Pro Tip of the Day

Fly the Challenge Virtually Free with TrueBlue Points

Here's the ultimate hack that could make your entire challenge essentially free: use TrueBlue points to book your flights instead of cash. JetBlue allows you to book flights with either cash or points, and crucially, both count toward your 25 destination requirement. Award flights are fully eligible for the challenge.

If you have the JetBlue credit card, you automatically get 10% of your points refunded on every award redemption. This means every 10,000-point flight only costs you 9,000 points net. Combined with the 350,000 bonus points you'll earn upon completing the challenge, you could theoretically complete the entire journey paying only the $5.60 TSA security fee per flight. If you don't have the Jetblue Card, consider getting it.- right now they are offering an 80,000 point bonus for new members! And if you're traveling with your spouse - have them get a card too - that's 160K points to use! A good friend of mine, "The Queen of travel hacks", Kerry, taught me this hack...once you get the personal Jetblue card, each of you apply for the business card too that's another 160K points for a total of 320K points! Ultimate hack, you get the credit card first, then refer your spouse, you'll earn and extra 10K points, then have them refer you to the business card - they get an extra 10K points - for a grand total of 340K points + the 700K points you'll earn in this challenge.- you earned over 1Million points!

The math is compelling: even if you spend 200,000-250,000 points completing the challenge, you'll earn 350,000 points back upon completion, plus the 10% refund from the credit card, plus any base earning from flights you do pay cash for. Many savvy challengers front-load their points spending early in the challenge, knowing they'll more than recoup their investment. Remember, after 15 destinations, you earn 150K points. So about half way through, you will reload your account to complete the challenge!

This strategy works particularly well for shorter domestic routes where award availability is typically good and point costs are reasonable. Save your cash for international flights or longer routes where award availability might be limited, but use points liberally for those short hops between East Coast cities or quick jaunts to the Caribbean.

The result? What appears to be an expensive travel challenge becomes essentially free flying, with 25 years of elite status as your reward. It's the kind of value proposition that makes the JetBlue 25 for 25 Challenge irresistible for points-savvy travelers.