Booking flights using rewards points and airline miles can be a fantastic way to travel, and save money along the way. But getting everything to work out just right, and getting a great deal while you’re at it, can be a real challenge. I found this out the hard way as I completed my first award flight booking.
My experience involved booking six flights on four different airlines using two separate award systems, spending five hours on the phone with Delta Air Lines, and having multiple moments during which I thought to myself “I have made a terrible mistake.” But would I do it again? Absolutely.
The Plan
My wife and I decided early on that we wanted travel to be part of our story. Though the pandemic and a new baby somewhat impacted our plans, we decided that this summer we wanted to take another larger international trip.
We wanted to go somewhere new, but also somewhere we would feel comfortable bringing the baby. The lack of a language barrier, our comfort level with the culture, and the fact that we have friends in country all drew us to the UK.
I also knew that we wanted to buy our tickets using points and miles. Similarly to how we did our Texas road trip last year, we could save hundreds, if not thousands, of dollars by booking our tickets using airline currencies — and perhaps even book premium-cabin flights.
The Great Search
I started casually looking for reward tickets a couple of months ago. What I found at first wasn’t particularly encouraging — I couldn’t find anything in a premium cabin on United or Delta for under 100,000 miles per person, each way. There was no chance I was going to burn that many points!
I decided to change strategies. I looked at booking flights on partner airlines with any and every airline I could think of — Air France, British Airways, even Latin American carrier Avianca. I tried different cities to fly into — Edinburgh, Cardiff, even Dublin. I tried different dates ranging multiple months.
The few flights I did find that were cheaper with points cost so much money in taxes and fees that it practically wouldn’t be worth it to use my points instead of just booking flights for cash. But finding something motivated me to keep looking. Finally, I looked into Air Canada’s program, Aeroplan.
Aero-Planning The Flights
I logged on to Air Canada’s Aeroplan website and started searching again. Finally, I found something — Business Class on Air Canada through Toronto to London for 70,000 points per person! The connecting flights may not have been business class, and the prices were one way, but that was okay. There w were multiple options for dates, and the long, overnight transatlantic flight was the one I was looking for. (Hold that thought.)
I decided to book the return flight separately, in economy class, so I started looking for return flights. I couldn’t believe how highly priced even the one-way economy tickets were, even with points. Once again, I looked on various airline programs using various departure cities (preferably not London due to the city’s incredibly high departure taxes).
After another hour or two of searching, I finally found a points ticket home with a decent date. The flight was through Delta’s loyalty program on Canadian carrier WestJet for 35,000 points per person. A bargain? Perhaps not. But compared to the cash prices, it was a great rate. Because of how hard-to-find the return flight was, I decided to book it first. Boy, am I glad I did.
The Phantom Award Ticket
I made the one-way points transfer from American Express to Delta, and went through the normal booking process. I entered my payment information for the taxes and clicked “Confirm Purchase.” The Delta website spinned for a little longer than I expected it to. Then, instead of the “Ticket Confirmed!” landing page, a message popped up in tiny font at the top of my screen, which was showing an otherwise normal Delta home page.
“Sorry, someone else just booked the ticket you were trying to book.”
And I thought…
I have made a terrible mistake.
I looked again at the website, and sure enough, the ticket was still shown as available. So I went through the whole process again. Maybe it was a fluke.
Nope. The same error message popped up. I tried again and again, but it quickly sank in that I might be out 70,000 American Express points. So I called Delta. And waited on hold. And waited on hold. And worked on a blog post. And waited on hold.
It took over two hours on hold and a manager to tell me that there was, in fact, no way to book the ticket I was trying to book. The manager couldnt even book it manually himself. The booking was being blocked on WestJet’s end. They had issued the award ticket to someone (not me), but had not updated their award availability to their partner Delta. The ticket was, in fact, gone. I thanked the manager for his time and hung up.
There were two other dates the following week that had the same price. I tried one of them — the same error came up. Apparently this is a thing that happens with Delta-WestJet partner awards.
Finally, on the other available date, I got a booking to go through. Success! It was 1 AM by now, so I went to bed. I’ll book the Air Canada ticket in the morning.
