How to Think about Strategically Booking a Flight

Strategically booking a flight doesn’t have to be an arduous experience. Sure, it seems rather complicated and you often hear about people finding the deals of a lifetime. In reality, it’s all about learning some simple strategies and having some patience in your searches and flexibility in your travel plans.

Booking flights and getting the best bang for your buck is a very strategic process. I have frequent flyers miles with many programs, some are more valuable than others, so it’s important to know which ones are the best to use for certain flights and there are some math formulas you can employ to decide whether going out of pocket or using miles make the best sense but knowing your travel goals is really the best way to make these decisions.

Miles are important to travelers in many different ways. If you travel once a year, your 30,000 mile stash is perfect for a free domestic flight. If you travel often, you may not want to cash in your miles if the flight is cheap enough but use your flights to accrue big reserves for 70,000 award flights to Asia. I use sites like Milez.biz to calculate award flights through a variety of programs.

The biggest question I get: How do you know when/if to use your frequent flier miles or just to buy the ticket?

Here is how I think about strategically booking a flight:

• Pick where I want to go at high level (usually my home city and desired arrival city)
• Choose a huge window in off-peak season – March & Nov are good months for off-peak Europe
• I run flexible date searches (Skyscanner is amazing at this) and if not available I usually use Tuesday as my departure day
• I jot down the best days to fly and what cities offer the best arrival time and which flights actually accrue the most miles (connections count toward your flight mileage).
• Are there alternative cities to fly out of/into? Some cities are just cheaper to fly into and out of and can save you hundreds of dollars by opting for them. For example, big US hub like NYC, DC and Boston are cheaper to leave from and arrival countries such as UK and Germany tend to be cheaper than countries like France and Italy.
• Are the tickets reasonable or does it make sense for me to use frequent flyer miles?
• Do I have enough miles for a one-way (OW) or RT flight?
• I run the numbers. How many miles will I gain from these legs if I pay for them? [cost of ticket / miles gained = price per mile] vs Using my frequent flyer miles

For example, I want to go to Paris and Amsterdam next March so I looked up RT flights from my home in Charlotte (CLT) to Paris (CDG) and also to Amsterdam (AMS). The cheapest flight was around $980 and had 2 connections and the 1 connection flights were in around $1100. I then created a multi-city flight itinerary from CLT-AMS-CDG-CLT but those flights were $1150+.

Unsatisfied with the prices, my next step was to check OW flights from CLT-AMS & CLT-CDG and AMS-CLT & CDG-CLT, these flights came in $649 and a whopping $900+ from either Amsterdam or Paris back to Charlotte.

So, if you still with me, my current best (and cheapest) option with one connection is about an $980 RT flight with 2 long connections or an $1100 (1 connection flight) from CLT to either AMS or CDG on March 1-9.

Digging deeper, it’s time to see if using frequent flyer miles is a better deal than shelling out $1100. I have some accrued miles on American, so I looked into off-peak flights to Europe in March. American has OW flights for 20k + $85 in fees (to either AMS or CDG), so it would cost 40k miles and $170 to fly back and forth to Europe. I have 40k miles from an American Airline credit card signup bonus, and since they technically didn’t cost me anything to acquire (except for meeting the minimum spend), they could be the best option.

First, let’s consider a couple things:

1. The mileage earned on purchasing the original RT flight (either the Paris RT or Amsterdam RT) + credit card miles (for using a miles credit card to buy the ticket) is around 11,000, which is ½ of what I need for another OW flight to Europe in off-peak season. I used a mileage calculator to figure this out.
2. The price per mile for this trip is 10 cents [$1,100 price of flight / 11,000 miles accrued ] – that is HIGH.
3. If the flight had been $650 RT, I would have paid 5.9 cents per mile, a much better deal.
4. I could use a combo of miles for one leg (CDG- CLT) and paid for the cheaper 2nd leg (CLT-AMS), but using the math, those miles would have cost 10.4 cents [$649 price of flight + $85 fee / 5800 miles accrued + 1250 miles earned from my credit card]

After weighing on all my options, the best and smartest play is to use my 40k American Airline miles and pay $170 for the flight. Even though I won’t accrue any miles for the trip, I should get 340 miles for using my miles credit card.