We look at award booking services and talk to the experts behind them.

Booking award tickets can be a time-consuming, arduous task that can require a surprisingly sophisticated level of knowledge and skill. Those who don’t know about the intricacies of partnerships, routing rules and all of the possible itineraries may come to the conclusion that award flights are nearly impossible to book. And it is true that you may not be able to fly on the exact dates on the exact route you want, but there are more options than may be immediately apparent.

Booking a simple roundtrip domestic flight on the airline with which you have miles is fairly easy. Even a flight on a partner flight can be straightforward, especially if award flights on the partner are available to book online. The challenge comes when you want to book a complicated award itinerary including partners, stopovers, open jaws or any of the other creative ways to piece together a dream vacation. And if you want to travel during a peak travel time or on a very popular route, it will be even more difficult. Miles can be tremendously valuable only if you know how to redeem them like a pro.

In 1987, AwardPlanner was the first award booking service to come to the aid of travelers who loved the thrill of earning miles more than the hunt for award tickets. The service was started by Randy Petersen, editor of InsideFlyer magazine, and charged an annual fee of $99.95 for the primary member and $19.95 per year for family members. And the fee was the same whether you booked one award or 20 awards per year. The service ended on March 15, 2007 and in the last six years, several new services have launched to help members use their miles and points.

Ben Schlappig was one of the first to fill the void in award booking assistance when he started booking awards for people informally about five years ago and under the PointsPros name since June 2010. Gary Leff launched Book Your Award in October 2009. Since then, over 15 other services have joined them to offer their expertise in award booking.

For travelers who don’t want to spend the time to acquire an in-depth knowledge of the various programs and airline flight routes but still want to maximize the value of their miles, award booking services can help you with your award travel. Their fees range between $60 and $200 per passenger, per trip, so they aren’t inexpensive, but their fees may save you both money and miles, not to mention the time involved with searching for awards and the frustration of interacting with customer service agents who may not have the motivation or know-how to help you.

We contacted the award booking services to find out more about what they each offer and asked about their experiences booking awards for clients.

Award Booking Service Plans 

Most award booking services do not charge a fee unless they are able to find you an award ticket that fits your specifications. But they do expect payment if they find an award that matches your request. So before you request help with your award search, be clear about what you want and be prepared to book a ticket if they find what you are looking for.

There are a couple of services that charge a fee upfront. The UPGRD.com Award Expert Service has several different options and customers can choose an award telephone consultation for $150 an hour that is bookable in 20-minute segments. Customers who choose this service can ask questions about award travel and get advice on award travel, specific or general, including routing options, preferred programs, mileage earning strategies and credit card tips. This option is only for advice and information, however, and the fee does not include booking an award ticket.

Cranky Concierge award booking service charges their booking fee upfront, before they begin searching for flights, but only if they think they will be able to find an award ticket. Brett Snyder of Cranky Concierge explains, “We will talk to someone first and get a feel for whether or not we think it’s going to be possible. If not, we will discourage them from signing up for the service.” Most of the time, however, a suitable award ticket can be found. Snyder says, “It’s very rare that we can’t find something that will work for a client. I can only think of a couple instances over the last couple years.”

Cranky Concierge is also a travel agent and can help clients purchase tickets if they don’t like the award options and will monitor their flights as well. The flight monitoring service includes monitoring for delays and cancellations, finding alternate options when flights are canceled or delayed and working with airlines to get you rebooked, among other services. Snyder explains, “All of our fees include our signature flight monitoring service. We assign a concierge to monitor flights and help if anything goes wrong along the way.”

Justin Goodman of We Fly Free requires upfront payment via PayPal but if he isn’t able to find an award that suits the needs of the client, which is “very, very rare” he says, he will refund the amount paid.

All of the award booking services will book the award ticket for you if that’s what you desire. Some services will charge a fee to search for the award and a separate fee to book the award. Most people hiring an award booking service prefer to have the flights booked for them, but you will need to provide your PIN or password for your frequent flyer program and provide a form of payment for the fee charged by the airline. For those who don’t want to share this information, you can take the information provided by the award booking service and contact the airline yourself to complete the booking. If you do decide to provide this information so that the award can be booked for you, you can always change your FFP account password after the flight has been booked for an extra layer of security.

