I didn’t see this coming! JetBlue is offering 350,000 points plus 25 years of status to anyone who flies JetBlue to 25 destinations by the end of this year. Stephen published the full details here. If we hadn’t already announced our 2025 team challenge, 100K Vacay, I’m sure this would have been it. Within our team, I know that Nick is interested in pursuing the JetBlue deal. He’s talking about finding the cheapest way to accomplish it with his whole family. I have no doubt that it’s possible to come out well ahead by sticking with cheap multi-stop flights. I also think that it would be torturous to do so. I’m thinking about it differently… Can my wife and I do this in style? Is it possible to cobble together enough fun trips by the end of the year so that we’ll actually enjoy the process?
Why bother?
JetBlue has been suffering financially, so it might seem ridiculous to pursue lots of points and many years of elite status with an airline that might not even exist five years from now. Additionally, from my home airport (Detroit DTW), JetBlue only flies to two destinations: New York JFK and Boston BOS. Even if JetBlue was doing well, it could reasonably be considered insane to pursue points and status with an airline that has so few routes for us to fly. My thinking is this: if JetBlue gets bought by another airline, things might work out well. Let’s say United buys them, for example. If that happened, I think there’s a great chance that JetBlue miles would become United miles, and an OK chance that however many years of JetBlue elite status that is left would become that many years of United Premier Silver status. And, most importantly, this seems like a fun challenge!
JetBlue’s route network makes things difficult

As you can see above, JetBlue flies to a lot of places, but the vast majority of those flights are from/to either New York JFK, Boston, Fort Lauderdale, or Orlando. So, once you’ve added those hubs to your 25-destination collection, you’ll have to revisit them in order to get to new destinations. For me, flying out of Detroit, I would have to fly through JFK or Boston every single time unless I use another airline to position elsewhere.
Just for fun, I tried to build an itinerary to see if it’s possible to hit 25 destinations in a single epic trip without any backtracking. I didn’t succeed. I was able to come up with an 17 destination trip, though. And, I’m sure it’s possible to squeeze in a couple more. You could probably get to 25 destinations if you slightly relax the “no backtracking” rule that I enforced on myself. Note, though, that I don’t know if this is really possible since some of these flights end in October and others start around then…

7 Destinations thanks to trips already planned
My wife and I have three trips to Europe and two trips to Buffalo that we plan to take during the eligible window for this promo (i.e. by the end of this year). If we fly at least in one direction on JetBlue for each of those trips, it’s possible for us to get 7 qualifying destinations out them:
- New York, JFK: Easily obtained since it is on the way to or from most other JetBlue flights for us in Detroit.
- Boston: Also easily obtained as a way-point between Detroit and other destinations
- 3 European destinations: We would have to change our outbound plans for each trip to fly from JFK or Boston to Europe, but could return as originally planned. Ideally I’d find ways to book JetBlue Mint Business Class cheap enough for it to make sense. As I’ve written before, JetBlue Mint is really nice!
- Buffalo: We could fly one-way to Buffalo (via JFK most likely) for one of our two trips there.
- Detroit: As long as any of the above trips include a leg on JetBlue that returns us to Detroit, then Detroit would count as a destination.
12 more via the Caribbean…
Once JFK and Boston and my home airport are accounted for, it’s not easy to rack up more than 1 destination per trip since most flights go to/from JFK and/or Boston. Plus, I’m not a fan of flying a lot of extra legs if we can help it.
One approach we can use is to separately position to somewhere in Florida then fly JetBlue from a Florida airport to a Caribbean destination or Mexico, then fly back to the same or another Florida city, then separately fly home. For example, we could position ourselves to Orlando, fly JetBlue round-trip Orlando to Punta Cana. That would add two destinations to our count (Orlando plus Punta Cana). Even better, we could take advantage of the few short-hop flights within the Caribbean. For example, we could fly Orlando to San Juan, then San Juan to Saint Croix, then retrace our steps home. That would give us three destinations in one trip.
Let’s assume that I can cobble together 2 separate Caribbean/Mexico weekends where we add 3 destinations to each one, and 3 more weekends where we add 2 destinations. That would give us 12 more qualifying destinations.
The final 6…
Let’s assume that the final 6 destinations will require 6 more trips. Based on where family and friends live, and places we might like to go anyway, I could imagine flying to each of the following JetBlue destinations from Detroit, either through JFK or through Boston. We would probably return home directly on a different airline, when possible:
- Providence, RI
- Hartford, CT
- Washington, DC
- Charleston, SC
- West Palm Beach, FL
- Fort Myers, FL
We could also do longer distance flights towards the west coast, but that will mean first going east to connect in New York or Boston each time and will obviously make the travel much longer.
Is this realistic?
Beyond the travel we already have planned, the outline above would require that we find 11 more opportunities to travel. With 6 months ahead of us, that’s just shy of 2 additional trips every month. My wife works full time and her job isn’t nearly as flexible as mine, so that would mean being away pretty much every other weekend through the end of the year. But it’s actually much worse than that because our existing travel plans already dictate that we’ll be away for 7 or 8 weekends. So, we would really be looking at being home only one weekend per month through the end of the year. That sounds exhausting.
Back to the drawing board…
If my wife doesn’t want to do this epic mileage run with me, then I could probably plan trips where I do nothing but fly around on JetBlue for a few days and I could rack up maybe 4 to 6 destinations on each trip. Or I could go plant myself for a while at a hub like New York or Fort Lauderdale and fly back and forth each day to different destinations. Nope. I don’t want to do that. That sounds miserable.
So… I’m not ready to admit defeat yet, but I’m not sure what my way forward will be. This is one of those once in a lifetime opportunities that I’ll probably regret if I don’t do it. At the same time, I don’t really want to devote the rest of the year to JetBlue.
What do you think? Should I give up on this? Argue your case. Should I push forward? Give me ideas for how to make it happen with as little pain as possible. Please comment below.

