Thanksgiving, Christmas, ski season, and that point in winter when somewhere warm starts sounding really good all have a way of feeling far away until suddenly they’re not.
Now’s a good time to see what the options look like.
That doesn’t mean there’s a magic deadline for booking. A flight that costs a ton of miles today could cost less next week. It could also cost more, and sometimes a great option pops up at the last minute. Award prices change, and there’s no reliable way to predict exactly when the best price will appear.
But waiting isn’t the only option.
Depending on the airline and the type of award, it may be possible to book a flight that works now and change it later if something better comes along. And if nothing looks good today, there are ways to keep an eye on the trip without searching for the same flights over and over.
Here’s where to start.
Start With the Trips You Know You’re Taking
Thanksgiving with the family is a very different trip from a January ski weekend or escaping somewhere warm in February.
For a holiday, wedding, or another event already on the calendar, start by looking at the options now. Someone who needs to fly the Wednesday before Thanksgiving and return Sunday has much less flexibility than someone who wants to spend a few days on a beach sometime this winter.
Look at both the cash price and the number of points or miles required. That gives you a baseline, even if you’re not ready to book right this minute.
More flexible trips open up more possibilities. A ski trip might work over several weekends. A warm-weather getaway might work in January or February. Try moving the dates, checking nearby airports, or looking at another weekend.
PointsYeah makes it easy to scope out your options without starting a new search every time.
Flight Search
Hotel Search
And if the destination isn’t set either, let what’s available offer some inspiration.
PointsYeah’s Daydream Explorer shows destinations that can be booked with points from a selected airport. Instead of searching for one place at a time, it can answer questions like, “Where could I go for a long weekend in January to escape the cold?” or “Where can I fly with my points for a ski trip this winter?”
Finding a flight that works doesn’t necessarily mean the search has to end.
Some airline loyalty programs allow award tickets to be changed or canceled without a fee. That can make it possible to book a workable option now while keeping an eye out for something cheaper or more convenient.
American Airlines is a good example. AAdvantage doesn’t charge change fees on award tickets, although changing to a more expensive award means paying the difference. American also allows eligible awards to be canceled before departure with the miles reinstated at no charge.
Say a Christmas trip costs 25,000 miles today. A few weeks later, the same flight becomes available for 18,000 miles.
The trip stays the same, but 7,000 miles go back into the account.
PHOTOSVIT / ISTOCK
But this is something to check before booking, because every loyalty program has its own rules.
Delta, for example, treats Basic award tickets differently. Basic awards originating in the U.S. or Canada aren’t refundable after the 24-hour risk-free cancellation period, and changing or canceling one comes with a fee assessed in miles.
Other programs have their own policies, and certain bookings can have additional restrictions.
That flexibility can be especially useful for winter trips that aren’t completely settled. Maybe the ski weekend depends on snow conditions, or a warm-weather getaway could move by a few days. If that’s part of the plan, check the rules before booking rather than assuming an award can be changed later.
Don’t Like the Price? Track It
Sometimes there isn’t anything worth booking yet.
Maybe the Christmas flight costs far more miles than expected. Maybe there’s nothing available for the ski weekend. Or maybe the only flight to somewhere warm leaves at 5 a.m. and connects twice.
Waiting can make sense in those situations. But it doesn’t have to mean running the same search every few days.
A PointsYeah Points Price Alert can track a trip and send an alert if the points price changes or something new becomes available.
There’s no guarantee a better option will appear, but the alert can do the checking in the background.
Keep an eye on the cash fare, too. If an award still costs more miles than expected but the cash ticket drops to a comfortable price, paying cash may make more sense.
Points and miles are another way to pay for a trip. They don’t have to be used every time.
DORADALTON / ISTOCK
Check the Hotel Before You Book the Flight
A great flight deal can become a much less appealing trip once the hotel search begins.
That’s especially important for fall and winter trips. College football games, parents’ weekends, Christmas markets, holiday events, ski season, and long weekends can make hotel rooms unusually expensive on certain dates.
A cheap flight to a ski destination, for example, isn’t nearly as exciting if every hotel nearby costs $700 a night.
Before booking a discretionary trip, check the hotel rates alongside the flights.
The hotel might change which weekend makes the most sense. It can also change where points are most useful.
For example, a reasonably priced cash flight paired with an expensive ski resort might be a good opportunity to save the airline miles and use hotel points instead. If hotel rooms at a warm-weather destination are inexpensive but flights are costly, the opposite might make more sense.
There’s no need to pay for every part of a trip the same way. Points can cover the parts where they’re most useful, and cash can cover the rest.
A Thanksgiving trip, Christmas vacation, ski weekend, and February escape don’t need to be planned the same way.
Some trips come with dates that can’t move. Others might have an entire season to work with.
Start with the trips already on the calendar and check both points and cash prices. For a more flexible getaway, see what happens when the dates or destination change. And before booking an award that might need to move, find out what the change and cancellation rules allow.
If nothing works yet, that’s useful information, too. Set an alert and keep looking without having to start from scratch every few days.
There’s no way to know today whether the best fall or winter award will appear tomorrow, next month, or a few days before departure. But knowing what the options look like now leaves plenty of time to decide whether to book, wait, or change the trip entirely.
