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 booked JFK-BOS-MVY-DCA-PBI for 23,900 pts
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!
ChatGPT did it in 3 sec. Not sure if it’s right:
Leg
From → To
Destination #
1
JFK → BOS
2
2
BOS → ORD
3
3
ORD → DFW
4
4
DFW → DEN
5
5
DEN → LAX
6
6
LAX → BUR
7
7
BUR → SAN
8
8
SAN → PSP
9
9
PSP → PHX
10
10
PHX → BZN
11
11
BZN → HDN
12
12
HDN → ORD
(waypoint)
13
ORD → BNA
13
14
BNA → MSY
14
15
MSY → FLL
15
16
FLL → MIA
16
17
MIA → NAS
17
18
NAS → AUA
18
19
AUA → PUJ
19
20
PUJ → SJU
20
21
SJU → DCA
21
22
DCA → RDU
22
23
RDU → PIT
23
24
PIT → PVD
24
25
PVD → PHL
25
See the numerous comments on this post and Stephen’s original post full of non-existent routes generated by ChatGPT.
I should’ve read first. Just as a first reaction I thought this would be really good for AI to figure out. Many others beat me to it!
Your route map is very inefficient.
1) All the northeast airports are easy to transit between via amtrak or car. So LGA, ISP, ORH, PVD etc. should all be in your route map somewhere. BUF and ROC are easy to get between so if you’re going to Buffalo anyways, seems obvious to check off ROC
2) Your Puerto Rico strategy is completely misplayed. It’s a tiny island and 3 airports are served there, so you should not be flying into and out of the same airport. And SJU flies to way too many unique destinations to flying into/out of TPA/DCA. One obvious example is to not waste 4 “easy” airports (MCO, TPA, EWR, DCA) on SDQ and SJU since you can just fly between those 2 directly.
Something like MCO –> PON//SJU –> SDQ –> EWR gets you an extra destination (PON) while still leaving TPA and DCA to use elsewhere in your routing
Departure airports don’t count. So if you fly into BUF and bus to ROC to fly out, you aren’t getting credit for ROC, so it’s the same thing as if you had flown back out of BUF. Similarly flying MCO-PON//SJU-SDQ-EWR only gets you three (PON, SDQ, and EWR), as you wouldn’t get MCO or SJU because you aren’t flying into them.
Why are you going to Buffalo two times? Most tourists just come here to see the falls, or to go to Rochester with their kids for a daytrip to the museum of play (ROC also has Jetblue flights so if anyone is planning the challenge it’s worth visiting that museum it’s really impressive).
Anyway when you’re in BUF make sure to check out Wingnutz, it’s the best Buffalo wing place, don’t go to Anchor Bar or Duffs, those are for tourists!
Anyone who thinks this would be torture in economy should read about the United FF who did 3 or 4 million miles in a few years. Imagine US- Singapore 95x in economy as just ONE route of many.
I’m wondering, with an entire family, how many times someone in the family would pick up an illness on a flight. I think that’s how I got bacterial meningitis.
I think FM should do it, if only for the content. But having Nick do it might be good enough for that purpose.
As for the cost/benefit, I think the points have a reasonable chance of surviving any purchase / merger — say 50/50 chance that the points will be around in some form for 5 to 10 years (but, of course, their value is likely to go down over time). They might even get a little more valuable if they transfer one-to-one to whatever airline picks over JetBlue’s corpse. I doubt the 25 year status guarantee would survive a merger, so you might be better off there if JetBlue remains independent but grants some status benefits on United from the partnership.
If you can do the challenge for $5,000 and consider that as a straight up purchase of points, then you’re paying 1.43 cents per point, more than they’re worth. I know it’s possible (in theory) to do it on awards for fewer points than you’d earn, but not that much fewer that it would be a huge win. The question is how much you value your time. If you simply love being on airplanes, or if you travel full time and can be in any JetBlue destination for whatever you do, or if your job is being on airplanes and writing about it, it might make sense. But if this is going to have to come out of weekends and work time, I can’t see how it adds up.
But if you pick 15k miles as your annual Mosaic1 bonus then you’d get additional 375k points over 25 years bringing your cost down to 0.69 cents. Plus you’d have some points earned from actual flying (unless you go on awards).
I’m not willing to assign a value of 1.3 2025 cents to a notional 2050 JetBlue point. Not sure how to value that particular item, but I think the odds of that benefit surviving for 3 years, let along 25, are pretty slim — even in the unlikely event that United grants 25 years of silver status when it absorbs JetBlue the Perks You Pick program won’t survive.
But even at a greatly reduced rate of, say, 0.75 cents per point while I might buy some JetBlue points at that rate for cash I wouldn’t give up all that time (and opportunity cost to rack up EQMs on other airlines) plus the cash.
Do flights sold as JetBlue flights but operated by someone else (e.g. BOS-ACK on Cape Air) count for this?
No.
Stephen’s post has all the detailed rules. Those flights would not count.
Is there any way to find all the JetBlue flights that are served by 2 or more different airports? That way you wouldn’t need to backtrack and would pick up multiple destinations.
According to ChatGPT:
Here are the JetBlue origin airports that serve two or more distinct destinations, listed by their airport codes:
• JFK (New York–John F. Kennedy)
• BOS (Boston–Logan)
• FLL (Fort Lauderdale)
• LAX (Los Angeles)
• EWR (Newark)
• LGA (New York–LaGuardia)
• MCO (Orlando)
• BDL (Bradley–Hartford)
FLL, JFK, BOS are hubs have the most flights
SJU and MCO seem to have the 2nd most destinations
Many Northeast cities fly to 5 or so Florida airports
It doesn’t seem like ChatGPT is very good for this kind of thing right now unfortunately as it hallucinates so much by either coming up with information it makes up entirely or by being incomplete. I’m sure it’ll get better over time, but for this kind of function right not it’s too unreliable.
e.g. There are many other cities flying to 2+ destinations such as DTW, TPA, SJU, DCA, SDQ, CUN, SFO, etc.
