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When we first started travelling our usual process was to search places like Kayak.com for flights and Hotels.com for our hotels. Seems logical enough: when trying to save a little cash we’d go to the places that made it easy for us to find lots of results at reasonable prices. Same? Okay, good.

What we eventually found out was that there are better ways to book travel plans. To clarify, by ‘better’ we don’t necessarily mean less expensive, so if that’s your main goal then perhaps stick with what works best. However, after traveling a bit, we found that the actual travel experience can be better when you book directly with different companies. Let’s go through a few quick examples.

Hilton, Conrad & Crockfords Resorts World – Las Vegas

Hotels.

Like most of our friends, we used to be pretty loyal bookers on Hotels.com. We could typically find a low-cost, no-frills room wherever we wanted to go. Then, on our first trip to Scotland, we befriended a hotel manager who got a disappointed look on her face when we told her our process when she asked how we found them. Yes, we often got the lowest price from Hotels.com (or other, similar websites), but she told us they take a pretty high percentage of the booking, so the hotel itself made less on the sale than if you book through them directly. We also learned that many hotels, particularly smaller and independent ones, don’t put their better rooms on those websites, specifically because they don’t get the same return on them. Plus, we’ve found that if you book directly and something happens, the hotel staff are more likely to work with you than if you book through some third-party site.

The same goes for major hotel chains. A few years ago, when the Pandemic was really revving up, we started noticing what people were saying about their experience with major hotel brands, specifically if they needed to change or cancel a reservation. Many hotel brands weren’t exactly open to working with people when life happened, and so in many cases they were out of luck when trying to make a change. Or, if a change was possible there were always fees charged to do so. Except one: Hilton. (Disclaimer: there were probably others that took the Hilton approach, this one just stuck out to us) Not only did Hilton not charge cancellation or reservation change fees (unless you cancel or change within 24 hours of your stay as a loyalty member), but they were also really easy to work with to make those changes. In fact, most of the time you can do everything you need through their app, it’s super easy and user-friendly, no hours on hold required. So, we started being more intentional about staying with them when we travel within the US and stay in major cities abroad. During 2020-2021 Hilton made it easier to earn and maintain their Diamond level of status, which has all kinds of perks we find valuable and so we’ve stayed with them since. Could we find less expensive rooms through third-party sides like Hotels.com? For sure. But we’ve found the folks at Hilton are happy to help, and more so when we book with them directly rather than third-party and being a loyalty member often gets you a great room at a discount price. Plus, we’ve racked up a pile of loyalty points that we can’t wait to use on a free vacation, we get free breakfast or hotel credit for food, and a plethora of other perks. Just something to consider.

Over Lake Michigan headed for Chicago

Flights.

Just like with hotels, there are loads of third-party websites you can scan to find rock-bottom prices on flights. In a prior life, we did that, too. Trouble is, that often means you’re flying with different airlines. Sound familiar? That, in turn, makes it very difficult to earn status with any one airline. By ‘status’ we mean being able to use your frequent flier miles, become eligible for upgrades or perks, fly with free checked bags and so on. I’ll say that again: the more you fly with multiple airlines, the harder it is to earn status with one of them. Makes sense, right? As with hotels, it’s also true, at least in our experience, that airline customer service agents are more willing to work with you (and obligated, in some cases) if you’ve booked with them directly rather than third-party. That comes in handy if your flight is delayed getting out, causing you to miss your connection.

So, after a while of buying tickets third-party, we started paying more attention to the experiences we had during our flights. As it turns out, we enjoyed our experience with United Airlines more than anyone else. Because of that and where we live (often flying to their Chicago or Houston hubs), for most of our travels that’s where we head to book our flights: the United website. Can we find less expensive flights from third-party websites? Absolutely. But again, the benefits of booking directly, accruing miles, earning status, and having better customer service are worth the sometimes slightly higher price we’ll pay to book directly with the airline.

As a sidenote: interested in jumpstarting your status with your favorite airline? You might consider checking out cobranded credit cards (a regular card like Visa that gains you points with a particular company, in this case an airline). Want to learn more? Our friends over at 10X Travel will be happy to help.

Overall.

Much of the information we share on this blog is focused on saving money while traveling internationally so we can do it more often. That’s something we’re passionate about and want to share with you. At the same time, there are times to focus on hunting around for the best deals and there are times to recognize when there’s value in paying a little more and booking directly with companies to get the discount or loyalty points in the long run. We do both because that’s what helps us travel the way we like best.

Just so we’re all on the same page, our goal is to share our process with you, not tell you what you should or shouldn’t be doing. So, if your goal is to save as much money as possible and booking through third-party sites works for you, then keep on keepin’ on. However, if you’re open to unlocking the value of booking directly with companies, even if it’s a little more expensive in the short term, we just want you to know about the option. And as G.I. Joe says, ‘knowing is half the battle.’

Happy travels!

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PLUS - We'll send your our Essential Carry-On Packing List for less stuff and more adventure!

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