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Our Award Booking Service has been rocking and rolling lately. Busy frequent flyers love the personal attention we give each itinerary, as well as our expert knowledge of award programs.

The MileValue crew has a battle-tested recipe for award booking success. By following a few easy tips, doing your homework, and being flexible, you too can be an expert award booker–and get yourself your dream trip.

Emirates First Class Suite

What are MileValue’s eight tried-and-true tips? How can you book an award like the pros do?

#1 Collect versatile points that transfer to many airlines.

This might seem like a no-brainer, but it’s a critical point to reiterate. The big three are:

Search for award space on or British Airways’ website, for example, and then transfer your Chase Ultimate Rewards to those programs instantaneously to book the space you’ve found.

Constructing an itinerary often means thinking outside the box, and flexible points exponentially increase the potential for finding award space. Check out Tahsir’s post, Membership Rewards Transfer Options: Singapore KrisFlyer, for a great example of the value of flexible points.

#2 The looser the time frame, the more fruitful the search.

The perfect companion for a huge balance of flexible points is an open travel schedule. What’s the hardest award to book? The one with fixed travel dates.

For example, many airlines aggressively restrict award space between the Friday before Christmas and the Sunday after New Year’s–December 20th and January 5th this season–the perfect window for the US holiday break. Having flexibility in your schedule, even if it’s only plus or minus a day or two, often means the difference between snagging precious award space and being forced to pay cash for tickets.

Shifting dates was the only way I could book my family of five to Italy for Christmas using miles. We are leaving right before the 20th and returning around New Year’s Day.

#3 Some of the best award space opens last minute.

Waiting until the last minute to book an award isn’t for the faint of heart, but is often the best way to get premium cabin seats.

Lufthansa is the most notorious airline for this practice of releasing seats near departure. Scott even wrote about the Star Alliance carrier’s tactics in the posts, The Poorly Kept Secret to Finding Lufthansa First Class Availability and How to Find Last Second Lufthansa Award Space.

Below is a sample route from Washington-Dulles to Frankfurt. Most days in the next week have Lufthansa First Class award space on their new 747-8.

Lufthansa isn’t alone in this exercise, though. Oneworld carrier Cathay Pacific will hold back first class award space until the last minute. They are showing great availability this week between San Francisco and Hong Kong for instance.

#4 Book the flight first, then grab the cruise/tour/hotel reservations.

In the same vein as fixed travel dates, having a confirmed hotel reservation or organized tour can hamper award booking success. You will be at the mercy of award space on the exact dates of your check-in and check-out.

If you somehow snag rare first class space on the Qantas A380, you can then start to build your trip Down Under. Everyone is competing for the same scarce award space. What you see today likely won’t be there tomorrow. If it’s a once-in-a-lifetime experience, book away!

Others may disagree, but I always focus on the scarcest resource, flight availability, before delving into accommodations. After all, there are no shortage of hotels, hostels, and rented rooms in most cities. And many hotels allow you to use points if any rooms are still for sale, so hotel award space disappears much less quickly that flight award space.

#5 Know the rules of each program. Be an expert.

Want an stopover on your American Airlines award? Want to fly from the US to India via the Pacific on American’s oneworld partners? Make sure to study The Five Cardinal Rules of American Airlines Awards.

Want to add a free oneway to a US Airways award? It’s possible, but it requires some trickery. You should scour the great post, Master Thread: Free Oneways on US Airways Awards before beginning.

Each program has different rules and restrictions, and it’s important to be armed with knowledge of the frequent flyer program whose miles you want to use. After all, the phone agent doesn’t get paid extra for helping you book your award, so you are the only one with the incentive to know this stuff.

#6 Maximize your routing. Use stopovers and open jaws.

Paid international tickets usually don’t have the same lenient routing rules as award tickets. Through the use of stopovers and open jaws, you can stretch the value of your miles and see multiple destinations on one ticket. For examples, check out my two posts, Anatomy of an Award: US to Asia via Europe in Business Class for 90k Miles and Anatomy of an Award: Nine Segment First Class Award through Europe and Asia.

Scott is the king of maximizing his award tickets. Check out his incredible post, How to See Seven Cities on One 12,500 Mile Award.

#7 Search segment-by-segment. Find the most difficult (usually the longest flight) award space first.

Plugging “Topeka, Kansas to Geneva, Switzerland” directly into an airline’s award search engine will likely yield nothing at all. Find the transatlantic award seats from Chicago, New York, Washington D.C., Detroit, or Atlanta first and build your trip from there.

If all else fails and you can’t award space from your home airport to the international gateway city…..

#8 Consider a cash positioning ticket to open up options.

Delta SkyMiles are often frustrating to redeem, but they have their strategic uses. Scott detailed many of those uses in his post, The Coolest Thing You Can Do with 25k to 150k Delta Skymiles.

Unfortunately, Delta is extremely stingy with domestic award space. You might be able to book your dream trip from Los Angeles to Sydney on Virgin Australia, but you can’t find any space from your home airport to LAX.

Purchasing a cheap domestic ticket with cash–or better yet Arrival Miles or ThankYou Points–can turn your dream trip into a reality. Just remember to leave plenty of time for delays or cancellations.


Award booking can be off putting to most frequent flyers. Earning the miles through manufactured spending and credit card sign up bonuses is the easy part. When it comes time to book, travelers are often left frustrated.

By following the steps above, you can put yourself in the best possible position to snag that dream itinerary. Just remember that flexibility and creativity goes a long way in this game.

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