How and When to Book Your Travel

2018 has officially been dubbed the Year of the Wedding. We thought we hit our peak in 2016 with 6 weddings, but this year we have officially been invited to 9, though we will likely only attend 7. Not only do all these wedding come with the usual costs of gifts, hotels, etc., but nearly all of them are a flight away. This isn’t just because NFF Jr. is easier to travel with on a plane than in a car. We have weddings that span Massachusetts in the north, to Wisconsin in the west, to Houston, TX in the south.

All of this travel has got me thinking about the best way to minimize our travel costs. Now, I have a confession to make. I’m a bit if a data nerd. I hear the words “statistical analysis” and I immediately get excited. Most sites I’ve been to who claim to know the best times to book flights often sorely disappoint. They’re usually too specific (“buy the third Tuesday before your travel”) with no acknowledgement that not every flight is the same. What about winter versus summer, holidays, etc?

Time until Departure

That all changed when I came across, a travel blog which has done a great statistical study around buying the cheapest airfare. Using data from over 900M tickets, CheapAir has boiled the buying timing down into 5 zones:

  • First Dibs: 6-11 months out
    • Pros: Full choice of flight options and seat selection
    • Cons: Cost
  • Peace of Mind: 3.5-6 months out
    • Pros: Mostly full choice of flight options and seat selection
    • Cons: $20+ premium for the choice
  • Prime Booking Window: 3 weeks – 3.5 months
    • Pros: Best bargains, within 5% of lowest price
    • Cons: Smaller flight selection and tighter seat options
  • Push Your Luck: 2-3 weeks
    • Pros: Possibility of a lucky break to find low fares to unpopular destinations
    • Cons: Booked flights for popular destinations or higher fares on average
  • Hail Mary: 0-13 days
    • Pros: Few to none
    • Cons: Premiums of $150 more on average for your flight


Across all flights, the cheapest day of the year to buy your flight is 54 days in advance of your travel date. However, the seasons can have a significant impact on that figure, so it’s important to know how to adjust your ideal range.

Winter: The ideal day to buy in winter is 54 days in advance, the same as the overall average. Therefore, we don’t need to make any adjustments to our ranges.

Spring: The ideal day in spring is 75 days in advance, a full 3 weeks earlier than the average case. This could be a big difference, particularly if you often find yourself in the Prime Booking Window / Push Your Luck zones.

Summer: The ideal day in summer is 76 days in advance, nearly the same as Spring.

Fall: At just 47 days, Fall has the shortest time between lowest fare and takeoff, reducing the averages by 1 week.

Booking my Flights

I have to admit, while I really do like saving money, I am also a planner. Before reading this article, I would have no qualms about booking the flights for our October weddings in February just to get it over with. So keeping that in mind, I am going to time my flights to be right on the border of Peace of Mind and Prime Booking Window, at 3.5 months adjusted for the seasons. I don’t mind paying a little bit of a premium to ensure that my wife and I can sit next to each other and share the NFF Jr. responsibilities.  So, below is my table for my prime time to buy my tickets based on travel dates:

Time to mark my calendar!

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