Is Airline and Hotel Loyalty Worth It?

“So how much is Delta Air Lines paying you?”

Somebody asks me that almost every time I walk off a stage. The answer is nothing. I am just a raving fan and have quite a few stories because of all the times they’ve bailed me out and created an extraordinary experience for me. In 13 years of professional travel, I have never been sponsored by them… well, unless you count the gift box they sent me for their 100th anniversary.

The big question I’ve been seeming to get more and more from speakers, consultants, and entrepreneurs is, “Is Airline loyalty worth it? What about hotels and cars?” That's what I want to tackle today.

I give my perspective on Airline Loyalty, Hotel Loyalty, and Car Rental Loyalty below.

A quick word on where I’m coming from, and it cuts both ways. I’ve held top-tier status with Delta, with Hilton, with Omni, and with Hertz. I’ve also had a program zero out my balance overnight and treat me like I’d never walked in the door. I’ve been at the top of these things and at the bottom of them, sometimes in the same month. That’s the only reason I have an opinion worth reading.

Airline Loyalty: worth it

Yes, airline loyalty is worth it. And probably not for the reasons you think. The SkyClub and the upgrades are great, don’t get me wrong. But that’s not truly what keeps me loyal.

What keeps me loyal is how I’m taken care of when everything is falling apart. Am I going to trust a budget airline to get me there? Am I going to be stuck in a queue of 244 other passengers, waiting my turn on a phone line with thousands of people on it? Or am I going to be with an airline that knows me and can get me where I need to be, even if they have to sacrifice their own dollars to put me on somebody else’s airplane?

This past week, I woke up to a canceled flight on my way to a conference in Orlando. But, with that was my new itinerary. They had rebooked me automatically and they transferred my complimentary upgrades, which was a rare, and pleasant surprise.

Here is the problem…with that new flight I was scheduled to be in the air at 30,000 feet at the same time I was to be walking on stage. So I quickly reached out and let Delta know my story.

In less than 10 minutes, they had me booked on a direct flight not to Orlando, but to Tampa. To top it off, they had ground transportation waiting that they covered. I got there with plenty of time to spare, checked into my hotel, got a little work done, and was still early to my presentation.

And it isn’t just that trip. A storm shut down O’Hare and my whole family was going to miss our connection through Detroit, so Delta put all of us on a direct United flight in the same fare class and we got home sooner than planned. Another Chicago snowstorm, they booked me on American. Snow out of Raleigh that wasn’t even their problem, American again. Many years back, JetBlue.

Thirteen years of loyalty to one airline, and a meaningful share of the times I’ve flown somebody else, Delta is the one who got me the ticket.

And the everyday math is better than people think. Last Friday my talk ended at 5:00, I did a book signing, hopped from the convention center straight to MCO, and grabbed dinner in the SkyClub. That dinner would have cost the meeting or me at least $20. This coming Monday I’m speaking in Atlanta in the afternoon, so I’ll grab lunch in the Sky Club, then dinner in the SkyClub before I fly out to Tuesday’s event. Two meals in one day, $20 each on the conservative side. That’s $40, just from flying the same airline. And that’s before the upgrades where the meal comes with the seat.

People often ask, "Is it worth having a connection?"

My unpopular answer is yes. In many cases, loyalty is worth the connection. The counterargument is that a connection is one more variable that can go wrong, be delayed, and blow up your day. Fair. But I also know the airline has my back and will make it happen. And given a longer connection and a shorter one, I almost always take the shorter one, because if it breaks I know I’m getting rebooked on the next one out.

Now, loyalty doesn't always pay off….there’s the day none of it worked.

It was March 6 of this year. I had finished a day of speaking in Memphis and I was trying to get to my brother’s wedding weekend. That’s when my beloved airline failed me. I have never seen a line like it, hundreds upon hundreds of people lining every terminal in Atlanta. I am a Diamond Medallion. I am a Million Miler. But that day I was a guy with a phone that wouldn’t connect me to anyone, looking at a line that wasn’t moving. I had to book my own flight on Frontier, and it took three days for my bag to get back to me. I rolled into a morning rehearsal after being up all night, completely tired, in yesterday’s clothes, with no suitcase.

That could happen on any airline. But I do know all of the times that I have been saved because I have been loyal. It's a reciprocal relationship, and the second it becomes a one-way street, I might start shopping for a new airline.

Hotel Loyalty: only sometimes worth it, and mostly not your call

Here’s where I waffle. Hotel loyalty absolutely can pay. The problem is that as a speaker, most of the time it isn’t your decision to make.

