Travel Tip: How to Book the Best Airfare

Booking travel has probably never been easier than it is today. But it has also never been more complicated! From travel agents to websites to apps, there are a million […]

Written By Rob Knight

On November 26, 2019

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Booking travel has probably never been easier than it is today. But it has also never been more complicated! From travel agents to websites to apps, there are a million options and opportunities for finding the perfect itinerary within your budget. Often the hardest part for me is striking a balance between itinerary, service, rewards, and price. I don’t know if I have “the secret”, but maybe my experience can be helpful to you.

I’ll start with a specific case…

 I recently booked my flight to Costa Rica for my annual photography workshop in January, 2020. I’ve been making that trip for more than ten years and I am pretty familiar with the options, but that doesn’t mean I just booked the usual without doing some research. 

I haven’t seen any advantage in booking flights too far in advance. I keep an eye on the fares starting well in advance, but unless there is an anomaly that is super cheap I wait to book until a couple of months before the trip. I’m based in Atlanta, and Delta has two non-stop flights from Atlanta to San Jose, Costa Rica each day. The fare is generally $550-$750 depending on the day, the weather, or whatever unspoken metrics make airfare change from hour to hour. If I see the fare drop below $500 I buy it immediately. Otherwise I just wait until closer to the workshop. The Delta fare tends to be the price I measure all of the other options against.

I also check Kayak regularly. Kayak (the website and the app) compares fares from most airlines (including Delta) and gives a good overview of the options. You can only book with Southwest Airlines on their website, so I make a special trip to their site to check the fare. Sometimes they are incredibly cheap, but I find that they are usually within a few dollars of the Delta fare for where I want to go. If it’s only a few dollars more I will always take Delta because of the sky miles, medallion status, etc that I have accrued over the years.

So here is my starting point…

As of today Delta is charging $630 my Costa Rica trip. That’s non stop each way and my baggage is free because of my medallion status. Southwest is a bit over $600 as well. I would have a layover each way, so this basically counts that out. There’s no way I would pay the same price and have to change planes. 

The next airline I check is Spirit. I haven’t had great experiences with them in the past, but I was curious. I can go round trip from Atlanta to San Jose for $266! Seems like a no-brainer, but wait. I would have a layover each way including a six hour layover on the way home. Definitely not my idea of an ideal itinerary. 

The other issue to consider is that Spirit charges extra for EVERYTHING. You get a personal item for free, but you have to pay for carryon bags and of course checked baggage. My baggage both ways comes to an additional $180 bringing the total fare to $446. You can also pay extra for early boarding, seat assignment, and on and on.

Once I have all the pertinent information…

At this point if I was only buying my ticket I would have to decide between a direct flight for $630 and layovers for $446. On nine days out of ten I would pay the extra fare and take Delta. It saves me hours each way to fly direct. Plus I get sky miles I can apply toward future travel. I would imagine Spirit offers points as well, but I don’t have the same experience with them that I have with Delta. 

However… At the end of my photography workshop my girlfriend will be flying to San Jose to meet me. Her ticket on Spirit is $305 vs the same $630 that mine would be on Delta. She doesn’t need to pay for baggage because I’m going to take her two days worth of clothes with me in my big checked bag. That brings our grand total with Spirit to $751 vs $1260 on Delta. Thats not quite half price, but it’s a significant savings.

The other issue is the layovers. Remember there’s a six hour layover on the way home. By myself I would hate that, but with my favorite travel partner I’m sure we can find something fun to do in Ft Lauderdale for six hours! 

It’s a balancing act…

Sometimes the trip itself dictates the flights. Depending on where you’re going there may be limited options for schedule, stops, etc. If you’re lucky you have options. When you have options and a bit of patience you can do your research. With just a bit of research you can find the schedule and price that works for you. On the bright side, airfare is typically uniform from site to site, so you don’t really need to look beyond a few sites. If you regularly travel the same routes you will get familiar with the best times to book and the best sites to use. If you are going somewhere new it pays to ask folks who have been there. Whether they are people you know or the internet at large. Use whatever resource you can to take the stress out of booking your next trip!


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