Free Services

Occasionally an enthusiastic traveler will offer to help you search for awards for free, but offers like these are usually for a limited time only. It takes time to look for all the possible combinations of flights and airlines on several different dates and it can also take hours on the phone talking with customer service representatives. Most people booking awards expect fair payment for their services. BoardingArea blogger Canadian Kilometers offered a “Pay Your Own Price” award booking service for two months with all revenue being donated to charity. Within 24 hours, he was swamped with nearly 100 requests and had to raise the white flag, “UPDATE: I’ve been swamped with so many requests that should you wish to fill in the form, I am going to ask you to be on my ‘waiting list!’ I’m really sorry.”

Helping people with award tickets is a generous gesture you’ll see occasionally but they don’t last. If you’re having trouble booking an award, you can try posting your desired itinerary on Milepoint or FlyerTalk and ask for advice. And there is a wealth of information available online about the various booking tools available and how to use them, including ExpertFlyer, AwardNexus and KVS Tool. Concourse Z on Milepoint has a section dedicated to award tools under the Award | Reward Tools section. Several of the award specialists also provide information about award booking at their blogs. Gary Leff of Book Your Award and View from the Wing blog recently wrote a comprehensive post about how to approach an award search and the different search tools available at http://insideflyerus.wpengine.com/link/?9518.

Planning Your Trip

Before contacting an award booking service, you will need to decide on your destination, the date range when you want to fly, your preferred class of service, number of passengers, maximum number of stops and maximum layover time per stop. Indicate if you’re interested in a stopover or open jaw ticket. Also indicate if you are willing to fly from or into alternate airports or in a different cabin class. For international flights, there may be availability from or to a city that isn’t one of your preferred airports. It’s not uncommon to fly from a nearby city or fly into an alternate city that isn’t too far from where you want to go. Sometimes the most difficult segment to book is the flight from your hometown to the gateway city and it’s not unheard of to purchase a short flight to get to your award flight starting point or to catch a train on the other end for your final destination.

In addition to your preferred dates, it’s helpful to have a date range so the person searching for award tickets for you has a few days to work with. It’s always better if you can be flexible with your itinerary but if your dates are fixed, let the person know that as well. If they can’t find an award that you are satisfied with, you won’t have to pay the fee. But you will be expected to pay the fee if they find you an award that fits your specification. After all, you are hiring them to do the legwork. So be as specific as possible in your initial request.

Keep in mind that in addition to the fee you will pay the award booking service, you will also need to pay the fee charged by the airline to book the ticket. And the award fees are determined by your elite status, not the elite status of the person booking the award for you.

Also include the names of the programs with which you have miles or points and your mileage amounts and whether you have elite status since some airlines offer additional seat availability to elite members. It’s helpful to have miles in different programs, but if you’ve concentrated all of your mile earning in one program, that will narrow down the search to one airline and its partners. The award booking services will also let you know what information you need when you contact them with your award request.

Having Realistic Expectations 

Booking an award ticket is different from purchasing an airline ticket and you may need to modify your plans to match what is actually available. Experts in award travel booking may be skilled with navigating the world of miles and points but they aren’t magicians. Ben Schlappig of PointsPros says, “If someone wants to have four people go from New York to Sydney Dec. 26th to Jan. 3rd with no flexibility, that’s basically impossible. But in general, if people are open to making additional connections, splitting the party amongst flights or cabins, or spending a night en route, we can nearly always find something.”

Award success is dependent on what’s available and while flights can usually be found, they may not be your first choice. Leff explains, “We can usually find something that will work, the question is whether the best available award itinerary matches the desires of the client—so if someone wants nonstop flights, that may not be possible, or if they want first class the best that might be doable for the number of passengers and dates of travel could be business.”

Scott Grimmer of MileValue points out that passengers flying on award tickets don’t always have access to the best seats and routing. He says, “It’s important to remember why airlines issue miles. They sell the miles, then they allow them to be redeemed for seats that would otherwise go unsold. That means getting the most desirable flight is often impossible. But I relish the difficult requests where the person writes in half expecting me to say there is no award space. Because when I find space for that person and help send them on a dream trip, I know I’ve done some good.”

