I'm sorry, fellow millennials … you're going to hate this next sentence: To get the best deal on award flights, you occasionally have to call someone to book your flights.

Yes, you may have to actually pick up the phone and speak to a human being to get it done.

I'll admit it: I avoid picking up the phone whenever I can, so the normal route of booking flights online over the last decade and change is a godsend. But it's undeniable – and becoming increasingly clear – that some of the best deals in award travel are best (or only available when) booked over the phone.

Sometimes, you just can't book a certain flight online, period – as is the case with the recent goldmine we discovered booking Hawaiian First Class flights to Honolulu (HNL) for just 26,000 miles using Finnair Avios, booking American Airlines or LATAM-operated flights via Finnair, and the holy grail of flight deals: booking ANA business class to Japan from 52,500 points via Virgin Atlantic. You might want to pick up the phone to put an award on hold before transferring your credit card points. And in some cases, dialing an airline might be an essential when you struggle to get a ticket to go through.

Fear not, millennials: This isn't as painful as it may seem! That thing in your hand makes calls, too, and it could get you the deal of a lifetime. 

 

Try Online Chat, Text & Social Media First

Luckily for phone-wary flyers like me, online chat features can connect you with an agent via text, which is something I employ all the time now.

It works much the same as picking up the phone in most cases, although you'll want to make sure you're not talking to a chatbot and are actually connected to a representative. Whether it's embedded in the airline's website or it's an actual text message function, these chat features typically start out with a chatbot until you ask for a representative. Be very clear about what you want with the bots. 

 

Finnair agent Sisu
Finnair's AI chatbot is named Sisu. You have to start chatting with the bot, when you'll be connected to a human once you ask for a “representative” in the chat. Finnair's chat feature comes in handy because Finnair Avios offer great rates on partner flights you can't find on their website

 

Starting out with the bot is an obvious drawback of these online chat functions, but there are tons of pros. For one, there's usually no miscommunication. When every piece of information is typed out and not spoken aloud between two people who could have a scratchy signal or a language barrier, it makes for clearer communication in many cases. 

For example, the airline I fly most as a Minneapolis-St. Paul (MSP)-based traveler is Delta. Delta has a line you can text message with and that's how I always communicate with Delta agents. When Delta makes you wait on hold for hours at a time, the chat agents are usually ready to respond within a matter of minutes or seconds. 

 

Delta chat feature
Delta's text with a representative feature is very handy. I almost exclusively chat with Delta agents instead of calling to avoid long wait times.

 

When You Might Want to Call or Chat an Airline

There are three reasons you might want to call or chat with an airline: 

  • You're having issues with the website
  • To confirm award availability and book a flight
  • To hold an award flight

 

Troubleshooting Website Issues

We love using partner programs to book flights, but some of the foreign partner airlines have lackluster websites compared to our U.S. airlines. Heck, sometimes our own airlines' sites stink.

You might go to book an award flight and run into an error when trying to book – a frustratingly common issue with some airlines like Air France/KLM. In these cases, I'd recommend picking up the phone and calling the airline.

An agent can use their system to get you booked quickly and efficiently instead of you refreshing and re-searching quirky airline websites and wasting valuable time and possibly losing out on your flight. 

Thrifty Tip: Before picking up the phone, try using that airline's smartphone app to book your award ticket instead. Those sometimes function better than the website itself.

 

Confirming Availability & Booking Flights

This is the obvious one. You have the points or miles and you want the flight booked. And while most award tickets are bookable online, a handful of partner workarounds aren't available online … but they can still be booked.

That's a great reason to get someone on the phone or by chat. 

The most frequent airlines you'll have to call or chat with to book partner award flights are Cathay Pacific, Finnair, and Virgin Atlantic – all points programs that have credit card transfer partners, which means your American Express, Chase, Capital One, Citi, or Bilt points can transfer to these programs, opening up new (and less expensive) ways to book flights. 

Here are a few of our favorite redemptions that you'll need to call the airline to book: 

  • Alaska/Hawaiian Airlines First Class to Hawaii for 26,000 Finnair Avios – must call or chat with Finnair
  • American Airlines flights with Finnair Avios – must call or chat with Finnair
  • American Airlines flights with Cathay Pacific Asia Miles – spotty availability online and much better over the phone or chat
  • LATAM flights with Finnair or Cathay Pacific – must call or chat with either program
  • LATAM flights with Virgin Atlantic – must call or chat with Virgin to book from Lima (LIM) to the U.S. only
  • Aeromexico flights with Virgin Atlantic – must call or chat with Virgin to book
  • ANA flights with Virgin Atlantic – must call or chat with Virgin to book (although these redemptions are exceedingly rare now)

 

large business class suite with dark seat padding and light woodgrain walls

 

In each case, booking with the partner airline by chat or phone call will yield you massive savings on the flights. I mentioned above that you can fly ANA's The Room Business Class from the West Coast to Tokyo from just 52,500 miles each way with Virgin. If you book with United, that same flight will cost you over 110,000 miles each way (and usually more!)

 

Holding an Award Ticket

It's become rarer and rarer over the years, but a handful of airlines allow you to put award flights on “hold” for 24 to 72 hours.

That can be critical if you want to lock down award space before transferring points, those transfers don't go through instantly, or if your points get stuck in limbo. Or maybe you're not sure if you can take a trip yet but want to put it on reserve while you decide.

