This is an as-told-to essay based on a conversation with Steve Carroll, a New York-based nurse practitioner who chased JetBlue’s “25 for 25” challenge to earn 350,000 points and Mosaic status for 25 years by flying to 25 unique cities by December 31. It has been edited for length and clarity.
Breakfast in Massachusetts, lunch in DC, dinner in Orlando, and back home by midnight. That was one of the epic days that my 10-year-old son and I recently flew — all for JetBlue Airways’ “25 for 25” challenge.
It’s been thrilling to plan and execute these trips, with layovers so tight we sometimes barely had time for a bathroom break. Finding a flourishing community chasing this challenge has been one of the best parts.
The promotion, created for JetBlue’s 25th anniversary, is simple: Fly to 25 unique cities in the airline’s network between June 25 and December 31, and you’ll earn Mosaic 1 status for 25 years plus a lump sum of 350,000 points.
There are some rules: You must connect your loyalty number to each flight; basic fares don’t qualify; flights must be operated by JetBlue (not its partners, such as Cape Air); and only arrival airports count.
Still, I realized it could be an unforgettable experience for my son Jackson and I. He already loves JetBlue (I think the TV screens do it for him), and his 100th flight ever was on JetBlue; we celebrated with cookies on the plane.
Courtesy of Steve Carroll
Plus, Mosaic status until age 35 means he and his friends could enjoy the perks — like free bags, complimentary drinks, dedicated security and check-in, early boarding, and seat upgrades — on future spring break or summer trips in college. (Editor’s note: You must be a Mosaic 3 member or higher to receive complimentary Mint upgrades and a Mosaic 4 for lounge access when JetBlue’s open in late 2025.)
The math also checked out. Completing the challenge would earn each of us a reward of 350,000 points, at least $3,500 in travel apiece, plus the additional points earned from our flights.
Combining the cash I’d have to pay plus the 100,000 JetBlue points I already had, the whole challenge would cost around $7,000, but I’d essentially be reimbursed in points.
I started the challenge already holding Mosaic, but securing long-term status gives me more freedom to put everyday spending on other cards and build points with brands like Hyatt via Chase.
JetBlue’s new partnership with United Airlines also means I can tap into reciprocal benefits on United — an attractive perk since we live close to the airline’s Newark, New Jersey, base.
To maximize our time, we mostly fly on weekends and sometimes take up to five flights across a Saturday or Sunday. We’ll end up taking closer to 35 flights overall because of the overlap at some departure and connecting airports.
Our flights so far stretch west to Los Angeles, north to Portland, Maine, and south to Fort Lauderdale. We’ve also checked off airports like Cleveland, Norfolk, Detroit, Pittsburgh, Manchester in New Hampshire, Raleigh in North Carolina, and Buffalo in New York.
Courtesy of Steve Carroll
Our most ambitious weekend was over Veterans Day in November, when we planned 18 flights and 11 new cities. The government shutdown, however, canceled five of them, but we managed to rebook and still add several new destinations.
Aside from those cancellations and a huge delay that forced us to postpone a trip, the challenge has been remarkably smooth. And we’ve met a great community of people also clamoring for 25 years of Mosaic status.
We recently flew in Mint business class to Los Angeles as our 23rd city and plan to complete the challenge on December 8 in Fort Myers, with about three weeks to spare.
Piecing together itineraries is like a game of Tetris
I already had a few JetBlue trips on my calendar to start, but then I created a master list of airports in the Northeast along with their city pairs. I live just north of New York City.
The goal is to create snaking routes that efficiently hopscotch across the US; we’re trying to avoid international flying. I’d sit up in bed when I couldn’t sleep and just map out my options.
Over time, I’ve figured out a few tricks: book one-ways, sit near the front, and choose the first and last flights of the day. Most fares average about $100 per person.
I have lounge access to make longer layovers easier, though I occasionally book “illegal” itineraries with very tight connections. Connecting airports, regardless of the time spent there, count as unique destinations.
Courtesy of Steve Carroll
But, before I risk it, I check the historical arrival times. One trip I planned included a 12-minute layover at New York-JFK, but we still made it because our flight from Hyannis, Massachusetts, landed half an hour early, as expected.
Weather-tracking helps, too. I adjust my flight if I anticipate a disruption, which my status allows me to do for free. An unofficial tool called “25for25.ai” has also been helpful; you can plug in your starting point and block destinations you’ve already hit.
Living in the New York area makes the challenge far more doable. Airports, like White Plains, LaGuardia, Newark, New York-JFK, and Islip on Long Island, are all considered separate, unique cities.
New York-JFK and Newark are especially useful since they offer so many connections. There’s also Hartford, Connecticut, and Philadelphia nearby. That’s seven of the 25 we could just drive to.
Smaller airports like Nantucket and Martha’s Vineyard in Massachusetts require more creativity because they offer limited frequencies.
One of our biggest travel days began in White Plains, New York, where we flew to Nantucket and had breakfast in town. We then headed to DC for lunch at the airport, and finally to Orlando for dinner, also at the airport.
My partner joined us on that trip, making it a family day in the skies. We crossed paths with about 15 other challengers on our legs to DC.
There is camaraderie in the challenge
What has been extremely helpful is the dedicated Mosaic Facebook group, where other participants in the challenge share routes and road warrior stories. It’s not hosted by JetBlue.
The challenge has fostered a vibrant and supportive community. (Editor’s note: JetBlue told Business Insider that over 500 people have completed the promotion so far.)
My son and I sometimes see other challengers on our flights and will eat lunch together in the airport between legs. We helped a family of four explore the town during our layover in Nantucket.
We exchange numbers with almost every person we meet so we can stay in touch. I didn’t expect to find such a large and enthusiastic community, but it’s become one of the best parts of the challenge.
I have a little tag on my bag that somebody made for me that says ‘JetBlue 25 for 25.’ When people see it, they’re like, ‘Oh, you’re doing the challenge.’
It’s been nice getting help along the way, and I appreciate being able to help others, too, cheering them on as everyone scrambles to finish by the holidays.
