Why Now May Be The Best Time To Book 2019 Holiday Travel

Filed Under: Advice, Awards

For many of us, early February means that we are one month into our new years’ resolutions, and that we’ve finally stopped writing “2018” on any document that we sign. But if you’re in the points and miles world and you tend to travel during the Christmas/New Years holiday, this actually be the best time to start booking award travel.

Booking flights

If you’ve been in this hobby for a while, you’re probably aware that timing is key in booking awards, especially during peak times. But just as a reminder, there are two key times where you are likely to find the best availability:

I don’t know about you, but if I told my husband that we’re planning a trip, and we can’t book a flight until the week before departure, I would probably be traveling alone a lot more. But if you are looking to book early, now is the time to hop on holiday award space – if you can find it.

Outbound travel

If you’re looking to travel before or right after Christmas, award availability should be up and running by now. I’ve seen pockets of saver availability across all three major airline alliances, although I would act fast if you’re trying to jump on award space that gets released early.

Return travel 

Between the crowds, potential weather delays, and terrible award inventory, traveling home right after New Years is always a struggle bus. And for those of us trying to milk vacation time and get back to work – sometimes it’s the only option.

The weekend after New Years’ is typically the worst of the year for award travel, with everyone and their dog returning home from vacations all over the world. Award calendars should be releasing availability for these dates (January 4th and 5th, 2020) this week, so keep an eye on the calendar and don’t be afraid to book early if this is your preferred week of travel.

Alternately, if you can extend your travel even by an extra day or two, you should have some much better options at your disposal.

Don’t forget to check partner availability 

If you’re looking to book an award through a specific currency, don’t assume that all partner availability will show up. Anyone who has ever booked through AAdvantage probably knows to check the British Airways site for OneWorld availability. You can also use the JuicyMiles search tool to avoid having to go through every partner site to find award space.

But beyond that, you may want to look at the carrier’s own website, particularly if you’re trying to book unicorn-type seats on the first day that they become available. For example, Japan Airlines typically releases two first class seats on the furthest possible booking day, but their award calendar is a day behind American Airlines. So if AAdvantage lets you book flights through January 1st, JAL only lets you book through December 31st (even with the time zone differences).


Redeposit fee considerations

Even if you’ve found your dream award, a lot can happen in 330 days. But if you’re feeling a little hesitant, keep in mind that award tickets can be changed or canceled at what is usually a marginal cost. The most expensive redeposit fees are charged by United, for $200 a ticket if you do not have MileagePlus status, but many airlines charge less than $100 per ticket. 

While no one wants to pay a fee to cancel a ticket, if you’re unsure about booking so far out, even $200 per person seems like a marginal “risk” to take on an award itinerary that may retail for five figures.

Furthermore, many airlines waive or significantly reduce redeposit fees for their elite members, making it even easier to commit to an itinerary without any “buyers’ remorse.”


If award availability during peak holiday travel is scant, then cash hotel prices tend to be certifiably bananas in popular vacation locations. I find that if I’m comparing points redemptions to cash prices, the week between Christmas and New Years’ is one of the best times to get a better point redemption value.

And it’s not uncommon for hotels to sell out months in advance during this peak time.

Furthermore, if you’re riding the Marriott Bonvoy train, keep in mind that they haven’t introduced “peak” award prices yet, but they sure as heck are about to. So while award availability at hotels is typically better than airlines, I would still lock in the lower rates while you can.

The St. Regis Maldives will increase from 60,000 to 100,000 points per night during peak travel times.

And whether you’re using cash or points, hotels typically have much more relaxed cancellation policies as long as you stay away from prepaid rates.


As someone who almost never books flights more than two weeks out, I would probably be scoffing at this article right now if it wasn’t targeted at busy holiday travel. But by booking ridiculously far in advance, I was able to land a pair of ANA first class tickets from Washington-Dulles to Tokyo-Narita at saver-level availability in late December.