When to Start Your Award Booking

When it comes to looking for award tickets, nearly everyone agreed that earlier is better and you should start looking when airlines release their schedules, which is usually around 11 to 12 months prior to travel. In other words, the best time to start looking for summer travel is the summer before you want to fly. Matthew Klint of UPGRD.com says many airlines release award seats nearly a year before the flight date and “more seats may open as times goes on, but if you know where you are going there is no harm in getting started early—you just might luck out.”

However, not everyone can plan that far in advance and there are other sweet spots for award availability. Snyder says, “We don’t think people need to start searching that early in most cases. And often, the best availability is found close to departure so those who want to travel even at the last minute will often find good options.”

Leff says, “Some award seats usually open when airline schedules do (varies by airline, usually between 331 and 355 days prior to travel) but that may not be when most seats are available since airlines want to offer those seats as Saver awards that they won’t sell for cash—and their ability to predict 11 months out is limited. In general, I find the best award space six months out, but also at the very last minute in the days before travel when airlines know which seats are about to go out empty.”

Leff is not alone in his last-minute strategy. Justin Goodman of We Fly Free says that other key times to look are “a few days or weeks before travel as airlines scramble to fill seats that almost certainly would go unsold” and “around one month out when airline computers start to become pessimistic about the chances to sell out a given cabin or flight.”

Also keep in mind that award availability is always changing. Ari Charlestein of First Class and Beyond says, “One day seats are there, the next day they’re not.”

In general, start early if you can, but six months out, one month out and just a few days or weeks prior to departure are good times to check for award flight availability. Booking so close to when you want to travel may be nerve-wracking and the uncertainty may not appeal to everyone, but nearly every award booker we spoke to agreed that awards do in fact open up at the last minute. Bryce Burchfield of 0 (Zero) Hassle Awards said, “Some airlines like United are great about releasing more award seats right before departure, and I have had recent success booking award tickets with them only a few days before departure.”

The Best Miles to Collect 

If you have United or US Airways miles, you may have an easier time getting an award ticket. We asked the experts which airline/alliance is the easiest to work with to find award seats and the majority said United MileagePlus and Star Alliance, although award seat availability also depends on where you want to go.

Omar Ghumrawi of Premier Award Bookings said, “United MileagePlus is generally the easiest to work with being they are part of the Star Alliance, the largest airline alliance. United also does not impose fuel surcharges like most, if not all, foreign frequent flyer programs as well as Delta and American, who sometimes charge fuel surcharges on redemptions on certain carriers within their own alliances.”

Schlappig adds that “Star Alliance has the best options to Europe by far, but each program has its own idiosyncrasies in terms of booking that space. American miles are a great option for Asia or for South America. Delta SkyMiles are still a good choice for Australia, though a great deal of date flexibility is required there.”

Klint pointed out that “Air France/KLM Flying Blue and Delta’s SkyMiles program are go-to programs if you hold AMEX points and are in need of last-minute travel or a large number of seats, particularly to Europe.” And now that Alaska has introduced one-way awards, he says, “the opportunity to mix and match carriers on a single itinerary has made that program much more valuable and easier to find an award seat on.”

But all miles can ultimately get you where you need to go if you’re flexible. Burchfield says, “While United is great about releasing plenty of award seats, I really don’t see that much difference in being able to find award seats across the various airlines. I’ve heard plenty of complaints about finding awards with Delta SkyMiles, but given a little flexibility I haven’t had many issues with them. Case in point, I had success booking a client to Mauritius and back in low-level business class, and was even able to book it completely online!”

Where to Go? 

We asked the experts for destinations that were relatively easy to book with miles and Europe and Asia came up as the easiest to book and were also two of the most popular destinations. Charlestein said he loves booking “transpacific awards because of the sheer number of options (with every alliance)! Whether it’s from Vancouver, San Francisco or Los Angeles on the west coast, or Chicago, Minneapolis or Dallas in the middle or New York or Boston out east, flights to Asia—even multiple seats in first/business class—are seemingly limitless.”

He continued, “Let’s not take this too far out of proportion though. There are obviously times when even the most heavily flown routes show zeros across the award board.”

