Delta Airlines: BOS-HNL

Winter’s finally here in Boston.  We got spoiled a little bit in December and November, as Mother Nature spoiled us with a little more warmth than usual.

Now it’s zero degrees with windchill, ahh that’s more like it.  So, who wants to go to Hawaii?

I know, me too.  Unfortunately it’s not me going, but my brother.  However, he’s entrusted me with booking the flights, which lets me experiment a bit.  Lucky for him, I actually love finding the cheapest flights, analyzing the routes and travel times, and figuring out the best way to get from Point A to Point B.

The Details

Airline:  Delta, he has a $1,000 flight voucher to use towards this trip

Airport:  Boston

Passengers:  2

Time Frame:  mid-February to mid-March

Duration:  1-2 weeks

Destination(s):  4 -5 days on O’ahu, 4-5 days on Maui, 4-5 days on Moloka’i

There’s also an emphasis on reducing cost.  He’ll be flying economy, and would like to reduce travel time, layovers, etc. but lowest cost wins in general.  He has no miles, and doesn’t want to deal with taking out credit cards or anything else, so we’ll be looking at dollar value.

…looks like I’ve got my work cut out for me.

The Plan

After experimenting a bit with routing and itineraries, the best plan is this:

  • Starting with Boston (BOS) – Los Angeles (LAX) – Honolulu (HNL)
  • Then HNL – Kahului (OGG)
  • And finally OGG – LAX – BOS

Some of the other routing options included Atlanta and Minneapolis/St. Paul, but those would have meant a much longer final leg to get to Hawaii and back. As always, I used Great Circle Mapper for this map.



The first segment is Boston to Los Angeles, and then on to Honolulu.  There’s a long (almost 4 hour long) layover in LA, but all in all, not bad.  The cheaper flight is worth the longer wait.


Honolulu to Kahului (on the island of Maui) is only a 40 minute flight, and will be operated by Hawaiian Airlines on behalf of Delta.  While on Maui, he’s going to take a ferry to the nearby island of Moloka’i, and spend some time there for a few days.  The majority of his trip will be on these two islands.


Most of the flights out of Kahului seem to route through LA on the return home too.  This is great for multiple reasons.  One, he won’t have to backtrack to O’ahu before heading home, he can leave straight from Maui.  Two, since we were able to get rid of one of the flight segments we had originally planned on using (OGG back to HNL), we’re cutting down on his carbon footprint for this trip.  I know this may not make or break a deal for some of you, but I try to reduce my emissions when I can.  Three, it reduces the overall cost of the trip.  Booking a return flight out of OGG was actually cheaper than the return flight out of HNL.

After taxes and fees, the price for all flights is $590.38/passenger, or $1,180.76 total.

After a $1,000 flight voucher, he’ll be paying $180.76.  I’ve offered to put the charge on one of my credit cards for the miles.  Which card did I use?  I’ll be evaluating and posting about that later this week!


In planning this itinerary, we checked a couple of other options too.  First of course, was round trips BOS-HNL, but this made it more difficult and more expensive to see the other islands he wanted to see.  I did check other airlines, but only out of curiosity.  As I mentioned above, he had a $1,000 flight voucher for Delta, so that was obviously the clear winner.  I also looked at Kayak for inter-island flights, but didn’t find any to be particularly helpful or much cheaper anyway.

Without the voucher, I would have done a few things differently.  I would have checked more airlines, and encouraged him to rack up some miles before leaving, or at least to use a fixed-value card, like the Barclaycard Arrival+ I keep in my wallet.  That way, he could earn some miles and redeem them against his travel purchases, including the flights, ferry ride, maybe even some incidental charges once he got there.

I genuinely love planning trips, and look forward to doing so!  I jumped at the opportunity to help him out on this one.  My only regret was not having the time to tag along!  If you have any travel questions, or want some advice on planning, please let me know in the comments!  My brother thinks I’m crazy, but I actually enjoy pouring over flight itineraries and airline websites for an hour or two.

Here’s hoping you all get to go on an adventure soon!



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