As a speaker you’re often end up on the meeting professional’s room block, so you stay wherever they book you. The major downside is that a lot of times you don’t get the points for that room, or you get limited points.

So you might hop from one meeting at a Marriott to the next meeting at a Hilton, then to an Omni, then to a Hyatt, and then to some boutique hotel that doesn't even have a point system. And that just described my last October.

I remember speaking in the middle-of-nowhere, Iowa, and the closest hotel was 45 minutes away, and there was only one hotel in that town. I didn’t even have a choice between brands.

That said, if you do get to choose your hotel stays frequently, it pays to be loyal. I just found out today that I have quite a few free nights at Omni, because I’ve been speaking at a lot of Omnis. This year, I reached their top level, Iconic, I get an automatic suite upgrade and two room-level upgrades. Some of the nicest places I have ever stayed at are Omnis, and that’s the one I’m doubling down on. I had a sauna in one of my suites at an Omni once and some other outstanding amenities.

And then there’s the other side of it. I just tried to book a Hyatt in Utah for an engagement a few weeks from now. In 2024, and a bit last year, I did a lot of events at Hyatts. So, I expected to have some status. But I logged in and a big goose egg. ZERO. My points had expired overnight. Last year I was upgraded in a Hyatt and stayed in one of the best custom decorated suites I’ve ever stayed in. This year they treat me like I’ve never stayed before. I’m not saying I need those benefits. But it does nothing to garner loyalty.

Hilton is why I moved to Marriott. I was Hilton Diamond for the longest time, and apart from the Diamond parking spot, which was really convenient, I’m not going to lie, there was really almost no benefit. The room upgrades never happened. The late checkouts almost never happened. I normally had to ask for my welcome gift, which was free water bottles. Here is the catch, and it is plaguing all loyalty programs. So many people were buying the top-tier status by just getting a deluxe Hilton credit card that the loyalty became saturated. I'm not against using credit cards to get ahead. But the saturated market has made me switch to Marriott.

The constant unavailability of late checkout is what really got me. Plus, Hilton made breakfast a lot more expensive at their hotels, and their room credits barely covered a side of bacon.

I lean toward Marriott now, when it’s in my control. If the room is comparable and the amenities are comparable and the distance from wherever I’m speaking is comparable, I’m leaning Marriott, because they’re doing a little bit more for me.

Rental cars: not right now

Nobody has won me over.

For a while Hertz did. They gave me those upgrades, some sweet cars, convertibles to drive the Pacific Coast Highway, fancy cars more expensive than my first house as a complimentary upgrade. And now I don’t get any of that, even though I’m at the same level. I had a large group last summer, and they didn't even have the vehicle with enough seats that I had reserved. And I'm at their top-tier status.

Loyalty comes down to three things: redemption value, reliability, and convenience. Feeling special is nice, but it isn’t the point. Do I sound like a diva? Absolutely. But you’re buying my loyalty with those things, and right now nobody in the rental car business is buying.

What it costs, and what I’d actually do

None of this is free. The threshold to be a Diamond Medallion is $28,000 a year in Medallion qualifying dollars, through credit card spend and air travel. I exceed that every year. That’s the real price of everything I just described, and it’s the number to run against before you decide to chase a tier.

And I’m not loyal to Delta because it’s my only option out of Raleigh. Delta has a ton of directs out of here, but so does American. Southwest has a ton, Avelo has a ton, Breeze has a ton. If I were in some smaller town with limited options, that would be a little more concerning. And I do realize that.

So here’s what I’d actually do, whether you’re flying a hundred times a year or fifteen.

1. Concentrate. Pick one airline and stay there. When your points are scattered across programs, you lose real value in the transfer fees just getting them back together.

2. Check the numbers before you book. Cancellation and delay rates by carrier and by airport are public. Almost nobody looks at them, and then they call the result bad luck.

3. Never have one way in. On any trip that matters, know your connecting options and every airport within driving or train distance of the venue.

4. Match the connection to your recovery. Take the short connection when you know they’ll rebook you on the next one out. Take the long one when you know they won’t.

5. Tell the meeting professional up front. If you’re tight, say so before you sign. I can make that fit, but you’re going to fit between two things, here’s the risk, and here are my contingencies. Nobody has ever walked because I said that.

6. For hotels, follow your calendar. Put your nights where your events already cluster, and don’t chase a tier your calendar won’t support.

Until next time,

P.S. Tell me your Atlanta. The trip where you had the status, the tier, the card, all of it, and it still didn’t save you. Hit reply. Mine ended at a wedding rehearsal in yesterday’s clothes, and my brother has never once let me forget it.