Travis Sherry of Extra Pack of Peanuts says destinations in Western Europe and Southeast Asia are fairly easy to book. He says he gets the most requests for travel to Western Europe where he can usually find availability, “because there are so many major airports in that part of the world, and it’s so easy to get around using public transportation after you fly there, it’s a pretty good bet I can find something.” Similar to Western Europe, he says “there are a lot of big airports and major routes going through Southeast Asia, especially with Star Alliance, that most of the time, I can find something that goes there.”

As for the most popular destinations, Goodman breaks down the majority of requests into three common categories: “The family trip to Europe (Rome, Paris, London, etc.); a romantic getaway to Thailand, Bali, Maldives, Tahiti, etc. or a trip to see as much of the world as possible for as few miles as possible that includes lots of big cities and airline hubs.”

Leff says Italy in the summer and Australia/New Zealand in December-January are popular and Grimmer says Europe in the summer for two people in business class is a frequent request he receives. In general, Europe and Asia are popular, along with Australia. Avi Garg of Using Miles and Points said his most popular destinations are Europe and India and Schlappig says, “South Africa is insanely popular right now, which is such a difficult market for award travel. Anyone wanting to travel there should note they will likely need to route via Europe, and depending on their miles, may need to pay some significant fuel surcharges.” Klint says, “Paris, Sydney, Kilimanjaro and Johannesburg definitely round out the top four” from his clients.

A Trip to Anywhere

Some people will leave it up to the experts to recommend the journey and destination. Klint said, “One client asked us simply to send him and his wife on a round-the-world trip. We ended up booking the client on a journey to Beijing, Hong Kong, New Delhi, Cape Town, Buenos Aires, Machu Picchu and San José and were not only able to come up with an incredible award routing in business class that avoided the pricey fuel surcharges Aeroplan passes on when booking with many carriers, but were also able to advise about sights of interest, hotels and restaurants in each stop.”

Schlappig says he gets an open-ended request, “At least once a week! We try to open a bit of a dialogue and figure out what it is they are wanting to experience and choose a destination together from that point. After all, just because some place has great award availability doesn’t mean it will make for an enjoyable trip!”

Burchfield recommended Bali to a client who simply requested to go “somewhere exotic” and says he and his wife loved the trip. Justin Forer of Award Concierge says he had a client with 500,000 miles and points who wanted to take his son on a “‘a premium class flight on the A-380 for his birthday.’ Award Concierge was able to build a creative itinerary that included a leg on the A-380 and free stopovers in New York City and Paris. The client was delighted and made a two-week vacation out of the trip.”

Goodman tends to recommend Thailand, which is his favorite answer to the open-ended question because, “It’s easily accessible on miles, the marginal difference between booking a trip to Europe/South America and Asia actually isn’t very high and there are some fantastic true luxury properties in Southeast Asia that aren’t priced very high in their respective hotel chains’ category charts.”

Bargain Hunters 

For those members who want to take advantage of some of the “bargain” awards, we asked for recommendations on how members can save some miles. Several award bookers recommended the US Airways business class award to North Asia for 90,000 miles, describing the deal as “insanely good” and “phenomenal.” Goodman goes into additional detail about this award and explains this “‘mini-RTW’ in business class with US Airways miles for 90,000 miles is always popular. You fly US Airways to Asia via Europe and by the time you’ve built in your allotted stopover and a few 20-23 hour ‘layovers’, you can cover a lot of ground and fly very comfortably for 90,000 miles.” However, you’ll have to act fast and book this award before Dividend Miles merges with AAdvantage.

Ghumrawi pointed out that “off-peak redemptions in certain programs can save sometimes up to 40 percent of the miles needed. For example, US Airways and American Airlines both offer off-peak awards to Europe (US Airways redemptions for travel from Jan. 15 to Feb. 28 is 35,000 miles in economy instead of 60,000).” He also recommends adding an open jaw or stopover to your trip, which “will allow you to not only visit your ultimate destination, but also a city or country en route to or from there for no extra costs in terms of miles.”

