Yesterday I was in session with one of my patients and she expressed some anxiety about buying an international flight for July, wondering whether the best strategy was to book now or wait. It took everything in my power not to go into a full-on discussion of this, but unfortunately, that’s not my role as her psychologist! It’s a common worry for those wanting to get the best airline deal, and there are countless online articles about it. The bottom line is, you can never fully predict if and when the prices will go up and down so its always a gamble (although flight alert apps such as Hopper can let you know when a flight you are looking for has gone down in price, and they will also predict whether it will go up or down in the future based on historical data).

I was never one to gamble, so my preferred strategy is to book as early as possible – sometimes that means 331 days in advance, which is typically when the big legacy carriers release their flights. I know this is not for everyone, but it does work for those of us who have somewhat predictable schedules and know that there is a certain time every year when they can travel. Since I work for myself I can basically take off whenever I want, but my family’s schedules are not as flexible. My husband teaches at a college so the dates of his breaks are known well in advance, and my children’s are also fairly predictable. Given that, here are a few other reasons why I like to book early.

1. I have been searching airline prices for a long time, and in general I have seen this pattern (not always, but usually): release a very low price when the flights are first released (331 days in advance), then go up (maybe even a day after that), then go up and down until the flight. This has served me well 9 times out of 10.
2. If you book super early, there is a good chance that the airline will change your flight. If the schedule change is significant (usually more than 30-60 mins), you can change your flight FOR FREE to a different flight, even if originally that other flight was way out of your price range. AND that new flight can be the day before or the day after, thus extending your trip. This has served me well many times. Often when you are booking the cheapest flight (as I tend to do), you get some inconvenient times (like leaving at 5am, or having a really tight or really long layover), but the flights with the more convenient times can be hundreds of dollars more. Once the airline changes the schedule, though, you can pick which one of those more convenient flights works for you! For example, one year my husband and I were taking a quick getaway to Mexico and only had about 3 days there. About a month before the trip I received an email from the airline that they had changed the outgoing flight to leave about 8 hours later, thus we would lose almost a full day! I called them back right away, and they kept looking for flights a little earlier that day but none were ideal. I asked about leaving the day before and they were able to get us on an afternoon flight that day, so we would arrive about 9pm the day before we were originally scheduled to arrive. I had enough Orbucks (Orbitz points) to book a free room for that night, so we ended up actually gaining almost a full day on our trip, all for FREE!
3. If you are booking Award flights on American Airlines it ALWAYS pays to book as soon as they release the award seats, 331 days in advance. The award seats have a lowest price they will go and will not go any lower, so with American, the lowest they will be is 15k one way for an international flight. If you log on the day they release and find award seats at that price, even if they are not exactly on the day you prefer, book them. The reason is this, AA will let you change award seats FOR FREE  on an award ticket, as long as the departure and arrival cities are the same and the “fare class” is the same (e.g, it still costs 15k miles per flight – you couldn’t change and award ticket that you got for 15k to one that was for 30k). It is fairly common that over time, the airline will start to release more low cost award tickets, so if you have a method for monitoring this (I use expertflyer, I will explain more below how this works), you will be alerted when the other award tickets are released and you can change the flight. Then you can call them and change the flight to the better one.

I recently had a fun, roller coaster experience using all of these methods on a trip we are taking to Mexico this March (are you sensing a theme? We love Mexico!). Some of you may feel your eyes glaze over as I get into the nitty gritty details, but for the one or two of you who are actually interested, read on!

I have been to Mexico five times but only to the Yucatan peninsula. I would love to see more of the country and have really wanted to visit San Miguel de Allende (recently voted most best city in the world by Travel + Leisure magazine). My husband has a certain week off in March for his spring break and for some reason my kids usually get the Friday of that week off for a teacher inservice or something. So if we went that week they wouldn’t miss as much school. When I first started looking for award flights it seemed like an impossible task. College spring break time is almost as bad as the week between Christmas and New Years for finding affordable flights, even for places that aren’t your typical “wooo hoo spring break!” locales. At the time I had about 60k AA miles to spend. That is only enough for 4 one-way tickets internationally, so I theoretically had enough to get us there, but not enough to return. I did have this great perk through my Amex platinum business card, however, which is that if you use your membership rewards (Amex points) to buy a plane ticket on your preferred airline (this is something you have to pick in January and cannot change it for a year), AMEX will give you 50% of those points back, thus giving you a 50% discount (since then it has decreased to 35% points back). So I could use those points flying Delta on the way home.

