It’s Not Easy Getting an Unfair Advantage in Travel

flight deal

A Bangkok flight deal for the flexible traveler

I do a lot of media interviews and write a lot of short travel articles for others on how to get good deals on travel. Many times the writer or editor is looking for insider, little-known advice and what they really really want is some secret travel tip that’s going to save a bundle.

As I’ve said before though, the fundamentals of getting a good travel deal have much more to do with open variables than they do with any new app or secret trick.

I’m planning to take my wife to somewhere in the South Pacific next year for a big anniversary trip and I’m very confident I’ll do it for close to the minimum cost one can get. Not because I’m so extra savvy though, but because I’m going to cash in miles and I’m going to take advantage of seasonality. I’m pretty sure I’ll be able to get free flights for us because I’ve been banking miles on the airline alliance that will get us there and we can go almost anytime in April or May. That happens to follow the end of the “escaping the winter” big tourist season too. I don’t have my heart set on one particular hotel and I’m looking for places that are lesser-known, so I’m sure we’ll do okay on whatever hotels we choose.

(c) Carolyn Heller

(c) Carolyn Heller

Contrast that with someone who must go to Bora Bora, must travel certain days in the third week of March, and must stay at a specific resort on a specific beach. He will pay whatever the airlines and hotels are asking. He has no choice. He can mess with the margins a little, but he can’t fundamentally reduce what he’s going to pay. No app, website, or trick is going to be much help.

The reason flexibility and a willingness to buck what the crowd is doing will trump all is that otherwise the deck is stacked against you. Like a punter playing roulette in a U.S. casino, the longer you play the more destined you are to lose. The numbers are just not mathematically in your favor. The airlines have an army of people who breezed through advanced calculus figuring out how to change seat prices in real time to best ensure the chance of squeezing every possible dollar out of every seat.

The hotels roll out dynamic pricing daily and sometimes hourly to capitalize on a surge in demand or a convention announcement. Rental car companies do the same, always weighing their options against what competitors are charging in every market and how many cars are reserved already. Much of the repricing is done by algorithms on a remote server, with no human intervention. Trying to find an app that’s going to counteract this is like thinking you can be a successful day trader because you bought a second monitor for your Dell.

Hotwire and HotelTonight work for one reason: they offer empty rooms at a discount. Use those services in peak demand periods and they’re close to worthless.

So forget trying to gain an edge through technology and forget the idea that a trick like booking a plane ticket on a Tuesday night after midnight is some secret trick that will save you a bundle.

Instead do these things:

  1. Keep as many options open as possible, including the destination
  2. Research those options in depth, including looking at historic flight cost patterns & overall hotel costs
  3. Use a tool like Google Flights to quickly see what effect changing dates or airports will have
  4. Travel where the deals are now, not where prices/exchange rates are at record highs
  5. Travel outside of high season (or go where it’s not high season there)
  6. Travel away from the prime destinations (interior Mexico, rural France, Czech Republic outside Prague.)
  7. Get good  at turning most of your spending into airline or hotel points
  8. Assume any travel article with “insider tips” or “secrets” in the title is going to be a disappointment and reread this list instead
  9. Put away your phone and enjoy where you’ve just spent all this time, money, and effort to reach



  1. Brock 09/15/2015
  2. Izy Berry 09/17/2015

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