I’ll make a confession: unlike most of my colleagues here, I’ve actually never flown a true international first class flight, so needless to say I’m ridiculously excited for the experience – which I’ll be sharing roughly a year from now 😉

ana first class 777

(Side note: if anyone has travel recommendations for skiing on Sapporo Island, by all means send them my way!)

Hotel bookings will follow shortly, but right now I’m looking at either the Sheraton Hokkaido or the Kiroro Hotel, both of which retail for 35,000 points a night and are showing standard prepaid rates at $500-$570 per night. Yikes.

Bottom line

Holiday travel can be stressful enough as it is, and booking award tickets during that time can often add to the frustration. But with enough advanced planning, and a willingness to commit, there are some gems out there to be found.

I think it goes without saying that your mileage will vary greatly during peak travel times, but with most programs, you’re probably more likely to have success now than you will in even a month or two.

Given that this is the week that most award availability opens up for the week after New Year’s, I would come up with a game plan quickly so that you can book award travel on the day that it opens up. Be patient,  hang up and call again if you have to, and don’t be afraid to lock something in if you are comfortable with the redeposit fees.

Good luck out there, for all of you advanced planners!

How far out do you typically book award travel? 

  1. I did SFO to Japan on ANA First Class (booked with Virgin Atlantic miles, mostly xfered from Amex) last winter to ski, actually. Everything lived up to expectations 🙂

    If you backcountry ski, I recommend Black Diamond Tours, who I used. Recommendations for resort skiing (from friends there) are Rusustsu near Niseko (great tree skiing) and Kokusai near Sapporo.

  2. Sapporo is not an island. It’s a city on the island of Hokkaido. For ski resorts in Hokkaido, be heard that the resorts near Niseko are great. Friends were there over Christmas and had a blast.

  3. I’m deep in my 2019 December planning. A continuous point of frustration I have is when the US carriers where I have mileage balances don’t allow booking early enough to capture the inventory when it is released. For example, United allows bookings of award tickets max 337 days in advance. However South African airways releases award inventory sooner than that, which I can see using ANA or Lifemiles to search. I watch in agony as that inventory is snapped up, and none is left by the time 337 days rolls around and I can finally use my United miles to book. There are many similar instances afflicting other programs (AA and BA is another one).

    Would you be able to provide a list of programs that allow you to put bookings on hold to block the inventory while you wait for that booking window to open up by alliance? I.e. if ANA would let me hold a booking for a week like AA does, then I could use that to hold the inventory. Then cancel that booking when 337 days came and rebook immediately with United.

  4. There is no need to pay $500+ for a sub-standard Sheraton on Hokkaido.
    You should be able to get a non-chain 4* hotel with a decent sized room for under $150.

  5. I’m in the “book when it opens up” group which means most of my 2019 travel plans were booked back in 2018. It hasn’t been as effective in recent year, and there is definitely some downsides, but ultimately it’s been my favorite strategy. Think the strategy works for me on a psychological level. I like having something to look forward to. When I’m feeling bored or have had a long week I research things to do at the destinations I’m heading to later in the year. I like also not having to worry about the mandatory details of a trip (how we’re getting there and where we’re staying). This means I can focus on what to do in the destination. Planning ahead also means I tend to find premium flights and hotels during peak season. I booked the Conrad Bora Bora for Nov 2019 (not peak but holidays) when availability opened up. Despite being 9 months away it looks like no basic rewards are available. They might open up more availability as it gets closer and they have unsold rooms but knowing I have something booked means I don’t have to take that risk.

    The downside means I’m sort of stuck with plans that sometimes don’t work out. Usually that means that I’m just not looking forward to it as much as I was a year ago. Another downside is I can’t take advantage of those cheap flight deals that come up during the year since they usually require traveling in the near future. Despite having a flexible job that encourages vacation and remote work I’ve already scheduled time off throughout the year.

  6. Late to the game… I booked my Christmas and New Years for two people on Star Alliance and Skyteam last week. Virgin, United and Delta all bookable. Almost no inventory… but got what I needed. The only ones not are oneworld. This post should have been done 2 weeks ago… but lucky for me.. you did not,

  7. It’s a little late for Christmas or NYE, isn’t it? I finalized my NYE plans a little while ago: two couples, all business, South Africa.

