Saving Miles Rebooking Flights

In March, my wife and I will be going on a week long family vacation cruise in the Caribbean, leaving from New Orleans. Ever since knowing we were going on a cruise, I have been obsessively planning our flights and hotel stay. I want the best deal!! We decided we were going to book 2 extra tickets, for my wife’s cousin and her new husband as wedding gifts. I’ll give a detailed breakdown of everything in a future post.

In October, I was able to book 4 roundtrip tickets from Boston to New Orleans on Southwest for a little under 80,000 miles. My miles were originally Ultimate Reward Points that I transferred from my Chase Sapphire Preferred account over to my Rapid Rewards account. Those flexible points are so valuable!

While most airlines charge a fee (it can be a hefty fee!) to change your itinerary on award or paid tickets, Southwest does not. This is extremely valuable, because you are safe to book your tickets immediately and if you find the flight cheaper, you can simply cancel and rebook. So, don’t be afraid to book your flight on Southwest once you decide on a trip!

Since I originally booked this flight, I have kept an eye on the prices of flights and was hoping prices would fall. There’s a smaller airport north of Boston that is closer for us, but usually cost a little more to fly from, that I was watching as well. Since October, the cost of flights haven’t really changed, but I was able to find a better deal today and jumped on it!

As I was checking flights from the Southwest App, I saw I could book flight from Manchester to New Orleans for less miles and prevents me from driving the hour to Boston (I hate driving in Boston!). It was only going to cost 7,944 miles per person to fly from Manchester to New Orleans. When booking the return flight from New Orleans to Manchester, it was 11,330 miles per person. It was going to cost less than 20,000 miles total per person! That’s a good deal to me!

My Phone Search from MSY-MHT
My Phone Search from MSY-MHT

It just so happened that when I went to rebook the flight, I noticed I only selected 1 passenger, oops! When I changed it to 4 people the price suddenly changed to 12,633. That’s a 5,200 mile (roughly $80-$85) difference overall for all 4 people flying! So I took a screen shot and decided to call and see why the price changed.

Price Difference Moments Later!
Price Difference Moments Later!

It was the first time I have called Southwest, but I was pleasantly surprised when someone picked up in 20 seconds. I was definitely expecting to be on hold for while.

When I told the representative what happened, he told me that there were only 3 seats left available at 11,330 miles. I quickly did the calculations and realized I would still be saving over 1,000 miles. Coupled with the time and cost saved by not driving to Boston, even with the slight increase for the 4th person, I decided to do it. I told him I wanted to book the 3 remaining seats at the 11,330 mile cost and the 4th ticket would be at the 12,633. I had all my information ready, flight numbers, layover locations and times of the flights. He was able to change this in a matter of minutes.

When it was all finished, I immediately had a little more than 1,000 Southwest miles refunded to my account. Currently, the total cost for 4 roundtrip tickets is 78,399 miles and $44.80. The total out of pocket cost would have been close to $1600 for 4 tickets!! There is no way I would have spent that much money for those flights! Thankfully, we have accumulated enough points and miles to only pay taxes and fees!

I’ll still keep an eye out for the cost to possibly (hopefully) drop again. If it does, I’ll be re-booking the flight once again.

Do you keep an eye out for price changes? Have you been able to re-book your flights and save money or miles?

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