The most work I've ever had to do for a reservation.

 

While Adam and I were in the Dominican Republic we had a conversation about future trip and how I would like to take one, really great trip with just my parents.  Adam was amenable and agreed that, even though mom and dad are still in great shape at 69 & 75 years old, we probably shouldn't put that idea off for too long.  

We first looked at renting a beach house in Puerto Rico, mainly to avoid the hassle of international  travel in the COVID-19 era.  After researching houses and activities for a couple of weeks though, the destination felt, well, forced.  

One of the lures though had been that we all had plenty of JetBlue TrueBlue (JBTB) points to cover the flights.  So as I cooled on the idea of Puerto Rico, I started browsing other options bookable with JBTB points.  Rediscovering the unique partnership between JetBlue and Hawaiian Airlines made things very interesting, very fast!  Mom and Dad had enough points to fly round trip, first class from Boston to Hawaii; we had enough for one way in first class and were willing to pay for the other leg.  

It is worth mentioning that Mom and Dad visited Hawaii nearly 50 years ago as newlyweds traveling with my Allain grandparents.  They have talked about it ever since and it was no secret in our family that they had always hoped to go back.  In recent years, it just didn't seem practical.  But now, the idea of mom, dad and I going to Hawaii, together with my spouse, is something of bookend, legacy trip pipe dream.  Which is all to say, I was heavily invested in making it happen.

It took little effort to get the go ahead from mom and dad;  and just as quickly I learned a new and valuable lesson about booking "award tickets".  We've been spoiled by years of using JBTB points ON JB flights where redemptions are based on ticket value not traditional "award space".  Even our newer swanky Chase Sapphire Reserve card had lulled us with the ease of using our reward points for travel.  On the upside, it was not long before I stumbled across a saving grace online tool - the Expert Flyer website.  

The downside was that I realized, no matter how many "points" you have at your disposal, award availability in coach is tight and in first class virtually non-existent.  It was a disappointing lesson, but using Expert Flyer did help me build a spreadsheet to discover the best possible change we had for booking 4 roundtrip tickets in coach.  

Not wanting to waste time (or suffer more disappointment), Mom and Dad kept me company on a Tuesday night while I called JetBlue customer service - the only option for redeeming JBTB points on Hawaiian Airlines.  

• <1 minute to have call ring through and select virtual queue option for a callback
• 75 minutes estimated wait time for callback was accurate...but...the agent who picked up said that a supervisor had to be the one to book this type of award redemption ticket. 
• 2h10m on hold waiting for supervisor.
• 25 minutes to complete transaction once supervisor came on the line (and she was a superstar once we got on the line!)  
• Total - roughly 3 hours and 53 minutes of phone time time to book our tickets

The payoff?  We booked 4 round trip tickets from Boston to Kona for $21.50 each!  Yup, a grand total of $86!  (and 120,000 JBTB points per couple) Even I was shocked!  I though for sure we'd get dinged with at least a few hundred dollars in taxes and fees since the purchase price for our itinerary was around $700 per ticket! I almost gave up on the call about 5 times, threatening to just "buy the damed tickets!"  Dad was tempted too as he mulled over the numbers in his head.  Patience absolutely paid off for this round!  Considering the huge savings, the phone time was an exceptional return on investment time wise.

Having confirmed with the JB agent that we were eligible to upgrade to Comfort Plus seats for a fee - a dealbreaker considering we were flying long haul from Boston to Honolulu.  Seat selection would be the next day's task.   

Wednesday morning I was not able to complete the transaction to upgrade seats.  No worries, the JB agent mentioned that sometimes it took 24 hours for everything to pull into the HA website.  I tried again in the afternoon and appeared to be successful - sort of.  Comfort Plus seats were now listed on our itinerary, but I did not receive receipts for the purchase, and no charges posted on my credit card.  

I elected to give it another 24 hours, then Thursday afternoon opened a Chat box on the HA app in an effort to confirm that payment had been processed.  Hours later an agent responded in the chat  indicating that payment did not process and attaching a secure form to complete the transaction via chat.  Unfortunately, by the time I saw the message the next morning the link had expired.  Back to square 1. 

Friday morning at work I opened a chat box again and by the time I got home that afternoon still had no response.  I submitted the same request through the text option, 2+ hours and no response.  I think I sent an email in there too, but at this point it is all running together a bit.  

I gave up and opted to call knowing that I would be again waiting.  

My first 10 attempts to call were met with a busy signal, but on 11 the call rang through.  The automated system estimated 30 minutes of hold time to reach an agent.  Only 30 minutes?  Great!  Just like the JB call on Tuesday, the estimate was right on.  Also like the JB call, I was immediately put on hold again after explaining the reason for my call.  

• 30 minutes on hold to reach an agent
• 45 minutes on hold to reach an agent who could do what I needed
• 30 minutes (on and off hold, but at least with the same agent) to make the necessary payment for the upgraded seats.  

While I was still on the call the charges posted to my credit card and the seat assignment remained unchanged when I looked at our itinerary online and through the HA app!  Finally!  

Maybe... 

For some reason the upgrade ended up costing $80 more over the phone than it said it would online.  There is a confirmation number for the "seat upgrade receipt" online, but the link is inactive and I cannot view the receipts to figure out why.  As directed on the HA website, I've now emailed a specific department asking for the receipts to be emailed to me.  My guess is that there was some flat fee per ticket for making the changes through an agent.  But that hardly seems fair given that the website's own errors were the reason I had to call in the first place.  

I'd like to say we're all set now with everything neatly arranged and confirmed, but my gut says that there is still more work to do on the air travel portion of this adventure...

Edit: There was more work to be done.  After multiple efforts between the website and mobile app to get our receipts, I emailed HA stating that the link didn't work and asking for PDF copies.  They sent me an automated response with a link to the website.  Repeat.  Another automated response.  Finally with the 3rd email saying the same thing a human apparently saw my message and now I have copies of our receipts.  Still not sure why the seat on the first flight were billed at $209 each instead of the $179 listed on the seat map, but I am too spent to pursue it further.  

Edit 2:  1/29/22... 7pm call with Caller ID saying Hawaiian Airlines so I picked up.  The representative was calling because we were, in fact, overcharged for our extra comfort seats and their system automatically refunded my card.  Good thing they called, I never would have noticed it.  The card has now been recharged with the correct amount, email confirmation received, and hopefully no more surprises!