I’m definitely considering this for the fun of it. First, I need to get from PDX to BTV via JFK later this month, but could do it the slow way.
Using {redacted} to help parse actual data and real flights that really exist, I think I could do this run:
Friday, position PDX to LAX (not jet blue, any will do).
Then… Friday LAX to FLL (jetblue, there are 4, any will do)
Saturday, FLL to CHS to BOS to SYR. (jetblue)
Sunday, SYR-JFK-BUF-JFK-RDU-JFK.(jetblue)
Sunday night JFK – BTV Delta flight for7500 pts, virgin atlantic.
I think this will net me 7 jetblue stops.
Greg, just as a heads-up it appears that you turned off comments on your article yesterday entitled ““New” Chase Sapphire Reserve vs Sapphire Preferred”. I wanted to respond to one of your readers who asked what benefits still exist for the old CSR card (for those who are grandfathered). I believe they are as follows (as I’ve wondered the same thing):1) 50% multiplier on Chase Travel
2) 3x on ALL travel
3) $10 Lyft credit monthly
4) $10 DoorDash credit on non-retail 2x/month and $5 credit 1/x month
For CSR Exclusive Tables it appears you get access to them to make reservations but you do NOT get a credit until October.
I believe the CSR deal on Peloton equipment expired. The Peloton $10/monthly credit on the subscription will start in October.
Would you be able to add this to your article yesterday? Of course, if I missed anything, please feel free to add. Thank you!
Thanks! I’ve fixed the comment issue. I’ll look into adding that info when I get a chance
I’m torn about this as I’m ORD based, but have free time to make this work and am hopeful that the points would become somehow useful on United as well at B6. Could also status match beforehand to Mosaic 1 to get free Same Day Switches and bring down prices. Question for regular JetBlue elites: if I’m on a PNR with P2, can I Same Day Switch the two of us at no cost?
Question, let’s say you did the challenge for 25 destinations. You would get it mosaic 1 for 25 years. If within the 25 years there was a status match from any of the other domestic airlines would the status match work? Being the bottom status I would assume you would get the lowest states for each airline you match to?
As someone who is never able to hit airline status could this worth it?
Yes it would probably be possible to do some status matching to bottom tier status over the years. In some cases, though, the airline asks to see proof of activity in the program that you’re matching from so if you haven’t flown JetBlue in a while, it might not work.
What brings you over to Buffalo? Any chance for a small meetup?
Visiting family. No, I don’t think I’ll have time.
Could this be a potential good use of either (1) CSR portal bookings at 1.5cpp (or 2cpp if you get the boost) or (2) using the Biz Platinum for 1.54cpp? My understanding is that B6 values pegs their miles to about 1.3cpp, so that may represent greater value than using cash (or regular points)? (Also possible that I’m way off here, the idea just popped into my head).
Definitely could be a good use, yes
I think you should do it. If nothing else to differentiate yourself from all the points and miles bloggers talking about it then sitting on their hands. Your existing plans will already get you about a third of the way there. Plus, a lot of us dream about such things but time, money, and location constraints conspire to keep it as a dream whereas we could do it vicariously through you. It would also make fun reading and show that you’re willing to have fun by doing this on a lark.
I love that image of Greg so much. Miles maximization math version of this meme

The JetBlue promo is more of a true challenge since FM does not create any of the rules.
I like the way you think! I went through the same thought processes and built up a trip that got close to 21 unique destinations but I had to backtrack some due to the hub and spoke system (I didn’t include Europe because I was trying to minimize cost and distance). For two of us it was looking to be around $5-6000 assuming we picked the cheapest flight options between two points. Ultimately, I gave up. Seems like quite a hassle and I already have other trips planned for this year. I like the idea of making it fun, like spending some time in the Caribbean, etc. If you do come up with something that you think will work I look forward to reading about it!
I am so glad this is not this years challenge. A bunch of content about flying JetBlue around the US is not compelling to me at all. JetBlue is a minor airline that has a very small network that we are all very familiar with.
Oh man — you or Nick have to try. This is awesome.
If FM is looking for suggestions for site functionality improvements, I would LOVE an option that auto-hides any comment containing “ChatGPT” 🙂
Ha! And while we are at it I would love an extension that blocks all the garbage AI articles that BoardingArea has been spewing out.
I booked JFK-BOS-MVY-DCA-PBI for 23,900 pts
As a one way?
I booked jfk- BoS mvy as one itinerary and mvy- dca – pbi on another
All same day
Think will do pbi – isp cheap to go home next day
I think the FM team should defer the currently planned team challenge a year and make a team challenge out of this unique opportunity now.
A refrain on the blog is how, in the miles and points game, one should be willing to switch plans when better opportunities arise. For instance, book a cancelable placeholder flight or hotel while keeping an eye open for a better option if space opens up.
We readers who agree with and have benefited from that approach would love to see the FM team make good use of it in this instance as well!
I would prefer this year’s challenge be “100K Vacay”, as this (the Jet Blue opportunity) is too similar to last year’s SAS challenge and less broadly applicable (mostly East US routes, w/ some Midwest / Europe / Caribbean, and only a couple of West Coast ones).
I’ll certainly enjoy reading about it if Nick and / or Greg decide to do it, but I agree that the current competition is more broadly applicable.
I like your thinking there but no, we’re sticking with 100K Vacay