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Wednesday, April 13, 2016

My general approach to booking flights (both paid and award)

There are many ways to skin a cat so I'm in no way implying that this is the correct way you should go about booking travel but I just wanted to share my general approach and offer some tips.

As I seem to have become the family expert on award travel as well as finding the best deals and discounts on flights and hotels I am usually the one in charge of planning as well as booking all the travel arrangements. This can be both good and bad as I've pointed out in a previous post. However, I have learned quite a few lessons along the way but usually as a result of the many mistakes I've made.

Step 1 - Figure out a destination and general time frame

Now this should seem obvious but is probably the most difficult step in the process. This is especially true if you have multiple parties involved which is usually the case and are trying to juggle multiple work schedules. Luckily, in my case it is usually just my husband (who is retired) and myself going on trips which makes planning much more simpler. You'll also want to consider the season of the destination you're visiting. For example, while I was able to score some cheap saver award tickets to Germany last month it was still rather cold there so I probably would have enjoyed myself much more if I didn't have to bundle up in 3 layers just to walk around the city.

Step 2 - Search Google Flights

Google Flights is probably the greatest single invention in my opinion and is usually my first go-to site when planning trips. You just plug in the names of 2 cities and the dates you want to go and a calendar of potential prices pops up that you can easily scroll through.

Here is an example of some random dates I plugged in from Indianapolis to Kauai in June-July. As you can see the lowest prices are highlighted in green and there is even a price graph that will tell you what months are the cheapest to purchase tickets. If you're feeling adventurous there is even an option to view a map of the world to get an idea of where you might go for cheap.

My general strategy is to try to leave/arrive mid-week such as Tues-Thurs because I find flights tend to be cheaper during those times. The flights and airports are also less crowded because you are fighting with all the business travelers.

Step 3 - Decide whether you are paying with cash or miles

The next step in planning is deciding whether you want to finance your trip with cash or miles. This is going to depend on many factors such as how cheap the flights are in cash, your current stash of miles and which airline they belong to, and the type of fare you intend to purchase. The general rule of thumb is you get more bang for you buck if you use your miles for higher fare classes such as first/business class as opposed to economy since the price of these tickets usually increase exponentially while the cost in miles do not. However, if you're like me then you actually need to value these tickets at that cost to get their true value and sometimes it can be more advantageous to book multiple trips in economy instead of just one luxurious trip in first class. I generally try to save my miles unless I can get a value of at least 2 cents per point which is where I value most of them, and since flights are so cheap these days I find myself using cash more and more. If I do decide to use miles to book award travel then I will use a tool such as AwardAce to find out which airline provides the cheapest option. Read about an example I used here.

Step 4 - Decide which portal you are going to use to purchase your tickets

American Express travel portal at

If you do decide to purchase your tickets with cash then the next step is deciding how you intend to accomplish this. Again, there are pros and cons to each option you choose and I find myself constantly switching between different methods. For example, I generally try to use either the American Express travel portal or Chase Ultimate Rewards travel portal if possible because you get an additional point for doing so. This is in addition to whatever bonus your credit card offers for flights/travel so if you used your Chase Sapphire Preferred card you'd earn a total of 3X points per dollar if you used the Chase portal. However, these portals don't always offer the best prices as others have tested. You also don't have the option of cancelling or making changes if your plans change which would be possible with some other third-party booking companies such as Orbitz.

Step 5 - Consider travel insurance

Now this is very dependent on how risk-averse you are and personally I have never bought travel insurance although wish I had on a couple occasions. The main reason I don't consider travel insurance now is because I tend to use my Chase Sapphire Preferred card for travel purchases which offers many travel protections such as Trip Cancellation/Trip Interruption Insurance, Primary Auto Rental Insurance, Travel Accident Insurance, Lost Luggage Reimbursement, Trip Delay Reimbursement, and Baggage Delay Insurance. Luckily I have never had to utilize these services yet but prior to having the Chase Sapphire Preferred I almost missed a Hawaiian cruise and would have been out over $5,000 if my family member who is a travel agent hadn't rescued the day. If you don't have a credit card that offers travel protection, then there are many companies that provide the same type of coverage such as Travel Guard which is the company that Costco works with for their trips.

Step 6 - Relax and enjoy!

Hawaiian beach

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