When, Exactly, Should You Book Your Holiday Travel?

Yes, it is possible to book holiday travel with miles. Here’s how.

If you want to redeem miles for holiday travel, it can be a challenging experience (especially if you’ve got the family in tow). So when, exactly, is the best time to make an award reservation? The answer is not simple because a variety of factors come into play.

Like normal airfare, mileage pricing can fluctuate based upon market conditions: how full the flight is and how full the airline predicts it to be. Even if you search for an award seat 11 months in advance (when many airlines traditionally make flights available for sale), you won’t find saver space easily for holiday travel. Getting a seat on the day before Thanksgiving is as rare as finding a four-leaf clover.

But there are free seats out there. The key is to be patient and flexible. Here are a few tips that might help you score that free ticket during the busiest travel times of the year.

It might be easier if you…

Consider looking at alternate dates, as there could be more free seats on the actual holiday itself. Domestic and transatlantic award seats are hardest to come by on Fridays and Sundays when business travelers are en route, but traveling around the holidays is busy anyway so prepare to be flexible. Be sure to check nearby airports as well.

Search for one-way tickets first, which might be an easier way to spot award space.

If you follow this column regularly, you know how valuable having elite status can be. Not only do airlines make more award space available to elite fliers, but many change and cancellation fees can be waived. This means that if you have an elite flier in your family, let that person be the one to make the reservation using their miles. If something better comes along, the elite traveler has more flexibility to make changes.

The best approach to booking award travel is to begin the search as soon as you know your travel plans. Award space might be there, but if not, it pays to keep checking because space can open up any time before the flight. It becomes a bit of a waiting game, but keep checking.

Lufthansa, for example, is notorious for opening up greater first-class award space within two weeks of departure. For many fliers, that might be cutting it a little close, but many airlines commonly create more award space closer to departure, a time when airlines realize there may be plenty of empty seats.

Don’t be shy about hanging up and calling again when speaking with a phone agent if he or she insists there is no space. Not all agents with various airlines are familiar with the immense roster of partners (within the alliance and not) that are eligible for award travel. Be sure they search all partner airlines, and remember that airline websites often exclude award availability with some partners.

When booking award travel, flexibility and patience are necessary. To travel for free, you have to be willing to give up a little peace of mind when booking flights.

The goal is to book awards at the lowest saver level, but if you absolutely must travel on a specific date and flight, airlines have made it easier by charging more miles for that “last seat availability.” It’s not the best value, but it is usually an option. For example, a domestic round-trip flight on Delta should cost 25,000 miles, but the airline might make it available for 50,000 miles.

Experts weigh in

Rewardexpert.com conducted an extensive study of saver award flight availability from Buffalo, New York. The results, yet to be fully released, show that award space is often released proportionally to the size of an airline’s operation in a given city. The gist of Reward Expert’s survey found that in the second half of the year, September and October were among the cheapest months for domestic economy class redemptions while November (probably due to holiday travel) was most expensive.

Cheapair.com conducted its own meticulous study on purchasing airfare and found that the best time was in the 40- to 60-day advance range for general airfare purchases. But it’s a whole different ballgame when booking award travel, although it does point to when there might be a jump in reservations (which can lead to greater or fewer award seats based upon booking patterns).

There is no best time to book award travel, but when it comes to the holidays, there is less of a chance for award seats to open up at the last minute since demand is always high during those periods. Instead, begin your search early.

One caveat: If you are booking travel on JetBlue or Southwest, watch for airfare sales at any time because award ticket prices are based upon the ticket cost. So when fares are cheap (as is the case when you book early), the cost in miles or points will be equally cheap. Southwest doesn’t charge change or cancellation fees, so no worries if your plans change.

It’s not just with airlines, either. Hotels in popular urban destinations are controlling the room inventory that gets allotted to point redemptions. For example, the new London House Chicago, part of the growing Curio Collection by Hilton, is seeing huge interest in its riverfront location for the holidays (the rooftop bar and lounge will be a shoe-in come New Year’s).

“Downtown Chicago is great during the holiday season and since opening in late May, we continue to see an uptick in reservations,” says general manager Jermaine Anderson. “Travelers are looking ahead to secure rooms a few months in advance.”

Hotels are more generous with their room allotment going for points than airlines are, but it still pays to book early because the points rate can go quickly. Also, hotel companies like Curio Collection by Hilton are more lenient in change and cancellation policies than airlines are.

Traveler’s toolbox

There are services that handle the nitty-gritty details of booking award travel. Expertflyer.com is an invaluable tool: It searches award space on dozens of airlines and also allows you to set an alert for when an award seat becomes available. This keeps you from having to check back daily. The website has a subscription fee, but it gives new users a free trial period, which may be just what you need to do your homework.

Awardace.com has an amazing calculator that tells you the cost of an award flight across multiple airlines and alliances. This one tool can help you save miles when trying to decide which program to use to make a reservation.

Bookyouraward.com can save you time and energy by determining the free travel options based upon the points and miles you have. These types of services are familiar with particular routes that are more likely to have award seats, which can get you in the air on the cheap.

 >>Next: How to Take Your Dream Trip with Airline Miles