Oh, Canada…
So, of course, the next morning I got up and jumped back on my computer. I was much more confident with this booking — there was award space on dates that would work with our adjusted Delta itinerary which was marked “Business Class (Mixed Cabin).” So, once again, I made the one-way points transfers, this time some from both Chase and American Express.
The transfers both were instant, and my Aeroplan point balance was now 143,000 (the extra 3,000 points to cover a 2,500 point lap infant add-on). So I selected the correct flights and started the booking process. It wasn’t until I reached the seat selection screen that I realized my second mistake.
The website would let me select Business Class seats for the Chicago to Toronto leg, but was only showing me the Economy Class cabin for the Transatlantic flight. I couldn’t get the seat map to come up for the Business Class cabin. Finally, I found, in small print near the bottom of my screen: “Business Class ORD-YYZ, Economy Class YYZ-LHR.” And I finally realized that the”Mixed Cabin” description indicated that, at least for the flights I had picked out, the overseas leg, the whole point of me going to all this extra effort, wasn’t Business Class.
I have made a terrible mistake.
Finding What I Actually Wanted
I pulled out of that booking pretty quickly. Then, armed with my 143,000 Aeroplan miles which I couldn’t send back to Chase or Amex, I set out to find something more amicable. But nothing was coming up. All of the flights were either “Mixed Cabin” and really only Business Class for one short connecting leg, or cost way too many Aeroplan miles for it to be worth booking.
I had to look at different dates to find something that would work for the right price. Finally, I found something. Business-class seats for a long-haul Montreal to London flight! Sure, we’d have a nearly six-hour layover in Montreal, but it would be during the baby’s naptime and we would have access to the Business Class lounge, so it seemed okay. The tickets were a week after we had planned, though, so I would need to try and change the return flight.
Back to You, Delta
I went back to Delta.com and looked at what was available. Delta lets you change flights (even reward flights) online, which is pretty cool. But I kept running into the same issue as I had before — the phantom availability for the WestJet flights, the only flights that were the same price as the ones I had booked already. The flights on a day that would work with our travel schedule were showing up, but when I tried to book them I would get an error. I copied down the flight numbers I wanted to switch to, and resolved to call Delta.
The robotic voice on the other end of the line told me that my wait time was approximately 1 hour, 43 minutes and that they would call me back. Great.
No less than two and a half hours later, I finally get a call back. I do my best to kindly explain the situation and tell the agent the flight numbers I’m trying to change to. I even tell her that if one date wasn’t available, another date adjacent to it which was also showing availability could work. She put me on hold.
I sat on hold for what seemed like an eternity, until she came back on the line. “Sir, would you be open to another day earlier?” I said yes, but my only thought was that all the award availability had to be gone. After all, when I had looked before, nothing was showing available on the day before the dates I had given the agent. She put me back on hold.
Finally Booked!
Another while later, the agent comes back on the line and tells me to refresh my Delta app. “Here’s what I was able to get you… two tickets, for the same price, on the next earlier day.” My app confirmed the booking. What?! I thanked her over and over, and she hung up.
The only thing I can imagine happening behind the scenes is that the Delta manager had called over to a WestJet manager and asked them to open up additional award space on the days we wanted to fly. Maybe there was some negotiation or I-O-U that was cashed in, or maybe this kind of thing happens all the time. I don’t know. But whatever the case was, the tickets were booked, and we were going to Europe!
The thrill of accomplishment washed over me. I couldn’t believe it after the whole nerve-wracking process, but it was done.
Lessons Learned
There are definitely a few things that I would do differently the next time I book a reward ticket. Here are my lessons learned:
- Book early. It would’ve been way easier to find affordable award space if I had booked three months ago!
- Read the fine print. Make sure I know what I’m booking before I click “Book” — cabin classes included.
- Be flexible. If things don’t work out perfectly the first time, I’ve got to be willing to pivot!
- Be patient and kind. Things might just work out better if I am.
It can be a big challenge to find a great deal on an award ticket. But when you save thousands and get an amazing trip out of the deal, it can all be worth it. Stay tuned for my review later this summer.