Some Days You Love The Miles Games, Other Days You Hate It – Today Was Both

I write this from somewhere over the Pacific while lounging my first class suite on JAL 1 from San Francisco to Tokyo-Haneda that cost me a whopping $5.60 out of pocket. At the moment, I am pretty darn happy with the miles game. But had you asked me about it at any time over the last ~72 hours, I would have told you I hated it. I write this post for two reasons – 1) to share with you how frustrating the points and miles game can be; and 2) to tell you to always stick with it because there is almost always a way to make it work.

I guess I need to provide some background on this trip first. One of my best friends and my college roommate is getting married in Chongqing, China. I was not able to attend the ceremony they had in the States, so I decided to hop on a plane and travel half way around the world to properly celebrate with him. I figured while I was over in this part of the world, I might as well make a bigger trip out of it and check out Tokyo, Hong Kong and Singapore. I have been to Tokyo and Singapore before, but never Hong Kong. Plus it offered a good excuse to write some reviews of some products I have wanted to do a formal review of.

I have had my main flights to and from Asia locked in for months now. I was originally supposed to route Orlando (MCO) to New York (JFK), then on to San Francisco on the A321T transcon in first class where I would pick up the amazing JAL 777-300ER for my first class flight Tokyo. I had planned on reviewing the A321T and the Flagship First Lounge in JFK during that routing. That was until Winter Storm Jonas decided to change those plans. And thus began the adventure that has been the last 72 hours of my life – a.k.a. the first time in my life I have ever contemplated throwing in the towel on trying to make travel work.

Cancelled Flights

While I have had the main flights to and from Asia locked in for a few months now, I have been closely monitoring some of the other segments – mainly the Hong Kong (HKG) to Chongqing (CKG) and back segments and the Hong Kong (HKG) to Singapore (SIN) segment – in hopes that Cathay Pacific would be opening up some of those flights for award tickets. Up until ~72 hours ago, Expert Flyer was showing plenty of seats available for purchase on the Dragon Air (a subsidiary of Cathay Pacific which is bookable using miles from any of the OneWorld partner airlines) flights to and from Chongqing. Based on what I had been seeing with what space was being opened up and when, I was confident the space would open and we would have our last minute tickets to Chongqing. Until Cathay Pacific zeroed out the flight ~72 hours ago…$@&$~!!!

Zero Availability

So thus I am brought to my first point on the points and miles game – it can be frustrating as hell! Sometimes the award space you want simply does not open up. But it is important to remember one thing – there are plenty of other options out there! The first thing you want to do is take stock of the points and miles that you have available at your disposal. From there I systematically went through each and every airline that was a transfer partner of any of my points or miles and checked to see what my redemption rates were going to look like. After I knew who offered the best redemption, I started checking every airline that was an option, starting with the least expensive option. Unfortunately, award availability was not very good on any of the airlines so I went back to the drawing board.

Zero Availability BA Availability

I next did a search on the ITA Matrix to see what a paid ticket would run me. I found a pretty inexpensive business class ticket on Hong Kong Airlines, which I have heard mixed things about, so I decided that since I could not find many actual formal reviews of the airline online, that I would go ahead and book it. That still left me with an issue of getting to Chongqing though. Paid tickets were running around $400 for coach and I was having a hard time justifying that. Finally I came across a great direct flight using my Delta Skymiles (I guess they are not completely useless after all!) from nearby Shenzhen (SZX) airport that would get me into Chongqing exactly when I wanted to arrive. Except when I tried to book the flight, I kept getting the message that the space had already been sold and to select another option. But every time I tried to go back and look at other options, that flight remained open and bookable. Weird.

So I ended up calling the Delta desk to help me with the booking. The Delta CSR was able to see the seats, but she was unable to get them to ticket. After 2 hours on the phone with Delta, I finally threw in the towel and decided to try another way. Within 10 seconds of hanging up with Delta, and already frustrated, I received an automated call from American Airlines informing me that due to Winter Storm Jonas, they would be cancelling my flight to JFK and from JFK to SFO. Crap…

Yelling at Phone

Since AA cancelled my flights, I knew there was a pretty good chance they would let me book into any open flights with first class seats available. I needed two and I wanted something cool to review and comfortable to fly in. As I have previously written about, AA operates some internationally configured aircraft on routes like Orlando (MCO) to Miami (MIA) and Miami (MIA) to Los Angeles (LAX). There just so happen to be two first class seats on the MCO to MIA flight on a 767-300 with fully lie flat seats and two first class seats on the MIA to LAX flight on a brand new 777-300ER with AA’s Flagship First. I have previously flown AA’s Flagship First on a few routes, but my girlfriend never had, so I figured it would be a nice way to go.

AA 777 (2)

Even though Winter Storm Jonas was causing call times to be astronomical at AA, since I am a Platinum elite, I was able to get through after only 20 minutes. Within 5 minutes the super helpful AA CSR had rebooked us on our new routing. Awesome!

