How I Nearly Lost My JetBlue Points Booking—and How a Supervisor Saved the Day

They say that if you’re on the East Coast, JetBlue is king—free Wi-Fi, unlimited snacks, and roomy seats. But even JetBlue’s vaunted award chart can trip you up: when I tried to transform 13,000 Chase Ultimate Rewards points from my Chase Sapphire Reserve® into two 6,500-point Boston→JFK tickets, the website glitched and nearly stole my seats.

Here’s how a savvy supervisor got me back on track.

The Plan: Boston to JFK to Frankfurt

Since I have a Singapore Airlines business class flight this summer departing from JFK, I needed to find a way to get to New York from Boston. After exploring tools such as pointsyeah.com, roame.travel, and seats.aero (websites dedicated to finding, valuing, and booking award flights with miles from various airline programs), I found a flight from Boston to JFK with JetBlue at 6,500 points one way.

I also had the option of booking a 8,300 point Blue fare. I decided against this because I knew I was not going to make any further changes to my flight and was comfortable not picking a seat (also, wanted to be frugal with my points). Furthermore, when it comes to bags, Blue fares have the same rules as Blue Basic fares. You get one personal item and a carry-on bag.

Before booking this flight, I made sure to check cash prices for similar flights. The cheapest I found was $99, making the points flight a great deal!

Why is this such a great deal?

Well, comparing the points fare to the cash fare puts my 6,500 points valued at 1.52 cents per point (CPP). A solid deal since JetBlue points are valued at 1.3 CPP according to frequentmiler.com.

After going through my options, I then made the decision to transfer 13,000 points from my Chase Sapphire Reserve® card to JetBlue using my TrueBlue number so I could book two one way tickets for me and my girlfriend.

Glitch in the System

Now here’s where it gets frustrating. I tried booking the flight on JetBlue’s website and I received an error message saying “Fare not available, please restart your search.” I figured someone snagged the flight right before I got on the site.

But, that didn't seem to be the case. When I returned to the page to book, the 6,500 point flight was still showing as available.

Round One with Customer Service

After failing to book online, I then decided to call JetBlue’s customer service line. When the agent picked up the phone, she had me slowly go through the whole process of how I booked my flight, just to come to the same result. I decided to ask for a supervisor.

Round Two

As soon as I got on the phone with the supervisor, I noticed the points booking disappeared! Strange. However, the supervisor was much more professional and helpful. Instead of me going through the process on my end, she tried it herself. No luck.

There seemed to be a glitch on the site, not showing that points availability was gone. The supervisor explained and confirmed to me that there was indeed a glitch on the site, showing the same error message for her.

She then tried booking me on an earlier flight for the same day. Success!

Final Remarks

Moral of the story? Booking with points CAN be easy but oftentimes it requires work. And sometimes it requires getting an agent on the phone to book your travel. Stay tuned for my article about booking an American Airlines flight via the Qantas program…