Tips for Making Travel Decisions That Save Money and Reduce Stress

by joeheg

I remember how I felt when I heard the simple idea that has changed how I travel. I was trying to save money everywhere I could and spent more time getting from place A to place B or not buying something that would make my travel easier or more enjoyable. I’ve stopped worrying about every little expense, and the change makes my travels much better. I don’t stress over every decision. I don’t spend hours figuring out travel plans when a simpler, slightly more expensive plan is available.

I realized Sharon and I have been making these decisions that deal with our bigger travel plans for years. What flights will we take? Which hotel should we stay at? What size car should we rent and from whom? As we’ve gotten older and traveled more, we realize it’s often best to spend a little more to pick our spots where we’ll get the best return. All these factors are the same if I’m booking with cash or miles and points.


The primary decisions you need to make when booking an airline ticket are:

  • What airlines do you want to fly on
  • Do you want to have a non-stop or connecting flight
  • What time do you want to fly
  • How much luggage do you need to bring

I’ve already written about how to find cheap airfare. However, we don’t always book the cheapest airfare. Among other reasons, there are airlines, due to personal preference, we won’t fly on.

Regarding flight times, we’d previously taken the 5 AM flight to save some money, but that time has passed. We now prefer to pay a little extra to leave around 10 AM or later because that way we can keep our dog home one more night and drop her off at “camp” on the way to the airport (which also saves us the cost of one-night boarding). (Note from Sharon: it also means I won’t be quite so crabby in the morning because we’re not waking up before the butt crack of dawn to get to our flight on time)

If we have a choice, we’ll take a non-stop flight. Luckily, Orlando Airport has no shortage of cities we can fly directly to.



a map with many pointsa map of the world with many pointsThat doesn’t mean we won’t take a connecting flight; moreso that we often don’t have to because the non-stop flights are usually cheaper.

The luggage question is one that we’ve just needed to start considering. If the best fare for us is on an airline where we’d have to pay for a checked bag (or an airline like Frontier where we need to pay for a carry-on bag), we’d need to consider that. While we could also save money by booking a basic economy ticket, we’ve decided that type of travel is not for us.

No trip is the same. For some of our travels, flight times are flexible; for others, we must be somewhere by a specific time. The more important it is for us to be somewhere, the more willing we are to pay the extra for the flights we need. I wish I could put a number on it, but it varies. Sometimes we’ll pay $50 more for the perfect flight time, but we might not want to pay $25 to save a few hours.


If you’re taking a more extended trip, your hotel bill may be higher than your airfare. Lucky for us, we don’t have a bunch of requirements when it comes to hotels. We’re just as happy staying at a Waldorf AstoriaCourtyard by Marriott, Candlewood Suites or a cabin at the Grand Canyon. If we never stayed in another five-star hotel for the rest of our lives, it wouldn’t bother us. We will choose what’s most important for us on each stay. It could be that I found a great deal, or we might want to stay at the same hotel as our friends, or we may need a hotel room that has a full kitchen with a freezer (so we can bring home Texas BBQ). Each one of those has been the deciding factor in past hotel stays. We may have paid some extra to get what we wanted, but not much.

I know that when it comes to hotels, I try NEVER to book a prepaid room (although I have on a rare occasion). On the other hand, I can’t remember a time when I booked a prepaid, non-refundable room. For starters, I usually can get almost the same rate that I can cancel if needed and pay at the hotel by booking with an AAA rate. It’s worth the few extra dollars not to pay the hotel months in advance.

Car Rentals

I like to think that this is where I’m willing to make the most concessions to save money. While I used to spend hours trying different combinations of codes and coupons, I now let Autoslash find the lowest prices for me. I use a credit card that provides primary LDW coverage and always decline the gasoline option. I only reserve the smallest car I’ll need for the trip (and I have no problem putting luggage on the car’s back seat).

There are some choices that I’ll make that may cost us more money:

  • If there are on-site and off-site rental locations, I’ll always try to rent at an on-site location. There’s the time saved when renting, and that’s even more important when returning the car – it can make a huge difference. I’m not sure how much more I’ll pay, but I’ll pay for the convenience.
  • I’ll choose a company where I can pick my car if possible. Since Sharon can’t drive all vehicles (Note from Sharon: I’m like a candy bar – I’m fun-sized!), we try to choose the ones we both can drive.
  • Renting from a company that lets me add Sharon as an additional driver for no charge is nice and may cause me to pick one place over another. It’s not something we’re going to pay much extra for though.

