Completing the JetBlue 25for25 Challenge: Some Numbers and Reflections

As I bounced around the east coast the past six months, collecting destinations as part of JetBlue’s 25for25 promotion two key questions kept coming up:

1. Are you going to finish?
2. Is it worth the cost?

The first one was easy: I didn’t start until I had a plan to complete the challenge. Not finishing wasn’t really an option for me, even knowing it would not all go to plan. I had backup routings in mind and extra travel days ready to allocate. Good thing, too, as I used many of them.

The second question remains a bit more challenging to answer.

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Reviewing my inbox, it appears I booked 80 different JetBlue itineraries directly (and one through an OTA) to complete the quest. I canceled many more than I flew. But that was, in some ways, part of the fun. Whether repricing previously purchased trips as fares dropped or adjusting the routing to make it to the finish line, the booking and rebooking different itineraries as my plans changed, and as JetBlue’s operations dictated.

An Initial Setback

I knew things would not go perfectly. I just didn’t expect a complete collapse on day one.

My plan started with a quick overnight trip, collecting five airports along the way (ORF, BOS, PQI, SAV, MHT). Alas, the aviation gods had other plans.

A thunderstorm blew through as we were boarding which was a small problem, but recoverable. The three hour mechanical problem was harder to sort.

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It also exposed JetBlue’s less-than-stellar approach to handling travel interruptions.

It denied any responsibility, even in cases where the carrier failed to deliver passengers on time. I spent the first two hours of the delay trying to undo the mess that would cause me.

And then I simply bailed.

I made it home, about eight hours after I left, having spent ~$110 on ground transportation and collecting zero of the 25 destinations. On the plus side, because I had booked everything as award trips I was able to easily refund those bookings. I seriously considered bailing on the whole thing, as I was still not convinced it would be worth the cost.

The silly side of my brain eventually won out, however, and I was soon back at the airport, ready for round two.

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Staring Over

Three weeks later I was back at Logan, ready to try again. A long weekend of bounding up and down the east coast was supposed to score me eleven destinations. Once again, however, the travel gods had other plans.

A 38 minute connection in Tampa could have worked just fine, had we made it out of JFK on time.  A mechanical delay, however, once again left me several hours delayed.

I swapped a well-timed Tampa-Providence-Fort Lauderdale trip for a replacement Spirit Airlines ticket, purchased while in the air en route to Tampa, losing another two destinations from my plan.

That $150 deviation got me more or less back on track, and a much better night’s sleep than was originally scheduled. Probably a good thing in the end. Fortunately, the rest of the weekend went well bouncing up and down the eastern seaboard, netting nine of the total needed.

A Pair of Replacements

After losing the initial five cities I back-filled with a couple mid-week day trips, picking up two destinations at a time. Fortunately that included staying on the same plane for all four flights one day; no chance of missing a connection on that trip.

Routing from Wilmington, NC to Miami via Boston is incredibly out of the way, but it fit my needs. Alas, it was impossible to book as a multi-city trip. Turns out JetBlue does not sell a number of itineraries, even those where it has fares published.

To wit: BOS-ILM r/t can combine with BOS-MIA r/t just fine from a timing perspective. (CLE/ORF also works, for those still planning trips). And the prices aren't good, but also not terrible and that date worked for me. Booking as a multi-city should shave $80 off the combined fare.

— Seth Miller (@wandrme.paxex.aero) 2025-07-30T19:17:02.196Z

That trip also happened to be on the last JetBlue flight out of Miami, slightly on purpose. Again, a significant mechanical delay, but it got the job done.

And got me to 15 destinations, the first of the three milestones for the challenge.

Work and Stuff

Adjusting a couple work trips added a few more destinations to my tally. That included catching three airports on a simple trip to DC.

Rather than flying straight to Washington I made a pit-stop in Philadelphia, including dinner with a friend and then a ride on the new Amtrak Acela train (I was not impressed). The way home was even more circuitous, flying to Fort Lauderdale and back to Worcester, followed by a train back to Boston.

I also had a family trip to DC, which included a diversion to BWI and picking up the BWI-DCA line. Sadly I did not get credit for the BWI landing.

