EXTREME? I Had Five Different Tickets Booked For Our Flight Home This Week

It still amazes me how much a seemingly small change during the pandemic has come to my rescue so many times.  Near the beginning of the pandemic virtually all US airlines eliminated change fees.  United went first, Delta and American quickly followed suit.  At the time it wasn’t something that moved the needle because nobody was traveling.  But, I had the sense then that this would be a big deal.

One of the biggest benefit to elite status was the ability to reduce or waive some fees that airlines typically charged.  At the highest levels of status many of those nuisance fees were reduced to zero.  The move by airlines to eliminate change fees took away one of the most valuable benefits of top-tier elite status, especially in an environment where free upgrades to first class are virtually nonexistent.  But, that change also democratized one of the key strategies I use when I travel.  Booking multiple tickets without any penalty to change/redeposit opens up options for folks who only travel occasionally.  Here’s a brief look at how and why I booked four sets of backup flights to get us home earlier thi week.

Delta Connecting Flights

I had been searching for an alternative to our scheduled United flight the following morning.  My searches had started with American Airlines since they operate Orlando (MCO) to Washington-Reagan (DCA) nonstop.  DCA isn’t the closest airport to home, IAD is.  But, it’s close enough.  Since I couldn’t find any American nonstop flights my next option was Delta connecting flights.  With a healthy stash of Delta SkyMiles, I found a connecting flight that left around 7pm, passed through Atlanta (because, Delta) and got us into DCA close to midnight.

American Airlines Connecting Flights

I wanted a backup option in case something went wrong with our Delta flights, and I was still hoping to get us home a bit earlier.  It would take us an hour to get from DCA to IAD to pick-up our car, so we wouldn’t be home until after 1 am.  I managed to find a connecting flight out of MCO that took us to Miami and then finally on to DCA.  That flight landed a bit after 10pm.  Still not perfect, but better.

JetBlue Nonstop to DCA

One of the strategies I use when searching for awards is to look for fewer seats than I need.  We always have the option of splitting the family up into groups of two (one parent, one kid), but I also use this approach because inventory is fluid.  While I was feverishly checking for nonstop options I found two seats on a nonstop flight from MCO to IAD.

As it turns out, it was a JetBlue flight.  American only had two seats but JetBlue has more of a revenue-based program, so I was able to grab four seats from JetBlue using some orphaned points I had there.  You can also transfer Chase Ultimate Rewards points and American Express Membership Rewards points to JetBlue’s TrueBlue program, though I don’t think it’s a great value.

At any rate, a 6pm-ish MCO-IAD flight was perfect for us.  We’d have time to visit with friends in Orlando and still be home in our beds before midnight.

United, Just In Case

I still had my original nonstop flights home the following day on United in case things went sideways.  But, I figured it was worth trying to have a United option in my back pocket for our preferred day of travel.  I couldn’t get the United app to ticket what I needed, so I had to call the 1K desk.  The agent I spoke with found me a more affordable option that connected in Chicago and ultimately had us ending up at IAD.  It left a bit earlier than I wanted, but I grabbed it just in case.  And, I’m really glad I did.

Five Flights, What Could Go Wrong?

Two United, A JetBlue, An American and a Delta flight.  The first domino to fall was the Delta flight.  The Flighty app (my favorite travel tool right now) alerted me that our outbound Delta flight from MCO to ATL was delayed.  That would likely mean we would misconnect in Atlanta and be stuck there overnight.

No problem, the JetBlue was really our primary option.  I went ahead and canceled the Delta flight since it wouldn’t be a viable option.

At this point, we were having lunch with a dear friend.  Once again, my phone lit up with a Flighty notification.  This time, our JetBlue flight was delayed four hours.  Yikes!  It was time to pay the check and move quickly to the airport.

We had plenty of time to make our American flight without rushing, but time was running out to make the United flight.  At that point, I leaned towards taking the United flight but both were timed similarly in terms of when we’d get home.

The decision was quickly made for me when I got another alert that one of our American flights was delayed.  I didn’t even take the time to figure out which one was delayed.  I canceled while were sprinting to the airport.

The Final Two Pennies

As we settled into our seats on our United flight, I struggled with crappy internet connectivity to get our Jetblue flights canceled.  As the dust settled and all the flights were canceled, I had a brief moment to look back on everything I booked (and canceled) over a five hour period.

The reason this strategy works for me is because I choose to keep a healthy balance of points and miles in my various accounts.  Many folks will tell you this isn’t an optimal strategy, that you should burn your points as soon as you earn them.  Plenty of logic there, but a bit of elbow grease and some available miles helped us get home when we wanted to.

You’ll obviously have to consider whether holding on to enough points to book backup itineraries is worth it.  At a minimum you should think about the flexibility of free changes.  Even though the airlines say they’re gone forever, we’re smart enough to know they’ll be back in some form, someday.  For now, that flexibility can be your key to finding the perfect vacation, or the right strategy when everything seems to be working against you.

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  1. and now you’re about to find out the headache many of us are going through. the refunds of points and fees don’t actually work on most flights. I had 8 cancellations this month and 6 did not process as they were supposed to on United but instead somehow went into “Future Flight Credits”. I had to phone United and one-by-one get them refunded. What an unnecessary pain their IT hasn’t caught up with their new policy.

    1. Tasso, far be it from me to argue United has good IT. However, their mileage returns generally tend to be more reliable than cash tickets.

      For now, all my points and miles are back in their respective accounts and I’m waiting for the taxes to be refunded.

      But, your point is well-founded. Technology is not a strength of pretty much any airline.

  2. What about the moral implications of holding a bunch of award inventory that you’re not going to use? For a revenue based program that’s not an issue but keeping multiple saver options from everyone else because you want a third or fourth fallback comes across as giving everyone else a big middle finger. Would you be okay with someone arranging a business meeting with you if there was only a one in five chance that the person would actually show?

    1. I’ve thought about it. Doesn’t bother me personally but I get the argument. In the end, the airlines are allowed to overbook. Plenty of other policies are very one-sided in the airline’s favor. I don’t view it as giving someone else the middle finger, especially since some of the rates I was willing to pay were decidedly not saver inventory.

      1. Sorry, I was really unclear. My concern isn’t for the airline, it’s for other passengers. If you were paying 25K or more per person for economy seats then you were certainly not getting any saver space, and taking up saver space at the expense of other passengers on multiple itineraries was my only concern.

          1. I agree with Christian. And with you writing about it, there will only be more people doing it. It’s odd that you felt ok writing about such an unethical activity.

          2. I don’t feel it’s unethical. I doubt anyone was hunting for the rates I was booking. Also can’t say I have much of an issue with someone booking a backup flight on another airline if they have the points/miles to do so.

    2. Valid concern, but IMHO not something I’d lose sleep over. Airlines overbook all the time. Schedule change – esp. air system wide ones – always leave passengers on standby, and those standbys will get freed seats. Do what it takes to get home.

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