Trip Planning 101: Pt. II – Buying Airplane Tickets

This post is part of a series on planning a trip. The last post covered choosing a destination.

Once you have chosen your destination you can start on the biggest road block – buying plane tickets. For me, this is often the “pulling the trigger” moment which can be nerve wracking. Tickets can be a huge chunk of money and are for the most part non-refundable.
Searching For Ticket Prices
To help ensure that you make the best decision possible it’s a good idea to do a little research and price comparison. This will be easier if you have very set dates. If your dates are more flexible, you will want to make sure you are tracking ticket prices to see when the best fare is available. I always recommend starting first at In addition to finding some of the lowest prices, kayak will also allow you to search for flexible dates and filter by a variety of different criteria. My other favorite feature of kayak is kayak buzz which allows you to pick a departure place, a time period and a general destination (“Europe” or “World Cities”) and see what low fares have been found recently. For example, right now I search for flights leaving from Washington “anytime” and found a $220 round trip flight to the Caribbean.
After a little searching on Kayak you will have a general idea of around what the flight should cost. This will allow you to search around for a possible better deal. This means going to the carrier websites (Delta, United), other bargain flight locators, etc. It’s also a good idea to see if you can get a ticket using miles or other rewards points.
Open Jaw Itineraries
My number one recommendation is that you get outside of the “round trip” pigeon hole. I find that people usually automatically assume that this is the way they should purchase their ticket. However, in my experience flying an “open jaw” (fly into one city and fly out of another) itinerary is often the best use of both your time in money.
When I visited Israel and Jordan last summer, we flew into Amman, Jordan and out of Tel Aviv Israel. We knew we wanted to visit both countries but this allowed us to avoid backtracking. Not only did we save valuable vacation time, we avoided an extra border crossing. The ticket ended up being slightly more expensive than a round trip ticket (around $100) but you have to remember that we would have been required to find and pay for transportation back to Amman from Tel Aviv. This means we probably ended up breaking even.
Most travel websites allow you to search for these tickets using the “multi city” option. Just make sure that the cities you chose to fly in and out of make sense for your itinerary. When visiting Croatia this summer, we decided to fly into Sarajevo in Bosnia and Herzegovina and out of Zagreb in Croatia. We also planned to visit parts of Slovenia. As it turns out, flying out of Ljubljana, Slovenia would have made a lot more sense and would have avoided us having to back track back into Croatia. Ideally you want to plan your itinerary with little to no backtracking necessary.
Think Outside the Box
The conventional wisdom would say that you would book your flights from your city of departure and into your destination, and most of the time that will be your best bet. If you live in a city with a major airport and are flying to another major hub your flight options will be multiple and cheap. Unfortunately, not everyone lives in NYC and not everyone is planning on visiting Frankfurt, Germany. That doesn’t mean that you can’t take advantage of these flights. My advice is to check out the cost of flights from large cities to your destination or the cost of tickets from your home to cities near your destination. Maybe a flight to London is $900 from Dulles but its only $650 from NYC. It’s easy enough to catch a cheap bus to NYC the day of your flight and save $250.
When I visited Morocco in May of 2010, tickets were around $1100 round trip. We were able to find round trip tickets to Madrid, Spain for $600 and then took Ryan Air to and from Morocco for only about 14 Euros each way. We were able ot save at least $400 and got to spend a wonderful day in Madrid.
Words of Caution
The advice above is all based on techniques that I have used before and I would recommend at least considering these options. However, once thing to consider is the added stress and effort required in some of these bookings. Always consider how much your time is worth before booking an option that will only save you a few hundred dollars. A bus ride to NYC might not seem like a big deal now, but you may be kicking yourself when you get off a transatlantic flight and have to board a four house bus. Another thing to keep in mind is that airlines won’t honor other airlines cancellations and delays. So if you have to make a connection with a budget airline and your other flight is late, you may be out of luck.
On the aforementioned trip to Israel I booked the cheapest available option – It was a full $100 cheaper than the other flights. Just one problem, it had a 12 hour layover in NYC. $100 seemed like a ton of money at the time of booking so I figured it was worth the layover. I was kicking myself 5 months later as I killed hour 7 at JFK – and I probably spent close to $100 on food and drinks while I waited, not to mention the time I lost.
Ultimately, 50-100 is not worth antagonizing over. If you keep waiting for the absolute cheapest fair you could wait forever. If you find a ticket that is reasonable and fits your schedule you should go for it. Then you can sit back and start the fun part – planning your upcoming vacation!
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One Response to Trip Planning 101: Pt. II – Buying Airplane Tickets

  1. Anonymous says:

    Such great advice. Thanks for giving us step by step instuctions. Super helpful!

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