Burchfield says, “120,000 Delta miles for roundtrip business class to either the Seychelles or Mauritius is tough to beat!” Klint recommends “Flying Blue (Air France/KLM) Promo Awards to Europe that often are a steal, even with the fuel surcharge ($600+ per roundtrip) factored in. For instance, this summer you can fly from Detroit, Minneapolis, Washington, Montreal or Houston to Paris or other cities in Europe for 62,500 miles roundtrip in business.” And another program across the pond can get you to Ireland for 25,000 miles. He says, “A gem of the British Airways Executive Club program is travel between Boston and Dublin for 25,000 Avios return in coach or 50,000 Avios in business class and no fuel surcharge.”

Grimmer gave us a list of his favorite bargain awards, which include the following:
– 40,000 American Airlines one-way first class between Europe and the Middle East. You can fly Etihad first class or Qantas first class on an A380 for eight hours.
– 30,000 US Airways roundtrip business class within South America. Argentina to Colombia is pretty far.
– 12,500 Avios one-way economy between the West Coast and Hawaii on American Airlines or Alaska Airlines flights.
– 25,000 Delta miles roundtrip plus a free one-way economy class flight within the U.S. (three one-way flights) by using a free stopover on domestic flights on valid connecting cities.
– 19,200 Southwest points for two one-way flights anywhere in the U.S. by exploiting the point transfers from Southwest to AirTran during the merger. You can transfer 19,200 Southwest points to 16 AirTran A+ Rewards credits, which can be converted back into the old Southwest credits for a capacity-controlled roundtrip award to anywhere in the U.S.
– 110,000 US Airways roundtrip to Australia with a stop in Asia one way. (U.S. to Asia roundtrip is 120,000, so adding flights decreases the price.)
– 17,000 Lufthansa miles for one-way in domestic business class (the best use is the flat bed p.s. service offered by United between LAX/SFO and JFK).
– Adding a free one-way flight to every award I can means three trips for the price of two. Certain AA, DL, US and UA awards allow an extra one-way trip within the U.S. and Canada for no extra miles to be tagged on to an award. Grimmer explains how to do this for American Airlines on his YouTube video at http://insideflyerus.wpengine.com/link/?9519.

Looking into the Future

The latest trend in frequent flyer programs is revenue-based awards where the number of miles required for award tickets fluctuate along with fare prices. While an increase in revenue-based programs would change the way awards are priced and their availability, Schlappig doesn’t think it will fundamentally change the value provided by award booking services. He says he doesn’t currently book awards for revenue-based programs very often right now because “there honestly isn’t much value we can add to a booking on Southwest, for example. However, if all the airlines and credit card programs were to move to a fixed-value system we would certainly stay in business, in my opinion. I think our knowledge of routes and products would be beneficial regardless, and that expertise could be even more valuable if there were to be a dramatic shift in the landscape.” Leff similarly isn’t concerned by a shift to revenue-based programs “… because there are many many programs around the world. I may focus more on high-value programs life Avianca’s LifeMiles. I get great results from Singapore Airlines KrisFlyer, and though they’re frustrating to work with, Korean Air SKYPASS. Big spenders with points in credit card programs that transfer to miles have lots of international airline options to work with. The nature of frequent flyer programs is to change, and we’ll keep working to stay one step ahead.”

Expert Award Tips

We asked the experts if they had any tips for customers on how to make the award booking process easier and quicker. We compiled a list of their responses to help you with your next flight award if you decide to contact an award booking expert or book your flight on your own.

The best way to make the award process easier is to be flexible with your trip parameters. 
Brett Snyder, Cranky Concierge

Before you start planning, it is best to catalog all the miles and points that you have across all the programs you participate in, including airlines, hotels, rental cars, credit cards and even trains, as they all might be useful for your trip. Award travel should be about adventure and exploration, using your miles and points to go places you only dreamed of … so the most important tip is to be flexible with your dates, connections, travel times and airports. If you are flexible, you will find that it becomes significantly easier to get real value out of award travel bookings.
Justin Forer, Award Concierge

Try to plan your travel goals very far in advance. Even if you don’t know exactly where you want to go (maybe you only know “somewhere in Europe”), it’s a whole lot easier to plan what type of miles you need to be stashing away if you know generally where you want to go. And if you can start looking for award space the day it becomes available (and keep monitoring it), you maximize your chances of finding an itinerary you really like. 
Justin Goodman, We Fly Free

