Sunday Reader Question: How Do You Book Complex Awards?

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TPG reader Jim asks:

“How do you guys always book those multi-segment awards for the low mileage amounts?  I use Expert Flyer and can find the segments I want, but If I try to book it, it seems like it will charge me for each segment individually and not as a single 25,000 domestic or 40,000-60,000 international.  The same question applies to the milage runners who will find these tricky routings for a low price.”

Firstly, when I book complex awards, they are almost always over the phone. Most airline websites are quirky for even normal awards, let alone complex multi-leg itineraries. I have had success with and, but it takes a lot of finessing. In general, I find all of the availability leg by leg by using one of the many tools like ExpertFlyer and the ANA Tool (Star Alliance). Once you have the availability down, then go to the website of the airline whose miles you are using and attempt to replicate it via the “Multi-city tool.” Here’s how to access that tool for each of the following frequent flyer programs: -> Use miles for Flights -> Multi-city tab. has a lot of partner award availability, but I often have issues with multi-city awards, so I usually end up calling 1-800-361-5373 to get awards booked. -> AAdvantage -> Redeem miles -> Book now -> Then select the multi-city button. only shows American availability so this is pretty useless. AAdvantage Phone reservations: 1-800-882-8880.
British Airways:  Multi-city itineraries need to be booked by calling the Executive Club (soon to be Avios) reservations desk at 1 800 452 1201 and it is only open from 7:30am-8pm eastern time daily. –> Multiple destinations -> Then add in legs using the “+ Add Another Flight to Your Trip” then at the bottom select the Reward Travel button right above the Search button. Onepass reservations: 1-800-621-7467 -> Skymiles -> Use miles -> Award ticket reservations -> Multi-city. I don’t know where to begin with describing the level of quirkiness with Delta’s system, but it can be extremely frustrating. Sometimes you need to click “Start over” to refresh the screen and then real results will load. More aggravating is finally getting it to build a complex trip and then getting an error that the fare sold out. only supports Delta, Alaska, Air France, KLM, and Alitalia availability. Skymiles reservations: 1-800-323-2323
US Airways only has US availability and does not have the capability to book multi-city awards. You have to call reservations at 1-800-428-4322.

Some tips:
1) Usually agents will assume you know nothing. I tend to let them know up front that “this is going to be a complicated trip, but I’ve done my research ahead of time to make this as easy as possible for you, so thanks in advance for bearing with me! The trip will start in X city and end in X city with stops in X,Y,Z and some overnight transfers. I think the easiest thing would be to give you the flights by day and flight number, but you tell me what you prefer.” From that point they’ll usually get the hint that you aren’t a novice.
2) Don’t trust everything the agents say – they make mistakes all the time. I often have agents look at the wrong flights, class of service and date – all things which can throw off the whole trip. Whenever they tell me availability doesn’t exist for my dates I ask them to verify all of the pertinent information and most of the time it’s a simple error on their part.
3) If the agent is nasty or doesn’t feel like helping, don’t argue with them. Simply hang up and call again! That’s one of the tried and tested ways of getting what you want when it comes to miles and points.
4) Push the limits. You’ll never know what’s possible until you try.
5) Don’t sound like you are trying to break/bend the rules. Playing dumb sometimes works in your advantage.
6) Be very friendly with the rep. I casually mention the reason why I’m constructing crazy routings, “Oh yea my best friend lives in Hong Kong and I haven’t seen her in a couple years – I can’t wait to have 23 hours there in between flights!” I also ask the phone agents how they are doing- small things like that can go a long way. If a phone rep likes you they can hook you up – I even once had a Delta rep ask revenue management to release a low level award so it would work better with my trip.
7) If they find your crazy award and are ready to book it – pull the trigger! You may not get the same result twice and they get (rightfully) really annoyed when they do a ton of work to find someone an award and then they aren’t ready to book. Many airlines will allow holds, so go that route if it’s available.
8 ) Once you get the award booked, ask them to waive the phone ticketing fee since the award was not bookable online. One of the other tenets of the miles and points game is, “It never hurts to ask!”

For more information on the routing rules and for general tips on maximizing the value of your miles, check out these posts:
Using for Award Availability
How to Use the ANA Award Tool to Search Star Alliance Award Availability
Air Canada Aeroplan: ‘Round the World’ Awards
Maximizing Stopovers, Transfers and Open Jaw Ticketing on American
How to Use British Airways Miles: Post 8, The Art of the Stopover
Maximizing Stopovers, Transfers and Open Jaw Ticketing on Delta
Maximizing Stopovers, Transfers and Open Jaw Ticketing on United/Continental
Maximizing Stopovers, Transfers and Open Jaw Ticketing on US Airways

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