But only a small subset of airlines actually offer award holds – all with different policies. Some give you 72 hours or more while others require you to call back in within 24 hours to book or lose your flight. Here's a not-quite-exhaustive list:

  • Air France/KLM Flying Blue offers holds of up to 72 hours
  • American Airlines AAdvantage, which offers online holds of up to 24 hours
  • Cathay Pacific Asia Miles offers holds of up to 72 hours
  • Emirates Skywards offers holds of up to 48 hours
  • Singapore Airlines Krisflyer offers holds of 24 to 48 hours – it varies by agent
  • Turkish Airlines Miles & Smiles offers holds of up to 48 hours
  • Virgin Atlantic Flying Club offers holds of up to 24 hours

To put award fares on hold with these airlines, you must talk to an agent to hold them and then call the airline back again within the deadline to book before your hold expires. American Airlines is a major exception – it offers a hold function even when searching at aa.com.

 

Your Pre-Call or Chat Checklist

First things first: Before you call or even start on this checklist, you need to find the critical element of any award ticket: award availability, meaning you can actually book that flight with points.

Not every flight is bookable on every day when you book with partner airlines, so you need to use other partner's websites to find what dates are available before you call. The best example of this is to use American Airlines' handy calendar tool to search for availability with Alaska/Hawaiian, Cathay Pacific, Finnair, and many other Oneworld alliance partners. You won't find a calendar of availability like that on Finnair or Cathay's websites, so finding the space with American first is key.

Check out our favorite sites for finding award availability – and the best third-party search tools!

Once you have your availability in the crosshairs, it's time to assemble as much information about you and your desired flights as you possibly can. 

Here's what you should have handy before you pickup the phone or start your chat: 

  • The points or miles ready in your account
    • Never transfer your flexible points until you are on the phone with the agent and they've confirmed availability – more on that later
  • All of your (and traveling companions') personal information
    • Dates of birth, loyalty numbers, Known Traveler Numbers (KTNs), and passport information
    • More airlines are now requiring companions booked under your name to have their own frequent flyer account or even be saved as a companion under your account
  • Date of departure (i.e., Sunday, January 10)
  • One-way or roundtrip
  • Route: i.e., Seattle (SEA) to Honolulu (HNL)
  • Flight number: i.e., AS 121 or Alaska 121
  • Scheduled departure time: i.e., departing at 7:00 a.m.
  • Class or cabin: i.e., “First”, “Business”, or “Economy”
  • What you know the flight should cost in miles
  • A NATO phonetic alphabet handy
    • This is invaluable for relaying names and other details to agents, especially if there's a language barrier

 

nato phonetic alphabet key
The NATO phonetic alphabet is a lifesaver when talking to airline agents

 

Let me put it like this: You cannot and should not call the airline until you know exactly what you want to happen on this call. You should be as precise as possible about what exactly you want booked and the miles it should cost. 

The more information the better! You can't over-prepare for a call like this. 

 

How to Call or Chat With An Airline

Let's get your flight booked. To do so, we'll use the latest Finnair-Hawaiian Airlines flight as an example. 

Here's what to do and an example script for your call: 

1. Call Finnair or chat online with a live agent

Hello. I need help looking for availability to book an award flight using my Finnair Avios, please. 

2. Ask the agent to check for availability

Can you check for availability to fly Alaska Airlines, first class, using Finnair points?

3. Give the agent the exact route and dates you want. Have those flight numbers and departure times handy, too.

I want to book two passengers on the one-way flight AS 121 from Seattle (SEA) to Honolulu (HNL) on Sunday, Jan. 10 departing at 7:00am in first class. Can you confirm the rate and taxes and fees, please? 

4. Transfer points only after you've confirmed the flights are available with Finnair

Transfers are usually instant; just ask an agent to stay on the line until your points hit your account.

OK. I would like to book this flight. I am going to transfer the points to my account right now. Can you remain on the line with me and confirm when the points are in my account?

5. Have the agent confirm your booking and ask for confirmation numbers from both Finnair and Alaska/Hawaiian

Can you reconfirm the flights I'm about to book? (Flight number, route, date, number of passengers, rate, etc.) 

OK, go ahead and book those flights, please.

Could you please provide me with my confirmation numbers for both Finnair and Alaska/Hawaiian, please? 

And that's it! You've got your flight booked with an agent. The same process looks very similar when you use the chat feature. Here's an example of what we did with Finnair's chat agents earlier this month. 

 

 

Finnair agent chat

 

Calling Strategies

Here are two other important strategies to consider when calling or chatting with an airline. 

 

Hang Up, Call Again

This is the most important thing to keep in the back of your mind when calling an airline: If your call or chat isn't going well, the agent can't seem to help you, or you're not getting what you want, it's probably time to hang up and try again. 

Here's an unfortunate truth: Not all agents are created equal. I've had to hang up and call again four or five times in a row to get an agent who can do what I want.

Just recently, I was trying to get my Delta SkyMiles number attached to a Delta flight booking I made with Air France/KLM Flying Blue and it took me four different chats with Delta representatives to finally get my number attached. The first three agents told me that there was no way I could ever get my SkyMiles number on a flight booked with Flying Blue – effectively gaslighting me into thinking I hadn't been doing that exact thing for years now. The fourth agent? Put my number on my reservation in a matter of 30 seconds. 

If you've done your research and know you can book something or make a change, don't let an inexperienced agent tell you otherwise. Hang up and call again to get what you want!

 

Take it Slow: Confirm and Reconfirm

Once you have an agent on the phone or chat and have found the award space you want, it's OK to ask them to verify, re-verify, and re-re-verify your bookings, your dates, your passenger information, and more. Don't let a language barrier, a thick accent, or a typo irreversibly mess up your reservation. 

If the award space is super rare or time-consuming, just make sure you get the important stuff done (i.e. dates of birth and correct spelling of names) and have the agent book your flights. The rest you can handle later. 

 

Bottom Line

You can and should pick up the phone to book some of the best deals in award travel, so long as you're prepared and know what to tell an agent. 

Remember to over-prepare for your call by having all of your information and the exact award availability you want ready to go at booking.