Yes, you are definitely correct. I was hoping it would provide an exhaustive list of city pairs, but I was not able to get that info with my prompts.
Are you considering flying from London to the US on JetBlue to partake in this challenge?
I’m afraid not. It would be a really fun challenge to do, but I wouldn’t be able to get much use out of the JetBlue points and status in the next few years, so it wouldn’t be worth it unless we were doing it as part of an official FM challenge. I don’t think I flew JetBlue in the 15 years that I lived in the US, so it sadly doesn’t make any sense to do the challenge right now.
It’s a shame though as it would be fun. If we’d ended up moving to the Finger Lakes, NY which had been our plan previously, I might’ve been more inclined to seeing as that would’ve been an hour from Rochester and Syracuse that are both served by JetBlue, plus the NYC airports would’ve been drivable.
Bummer. Being near SFO, there is not a lot of JetBlue flights on the west coast. I think I’ve only flown JetBlue less than 5 times in my life, but somehow I manage to have about 180K JetBlue points in my account from CC sign up bonuses and points pooling.
Maybe British Airways or Virgin Atlantic will have a similar promo and you will be in the right place at the right time 🙂
Yep, I’m curious if BA will try to do something similar. It sounds like a lot of frequent fliers in the UK are really disappointed with BA’s recent changes to earning status and have been booking with other airlines. If that has a material effect, I can see BA launching some kind of challenge like this to get in on the action and try to win customers back.
To be fair this seems like a pretty hard challenge for a general-purpose model to handle. It would need a lot of domain-specific knowledge (like code sharing, schedule updates, partnerships, co-terminals, etc) to answer these kinds of questions.
Greg I’d consider crossing off more unique stops by self-positioning to some nearby airports (via one-way car rentals or other cheap flights/trains). For example it looks like Jet Blue has a Boston to Traverse City flight – while that is considerably further from Ann Arbor than Detroit, maybe you can tie it in with a stay at the Inn at Bay Harbor? Or get a cheap Delta flight back to Detroit. Jet Blue return flights to Cleveland and Chicago would you put similar distances from home. If you don’t mind the stops to visit those places along the way back that knocks another 3 destinations off your count.
There are similar opportunities to fly back from Florida on Jet Blue to a different destination if you live in the Northeast (flying back to Worcester instead of Boston, or Long Island instead of New York). But that seems rather circuitous for a return to Detroit.
Nantucket is also interesting for something like DTW->BOS->ACK->HPN/LGA all on Jet Blue and then take Delta direct back from either White Plains or LaGuardia. That would be another two destinations without as much flight time as one of the trips to Florida.
Fitting things in a weekend is where it gets tricky – I’m not sure how “fun” these extra stops or distances will be in only two days!
Great ideas!
The NYC- ACK-HPN is a great one as ACK is only northeast airport in which you can book from HPN . i have already booked this itinerary with a few extra legs
i should sat to HPN
Curiously absent on this Jet Blue offer is a Founders Card membership.
LOL
Actually, it’s a Perks You Pick choice, so you can get a Founders Club membership through this challenge.
Cancel your other “challenge.” This is it.
I agree. You can always do the other challenge next year. Win – win!
I think they should combine the challenges. Extra points in the existing challenge for accruing the most JetBlue destinations as part of the trip.
I have a strong feeling you or someone on this site will go for it regardless of what we think!
That being said, I think it’s really hard to justify this challenge unless you live near their hubs in the Northeast or Florida. Not living in those areas, I’ve only ever flown Jet Blue twice in my life, as it’s rarely the most convenient option.
Sure, they may get acquired by United or someone else, but they may just as easily not. Just look at Spirit and Frontier’s on again, off again disaster of a merger. I don’t think anyone should participate for the main hope of them getting acquired, as that’s just an expensive gamble.
Just looking at the value of your time, it’s hard to justify this even if you live in one of the hubs (which I do).
I originally thought we’d bring the whole family and use lap infant tickets, but a JetBlue supervisor said those don’t count—so our toddler would need his own seat. Realistically, bringing them sounds way more stressful than going solo, and we don’t have anyone to watch him. With five family trips already left on the calendar for the rest of this year, it’s a tough sell.
That said, I’m based between FLL and PBI, I have the transferrable points available, and I work for myself—so if I stick to same-day trips (avoiding overnights,) I’d love to find a way to make this work without building too much resentment at home. The hardest part is convincing my wife to stay back with a toddler while I fly around chasing destinations. (Her best friend works for JetBlue… maybe that earns me some grace? Lol.)
I’d love any thoughts on how to pitch this in a way that doesn’t sound totally selfish or crazy. Also curious how others are thinking through the math—since you can’t book Blue Basic awards and still have to pay taxes/fees, there’s some cash outlay here. Even using points efficiently, is Mosaic 1 for 25 years and the 350K bonus really worth it after the points/cash spent? I usually book with points anyway, and rarely is JetBlue the best option with points. Also as you mentioned, if JetBlue does get acquired by United later, is it probable they’ll even honor decades of status?
Excited to hear what others are thinking—and good luck to everyone going for it! We should come up with a way to recognize/signal each other in-flight haha. Feels inevitable that a few of us would cross paths mid-challenge.
From what I’ve found, we should be able to do it for ‘free’ by booking awards flights. Just need to average less than 14,000 miles per new airport and the miles earned will equal miles spent.