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Miles and Points are boundless – they can take you anywhere all around the world and most of the time you can save big, and even fly in First or Business Class where a ticket would normally cost thousands. When redeeming miles, it is important to understand how your frequent flyer program works and what their rules are and if they allow you to maximize your miles by creating custom award flight itineraries.

What is a Custom Award Flight Itinerary?

A custom award flight itinerary is a booking where you put together all of the flights by yourself instead of just going to the airline’s website and accepting the flights they offer. Custom itineraries are great when you want to:

  • have stopovers
  • have extended layovers (up to 23 hours 59 minutes)
  • route over a favorite city
  • try multiple airlines all on the same ticket
  • stretch your miles further and maximize your ticket

Custom itineraries can be basic or complicated – it all really depends on what you want to book and what the frequent flyer program allows.

How to Plan a Custom Award Itinerary

You can start planning a custom award itinerary by studying what your frequent flyer program allows and what airlines are available to you – of course, award availability will need to be there in order to book.

Firstly, you will need to understand the rules of the frequent flyer program you are using to book your itinerary. The most important aspect to understand is if they allow you to create custom itineraries or if they only allow you to book what they show you online. Programs like United and Delta only allow you to book what they show – from your origin to destination and if you want a custom itinerary, you will need to pay more miles.

If your program allows custom award flight itineraries, you will need to keep in mind a few key items:

  • what airlines are available to you and do they have award space?
  • what is the maximum permitted mileage flown between your origin and destination?
  • how many flight segments are allowed?
  • can you mix cabins?
  • can you mix airlines?
  • will the itinerary price in your favor?
  • are you able to route via a third region?

There may be more questions you need to ask yourself before planning your trip, depending on what frequent flyer program you are using.

For example, American Airlines AAdvantage allows you to create custom itineraries as long as they are on partner airlines (a booking with only AA flights won’t qualify). Some rules of AAdvantage include:

  • maximum of 4 flight segments on international awards
  • cannot route via third region, some exceptions apply
  • need to call in to book custom flights
  • no stopovers allowed
  • long layovers of up to 23 hours 59 minutes allowed
  • can mix cabins and airlines

Always check the rules before planning and searching flights.

Searching Award Flight Availability

When planning a custom award flight itinerary, you will need to search each flight one at a time and you will also need to keep in mind all of the rules of the frequent flyer program.

For example, if you want to fly from San Francisco to Athens and the program’s website only shows you award flights that are “simple” (like one connection only) and you want to create a custom itinerary, you will need to figure out:

  • what cities you want to transit
  • how long your layovers will be
  • will you or can you have a stopover
  • will your custom itinerary satisfy all of the program requirements

Going back to our examples, let’s say we are redeeming AAdvantage miles from San Francisco to Athens and when we search this city pair, the only options we have are one-stops, via London, Philadelphia, etc. Most people would be happy to book those, but we want to get creative.

The following, custom itinerary would price the same as the one above:

  • San Francisco to New York (AA or AS flight)
  • New York to London (AA or BA flight)
  • London to Madrid (BA or IB flight)
  • Madrid to Athens (IB flight)

In Business Class on partner airlines, both the simple itinerary and our custom itinerary would price the same at 57.5k miles in Business Class. Our custom itinerary meets all of AA’s rules which include a maximum of 4 segments, within the maximum permitted mileage, layovers of under 24 hours, etc.

You would find this itinerary and flights by searching each flight individually and then putting them together as one trip – a custom award flight itinerary.

Booking Custom Award Flight Itineraries

In most cases, you will have to call the frequent flyer program to book your custom itinerary. There are a tiny amount of programs that allow you to use the Multi-City function to create custom award flight itineraries that are correctly priced. For example, if you typed in our custom itinerary on AA’s website, it would charge you for each flight separately even if you meet all of the requirements for the booking to qualify as “one award” – so you need to call.

The best way to approach the task is to tell the agent you already found availability and “feed” them each flight separately and once they find all of the flights, they should be able to price the whole itinerary correctly and if it meets all of the requirements, it should price as one award at the expected price for this trip from origin to destination.

All in All

Creating and booking custom award flight itineraries is such a fun way to see more places, try more airlines, and really stretch your miles further. Why fly direct or with one stop when you potentially can have 5 layovers and see more of our beautiful world?

Custom award flight itineraries take your miles and points to the max when you are flying in Business or First Class on multiple airlines throughout the world – you can sample different products and have layovers in really cool places, all while paying the same price in miles as you would for a more direct routing. Remember that “hang up, call again” is your friend if some agents are hesitant to book a custom routing or if they quote you the wrong price – just remember to thoroughly research and understand the rules of the frequent flyer program.

Travel Miles 101 has partnered with CardRatings for our coverage of credit card products. Travel Miles 101 and CardRatings may receive a commission from card issuers.