4 Ways You Could Have Paid Less for that Flight

1. How to save $35 with one click.

2. Don’t forget about that time of month.

3. Cheat on your search engine right before the big day.

4. The only time being indecisive will save you money.

How to save $35 with one click.

Let’s say you are sitting in your small cubicle in downtown Boston on a Monday afternoon. The coffee machine has just broke and your boss just forwarded you an email chain of angry customers with a four word lowercase message and no punctuation- “take care of this”. Sounds like it’s time to plan a vacation!

As much as third party booking sites want to hide this fact from you, it is true. Using an incognito browser, a browser that hides your search history and identity, will often get you a cheaper price on your flight when booking through third party websites like Kayak, Expedia, etc. This is based on the cookies (see what are cookies again?) that these websites use to track your search history.

If you are monitoring a flight from Boston to Thailand, for example, and are searching multiple times a day for several days, airline booking companies can guess that eventually you are very likely to book that flight. In fact, they are even banking on you having an self-loathing episode when you see the price creep up $30 the next day and you think to yourself… it might jump even further if I wait any longer.

Let’s take a look at an example. I have decided I want to go to Thailand for two weeks because it’s far away, sunny, and I can get a full body hour-long massage for the price of a Venti coffee at Starbucks. I search in Kayak.com for such a flight in October. I changed the days I was going to leave a couple of times before arriving at the below results.

Looking at just the top three options, if I wanted a shorter layover I would probably consider either the second or third ticket option. Now, let’s put in the same exact search into an incognito browser (how to search incognito) which means no cookies are left and my search history is not tracked.

While the first two flights remained unchanged, the third flight, the exact same flight, jumped $35! While this might not seem like a lot compared to the flight price, I have seen differences much higher, plus that’s hard earned money you are just giving to Kayak as a gift! Keep in mind, in the first search, I was not even signed in to my Kayak account where search tracking is obvious, I was just searching on my normal browser.

Don’t forget about that time of month.

What is the cheapest day to buy my flight ticket? Older trends tended to pinpoint days of the week to fly domestically and internationally. There are plenty of pre-2018 articles citing mid week or a Tuesday / Wednesday as the optimal time to score a cheap flight. This has become less and less true as of late. According to research done by Kayak, January is the cheapest month to fly overall. Now I have not found this true yet…maybe because the article that took this information live coincidentally came out in January (hmm….). But, the study does list the best days to depart domestically and internationally in the U.S. which I have found some validity to. For the most part however, you can’t make blanket statements that are accurate for ALL destinations and flight types for day of the week to book.

But there are a handful general rules of thumb for purchasing flights:

  • Book at least 2 months in advance or more for international flights
  • Be flexible with departure/arrival days (try all of them). Kayak, Momondo Google Flights, and other major airline booking companies have great search grids for this.
  • Check the specific flights you want several times a week. The week’s pattern usually repeats itself and you go for the cheapest day the next week.
  • Avoid peak travel season for destination
  • Get uncomfortable. Late nights, early morning, more layovers, longer layovers, all almost always come hand in hand with discounted ticket prices. Just supply and demand.

Cheat on your search engine right before the big day.

Very intelligent people spent a lot of time and dollars to create algorithm-backed search engines to help you find the exact day, length of stay, fewest layovers, shortest layovers, preferred connections, and other amazing features. We must give thanks to these wonderfully useful tools. We must use them often and with enthusiasm. Look at this needle in the haystack find of a $561 round-trip flight to Thailand. She is beautiful and I might not have seen her without Kayak’s flexible search tool.

But once you find this gem and convince yourself you two are a dream match, it’s time to break her heart. Often times, going to the actual airlines website and searching for the exact same flight you found on the advanced search engine, will reveal to you the same flight for cheaper (in this case, AirAsia) . This is not always the case but rarely will the price be more expensive. At the end of the day, airline search engine companies are just trying make money.

Summary: Find cheap flights on fancy search engines. And then buy them at their source. Fall in love, but avoid loyalty.

The only time being indecisive will save you money.

Some people know this, many do not.

In the U.S., it is a government rule that if you are booking an airfare in the United States, U.S. Department of Transportation regulation requires that, as long as you’ve booked a non-refundable ticket 7 days ahead of your flight, you’re entitled to hold your reservation and the fare and change or cancel your reservation within 24 hours of booking, without paying a cancellation fee.

I first learned this rule the hard way. After using what little funds I had saved up for a Spring Break trip in college, I booked my flight to Cabo, Mexico. In my moment of horse-blinder excitement, I realized as soon as the confirmation page sprung open on my screen, that I booked the wrong dates. Sheer panic ensued as I furiously searched the web until I found this rule and called the booking agency to get refunded.

This rule can be leveraged to get cheaper fares. If you book a fare, you might as well check the next day to see if it dropped enough to make it worth your time to call customer service and change it. Airline customer service can sometimes be enough of a deterrent but hey, $100 is 15 hour long full body massages in Vietnam. Just saying.



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