Earlier this month, my wife and I took a trip to Grand Cayman. It was chilly and windy, which was unusual. A bit if a bummer, but there was no snow, so it beat New England by a long shot.
I fly infrequently now. Usually 1 trip to a warm climate during the winter, but that’s it. Throughout much of my working career, I traveled quite a bit. I usually found myself in an airport a couple of times a month. A lot has changed over the past few years.
Traveling frequently has huge benefits. I had points and upgraded status on several airlines. I boarded early (which means I always got overhead space), often got upgraded seating and had a free drink.
Sad, but this is all gone for me. Now I fight for overhead space, pay for my drink and squeeze into the middle seat.
But, all is not lost, there are some ways to make the travel experience a little less onerous.
Cost
It’s really hard to compare costs.
I’m going on a golf trip to Florida later this year, and I booked a JetBlue flight. Great news, I saw a flight for $99. Not so great, the lowest return flight was $246. Once I started booking, I realized that I wouldn’t be allowed to select a seat. If I wanted to select a seat, I’d need to pay an extra fee.
I generally avoid extra fees, but I feel like if I have an assigned seat, then the airline is holding a spot for me. I know they oversell, but I know seat 19C is mine. Without an assigned seat, they could be overselling the plane and I’ll be the guy waiting at the desk while they ask for volunteers to take a later flight. I have a tee-time waiting. I need to be on that plane.
And 2 clicks later, I find that I’ll need to pay for bags. I can jam a few day’s worth of golf clothes into my backpack, but that won’t work for my clubs. It’s $35 per bag. That’s another charge.
And then there are a whole host of other add-ons. More leg room, even more leg room, premium economy, business class….
I clicked a resounding “no” on all. I need to be on the plane and I need my clubs, but beyond that, I can manage a 3 hour flight with even less legroom.
Expectations
I went from Oh Great!! a $99 flight with an expectation that air travel will cost me less than $200 to Oh Crap. $400.
I didn’t book because I was so annoyed. And there’s nothing wrong with the $400 price. Driving would take me 24 hours and would cost me a lot more in gas and wear and tear on my car. $400 is a deal.
But not compared to $200.
Fly Angry
I took a few days to let my blood pressure drop and then I booked the $400 round-trip flight.
But I was definitely angry. I started thinking maybe I take the non-refundable fare, maybe I don’t get an assigned seat and risk losing my spot. Maybe I could rent clubs…All these could have been bad decisions.
On the other hand, it’s easy to say that I fly infrequently so maybe I should pay for a few upgrades. But then I get to the payment screen and I’m now at over $500.
For me, it’s hard not to go through this process and not get angry.
But, I took a few days, came back with a cooler head, and booked what I needed.
So tip #1 is to set reasonable expectations. We probably won’t end up paying the lowest fare and we’ll probably need to pay for some add-ons. Maybe think about what’s a reasonable cost before starting.
I’ve flown to Florida pretty often and friends constantly talk about trips and fares. I know to expect $200 – $600. Sometimes we’ll get a $99 fare, but don’t count on it.
This may prevent us from getting angry and possibly making a rash decision that we’ll regret later.
Requirements
Everything begins with requirements.
There are a million choices and great sites like Google Flights that help us explore all the options.
But sometimes the number of choices can be overwhelming. I find it helps to narrow things down a bit before starting my search.
On my Grand Cayman trip, I had 150,000 JetBlue points that were losing value rapidly. So that made my decision for me. JetBlue it is!
I spent a little time looking at Delta flight options for my Florida golf trip, but I’d be flying out of a different airport than my buddies and I’d fly in at different times. So I’d need to come up with transportation and then I’d need to get a hotel one night…it got complicated fast. I might be able to get a free flight using points, but the hotel and the car rental would eat into any savings.
So for me, in both cases, I needed to fly JetBlue. This narrows things down.
Often times we’re limited by dates. We only have 1 week off, or we’re coordinating with a spouse, kids, dog sitting….
If our requirements are specific, we have limited choices, but a site ike Google Flights can still help.