Skipping The Rental Car Entirely

We’ve been doing this more and more when visiting big cities. Most airports are connected to the downtown area by some mass transit, usually trains. If we can make it around from there by walking, taking other public transport, using ridesharing apps like UBER or Lyft or even using taxis, we’ll try and do that. Otherwise, we’d have to pay car rental charges along with the insane parking fees most city hotels charge.

Changing Travel Dates

I’m sure you’ve seen the pop-up box that says, “Travel 1 day earlier and save $45!” when looking for airfare. It sounds good, but we’ve hardly ever taken them up on the offer. In our case, I’ve usually had to put in for vacation weeks, if not months in advance. Leaving a day earlier would mean missing another day of work, already making this a money-losing proposition.

Here’s an example where you can fly at 7 PM the night before instead of 7 AM the following day for a party of 3 and the flights would be $50 cheaper per person—so $150 total.

Here are some costs you may incur:

  • Extra night of hotel
  • An extra day of car rental
  • An extra day of parking the car at your home airport
  • Extra cost of boarding animals
  • Extra night of meals away from home

This would be great for you if you don’t have any expenses (getting a ride to/from the airport, staying with family or friends, lost wages). Just consider that saving money on airfare by changing dates might cost you more in the long run.

Flying To/From Alternate Airports

If a city has multiple airports like New York, Chicago, or Los Angeles, I’ll be willing to fly to any of them for cost savings if it is convenient for the trip. We flew into Burbank when staying in Hollywood, and it was easier to get to our hotel and was cheaper airfare. I’ll also consider flying into an airport a little drive from our final location if the airfare is massively different. Three hours of driving is worth $200, but not $50.

I will occasionally look to see if flying out from another Florida airport, like Tampa, Sanford or Daytona, will be cheaper for us. It usually turns out that since Orlando airport is so popular, they typically have the lowest prices in the area because of all the competition.

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This post first appeared on Your Mileage May Vary


Christian October 4, 2020 - 12:36 pm

Some good insights. BTW I love the above map that shows all the nonstop flights from Orlando. Is there a website that does that for various airports? That would help a lot on trip planning.

Fathiss November 15, 2021 - 9:08 pm

I often do the prepaid with programs with status. I find these nonrefundable rates are more flexible than you think. Save the 20% or so and if plans change or if the rate goes down, simply contact and renegotiate. I just did that this morning with a nonrefundable car rate and they reimbursed me $101.19. I can’t remember this ever failing with some level of status in a program.

disdadisdisdis November 16, 2021 - 5:34 am

Yeah, I am kind of moving in the same direction as you guys.

Honestly, I’ve made the biggest mistakes planning vacations AFTER I learned about “O&D revenue management.” I used the ITA matrix to find the cheapest points of departures and destinations, learned about “skiplagging” and “1x strikes.” Ultimately, it did no good. Not only where you longer in the air due to positioning flights. But also, you sometimes needed to book an airport hotel to have enough buffer between the positioning flight and your actual ticket which exploited airlines’ O&D logic.

Once you added up everything, cost of hotel for layover, cost for positioning flights, etc., little saving remained. That little saving plus the extra miles earned for the more complicated routing usually do not outweigh the inconvenience. So I largely stopped doing it. (If I can save a couple of thousands on a first-class long haul flight by positioning myself somewhere, I might still do it.)

JoeH November 16, 2021 - 2:36 pm

The biggest shift for me has been with city transportation. It used to be cheapest option, even if it saved only $5. Now Uber or a Taxi is often the choice even for $20-$50 more when it saves time and hassle. The last subway connection that was 12 minutes walking while dragging carry-on luggage for the family was the final straw!

joeheg November 16, 2021 - 11:19 pm

The final straw was a walk in the freezing rain in Chicago to get the six blocks from the hotel to the elevated train stop when I could have called an UBER for less than $10.

Jim Lovejoy November 17, 2021 - 4:20 pm

I agree in general. However I’m not so eager to give up on off-airport car rentals. Back in 2017 we saved around $500 by
taking a $30 taxi ride and about 15 minutes longer total than the congestion at the airport. In fact, it might not have cost us any time at all because the rental was only a few blocks from our hotel.
I would only do it if it would clearly save not just hundreds but multiple hundreds for minimal effort.


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