That cluster of flights did push me over the 20 destination milestone, adding 200,000 more TrueBlue points to my balance.

A Final* Push

My final five airports were supposed to be pretty easy over three days. Work had other ideas. A few more cancelled and rebooked flights, including a very judicious use of the same-day change option for Mosaics, got me to 23 destinations and an overnight in Detroit during the ATC slowdown related to the government shutdown.

At least this wasn’t JetBlue’s fault, but it still sucked. And, once again, it showed the carrier’s lack of flexibility with IROPs. So I bought a walk-up ticket DTW-BOS to go home. I’m still fighting with my travel insurance over that reimbursement.

The Actual Finish

My final two airports that weekend were supposed to be Fort Myers, FL and Manchester, NH. Fortunately there are non-stop flights in that market and I found a cheap quick turn. I booked it on consecutive weeks, just in case things went sideways.

I met online friends for the first time on the trip, had a quick dinner in the terminal, and finally made it home, with my 25 destinations in the bag.

Of course, JetBlue didn’t really think so. The flight from Manchester to Fort Myers never credited in JetBlue’s systems, for me or for others on board. Eventually I got it resolved through back channels, but it was not seamless.

The Costs

The final tally of the trip was reasonable, but came in higher than expected with the extra trips and deviations. The tickets ran me 147,200 points (including the 10% discount for the JetBlue CC) and $1,483. Hotels and buses and such added another $1,000 to the tally.

The 200,000 points net I came out with are theoretically worth about $3,200-$3,500. And that’s before considering the 25 years of status.

Of course, I also had to spend all the time in air world.

Which is to say, I’m still not convinced that on a straight dollar basis it was a worthwhile play. Each of the 25 years theoretically comes with a Mosaic Perk; I typically select the 15,000 bonus points, worth about $220 in airfare. If that sticks around over the next couple decades the scales tilt more towards it being a smart “investment,” but that’s still not a certainty against the backdrop of the time involved.

But it certainly scratched an itch for me.

Some Other Thoughts

JetBlue does a lot of bragging about its on-board product and I spend a lot of time on airplanes and thinking about the seats and systems. More than 30 JetBlue flights in five months was a good opportunity to see how well the carrier delivers on some of those promises.

The FlyFi inflight internet system worked on every one of my flights. Performance was inconsistent, and there’s a notable difference between the old and new implementations (and the older setups are getting an update in a couple years). But it did work. Which is a step up from the inflight entertainment system.

JetBlue and Thales Inflyt made big promises on personalization with the “Blueprint” IFE platform a couple years ago. Most of it works, some of the time.

Notably, the feature allowing passengers to log in to the platform and save their preferences, including their favorite movies, only worked on about 25% of the flights. The option allowing passengers to set their preferred name on the IFE system was never implemented. The company says “the ‘preferred name’ feature in Blueprint is coming in a future update.”

I also spent a LOT of time working with JetBlue’s website and app. Basic functionality mostly works, but there’s plenty of room for improvement.

JetBlue does not really sell many trips with connections, and its systems are built around that approach. When displaying itineraries with a connection (e.g. RDU to DTW via JFK) some systems will show it as a trip to New York rather than to Detroit. The carrier still will not allow multi-city bookings via awards, in addition to not selling all the fares it markets, noted above.

The progress tracking for the challenge had issues, once it was finally implemented a few months into the promotion. The app routinely fails to update when flights are cancelled. The company’s year-end email had the wrong data for my most frequent airport, trips flown, miles flown, and elite status qualification.

Perhaps little things, but they add up to a challenging digital travel experience at many levels.

On the plus side, JetBlue did implement a cutover of its entire online booking platform in the middle of the challenge with relatively few disruptions, and most of the prior booking functionality is back online now.

A Community

Much like with the All You Can Jet promotion nearly 20 years ago, the 25for25 challenge launched many online – and eventually IRL – communities.

It was travelers helping each other, sharing adventures and travel tips. People made their own t-shirts and sweatshirts and scarves and pins and all sorts of other ways to celebrate and track their progress. That was great to see evolve and be a part of.

And I’m quite certain it worked in JetBlue’s favor, creating some short-term revenue and a longer-term brand loyalty for a couple thousand customers.