AA Status Cards

Flash forward to Saturday afternoon when we were scheduled to leave and all seemed good. No delays and no cancellations showing on our routes and the 777-300ER that had come in from Brazil was already parked at MIA. Perfect…I thought!

After an hour of delays on our flight to MIA, I started to get a little concerned as the gate agents were not giving us any updates. Concerned that they may cancel our flight, I tweeted out to the utterly amazing team @AmericanAir and asked them to protect us on a flight through Dallas/Fort Worth (DFW) which would get us into SFO with a little under 2 hours to spare. It turned out to be the best decision I could have made as about an hour later, the gate agents reappeared and announced that the flight was cancelled due to a mechanical issue. Cue the MASSIVE rush of people to the desks to get rebooked.

Since AA had already protected us on the flights through DFW, I simply called in to the Platinum elite desk and had them reticket us. The only problem was that there was only one seat in first class on the flight to DFW. No matter I thought, it is a less than 3 hour flight – I can tough it out. Just in case, I set an Expert Flyer alert in case an extra seat came available in first. When we tried to re-check in for the flight via the AA app, we were told we could not. Not wanting to exit the terminal and have to re-clear security, we opted to wait in the line for the service desk to have our tickets printed. When they printed my girlfriend’s ticket, they had put her in the coach seat and were not showing that she would be #1 on the upgrade list (don’t worry – I had every intention of giving her the first class seat). In fact, they were not showing that she would be on the upgrade list at all – nor that she was even eligible for a comp upgrade. I immediately got on the phone with the Platinum desk again and had them note in the system that since we were on a first class ticket, that she should receive the comp upgrade if space opened up and that due to her also being a Platinum with AA, that she would be #1 on the upgrade list. With that issue squared away, we headed to the gate, relieved that the day was finally turning around. Or so we thought…

At about 40 minutes prior to boarding, Expert Flyer alerted me that one more first class seat had opened on our DFW flight. Perfect! I quickly tweeted out to AA to ask them to put my girlfriend in that seat and sure enough, about 2 minutes later the gate agent asked for her to come to podium. This was the first time I had tweeted to AA to get something done, but I cannot say enough good things about the people who work AA’s social media account. They are absolute rock stars (more on this later). Thinking everything was good, we cued up to board the plane in desperate need of a pre-departure beverage.

AA 330 (edit)

Right before the boarding announcement for our flight was made, the gate agent called my girlfriend up to the podium again. Uh oh…

As it turns out, AA had forgotten to cancel her check-in from our previous itinerary and as a result, the system (or someone at AA ticketing) cancelled her ticket for the DFW flight. As we were getting ready to board… And the gate agent was unable to get the ticket reissued and pushed through for us. Thankfully he too turned out to be a rock star (and got some AApplause for his hard work) and quickly jumped on the phone to try and get the issue resolved. If we missed this flight, we would misconnect all the way to Tokyo! I again jumped on the phone to the Platinum desk and thus began a frantic 20 minutes trying to get the ticket issue resolved. During that time, the rock stars at the AA social media desk had apparently also realized there was an issue and started working on it – they even sent me a tweet to let me know when they had it resolved! With about 5 minutes to spare before they closed the doors, we boarded our flight to DFW.

Upon landing in DFW, we were informed that we did not have a gate to park at and that operations was working on getting us one. Our connection was about an hour and a half, so any delays would be costly. After about 45 minutes of sitting on the tarmac, we were finally given a gate and parked. We quickly hopped into the Admirals Club to see if we could get our tickets for our flight to Tokyo issued, but we could not. After a quick drink and a phone call to my parents, we were off to our gate where they were already boarding our flight to SFO. Thankfully that flight and our connection to our JAL flight went off without a hitch.


So this brings me back to my original two points – flying is not always fun and easy and sometimes you need to be prepared to be flexible. Always have a backup itinerary in mind if you can and above all else, be kind to the airline employees. ‘Please’ and ‘thank you’ go a long way with them, as does making sure you recognize those employees that go above and beyond for you. I still have not figured out how I am getting to Chongqing, but as the old saying goes – where there is a will, there is a way.

It is also important to remember why we play this crazy points and miles game. I am currently sitting in a seat that would have cost me ~$12,000 had I paid cash for it. I am surrounded by no doubt titans of industry and the business world who paid that amount for their seat. My seat cost me some miles I earned from a credit card sign-up bonus and $5.60. The cup of French press coffee that I am currently drinking would have cost me more than that at any coffee house in America. Let that sink in for a minute and let it be a reminder of why we play this game – even when it stresses us out to the extreme.

Final Thoughts

I cannot sit here and say today was not a day where I questioned my sanity and whether all of this was worth it. But I can tell you that as I sit here in my first class suite on my way to a explore a country I love and having paid a mere $5.60 out of pocket for this seat – yeah, it is worth the stress and the time because there is no way I could ever afford to do this otherwise. Safe travels my friends!

What is your worst travel day story?

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