    I did have to settle for Egyptair going to JNB, but I was delighted to get four seats on SA’s JNB-JFK route. It’s not the swankiest, and I had to cut our trip short by one day due to availability, but it is the most convenient route for us. Now I just need to cross my fingers and hope they don’t go bankrupt this year.

  8. @Sam — Aeroplan (and Amex MR points) is how I got 2 of my SAA tickets as soon as SAA released them.

    I have a lot more UR points than MR points, so I couldn’t just grab all four at once.

    I got lucky with the other two — they stuck around until I could book them with United miles. (My backup plan was to use BA and ease the pain of those fees by enjoying a long stopover in London.)

  9. I book in the final days before travel. Book the time, pack the bag, place it by the door, book a oneway to the destination and step into the waiting uber. What can possibly go wr

    The best part is the freedom in Bangkok to enjoy it as long as I like, then go home when I decide I want to. I don’thave a “return date” until I’m ready to return. Psychologically, I can recommend this highly, at least once, to you, if you think it’s scary. It is, but it’s also thrilling and different.

    One thing about last-minute award travel: you can take away all the fear beforehand. Go online today, search oneways from your city to Bangkok today, tomorrow, the next day, etc. Lots of availability! Okay, now search two months from now. Nothing. You can do this every day until it’s drummed into your skull that last-minute availability is always abundant.

    Except if you want CX and you only have Avios. In that case, enjoy your living room.

  10. Been digging around, but trying to use AA systemwide upgrades while traveling by myself to visit friends in Shanghai. Stupidly, nothing availabe and still a pain in the *** this far out – not willing to risk having to fly in cattle class that long. AA has truly made their EP program worthless. Will save my miles for when I retire in a few years and need one-way segments. Screw AA. Will earn miles and use them on better partners.

  11. Booked one way to Thailand for end of December on Asiana and Thai in Business for 2 adults and a baby($100). Booked it through Aeroplan and transfered 155K MR points. Still figuring out the return.

  12. Seconding what somebody above said about Rusutsu. Most incredible fresh skiing powder of my life, and the Westin is right there next to the ski resort, with indoor and outdoor onsen and just an amazing ambiance.

  13. I just booked 2 ANA tickets last week for November; there was only 1 date the entire month from JFK that had 2 tickets in first class. Lucky for us we had some flexibility in our schedule!

  14. I am also in the “book when it opens” camp. I have used this strategy for the last few years and it has worked for me. I finalised my Xmas/NY travel to YVR on CX weeks ago, even had to pay more points for business choice awards (rather than business standard) cos I could see seats been snapped up right in front of my eyes!

    We have just returned from skiing in Hokkaido! We were at Niseko and Rusutsu. Niseko is “wild” and ungroomed, with plenty of powder. Grand hirafu was very crowded 2nd week of January but the other parts of Niseko was not so crowded. If you are used to the facilities in ski resorts in North America, you will find it mostly lacking in Niseko. On the other hand, the food and cultural experience will be overwhelming (in a good way). Rusutsu was lovely to ski at, and will become part of epic from 2019. It is a bit more similar to a North American ski resort than Niseko, with nice grooming and better lift facilities. It felt a bit more upmarket than Niseko. The Hokkaido ski resorts are not big so I would definitely recommend visiting at least 2 if you can. I would suggest booking your accommodation way in advance, as there is only limited (and expensive) accommodation in resorts like Kiroro and Rusutsu (plenty at Niseko). Wherever you end up going I am sure you will enjoy skiing in Hokkaido, it’s different and I look forward to your trip reports!

  15. just a suggestion steph- when you title the article referencing “holiday” travel, it leads the reader to wonder what holidays youre talking about since there are so many!

    in this case u were referring to christmas+new years, so maybe changing the title to Christmas travel would be more helpful since we all know what time of year that is!


  16. Steph/Ben – Have you ever released a guide of when every airline releases award space (350 days, etc)? If not, would you please?

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