Which comes first: the chicken or the egg? Do you book flight or hotel awards first?

Spoiler alert: on this coming weekend’s Frequent Miler on the Air, the question of the week is the title question of this post. Readers Frank & Deana wrote in with this question:

Which comes first, the chicken or the egg? (Aka when booking a trip which do you typically book first in order to maximize value, the flight or the hotel?) Obviously, once one is booked it greatly limits flexibility to search for awards, adjust dates, seek upgrades, and compare competitors for the second. Some fabulous hotels/offers may justify accepting a 2nd, 3rd or worse choice in flights/itineraries and vice versa.

While we’ll each answer on tomorrow’s podcast, the question has stuck in my mind because I think it really speaks to the heart of award travel.

We’re deal hunters at heart

There are probably no statements that apply uniformly across all points and miles afficionados, but one thing that I think many award travelers have in common is that we are deal hunters at heart. Before I was a points-and-miles person, I was an online reseller, spending my free time finding things on sale that I could flip for a small profit on eBay or Amazon. Before that, I was combing the Sunday newspaper for coupons or if we roll back the clock 20 years I was comparison shopping with the ad from one store at another store or I was reading a website about all of the free or cheap things to do on my trip to Las Vegas. I blame credit my parents for my intrinsic appreciation of getting a good deal.

And so when I eventually stumbled on award travel, it was while looking for a way to get a good deal on flights. I was immediately hooked on the idea of getting “free” (or very highly discounted) flights and hotels by just spending money that I was already spending and getting the flights and hotels along with it.

My “deal-hunter” tendency has highly influenced how I have booked travel since long before I began playing this game.

That is to say that rather than deciding on a place for next year’s vacation, I was always deciding on a trip based on getting a good deal ever since I was old enough to be planning my own trips: We simply went where the cheap economy class airfares would bring us. One year we went to the Bahamas because JetBlue had a vacation package deal from New York that included flight and hotel for several nights for about the same cost as the flights alone. Another year we went to Ireland in January because flights were only $260 round trip (definitely not the ideal time to visit Ireland!). Yet another year, we went to Abu Dhabi because we stumbled on an airfare sale on Christmas morning offering tickets from New York to Abu Dhabi for $187 round trip. We never thought to plan a trip around a destination and time but rather we picked them based on cheapness affordability.

That desire for a good deal didn’t end when I found ways to book flights and hotels with points and miles. On the contrary, I think this hobby as fed that desire.

Hunting out a good deal first

I think the ultimate answer of the “chicken vs egg” debate for me is that the deal comes first. It doesn’t matter how much I’d like to see a place, I can’t bring myself to overpay. If I know that a saver award would cost 50K miles, I just can’t bring myself to pay 100K miles. It generally won’t matter to me even when I have millions of points and miles that I could afford to spend 100K miles, I just won’t do it if I know it is possible to pay 50K. Instead, if I could only find tickets for 100K, I’d let that trip wait for another day.

Again, it’s not because I can’t afford to use more miles but rather because I am obsessed with getting as good a deal as possible. That isn’t to say that I’ll never pay a little more than the bare minimum for convenience or luxury or both. In fact, I very regularly pay the premium to fly in international business class rather than economy because I feel like the experience easily justifies the price. By the same token, I am sure that there are some who would spend 100K in my theoretical example if it meant checking an item off of the bucket list or something to that effect (and even if it meant flying in economy as long as it meant not using cash). I can accept and respect that, but it’s not my jam.

And so I am most likely to go where the deal takes me. Instead of looking for the cheapest economy class airfares, I am now looking for award availability for four passengers in business class at the “saver” (lowest) level since we travel as a family of four. The rare chance to get four seats in business class to Fiji is why we booked a trip there that was meant to happen earlier this year (we ultimately had to cancel). Fiji hadn’t necessarily been on a shortlist of destinations we were considering but rather it was the opportunity that knocked and we tend to answer that knock.

That perspective would seem to suggest that I am equally likely to start with either flights or hotels based on a great award deal presenting itself, but in reality I think I have a clearer answer.

Flights are harder, so those are more often my first step in trip planning

Most places in the world that are visited by many tourists have multiple hotels. In many (most?) situations, there are numerous points-and-miles hotel options. At the very least, I can typically use Chase points at 1.5c per point or Capital One miles to reimburse a hotel stay. Since I am diversified in different award currencies (including hotel points programs), I am generally confident that I can find a hotel when and where I need to travel. There are obviously exceptions, but for the most part I know that I can find a reasonable hotel option using points in Paris or Rome or Bali or the Maldives or wherever. No, that won’t be true on New Year’s Eve or the night of a Taylor Swift concert, but most of the time I can find an option or three on the hotel side.

