This Flight Booking Mistake Cost Me Over $350

Sometimes shopping around for the best deal can backfire.

I'm the type of person who likes to compare as many options as possible when booking travel. My typical flight booking process involves several tabs open with different airline websites, where I'll look at prices in both dollars and, if I have any, miles. If I'm not sure what to buy, I'll wait and check back later.

Although my method has often worked out well for me, I recently ended up spending much more on airfare than I should have. And it was all due to a simple, avoidable mistake.

Fare today, gone tomorrow

My wife and I work remotely, and we travel around quite a bit to spend time living in different areas. After staying several months in Los Angeles, we finalized our next stop last month, and I started looking for flights to get us there.

Right away, I found a pretty good deal -- a flight with United for $323 per person. It was a reasonable price and nonstop, but it was also a morning flight, so it would've meant leaving early and fighting traffic to get to LAX. I figured I'd keep searching, and something more convenient would pop up.

Spoiler alert: It wouldn't.

I looked around when I had some free time that day, but I didn't find anything that checked all the boxes. I was also getting to the point of information overload. After looking at so many options, I was less sure than ever of what to do. Should I try to use my travel rewards or pay in cash? What if I flew out of Burbank instead? Just how far was the SNA Airport, anyway? (Way too far to be worth it, if you're wondering).

The next day, I checked prices again. As you may have guessed, the tickets with United were now much more expensive at $420 per person.

From bad to worse

I should've just booked the United flight. Instead, I made another bad decision to turn this entire booking into a real comedy of errors.

Now that the price had gone up on those tickets, I decided I definitely didn't want them. If I bought them at $420 when I could've had them at $323, I'd feel like I had overpaid. It's a fallacy, I know, but that was my way of thinking. The obvious solution, to me at least, was to find a different, better flight.

Of course, that didn't happen. With time ticking down and needing to book something, I had to grudgingly admit to myself that the United flight was clearly the best option. So I bought two tickets, now at $508 apiece. I earned more points on one of my credit cards, but I would have much rather saved $370.

How I could've handled this better

Looking back, the worst part of this situation was that I could've locked in the low price on the United tickets and kept shopping around.

The Department of Transportation has a flight cancellation rule that would've covered this. When you book a flight to or from the United States at least seven days in advance, you can cancel or change your ticket free of charge within 24 hours of booking.

What I should've done was buy the United tickets right away. Then, I could've used the next 24 hours to see if anything better was available. If so, I'd be able to buy that and cancel my United tickets. If not, I'd be safe, because I had already gotten tickets and wouldn't need to worry about prices increasing.

An expensive lesson

This wasn't my proudest moment, but it was a good learning experience. Here's what I took from my booking mishap:

• Flight prices can go up at a moment's notice. Don't assume that a deal is going to stick around until tomorrow or even later that day.
• If you find airfare that works for you, book it. You still have 24 hours to cancel if you change your mind or find something better.
• "Pretty good" is good enough. I wasted a lot of time looking for a perfect option that didn't exist, only to go with the deal that first caught my eye.

About a week ago, I found myself in a similar situation. It was late, I was shopping for airfare, and I found a good deal with Alaska, but I'd have to call my card issuer's travel portal to earn the most credit card points. So I called at 1:45 a.m. (yes, I'm a night owl) and booked tickets. Not only did I save time by booking the first deal I found, but I had peace of mind from locking in a low price.