My Huge Delta Upgrade Gamble Paid Off & What Those Flights Got Me!

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Delta Upgrade Gamble

Delta Upgrade Gamble

Last week I wrote about a gamble I took for my vacation to the Bahamas. No, the gamble wasn’t staying at Atlantis (although I think I lost on that one), but it was in hoping my daughter and I would score a first class upgrade on our flights to Nassau with my matched Delta Platinum status.

As a temporary Delta Platinum Medallion (I will drop to Silver when my Delta status challenge ends) I am eligible for a complimentary upgrade for myself and one companion. The problem was that my wife, daughter and I were all traveling together meaning someone would be left out. Additionally, if I booked all three of us on the same reservation then none of us would get an upgrade.

Paid First Class Was Actually Cheap

The one interesting thing about my flights was that paid First Class was not too much more than economy because there were tons of seats open. I knew there was a good chance based on this fact that I would get an upgrade along with a companion so I didn’t want to pay up.

Since I wanted us all to travel together though my gamble was to book my wife into First Class. This was the perfect plan on the surface since she would be happy either way (happy wife happy life), but it had some potential pitfalls. Mainly, our upgrades might not clear and my daughter and I would be sitting in the back for our long redeye flight.

Indeed as the flights got closer the First Class seats began to disappear. My Platinum status entitles me to upgrades as soon as 120 hours out, so I was on pins and needles as that date approached. Would my upgrades clear at 120 hours or would I have to sweat it all the way until we got to the airport? Thankfully the news was good.

Our Upgrades Cleared As Planned

delta upgrade gamble
Not a better email to get!

Despite there only being a few open First Class seats on both our LAS-ATL and ATL-NAS flights, our upgrades cleared for both legs right at the 120 hour mark. Better yet our seats were assigned together and in each case I was able to move my wife to across the aisle from us. My crazy plan worked exactly as expected.

While this story certainly is one that applies to me, it is a good example of how status matches, splitting up bookings, reading all terms closely and/or monitoring flight load levels can really pay off in the end. Yes, the 3 1/2 hour redeye to Atlanta that landed at just before 3am West Coast time sucked, but it sucked just a bit less because of those First Class upgrades. We did spend a few extra points to buy up my wife to First Class (I booked her flight with Chase Ultimate Rewards), but that allowed us all to fly up front without anyone feeling left out or cramped.

delta upgrade gamble
Ellie made great use of the space on our flights to sleep! 🙂

Locked In Status Through 2021

While everything went my way this time, I was completely alright with having to fly in the back, because I have learned that isn’t always the case. Things do seem to work out more often than not, but when making these types of grand gambles one must be willing to take a loss. I’ve been fairly satisfied with my Delta flights and my Platinum status. While I will lose the status, this flight locked me into Delta Silver status through 2021 and hopefully that will be good for something?!?

Can you think of a time you made a similar gamble and it didn’t pay off? Share your story in the comments!

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