Options
We can really start to save money when we don’t have a fixed date, airline, or even location.
While it will cost me $379 to go to Orlando tomorrow, if I can wait until St. Patrick’s day, I can travel for $99.
But even if I do have fixed dates, let’s say I have to go March 9-16, Google Flights can help me find the lowest cost airline.
Wide Open
But where we can really save some money is when we are completely flexible. Money expert Clark Howard recommends choose the location that’s on sale and then figure out why you want to go there.
I put in Boston as the departure city and no destination and I can see prices for various 1 week trips over the next 6 months.
Spend a few minutes. There are lots of tools and options for finding a discount.
Travel Sites
I tend to visit the usual suspects – Booking, Expedia, Kayak…I seem to get pretty good options and prices. Here’s what booking shows me for a flight from Boston to Fort Myers.
I can then filter a bit if I’m not happy with the flight that leaves at 7:15am, has a stopover and then arrives at 10:29pm. I could probably walk there faster.
And when I click in, it looks like I’ll need to pay extra to check a bag or to avoid cancel/change fees.
Aggregators v. Direct
So an aggregator like Booking provides lots of options across many airlines, but wouldn’t it be cheaper to book direct? The answer is a resounding maybe!
Reader Mike and I have debated this about hotel prices. He has loyalty points and going direct is his go-to. I usually start with booking or expedia.
I ran a little experiment on our flight to see the difference between booking and JetBlue. Going direct to JetBlue will save us 20 cents.
But this is a sample size of 1.
I typically start with the aggregator site and then go to the airline site to see if I can beat the price. Sometimes it’s worthwhile, sometimes not, but always good to check.
Refundable
Refundable base price tickets are scarce.
However, this tidbit can sometimes work well, and even if airlines don’t frequently offer reasonable cancellation options, hotels often do and rental cars will sometimes offer one.
Prices change frequently. There are a million travel advice sites and they all have their own scheme for when to book to get the cheapest flight. One intriguing one is to use a VPN to mask your location.
Sadly, I tested our BOS to RSW JetBlue flight from both India and from Nashville and got the same rate each time.
But I do know that they change from week to week. And they often get reduced right before travel if they have empty seats, empty rooms, or un-rented vehicles.
If we book refundable, we can continue to shop right up until the day we leave. If we find a cheaper rate, cancel and buy the cheaper one. If we don’t, stick with our original.
Trip Sites
Remember Groupon? Years ago, my wife and I were huge Groupon users. Then everyone got Groupon fatigue.
It’s still there and check out this deal.
I’m thinking of clicking Buy Now. I’m not sure I could spend 8 days at home for $699.
I read dozens of 5 star reviews, but the reviews are all about the booking process. I couldn’t find anyone who had completed the trip. This could be a risk.
I asked ChatGPT. Grok is ignoring me lately – he keeps saying High Volume.
Clark
We spoke earlier about my favorite cheapskate Clark Howard. He regularly posts travel deals on his site and his daily emails. Clark says.
We only share deals that will truly save you money.
I feel better that someone I read regularly and rely on for advice is vetting the trip. However he doesn’t promise that the hotels will be great and the transfers will be seamless.
Wrap Up
Travel in general, and especially air travel has become much less fun over the years. And airfare is a killer. The base ticket price alone will give us heartburn, but then we’re shopping for even more leg room, early boarding, seat assignment, check-in bags… It’s as complicated as buying a car.
The good news is that with the internet and all the travel sites, with a little effort, we can get a ton of information. This makes it easy to compare prices across providers and choose the best deal.
I did not talk much about using AI assistants like ChatGPT or Grok. I used Grok to help plan a trip and he was quite helpful with recommendations, but he was way off on prices and he missed the boat on a few things that were important. He was great at recommending spots on a rainy day, but not so great on recommending a quiet relaxing Caribbean island.
I love Google flights. It’s helpful when you know when and where you’re going, but it also is great to explore deals when we have flexibility.
I’m also a big fan of Clark, because I trust that he’s vetted the deals. Not so much with Groupon, but I’m intrigued.
Safe travels!