The True Cost of Bargain Flights

Even financial professionals are constantly reevaluating how they make money decisions. I recently attended MilMoneyCon25 in beautiful (and hot!) San Antonio. As I was booking my flights from the Nashville area, I went through my usual decision-making process. I generally search for the cheapest flights to wherever I’m going, and if the layovers or the time of day is especially awful, I’ll scroll down to the slightly more expensive options until I find the “sweet spot”- cheap flights but decent time of the day and not-too-long layovers. This has usually worked pretty well for me, but I’ve had terrible experiences for both of my trips so far in 2025, which has caused me to re-think my decision-making process.

March Trip

In March, I traveled with my two daughters to New England to visit family. The flight there was nonstop, but the return trip had an hour layover, which is about as long as I usually like. Our first flight from Boston to Fort Lauderdale was delayed due to a mechanical issue, which caused us to miss our connecting flight. It was good news for me that the cause of the delay was what the airline called “controllable,” meaning it was within the airline’s control (eg: not weather). The connection was a 6:45pm flight, and they had no seats available to our destination for the rest of the night. Or the next morning. Or the next afternoon. They could put us on the same flight the following day, 24 hours later. And no, they couldn’t give me our checked bags or the checked car seats back, because they were deep in the bowels of the baggage claim system.

So, there I was, with two young-ish kids, stuck in Fort Lauderdale overnight with only our carry-ons (which, fortunately, turned out to have most of our overnight things). The airline paid for our hotel and gave me a meal voucher, but even though our delay was 24 hours, the voucher was a one-time use- whether I used all of it or not, anything remaining would be void after the first purchase. We made the best of it (read: the kids had a blast, but it was stressful for me), but I would have preferred to not have what I called our “some-expenses-paid vacation in Florida.”

May Trip

Then last week, I had the immense pleasure of attending Military Money Conference 2025, more affectionately known as MilMoneyCon25. The trip there was uneventful, even with a layover, and the entire conference was amazing. My presentation, “Demystifying the VA Claims Process” was well-attended and went smoothly, and I loved catching up with friends and learning from other financial professionals in the military space.

That one-hour hop from San Antonio to Dallas? It turned into a six-hour saga. Ironically, if I’d just driven, I could’ve been there in 4 to 4.5 hours.

We left San Antonio about 15 minutes late due to storms over Dallas, but I still had 45 minutes left of my hour layover to catch my connecting flight. But as we approached Dallas, the storm shifted. Our original arrival route was closed, so we were rerouted north. Then that route shut down too, and the pilot was directed to circle the airport for the next 30 minutes while we waited for clearance to land.

Unfortunately, the plane had only fueled for a one-hour flight. After all the detours, we didn’t have enough to keep circling. So—surprise!—we were diverted to Lubbock. Yes, farther from Dallas than where we started.

We landed in Lubbock around 7 p.m., refueled, and then sat through a ground delay until after 10 p.m., waiting for Dallas air traffic control to give us the green light. By the time we got back in the air, landed, and deplaned at DFW, it was close to midnight.

Every flight to Nashville had already left. Customer service told me the next available flight wasn’t for 30 hours. My best option? Fly to Memphis instead—still three hours from home, but at least I’d arrive home within the next 12 hours.

I didn’t bother with a hotel since my Memphis flight boarded at 6:30 a.m. and I wouldn’t sleep well knowing I had to wake up so early. I found an empty bench in the terminal and tried to rest, but after a series of interruptions, I gave up around 4 a.m., after sleeping for only 30–45 minutes.

Thankfully, the flight to Memphis was smooth and quiet—half full and early enough that most people slept, myself included. I landed with the plan to rent a car for the final leg. But after three rental agencies had no one-way inventory available, I gave up and called an Uber. Another three hours and $250 later, I was finally home—nearly 24 hours after I’d arrived at the San Antonio airport.

Not only did my 6-hour trip take nearly 24 hours, but because of the sleepless night, I needed more recovery time than I'd planned on. I was completely unproductive the day I returned home, and only slightly less so the following day. I've been home for about 2.5 days now, and I'm only just starting to feel like myself again. Not the best ending to an amazing conference.

Lessons Learned:

• My time and sleep are now more valuable to me than money. Previously, I’d choose the cheapest reasonable flight with a short layover, but having these back-to-back experiences taught me that I’d rather pay extra for a nonstop flight or a flight a bit earlier in the day- when there would be some buffer for delays and I’d be more likely to still arrive the same day.

• I would now rather book my flights earlier out and pay the extra fee for trip insurance in case my plans changed. I wasn’t entirely certain of my travel plans until a few weeks prior to the conference, and by then, the good flights were sold out or too expensive. If I had booked my flights months in advance (when I made my cancellable hotel reservation), I could have gotten better flights earlier in the day… and possibly even a nonstop flight! The trip insurance is like any other insurance – you pay the premium just in case, but you hope you never have to use it.

• I’m glad we have a healthy emergency fund that can easily cover unexpected costs on a routine trip, such as my Uber trip. I spoke with an Active Duty Soldier who was also stranded in the airport who couldn’t get a flight out for four days! I suggested that he do what I was doing- fly into another airport within driving distance and rent a car to get home. He couldn’t afford the $100 or so that the rental car would cost. The unfortunate thing is that it would cost much more than $100 in food and lodging. Having an emergency fund gives you more flexibility and less stress when routine things don’t go according to plan.

Have you ever had a “routine” trip suddenly go awry? How did you adapt in that situation? What things do you consider and prioritize when making travel plans? Leave your comments below!