Now to find the flights. As I have said elsewhere, for international flights I often look for flights leaving from Newark, Philadelphia, or JFK because our home airport of Syracuse is very small and therefore we might have 2 layovers. I searched and searched and found one-way flights from PHL-BJX (the closest airport to San Miguel, about an hour away) for 15k miles each leaving the Tuesday of that spring break week, from PHL at 5am. This meant we would have to drive down to Philadelphia that Monday, stay at a hotel near the airport and get to the airport by maybe 3:30am? Yuck, but oh well. For the return flights, the cheapest I could find on Delta was a BJX-PHL leaving on that Saturday 8:45am from BJX and getting into PHL at 6:41pm. This was also not great because we would need to be at BJX at 6:45 am, which meant leaving our hotel in San Miguel around 5:45am. But this was the cheapest option. The one-way tickets on Delta were $388 per person which translated to 155,812 MR points, so after the 50% back I would have spent 77, 906 MR, which would be 19,476 MR per ticket. The only kind of crappy thing was that we would only be in San Miguel for 3.5 days now, given we would arrive Tues afternoon and have to leave at the crack of dawn on Saturday. Here is how that all changed over the course of almost a year, so that now we are getting 7 full days there!

1. First flight change: A little while after I booked the tickets, Delta changed the return flight time to an hour earlier – 7:45am! This meant we would have to leave the hotel at 4:45. Are cab drivers even up at that hour? The change was not significant enough to ask for a flight change, so we may have had to suck it up, until…
2. Flight cancellation: One day in September I pulled up my Delta app to check on a different flight, and in my upcoming trips list the flights to Mexico had disappeared! I freaked out for a minute and then called Delta. They explained that our original flight had been cancelled. I asked why they didn’t contact me to let me know, and they said they couldn’t because I booked it with a 3rd party (amex). I had a hard time believing this because my Delta skymiles # was attached to the reservation, and they have my contact info through that, but whatever. The agent was super helpful and was able to find a flight that left the same day (Sat) at 9:45 am and got to Philadelphia at 8:33pm. Woo hoo! This meant we didn’t have to leave San Miguel at 5:30am. We would still need to leave early, but it wasn’t as bad.
3. Second flight change: Then one day in November, I was contacted by Delta (by this point I made sure the reservation was linked to my contact info) to inform me that the flight had been changed again. I can’t remember what the change was (I think the layover was something ridiculously short, like 30 minutes), but it was significant enough that Delta would allow me to change my flights again, this time to whatever was open. Since I had wanted more time in San Miguel, I asked about flights on Sunday, and they changed our ticket to leave at 9:45 am Sunday, now giving us another FULL DAY there. I had wanted to check out Guanajuato, another  colonial town in the area that closer to the airport, but in our original itinerary, we didn’t have enough time to do two cities. Now we could leave San Miguel on Sat morning, spend the day and night in Guanajuato, and be closer to the airport to leave Sunday morning, #winning!
4. I wasn’t thrilled about the 5am flight from PHL to BJX on AA, but like I said, when I originally booked it, that was all that was available in the 15k award level. Enter expertflyer.com. This site offers a search engine that will search award availability for you, and if you pay for their premium service ($10 a month), they will continue to search for any award that might open up for the flights you want. This is well worth the $10 in my opinion. I had expert flyer searching for any award flights on the Sat, Sun, and Mon before that Tuesday we were originally scheduled to leave, and lo and behold! on one day on November a bunch of new 15K award flights were released! I was able to decide between several different flights, but ended up settling on one that left PHL on 3pm on Sat and arrived in Mexico at 9pm. The only problem with that was the layover in Dallas was super tight, 55 minutes! But I figured if we missed the flight we would be able to catch one the next day.  Now we had an extra 2.5 days there! I booked a Hampton Inn near the airport for when we arrived late Sat night for $50 (don’t worry, it got great reviews, these are just Mexico prices), and another hotel in San Miguel for 2 extra nights using Chase ultimate rewards points.
5. Now I was very happy that we would have 7 full days in our destination, vs 3.5. The only thing that was niggling at me was that 55min layover in Dallas. So, the other day I received a promotion from American where I have “Platinum Pro” status for the next 4 months! This means I get complimentary upgrades for domestic flights and can pay a small fee for myself and my companions for upgrades on international flights. I called to see about getting upgraded to first class on the flight there – at least we would be at the front of the cabin for when we would have to run to our connection. As I was chatting with the customer service rep however, she informed me that the upgrades don’t apply for award flights. Darn! I explained my concern to her that the connection was super tight, and she offered to look for a flight that left Philadelphia earlier. Luckily, she found seat availability on the 12:50pm flight from Philadelphia, giving as a longer layover of 3 hours. But since there is a Centurion Lounge in DFW, I don’t mind that at all! I don’t know how she was able to find this, since that flight had not been available previously at the 15k award level, but I’m not going to look a gift horse in the mouth!

So there it is, my long and winding road of being able to turn a 3.5 day trip with super inconvenient flight times into a 7 day trip with very convenient flights, with no change fees or money exchanged at all. I hope if you are still here by this point I have convinced you why it sometimes makes sense to book flights way in advance. It’s still a gamble, in that you never know for sure whether you will get a flight change that will allow you to book something else or if more award seats open up, but in my case the gamble paid off.