Airplane in the sky


Our honeymoon is really coming together! So far we have all of our flights and most of our hotels booked. We chose to fly in and out of JFK because of the superior award redemption options (Japan Airlines First Class and Singapore Suites), but we needed to get ourselves from Boston to JFK and back.

Getting to JFK

Crowne Plaza JFK
Starting the honeymoon of early!

We are flying to Tokyo on Thanksgiving morning which is obviously a hectic time at airports. I was nervous to fly from Boston to JFK on Wednesday night or Thursday morning in case of Thanksgiving-related delays. I guess the title of this article is a bit of a misnomer because we decided to drive to JFK instead. I’m sure the traffic will be bad on Wednesday night too but we’re planning on leaving late at night to hopefully avoid it. The cost of the rental car is $95.72 which adds to our out-of-pocket expenses slightly. We saved $208.16 by redeeming 35,000 IHG points for a room at the Crowne Plaza JFK that night.

Getting Back to Boston

After our luxurious Singapore Suites flight, we’ll be slumming it on JetBlue to fly back to Boston. We used 15,000 JetBlue points to book these flights. We paid $11.20 in taxes and an additional $2.55 in excise tax fees since I transferred 4,250 points from American Express Membership Rewards. This flight was worth $230.40 at the time of booking.

As with any positioning flight booked on a completely separate itinerary, we run the risk of missing our flight back to Boston if the SIN to JFK flight is delayed or any reason. It’s less risky on the tail end of the journey since it won’t mess up our vacation if we miss this flight…all we’ll miss is more work!

Final Thoughts

While flying directly from your home airport is usually the most convenient option, it sometimes makes sense to book a positioning flight or rent a car to go to a larger airport where you can get better award flights. We’re excited to fly first class for the first time, and this was only possible by positioning ourselves from Boston to JFK.

Honeymoon Stats

Points spent: 1,219,000

Total value: $66,780.97

Out-of-pocket cost: $1,722.23

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