Don’t just buy the cheapest flight – you might regret it

The cheapest flight can bring its own baggage

There’s a great number of online businesses which exist purely to get you the cheapest flight or show you how to find the cheapest flights.  And if you want to make the most of your travel budget, flight search engines like Skyscanner and Momondo can be godsends in getting you a great deal.

The obsession has gone even deeper recently, with apps like Hopper analysing cost patterns in order to advise you of the best time to book.  It seems to be written in folklore that midnight on Tuesday is the best time to find cheap flights, and yet Hopper themselves have been able to confirm that only around 1.6% of domestic flights in the U.S. are discounted at this time.  Even if you do get a ‘cheap Tuesday’ discount, you’re saving an average of $18.

The problem with this obsession over finding the cheapest flight is that you’re potentially missing great deals on better quality flights.  If you were buying a laptop, you’d be wise to look past the bargain $400 model if there was a $1,000 laptop discounted to half price.  And the same applies to flights.  You could easily find that by paying a little more than rock bottom, you make greater savings.

This is why I really like the flight quality score on Expedia.  In some cases you can see that by paying an extra 10% you’re getting a flight that’s twice as ‘good’.  The scores come from Routehappy, and they’re based on things like trip duration, food quality, and WiFi.

By buying a slightly better quality flight, you can still save money and avoid some of the travel nightmares that are all too common with buying the cheapest flight.  Here are some things you should factor into your purchasing decision.


Flight duration

The cheapest flight is usually longer, involving more connections.  Sometimes it’s extremely long, as much as double the length of the next price tier.

If you take this bottom-of-the-barrel flight, you might save yourself $150 to $200.  But at some point during the trip when you’ve spent a mind-numbing seven hours sat in an airport you might start to ask yourself if you’d have paid the extra to be there by now.

More connections also present a greater risk of missing those connections due to delays.  This depends on the layover time at each airport, which you should definitely check before buying.  The other thing that can go wrong with connections is that your baggage can go missing.  Obviously this can happen on any flight, but with more connections the chance goes up.


Hidden costs

These costs are not necessarily ‘hidden’ by the airline, but just hidden in the sense that they are external to the flight itself and you might not consider them.

If you’re bringing any sports equipment or other large items with you, you should check the fees before you buy your flight.  You might discover that the cheapest flight will charge you much more for your baggage, to the point where it almost completely cancels out your savings.  Bringing a bicycle to South America I discovered, for example, that Air Canada charges just $50 CAD while Copa Airlines charges $100 USD.

If you don’t get any free food on the flight, you might find yourself buying some on the plane or in the airport at an extortionate cost, particularly if it’s a long journey.

Also look at the transport available to you in the destination city at the time your flight arrives.  If the cheapest flight arrives too late in the day, you might lose your opportunity to take the free shuttle and have to get a taxi to your hotel or hostel instead, at much greater cost.


Cancellation policies

Cheap flights are often discounted by a third-party company, which imposes its own rules regarding changes and cancellations.  You’ll probably find less flexibility to change or cancel your flight when you’ve paid such a low price, and if your travel situation is somewhat unpredictable you’d be better paying the extra for that peace of mind.

The last thing you want is to have to write off the entire price of the ticket because you can’t fly on the day you’ve booked.



Generally speaking, more expensive flights give certain perks.  If you’re a frequent flier touring a continent going from place to place, these perks could be extremely beneficial to you in providing a more secure and comfortable experience.

The sort of perks you can expect include:

  • Priority check-in
  • Faster boarding
  • Waived baggage fees
  • Access to an airline lounge
  • Complimentary upgrades
  • Faster security screening

If you have a ‘digital nomad’ type lifestyle and need to service clients while you’re on the road, these perks are particularly useful.  They save you time at security, give you a more comfortable environment to work and often you’ll get free food and drinks.  The cheapest flight, on the other hand, just gets you there no a no-frills basis.


You get what you pay for

It didn’t come as a surprise to read that four of America’s most hated 15 companies are airlines.  The airline industry is one of the most complained about of all – pretty much everyone has at least one rant up their sleeve.

But how many of us can actually say we make calculated decisions when buying flights?  The bottom line is that you get what you pay for.  And while I’m not excusing airlines for poor service, I do believe that if you’re one of the millions of people who just hunt for the cheapest flight and choose purely on a cost basis, you might want to start making smarter decisions.

That said, flights are expensive and sometimes it just hurts to have to pay so much to do what you love. I’m not saying don’t buy the cheapest flight.  I’m just saying look at what it includes and decide if it’s really the best value for money.

If you’re on a tight budget, it’s a no-brainer to bring some food on the plane with you and make sure you weigh your luggage beforehand to avoid any nasty surprises at check-in. Think about better ways to save money on the flights themselves, like leaving on a different day or taking a different route. Some credit cards, like the American Express Platinum card, offer you excellent introductory bonuses and annual flight credit, plus lounge access and savings on car rental.

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