How I completed JetBlue’s viral 25-for-25 challenge for under $3,300

I’m no stranger to doing ridiculous things in the name of points and miles.

But with a one-year-old daughter at home, I can’t just drop everything and fly when award space suddenly opens up or someone spots a mistake fare.

That’s why I loved JetBlue’s 25-for-25 challenge from when it was announced in June.

The premise was simple: fly to 25 unique JetBlue airports by the end of the year and earn 25 years of Mosaic 1 status plus 350,000 TrueBlue points.

Being based in New York City helped.

I had access to five nearby JetBlue airports and a large chunk of the airline’s route network. After crunching the numbers, I realized I could come out ahead by strategically flying JetBlue for the rest of the year.

Here’s how I pulled it off.

Related: 3 quirks United and JetBlue should fix in the ‘Blue Sky’ partnership

Organic flights

The first step was easy: shift as much of my already-planned travel out of New York to JetBlue.

So when I went to preview the new United Club in Denver and San Diego’s new Terminal 1, I flew JetBlue to both.

Things got more creative in Salt Lake City. I had two back-to-back trips there. One to see the Delta Sky Club and another for the Amex Centurion Lounge.

On the first trip, I flew JetBlue to Las Vegas, then booked a Delta flight from Vegas to Salt Lake City (in a middle seat, no less).

On the second, I flew JetBlue nonstop to Salt Lake City.

Basically, doing everything I could to organically check off as many JetBlue destinations as possible. (Ironically, that Delta flight from Vegas to Salt Lake City cost more than the JetBlue flight from New York to Vegas.)

Even better: because I was employed by The Points Guy, I wasn’t personally on the hook for these travel expenses.

All told, I knocked out 12 destinations using trips I already had on the calendar through year-end.

A status “run” (or two)

To close the gap to 25, I planned a few status runs. Basically, flying around the JetBlue network purely to rack up new-to-me destinations, without ever leaving the airport.

Initially, I assumed I’d do one big run, earn the points awarded at 15 destinations, and use those points to offset the rest of the challenge. (That assumption turned out to be wrong. More on that below.)

The first run was wild, even by my standards.

I flew for 36 straight hours, through the night, with the longest connection being three hours in Nantucket — stop number two.

The routing went like this:

• New York → Boston → Nantucket → Washington Reagan National → Orlando → Santo Domingo → Fort Lauderdale → Cancun → Tampa → Westchester County

I had an “overnight” in Santo Domingo (aka just three hours), spent sleeping upright in a brightly lit Priority Pass lounge, blasting Caribbean music. (I use Loop Engage earplugs when I travel.)

I was even scolded for trying to put my feet up on the chair next to me.

Fortunately, I did this run with my buddy Sam Hollander, the CEO of Autopilot, which made it far more tolerable than doing it solo.

The goal was simple: maximize the number of unique JetBlue destinations in 36 hours while minimizing out-of-pocket cost. (My scripts crashed plenty of times trying to make it work.)

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By the end of that run, I had visited 12 destinations. By mid-September, I hit 15, thanks to two more from San Diego and a trip home to Florida for the Jewish New Year.

Related: Watch my first status run recap

A miscalculation

At that point, I thought I was in the clear.

Hitting 15 destinations earns the lowest prize tier of the challenge, 150,000 TrueBlue points. I assumed those points would post within a few weeks (after all, this is JetBlue IT), and I’d use them to cover the remaining flights.

Then I posted about this strategy on Instagram, and JetBlue’s brand account replied.

Turns out, you only earn one prize after the challenge period ends. You don’t receive the incremental rewards at 15 or 20 destinations.

That was a pretty big misread, especially for someone who enjoys poring over terms and conditions, but by then, I was committed.

So yes, I’d be paying (or redeeming existing points) for the remaining segments. And then came the sneaky mid-challenge devaluation.

But at this point, I was too committed to stop, so I kept going.

Another status “run”

By early November, I was at 20 destinations. I had one more booked for winter break and needed four additional airports to reach 25.

That meant one more run.

This time, I planned another 36-hour itinerary, but with a nine-hour overnight at an airport hotel instead of the terminal floor.

The plan was to arrive in Providence around midnight and depart the next morning for San Juan.

Naturally, I ended up booking during the peak of the government shutdown, and every single flight on this run was delayed by at least an hour due to FAA staffing.

The good news was that because everything was delayed, I didn’t miss any of my (even-tight-for-me) connections, including a 23-minute turn in San Juan.

The other silver lining: the Fairfield Inn near Providence Airport was so mediocre that I didn’t mind only sleeping three hours, fully clothed, above the sheets.

That run ended in Hartford, the closest JetBlue airport to New York that I hadn’t yet visited. I originally planned to take public transit home, but after the delays, I Ubered instead.

Hands down, the best money I spent during the entire challenge. I passed out for the two-hour ride.

Related: Watch my second status run recap

Only one “extra” flight

One thing I’m especially proud of: I’ve flown JetBlue 26 times since July 17, meaning I’ve only taken one flight that didn’t count toward the challenge.

That meant I could still requalify for United Premier 1K and American Executive Platinum on other trips, but more on that in my upcoming year-end recap.

Even better, that 26th JetBlue flight was unavoidable. I flew from San Juan to St. Croix, and the only way to get back to San Juan in time for my Hartford flight was to take the same aircraft back.

Total stats and my itinerary

If you made it this far, you’re probably interested in the full itinerary and how much each segment cost me out of pocket. I’ll break that all down below.

And if you completed the challenge too, let me know how you approached it in the comments. I loved running into other participants along the way.

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