On the other hand, I can’t make four business class seats to Europe or Fiji or anywhere else appear out of thin air: it can be challenging to find multiple award seats in a premium cabin on a specific day or even in a specific month. Succeeding in that arena requires flexibility. When traveling internationally, we value flying in a premium cabin enough to prioritize that experience. I know that someone who has always planned trips by first picking a destination would probably find it crazy to prioritize the availability of a premium cabin award ticket over where you’re going, but in our case we haven’t changed our trip planning drastically due to the points and miles game, we just traded one parameter for another. Whereas we used to plan trips around the cheapest airfares, we now plan around premium cabin award tickets — in either case, it is deal first and location second for us.

I think it’s worth mentioning that some will probably think that we “have priorities backwards” because of this approach. I can see the temptation to do that (or to punk rock your travel), but I’d argue that this approach has opened us up to destinations that we’d have never considered and that have led to some of our coolest travel memories. If I started with a bucket list, I’d surely have stuff like Paris and Rome on the list (places I’ve been and that I love!), but I doubt I’d have even thought to put Lithuania or Saipan or Malta or Oman or Niue on my bucket list. Instead, I have ended up in those places due to the chance circumstance of award availability or great cash deals sending me looking at a place I hadn’t known I wanted to visit or would enjoy so much. I tend to think that our approach to trip planning has led us to more serendipitous destinations. That’s not to say that my approach is better than creating your own bucket list and checking it off one by one but rather that I don’t feel we’ve been cheated by our focus on deals. My perspective might be different if my goals, age, and circumstances were different, but up until this point we’ve not focused much on checking places off of a list. I am content to think that I can get anywhere I want to go “someday” (and accept that “someday” may never come for some places).

Award travel is flexible, so it often doesn’t matter which comes first

Ultimately, it doesn’t always matter where I start planning a trip since award travel often provides the flexibility to change as needed.

My initial thought when reading the question was that it is easier to start your trip planning with finding hotels since hotel awards can almost always be cancelled with no penalty up until a day or two before the stay (with some rare exceptions). That means that there is often no risk in speculatively booking a hotel since I am typically using an existing hotel points stash (rather than transferring points) and I can always change or cancel later. If I run into some rare hotel availability, as I did when I found 5 nights at the Grand Hotel Victoria on Lake Como, I’ll book that hotel availability first and then commit to hunting out award flights (recognizing that if I ultimately can’t find flights, I can cancel the hotel without penalty up until the cancellation deadline). I’ll also consider booking multiple sets of dates intending to firm plans up as I find flight availability.

But as we talked out our answers to the title question on the show this week, I realized that I’m rarely booking hotels where award availability is scarce. Hotel award availability in general is much better than premium cabin flight availability, so it just rarely creates a measurable obstacle for me. Even in those times when I just can’t find hotel availability, chances are high that I can cancel flight awards with no penalty or a low penalty. That obviously varies by program, but many of the most popular award booking programs have no fees or the option to book a slightly more expensive award with greater flexibility. You can read more about award change and cancellation fees by transfer partner in this post.

It therefore doesn’t seem highly important to me which part of the trip to book first since I know that I can usually cancel one piece of the other doesn’t come through.

My approach will change as my family travel evolves

A final key note here is that my style is likely to change as family travel evolves in my household. With years of being tied down by the school calendar approaching us, I know that I am going to have to deal with time restrictions much more often than I’m accustomed to. For almost 15 years, my wife and I have worked online with a great deal of schedule flexibility. I recognize that being restricted by the school calendar is going to have an impact on future travel.

I’ve previously written that flexibility is a huge key to success with award travel and we are developing less and less time flexibility. On the plus side, we are very much accustomed to location flexibility. That’s going to continue to be a key for us as we move forward.

That said, I expect that we will often need to plan further in advance and book as soon as booking calendars open in order to find awards during school break weeks, which means we will almost certainly gain even more emphasis on starting with flight awards and accepting that we may need to adjust hotel expectations. I fully expect some readers to chime in and say that it doesn’t make sense to prioritize an 8hr premium cabin flight over the hotel where I’ll spend 8 hours a night sleeping for 8 straight nights, but that’s probably how we’ll do it. That doesn’t make it “right”, it’s just the approach that will apply in our household.

But ultimately, even as our approach evolves, I think that flexibility will remain a constant. We’ll remain flexible regarding location and we will continue to value flexible awards. By maintaining flexibility in those two arenas, I think we will generally continue to plan travel mostly based on where awards are available during our schedule openings.

I’m curious to hear from readers: which comes first for you?

As we discussed this question and as it has continued to swirl in my mind, I have become very curious to hear from readers. Please share your opinion in the comments: do you focus first on flights or hotel awards? What drives your award redemptions the most? Do you focus on availability of premium cabins like we do, or do you perhaps focus on finding destinations that are incredibly expensive to reach with cash but reasonable using points? I’d love to hear your answer to Frank and Deana’s question in the comments.

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