For complicated reward travel, calling may help


If you’re trying to book a complicated trip with points, it may pay to call but it won’t always reap the rewards you’re hoping

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Best strategies for rewards cards

The content on this page is accurate as of the posting date. Some of the offers mentioned below may no longer be available. Please review our list of best credit cards to find our current offers, or use our CardMatch tool to find cards matched to your needs.

They say that the definition of insanity is doing the same thing over and over and expecting different results. Calling an airline to book reward travel can feel insane at times, when you’re dealing with automated machines and confusing answers.

But what if you do the same thing repeatedly and the results really are different? That’s what happened to me this month when I called a foreign airline again and again to try to book a plane ticket using credit card reward points. Each time, I received a different story about what was possible and what I needed to do. It sure felt like insanity.

But I learned a few things along the way, too.

My saga started when my 16-year-old daughter was accepted to a summer program to study in Seville, Spain. She needed to fly into Madrid on a certain date in June and fly home to Charlotte from Pamplona, Spain, on a certain date in July. To buy a round-trip ticket would cost well over $1,000, but fortunately over the years, my wife and I have built up a reserve of points and miles using credit cards. Together, we have more than 100,000 each of American Airlines miles, Chase points, and American Express points. The challenge would be to find a way to get her to Spain and back using as few points and miles as possible. But I enjoy a good challenge.

Research flight routes, try partner airlines

Usually, the best advice on booking award tickets is to be flexible, but here, I had very little flexibility: I was working with set dates and cities. But I did have the flexibility of trying American miles or looking for seats on the international airlines that are partners with Chase and American Express.

Getting her to Madrid was no problem. It is a big airport with a lot of international flights. Using the award search tool on Dutch airline KLM, I found a ticket on Delta from Charlotte to Madrid through Atlanta for 25,000 miles and booked it.

The return would be much trickier. Usually, when booking reward flights, it’s best to do some research first to determine which airlines fly the routes you are looking for. You can usually get a good idea by using Google Flights, or even looking up airports in Wikipedia. Then, see how you can book those flights – either through transferring points to that airline directly or booking them through an airline partner.

Pamplona, though, is a small airport. It is served mainly by Spain’s national airline, Iberia. Iberia flies from Pamplona to Madrid. From Madrid, Iberia flies to a few U.S. cities, including Chicago, New York, and Miami, and one of its partner airlines, American, flies nonstop from Madrid to Charlotte. The good news is that you can transfer American Express points directly to Iberia.

The problem, though, was that on the date she needed to fly, neither American nor Iberia showed any availability for flights that started in Pamplona and ended in Charlotte. Online, for 5,000 Iberia miles, I could book her from Pamplona to Madrid, but not on to Charlotte. Or, for 65,000 American miles, I could book her from Madrid to Charlotte, but she couldn’t start in Pamplona. Often, airlines don’t make a lot of award seats available to other airlines’ reward programs.

As a backup plan, I saw that online I could book her from Pamplona to Madrid then Madrid to New York-JFK for 40,000 Iberia miles. But she would still need to get from New York to Charlotte.

When calling, be prepared to book

But I figured I’d call to see if there were better options. Sometimes, it makes sense to call, particularly on complicated itineraries. Airline websites often are ill-equipped to handle award flights on other airlines, or multiple stops.

To my delight, when I first called Iberia, the agent who answered said he saw space on American’s Madrid to Charlotte flight, and that I could book her from Pamplona to Madrid then Madrid to Charlotte for 42,500 Iberia miles. Perfect! But I hadn’t transferred the miles from American Express to Iberia, since I didn’t know what was available or how much it would cost. Unfortunately, transfers from American Express to Iberia can take up to 72 hours – and Iberia won’t place potential award tickets on hold.

But I was heartened – the first agent I called had seen space available on the flight I wanted for a low number of miles. I transferred the points, waited for them to post the next day, and tried again. That’s when the fun began.

Know reward rules when using points on others

The second agent I talked with said he couldn’t book award flights, so he transferred me to a department that never picked up. I called back. The third agent said he saw no way to get from Pamplona to Charlotte. Same with the fourth. The fifth agent, Daniela, was very helpful, and she labored for 35 minutes to make the itinerary work, and I thought it had. But when it came time to book the ticket, she said I had failed to list my daughter as a “beneficiary” on my Iberia frequent flyer account, so the computer would not issue the ticket. The beneficiary process takes 24 hours to register online, she said, and she couldn’t place the ticket on hold.

Over the next three days, after registering my daughter as a beneficiary, I called Iberia another 11 times in hopes of finding an agent who could book her all the way from Pamplona to Charlotte. Two said I had to email my request, so I did. But I also kept calling. One agent said he could only book me on American if it was round-trip. Two said they could only book the ticket to New York. Most said they couldn’t help me and referred me to the “Iberia Plus” department \u2026 which was never able to book me a trip from Pamplona to Charlotte using miles. When I asked if I could talk again to Daniela, even though I had her last name, they told me it wasn’t possible since they were in a big room in Madrid with several hundred agents.

Frustrated, I gave up. I went with my backup plan, booking her online to New York, then buying a ticket from New York to Charlotte on American using Chase’s travel portal for 8,300 points. It’s a separate itinerary, so if her plane arrives late or her baggage goes missing, we could have a problem.

Flexibility is key for reward travel

What did I learn? I knew online reservations have their shortcomings, but so do phone reservations. You might get different results every time you call. Unlike the old days, when a good agent could find ways to work around the computer system, today’s computers give agents little discretion. Flexibility really is important. It’s much easier to fly from big cities than small ones. Do your homework online before calling, and suggest alternative routes to agents.

Two days after I booked the ticket, I received a response to my email: “We are sorry to tell you that we cannot help you from this department. Please contact your customer call center. You can find the phone number in the link below.”

 See related: Booking a trip on two airlines has risks, 5 times you should call your bank about your card

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