Kate's on a Plane

My first sign-up bonus was 100,000 Chase Ultimate Rewards points from the Ink Business Preferred. Here’s how I used some of those points (and a few others) to book my very first* award trip. There’s an asterisk* because although this was the first redemption I made, it wasn’t the first points-funded flight I got to fly, not least of all because I didn’t even go on this trip!

My partner is from New York, and his family still lives there. His mom has long dreamed of taking our son to a Broadway show. So for Father’s Day, I cooked up a whole trip to send my partner and our son up to the Big Apple to see The Lion King on Broadway. I bought tickets to the show with cash, and here’s how I booked the travel for a holiday weekend in the fall.

Round-trip flights on JetBlue cost 22,000 points for the two of them. I cobbled together American Express points, Chase points, some Citi points that were lingering in my Citi account from my oldest credit card, a holdover from before I got into points and miles. Amex charges a small excise tax to transfer points to domestic airlines, so my out of pocket cost for the outbound flight was $19, including the excise tax and airline taxes and fees. Amex transfers to JetBlue at a 5:4 ratio, so I had to transfer 13,000 MRs to get the number of JetBlue points I needed. The return flight was just the usual $5.60 per person, since I booked the return flights with Chase and Citi points.

The cash cost for these flights would have been $375 round trip. JetBlue award flight prices are always correlated to cash prices for the same tickets, so the value here is pretty predictable. I rebooked these flights several times, and at one point the cost was as high as 34,000 points, but I got about one-third of those points back by monitoring cash prices and rebooking when they went down.

My partner has since gotten the JetBlue business card, and one of the benefits of this card is a 10% rebate on award bookings. It remains to be seen whether or not he will get 2,200 points back after the trip, because I originally made the booking under my JetBlue loyalty account. When I posed this question to a JetBlue customer service rep, they said that we wouldn’t get the rebate, but if there’s one thing I’ve learned in this hobby, it’s just how often customer service reps are wrong. 

I transferred points from Chase to book one night at the Hyatt Place New York Midtown/South for 20,000 points. At the time I booked it, the cash price would have been $601. This represents a value of 3 cents per point, which is pretty good! I sent an email about a week ahead of time requesting an upgrade, which was granted. My partner, son, and mother-in-law were treated to this view of the Empire State Building from their room.

The total cost for the flights and hotels for this trip would have been almost $1,000. My out of pocket cost was $30.20.

This is a trip that wouldn’t have happened any other way. Because we have family on Long Island, we would never spend the money to actually stay in the city. Not having to pay for flights freed up money for me to get them excellent tickets to the show. It was worth every point and every penny to be able to gift this trip to my partner for Father’s Day.