How to Book Flights Around the Holiday Season

It’s that time of year again – many people are booking trips around the world to fly home for Christmas. For me, that’s a trip from London to San Francisco – 11 hours in the air if it’s direct. This year, it also includes Conor booking flights from London to San Francisco to spend the holidays with me and my family. Booking flights can be daunting because of the price, but there are a few tips and tricks I’ve learned over the years.

Incognito Window is your best friend, because airlines are scammers and shady-ass corporations. The prices you see are different from prices I would see because they have your cookies – tracking what sites you’ve been on, how many times you’ve looked at flights before, etc. This means they can manipulate prices to get you to pay the highest price possible. Incognito doesn’t track your cookies or sites you’ve been to, for the most part, so I always book flights on Incognito. This is the Google Chrome word for it, but it’s basically a private browsing window. Super easy to access through the “File” tab when you have your internet browser open.

I usually book about 8 weeks out, unless I find a really good deal in the mean time. For some reason, six to eight weeks out from your desired departure date is the sweet spot for deals. The prices should be lowest around then, and will start increasing soon afterwards. I’ve booked flights anywhere from months out to one week out, and consistently six to eight weeks has the best deals. I haven’t booked my flights home yet, but right now the prices are really good and better than they have been for the past few weeks, even though I’m on the end of that six to eight weeks sweet spot. Usually, once I know I want to book flights, I will start keeping an eye on prices through Incognito Google Flights – though there are apps for this like Skyscanner.

Google Flights is a great way to plan your trip through their Date Grid. If you’re flexible on when you fly out and fly back this is a great tool to find the best roundtrip price around your dates. For me, flying back on the 29th of December is way cheaper than the early days of January. Just as flying out on Tues-Thu is usually cheaper than Fri-Sun. I use Google Flights in Incognito to find the best deals usually. There are some caveats.

Some things to consider when booking would be loyalty programs. My parents have flown with United for decades and now reap the benefits of being Gold members, so they always fly United. I, on the other hand, have no loyalties to any airline at this moment so I can be more flexible in looking at different deals, days, airlines, airports, etc. However, loyalty programs can be very beneficial, but they require, you guessed it, loyalty which doesn’t always translate to the best price for the trip. So for me, as a working professional on a minimal salary, the prices now outweigh any potential benefits I’ll have from loyalty programs in five years. With that said, I still have a member number (they’re free from any airline website) for every airline I fly with, which means I am still tracking any miles I fly with the airlines. Potentially this could lead to benefits, but without flying one airline consistently, the points are that helpful right now. If you are a loyal flyer, I would say keep flying that airline and look for their best deals around the dates you want to fly – they might even have holiday specials for frequent flyers. Additionally, if you consistently book holidays through sites like Expedia or Kayak and have been gaining points from doing that, I would say keep doing it! These sites help find the best deals and allow you to accrue points for benefits.

I recently signed up for Jack’s Flight Club, a weekly newsletter about the best flight deals. I booked my weekend trip to Rome through these deals. The newsletter is free to sign up for (though there is a Premium service if you want to pay to find out about more deals sooner – I don’t). It gives me a heads-up which is always nice to have. Some of the deals don’t apply to me at all, but some do, so I keep it in my inbox.

Dana’s Do’s:

  1. Use a private browser!
  2. If you can, be flexible on your fly dates to get the best deals.
  3. Best to book about eight weeks out, but keep an eye on prices leading up to that.

3 thoughts on “How to Book Flights Around the Holiday Season

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