am or 6 pm departure nonstop on Alsaka. Or a 10 a.m. flight that stops in Honolulu with a plane change that gets me in at 4:00 pm and supposedly adds about 1.5 hours to trip duration. I don't love getting up at 3:30 a.m. in December in Portland, but conventional wisdom is "fly early non stop." What do you all think?

Of course, despite all protestations to the contrary by Alaska, as I flyer its more $$$ and fewer choices since the takeover.

Answer

When flying from Portland (PDX) to Kahului (OGG) in Maui, your main considerations are convenience, arrival time, and overall travel comfort. Since the direct flight you preferred is no longer available, you’re left with either an early nonstop, a late nonstop, or a midday flight with a stop in Honolulu.

Options and considerations:

Early nonstop (7:00 a.m. departure): Pros include arriving in Maui earlier in the day, giving you more daylight for activities, and no plane changes. Cons are very early wake-up (around 3:30–4:00 a.m.) and potentially less sleep before the trip, which can be tough for some travelers.
Late nonstop (6:00 p.m. departure): Pros are a more relaxed morning at home, no rush to the airport, and possibly a smoother start to travel. Cons include arriving in Maui in the late evening, limited daylight for first-day activities, and potential fatigue from flying at the end of the day.
Midday flight with a stop in Honolulu (~10:00 a.m.): Pros include a moderate departure time, less early wake-up, and a chance to stretch legs in Honolulu. Cons include a longer total travel time, plane change hassle, potential delays, and arriving in Maui mid-afternoon, which can cut into your first day.

Additional factors:

Winter in Portland is dark and cold early in the morning, which makes the early flight less appealing if you’re sensitive to early wake-ups.
Nonstop flights are generally preferred for convenience and minimizing travel stress, but the early or late timing may offset the benefits if you’re not rested.
If you value getting on Maui quickly and maximizing your first day, the early nonstop is ideal despite the early start. If your first day is flexible or you’d rather rest on the plane, the midday connecting flight could be reasonable.
Consider airport logistics, such as parking or airport shuttle timing, which can make very early departures more challenging.

In summary, there’s no one-size-fits-all answer. Early nonstop is best for maximizing Maui time, late nonstop is best for convenience and comfort, and the midday connecting flight is a middle-ground option but adds some travel complexity. Since it’s a December flight, balancing comfort versus day-of-arrival energy is key.

Flying from PDX to OGG

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