Photo by Sir Mildred Pierce

When buying plane tickets, you want to find cheap tickets on a convenient flight, without spending a lot of time searching for them. If you’re in a hurry, you can learn how to do this by skipping ahead to the Cliffs Notes at the end. Otherwise, you can read all the gory details.

The more complicated a trip is, the more it pays to check out your options. Flying from Washington, D.C. to New York is pretty straightforward. Just check out some travel sites, play around with different dates (and possibly different airports), and it’s not hard to choose the flight that gives you the best combination of price and convenience.

But flying from Washington, D.C. to Osaka, Japan is much more complicated. That’s why I enlisted some experts.

Back in January, I planned a trip to Japan that I’m taking next week. While I had found some reasonably priced one-stop flights on CheapTickets, Orbitz, and Expedia, I was curious to see if veteran travelers could do better. Since my mom works with someone who lived in Japan for five years, I asked her to see if he had any advice on finding a good flight. He had some specific airlines in mind, but he didn’t find anything cheaper than what I had already found, nor did he find a nonstop flight.

It turns out that my mom also works with someone who derives great enjoyment from looking for good deals on travel. He would never just look at a few options and consider his search done. He would consider every possibility under the sun, and he was actually willing to spend a lot of time helping me find a flight.

He considered that I could fly into Tokyo and take a train. Or fly to Los Angeles, then switch airlines. Or fly into Toronto, then get on a Canadian airline. But after spending several hours looking, he didn’t find anything better than what I already had. However, he did suggest that I try Priceline.

When all was said and done, the best deal came from Priceline, which had a flight with a layover in San Francisco, for $188 less than the cheapest flight on CheapTickets, Orbitz, and Expedia. In fact, it was $350 cheaper than the same flight on those sites! Another nice feature I discovered is that Priceline lets you know if alternate dates or airports will result in a cheaper flight.

The Priceline flight was on United, and I found the same price when I went to the airline directly. I always buy tickets directly from the airline to save the $5 or so charged by some sites. Priceline doesn’t charge a fee for any published flights, but I figure you might as well avoid the middleman and possibly have better service or fewer complications.

Priceline still has their “Name Your Own Price” system that lets you bid on flights, and claims you can save up to 40% that way. The major disadvantage of doing this is the risk and uncertainty. You submit a bid blindly, not knowing the airline, times, or routing in advance. And if they accept your bid, you can’t cancel or make any changes. Also, if your bid is rejected, you can’t submit another bid until after the waiting period has passed. Furthermore, you don’t get any frequent flyer miles. I don’t know what kind of success people have had doing this, and Priceline has been moving away from the “Name Your Own Price” model in recent years.

Incidentally, Travelocity found a flight on Asiana Airlines for $54 less than the Priceline/United flight, but it had stops in L.A. and Seoul, and I really wanted to avoid two stops.

Ultravagabond Tim Ferriss has said that instead of booking flights far in advance, he gets better deals by booking at the last minute, when the airline is afraid the seat will go unsold. I tested this back in January, searching for a last-minute Japan flight on United. There was only one flight available, for $3,000 more than the far-in-advance flights, and with a 5 hour layover in Doha, Qatar (which means flying around the world in the wrong direction).

I checked again a few days later and found several last-minute United flights for $3,000 more, with a stop in San Francisco. However, when I checked on Priceline, I actually found some last-minute flights for $118 less than my far-in-advance ticket ($3,118 less than the flights offered at the same time on United). Remember when I said that my mom’s coworker thought of flying into Toronto? That’s what these flights did. But they also stopped in Vancouver, and I wanted to avoid two layovers.

Cliffs Notes:

1. You’re perfectly capable of quickly finding as good a deal as a veteran traveler could find.

2. Check Priceline first, because it tells you whether changing dates or airports will give you a better deal, and you can use this information on later searches. Naming your own price might not be a good idea because of the risk of unchangeable tickets, inflexibility of having to accept whatever times and routes they give you, and time required to resubmit bids that aren’t accepted.

3. Check some of the travel sites such as CheapTickets, Orbitz, Expedia, and Travelocity. They’re likely to be very similar, so don’t feel like you have to check more than a few. Also check Kayak and SideStep, which offer the advantage of searching multiple sites, though I would still search directly on some of those sites (tip from Barbara Swafford and John).

4. If you have a particular airline in mind, search for flights on their website. The price could be different from what’s listed on the travel sites, or the airline might not be included in those sites.

5. Buy your ticket directly from the airline to save money and eliminate the middleman. If you have an ethical problem with this, then by all means pay the extra $5 if that lets you sleep better.

6. Although Tim Ferriss has traveled all over the world and says booking tickets at the last minute will save you money, I didn’t find that to be true in this case. It might depend on where and when you’re traveling.

See also:

How to Fly Without ID and Skip Lines (Tim Ferriss)

How to Score Free Airline Vouchers by Reserving Overbooked Flights (Clay Collins)

• Free Ebook: Memoirs Of A Gaijin