How I Shop For Airfare


There are no road trips when you live out on a tiny island out in the middle of a big ocean. If you want to travel, you’ve got to fly.

I’ve read countless articles over the years on how to find the best airfares, and along with some of the advice I’ve picked up along the way, I’ve also come up with my own technique for finding the best ticket prices to wherever we’re traveling. Over the years I’ve always been able to find airfares for less, sometimes hundreds of dollars less, than what I initially budgeted for a trip.

One of the reasons I like to plan travel so far out, if possible, is that it gives me more time to figure out what’s going on, set up a budget, and save for our trip versus starting closer to when we plan to go and then getting freaked out by the prices I find.

I’m definitely not an expert when it comes to booking airfare, but here’s how I do it:

  • Research, research, research: Once we (or I) decide where we’re going, I start checking airfares, even when the trip is going to be a year away, like our trip to Japan next year. I always start with Kayak because the site lets me know the different airlines that fly to our destination, and by inputting several different dates once or twice a week I can generally get a ballpark estimate for what our tickets are going to cost. Kayak also has an algorithm that can sometimes let you know whether prices are expected to increase or decrease, which is helpful. If the trip falls within less than nine months. I start searching my travel dates immediately.
  • Set a price limit: Based on research, I set a limit for the highest price I am willing to pay per ticket, and use that price when I make my entire travel budget. The research is important to set a realistic limit. It makes no sense to tell myself I only want to spend $400 per ticket when prices are in the $800 ballpark and staying there. So far though I’ve always been able to come in under my limit, sometimes by a couple of hundred dollars. You can set up a price alert with Kayak and other sites that let you know when prices drop below your limit, but I’ve always been able to find great prices without the alerts.
  • Buying early versus buying late: I know there can be great ticket prices at the last minute, but when I’m traveling with the family, waiting until then is too risky. I might not be able to find seats for everyone, or we might end up scattered throughout the plane, not a good idea when you have children or you’re on a long flight. Typically, I am ready to buy tickets nine months before travel, if I can find a good price. Also, the earlier I buy, the better the seat selection.
  • Search everyday: When I enter my “buy window,” I’ll usually start checking in with Kayak every day, and will also start checking airline sites as well – they sometimes have better prices. Southwest Airlines doesn’t show up on Kayak so if I want to use them I have to go directly to their site. Once a day for a check is enough though. I’ve never found a “best time” or “best day” to find good fares. They can appear at any time.
  • Be flexible: It’s not always possible, but I’ve been able to save big a few times by being flexible about travel dates. When we moved to Kaua’i in 2014, because we had a lot of luggage we wanted to fly non-stop to Lihue from Seattle, and we planned to leave on the Saturday after the girls’ last day of school. But, one evening when I was checking fares for that particular flight, I saw that if we left on Thursday instead of Saturday we could save over $680 on our family’s tickets. The girls had to finish school two days early, and we had to pay $270 for two nights in a hotel since we couldn’t move into our pre-paid condo rental early, but it was still a $410 savings for being willing and able to leave two days early.
  • Time is money: Sometimes the cheapest fares are not the best. There is no way I want to spend 20 hours or more traveling to my destination, with two stops along the way and a seven-hour layover in some airport just for a cheap fare. I don’t want to spend hours waiting in some airport between flights. I also hate redeye flights with a vengeance because I don’t sleep well on planes (I am dreading WenYu and my trip to Colorado in two weeks – we are booked the redeye from Lihue into Seattle). I always check the total travel time before I book any ticket, find out where the layovers are and how long they will be, and whether our flight will arrive the same day as we depart, because I am more than willing to pay a little more (but still below my limit) for a shorter travel time.
  • Be ready to pounce: When I find a good or great price for tickets, with a good flight schedule, I buy them then and there. No hesitation, no regrets. I did feel a little unsure last year about buying our Mystery Vacation™ tickets to Phoenix so early, because they were just a few dollars under my limit, but the price never went any lower than what I paid. I had no way of knowing that at the time except I had been watching the price trends and had a feeling prices were not going to get any better . . . and they didn’t.
  • Brand loyalty: Although I’ll consider almost all airlines, we currently prefer to fly with Hawaiian Airlines if at all possible because we earn frequent flyer miles to cover the girls’ travel to and from college. However, if I find a great flight at a great price on another airline, I’ll go with that.
  • One more thing: If I have a long flight, and can upgrade to Extra Comfort or Preferred Economy or whatever the airline calls it, I will pay for it – I always add a little to our travel budget to cover this expense. Sometimes you can book the preferred seating when you purchase tickets, but with some airlines the upgrade can only be done when you check in for the flight. Prices for an upgrade range from $50 to $100 per ticket, but that five extra inches of leg room makes a real difference, especially on a six- or eight-hour (or longer) flight.

Believe it or not, I find researching, and then searching for a good ticket price a lot of fun. I love the thrill of the hunt, of finding a great price for the shortest travel time on my preferred airline if possible. I’m getting ready in the next week or so to start researching flights to Tokyo, but June will be around the earliest I will consider purchasing. I can be patient though if I need to be. I’ve had good luck in the past finding great prices for Japan flights, and with the drop in fuel prices this past year I’m keeping my fingers crossed that I’ll come up lucky again. I’m also going to have to start looking for tickets for WenYu and I back to the mainland when it’s time for her to go to school, but can’t start searching for those until we know for sure which college she chooses. And, I’m still hoping the fares for our June trip to Oahu will drop a little, but they’ve been holding steady for the past several months and I may, for the first time, have to purchase above my limit (and then cut our travel budget elsewhere).

2 thoughts on “How I Shop For Airfare

  1. You might also want to try Google Flights. It is less known, but will show you on a calendar, how much the best fares are for days before and after your dates. Makes it very easy to spot a hige savings by leaving a day or two earlier/later.


    1. Thanks for the GREAT tip. No, I didn’t know about Google Flights, but I’m always happy to have another source to check out when it comes to buying tickets for air travel. We’re usually stuck these days with particular travel dates because of the girls’ school schedules, but once they’ve all left the nest, Brett and I can be more flexible about departure dates. I love that many airlines now offer a similar service on their websites (Hawaiian does) – you can see several days’ fares at the top of the page, and see if it makes sense to leave earlier or later than planned.


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