Why you shouldn’t book the cheapest ticket

The cheapest ticket isn’t always the best choice. In fact, sometimes it will make your trip miserable.

Remote Airports

Maybe that ultra cheap fare is such a bargain because the airport you’re flying into is ultra inconvenient.

Many cities have multiple airports to choose from. Paris, for example, has Charles de Gaulle, Orly, and Beauvais. None of them are close to the city center but Beauvais is 80 km (55 miles) from Paris and the bus takes 80 minutes to get there.

Chicago has two airports, O’Hare and Midway. Both have good public transportation service to downtown. But, if your final destination is the northwest suburbs, O’Hare is the best choice. Likewise, if you’re staying on the south side, you’ll want to fly into Midway.

There are also regional airports to consider. Boston’s airport is Logan. But, if you’re going to the lovely city of Providence, flying into Logan will be a pain. They’ll tell you that the bus only takes an hour, but that would only be in the best of conditions. Fact is, traffic is often horrendous and you could be stuck for 2 hours or more.

For me, two of the most important factors are nonstop flights and access to public transport. Who wants to shell out $50, $100, or more for a taxi ride because the bus doesn’t run at night or the train is out of service, or worse, there isn’t any public transit at all?

Long or Bad Connections

You’re going to Europe! And you found a great price on airfare! Score!

You just have to make a connection in London. No problem, right?

Then, you read the flight info. Your connection arrives in Heathrow and departs from Gatwick.

Don’t even think about it! Here’s why this is a terrible idea.

First, you’ll have to go through customs at Heathrow. That’ll be at least an hour and maybe much, much longer. Then, you have to get the bus (there’s no train between the two airports) from Heathrow to Gatwick. It’s expensive and will take at least an hour and maybe a lot longer.

You’ll be starting your trip with a giant headache and you’re not even at your final destination. Ugh.

Then, there’s the siren call of the long layover.

Wait, you say. What’s the big deal? I can go explore the city on my 8 hour layover.

I know people who do this and recommend it. For them it works great!

For me, it’s a nightmare. That’s because you have to leave the airport, and if you’re traveling internationally that means going through customs. An hour on a good day, two or more on a bad one. Then, you have to get from the airport to the city. That might be 90 minutes or longer if you’re in a place like Paris where the airports are far from the city center.

And, don’t forget you have to get back. That’s another 90 minutes back to the airport, plus arriving 2 hours before departure. Now, your relaxing 8 hour day in Paris is an hour or two of stress.

Forget it.

Find the flight with a shorter connection. Or better yet, a direct flight.

Basic Economy

Basic Economy is the airline industry at its most cynical. We’ll reel people in with low fares and then nickel and dime them to death until their Basic Economy seat costs more than Business Class (just kidding, but not really).

Even if you’re planning on traveling without any luggage, you still get the worst seat on the plane. And, if you have to change travel dates (haven’t we all had to do that at some point in our lives?), you’re screwed. Forget it.


Have you ever taken an overnight train?

It’s a pretty enticing proposition. By riding the train overnight you not only get from point A to point B, but you also don’t have to pay for a hotel or Air BnB that night.

But, don’t make the same mistake I did.

Years ago I took an overnight train and just booked a regular seat. It was cheap and I was poor.

Of course, the ride was miserable. I was uncomfortable and couldn’t sleep. I arrived at my destination the next morning feeling terrible. And the worst part was, I was there for a job interview! Somehow, I pulled myself together enough to get through the interview and even was offered the job!

Anyway, if you’re traveling overnight, take my advice and book a sleeping compartment.

Bad Times of Year

I’m a big proponent of traveling during the off season. This is especially true in Europe where the most popular cities are unbearable in July and August with the crush of tourists and oppressive heat.

Spring (April and May) and Fall (September and October) are great times to be in Europe. Costs are lower, locals are less stressed, and there are fewer tourists.

However, some places might not be great during the off season, no matter the cost savings.

For example, many parts of India are swamped with monsoons between June and August. Same goes for Thailand from July through October.

Then there’s the Atlantic Hurricane Season. It runs from June 1 to November 30. On average, there are over a dozen tropical storms in the Atlantic, Caribbean, and Gulf of Mexico. That’s a storm every two weeks!

Of course, your chance of being impacted by a storm is relatively low. But, with climate change, storms are more frequent and more powerful.

So, if you decide to go to your Caribbean island paradise during hurricane season be sure to get travel insurance. And make sure it covers hurricanes.

Bottom Line

Before you book that deal of a lifetime vacation, ask yourself “why is this so cheap?” Yes, maybe you’re getting an unbelievable deal. Or, maybe, you’re booking a miserable middle seat with no legroom, laying over in an airport for hours, and arriving at an airport a hundred miles from your destination.

Author: Brent