Collect miles in programs where points transfer to a variety of airline frequent flyer programs (Chase Ultimate Rewards, American Express Membership Rewards, Starwood Preferred Guest). That way points can go wherever the best match between itinerary desires and award availability is most likely to be.
Gary Leff, Book Your Award

Have some flexibility, especially date flexibility, and plan ahead. Know the trip you want before you contact an award booker. Contact an award booker when you are likely to be able to answer emails quickly. Award space can change rapidly, so you’ll want to be able to give the go-ahead to put a great routing on hold before it disappears.
Scott Grimmer, MileValue

Be specific about what you want and have your points ready. The more specific you are about what does and what doesn’t work, the easier it is for me to either find your flight or write it off as not being possible. While I love the idea of “not caring where you go”, I find that even though people tell me that, it certainly isn’t usually the case. Having your points ready is always a major help. I can’t tell you how many people have come to me and said that they have 150,000 United miles, we’ve gone through, found the flights, and then I’ve heard “well, I don’t have them yet, it’ll be a week or two until they post.” Then, after they post, the flights we have looked into are gone. The client is heartbroken, and we’ve both wasted a lot of time for nothing.
Travis Sherry, Extra Pack of Peanuts

Flexibility is the key. I personally know it can be tough at times, but if you open up your time schedule a little bit—even just a week or so, and don’t mind a few stops along the way, most any award is possible.
Bryce Burchfield, 0 (Zero) Hassle Awards

Planning ahead along with flexibility are the two keys to find “aspirational” award tickets, as well as knowing which destinations you would like to visit. 
Omar Ghumrawi, Premier Award Bookings

Do your homework before contacting an award booking service. Check the airline’s website and call them to see if you can book it yourself. And when calling airlines, sometimes to get results you will need to call two to five times to find a knowledgeable agent. Only contact a booking service if you’re actually ready to book the award. Transferable credit card points (AMEX, Chase Ultimate Rewards and SPG) are great because you have many airline options. Be flexible with your travel dates if you’re hoping to use points. It’s hard to find more than three award seats on the same flight together. Be ready to split your party.
Dennis Konnov, Award Planners

When using an award service, give as much information as possible, including the amount of miles, date of travel and flexibility. About 60 percent of the requests I get are from customers who want to travel on exact dates or nonstop (or one stop).
Avi Garg, Using Miles and Points

Think about what is most important for your trip, and be open with that information. Whether it is more direct flights, the best products, the fewest number of miles, the lowest out-of-pocket costs or the easiest connections; award travel requires a bit of prioritizing, and it helps if we’re all on the same page. Also, if you aren’t realistically ready to ticket your flights within 24 hours, it probably doesn’t make sense to contact a booking service. Award availability is incredibly fluid, and many programs don’t allow us to hold space. It’s always sad when someone takes a few days to look over an itinerary, only to find the space is gone when they’re ready to book. 
Ben Schlappig, PointsPros

When you send us your request, if you also send us how each travelers’ name appears on his/her passports we will place tickets on hold for you if feasible (assuming, of course, we find an itinerary that matches your request). That way, you can review the itinerary we have assembled for you without fear of losing it. So many times we have been successful in finding itineraries only to see a client take a day or two to decide and then find the itinerary is no longer available. Award availability waits for no one. When you contact us, you should be ready to book immediately because there is usually not time to consider your options for more than a half day.
Matthew Klint, UPGRD.com

Be flexible. While I’d love to book an A-B itinerary on a nonstop flight in first class on your most preferred dates, we’re often at the mercy of the airlines and how generous or not they are with their award space and may have to compromise on some portion of the trip.
Christopher Wacker, Award Travel Consulting

My tip is to always send your most up to date miles/points account balances for ALL of your accounts. One program may have availability while others don’t. Be flexible!
Bobby Burns, Award Booking Service

There are a lot of DO-IT-YOURSELF resources out there, be it paid resources like ExpertFlyer and free resources like the airline websites. The answer lies in how much you know about the various alliances in order to efficiently utilize the miles.
Sunny Dhuper, World Class Perks