Where Do You Draw the Line to Save Money?

We’re planning another trip to Disney this year, and that means Bryce gets to obsess over small details (and start talking about himself in the third person.) At the moment, I’m looking at plane ticket prices (mainly because it’s too soon to start really looking at Disney prices, and I’ve got my fingers crossed they’ll be offering free dining again . . .)

Each time I look at these tickets, my knee-jerk approach is to find the cheapest tickets available and book those. But maybe I’m getting older or wiser (or just not as frugal), but I’ve been burned by that approach a few too many times in the past. It’s one thing to find the CHEAPEST FLIGHT YOU CAN, but then you still have to actually use those tickets.

In other words, it might seem awesome to save $150 a ticket by flying on an off day out of an airport that’s far away, with a 2 hour layover, on the red eye. But when it comes time to make that flight, and you’re stuck traveling or 12 hours for a trip that really should have just taken 6, you begin to wonder if it was really worth all the savings.

So it’s a balancing act. A few years ago, I think I would have gone with the savings, every time. It was the difference between being able to go on the trip or not, period. These days, when we’ve got a bit more extra money in the budget?

Let’s talk specifics.

For me to fly to Orlando, I can leave from multiple airports. The closest one is Portland, 1.75 hours away. Bangor is about the same, but it’s a regional airport. (Though it does do direct flights to Sanford, which is close to Orlando . . .) Then there’s Boston or Manchester, both about 3.5 hours away, though you can take a bus to Boston easily. (But if you take the bus, that adds on $150 of bus tickets for our family, which cuts into savings from flying out of Boston.)

There are no direct flights from Portland. There are some in Boston, but they cost more, so you eat up the savings you could have had if you go that route. (You’ve also left from Boston, which added a bus ride to your journey . . .)

But wait! There’s more!

We’re looking at Thanksgiving. And as everybody knows, Thanksgiving is a time when airlines like to hike their prices. So we can either fly at strange times for less, or pay more to fly when we actually want to.

Then again, there’s also Montreal. Canada doesn’t do that whole Thanksgiving thing, so we could fly at normal times for normal fares (non stop, even) . . . if we’re willing to drive 4.5 hours and make it into an international flight.

Add these all up, and there are so many moving parts, it makes my head spin. And how much money am I saving if I’m putting in 20-30 hours of my time just to save $150?

Which leads me to my question of the day: where do you draw the line, personally? Are you the sort of person who will go for the absolute cheapest, no matter what? Do you just ignore the ticket price and go when it’s convenient? There’s a lot of middle ground between those extremes, and I’m curious how other people decide where they fall in there.

Do tell.

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