The Hilton Honors ecosystem has a lot to be desired, and assuming you have been in the points-and-miles community at some point, you have likely heard people discuss the Free Night Rewards that are provided with co-branded American Express cards. Honestly? The praise is well-deserved. These certificates are far bigger than they are small, and they have a certain degree of flexibility that most hotel loyalty programs cannot even compare.

However, there is a catch that has been lingering long enough and it is that of the nature that leaves one wondering what year Hilton believes we are in. Let's break it all down.

Why The Free night reward by Hilton is so good

On the way to the annoying part, we have to pay credit to the credit. The Free Night Reward certificates offered by Hilton are impressive. Hilton continues to keep things refreshingly open as compared to certain hotel programs, which only allow you to get free nights on off-peak dates or at lower tier properties or on a laundry list of blackout dates.

Your Free Night Reward is redeemed on virtually any night of the week, and just about any Hilton property anywhere in the world. And by any property, we mean some fairly high-end choices that include aspirational resorts and luxury urban hotels, which would otherwise cost a number of hundred dollars per night. Taxes and the resort fees are also included in the certificate and this is a small detail that people should not overlook. A free night but you get hit with eighty dollars in fees is not so much free.

Want to extend a trip? You can add your certificate to other nights of the same reservation, and it is easy to make it fold into a longer vacation without the hassle of booking. It is the type of considerate elasticity that wins actual devotion of voyagers.

How Do You Actually Earn One?

Depending on the type of card you are carrying on the Hilton Honors Amex, the Free Night Reward is on the way.

The Hilton Honors American Express Surpass CARD will award you a Free Night Reward once you spend $15,000 in a calendar year. It is a good mid-range card and among average consumers, this amount is quite affordable.

Hilton Honors American Express Aspire Card is where things become interesting. It is the upscale co-branded product of Hilton, and it is full of free night prospects:

• Free Night Reward is automatically earned each anniversary year of the card, no expenses needed.
• The second Free Night Reward is provided after $30,000 in calendar year expenditure.
• The third Free Night Reward is achieved upon spending $60,000 during calendar years.

In the case of high spenders or small business owners who charge high amounts using a personal card, it is three free nights in the world-class properties annually redeemable. The economics of that alone can be used to explain the annual fee of the Aspire many times over.

One more thing to look at is current welcome offers on the co-branded cards of Hilton, which Free Night Rewards have been part of limited-time sign-up bonuses. Such promotions are in and out and timing of application can be significant.

And the next one is the Part That'll Make You Groan

This is where the narration takes an unwarranted curve. However, as much as Hilton does with these certificates, there remains one gaffing issue which has been raised by travel enthusiasts over the years and that is, you have to call Hilton to redeem a Free Night Reward.

Yes, you read that correctly. When you will be able to book a flight to Tokyo, reserve a car in Rome and check into a hotel in Barcelona all in ten minutes on your phone Hilton will still have you pick up a phone and talk to a live agent to one of its most popular cardholder benefits.

Hilton has improved to its credit. It is also a good thing as you can now see your Free Night Rewards and their dates through your online account. But to see your certificate and to be able to make use of it online? Two very different things.

The Booking Process as It Really Is

One of the most recent redemption experiences is a great example of how awkward such a process still is. The after the initial check online that there was a Standard Room Reward available at the target property, which is an important first step, as the certificates that are provided are only applicable to standard rooms, the second step was to call the Hilton customer service line at 1-800-446-6677.

This was followed by a multi-step phone conversation that was strangely bureaucratic given the fact that it was supposed to be smooth:

• Giving the explanation of the purpose of using Free Night Reward certificate.
• Waiting when the agent had to find the property and inquire whether it was available or not the same that it was already called in the online minutes prior.
• Choice of preferences of bed type.
• Waiting once more when the agent had to reassure the hotel on the phone.

The latter is a rather confusing step. When a regular room is available on the Hilton site, then why can’t it be confirmed to the property without further call? It is a question to which there is no satisfactory answer.

The free night was booked in, and the extra nights on the same stay were then booked separately online, in approximately three minutes. The difference could scarcely be overlooked. One certificate night total time on the phone: 16 minutes. Time that it would take to book the rest of the trip digitally: a fraction of that.

And, as I was about to hang up, the agent provided an opportunity of listening to a pitch by Hilton Vacations, their timeshare division, in place of 500 Hilton Honors points. It costs about 2 to 3 in point value and it is an easy pass.

This Fix Should Be Simple

Here's the thing none of this diminishes how valuable Hilton's Free Night Rewards actually are. Used strategically, a single certificate at the right property can easily deliver $300, $400, or even more in value. Hilton has also quietly expanded where these certificates can be used, including at a growing number of Small Luxury Hotels of the World properties now integrated into the Hilton portfolio. That's a genuinely exciting development for travelers who love boutique luxury experiences.

But that's exactly what makes the phone-only redemption process so maddening. The product is excellent. The delivery system is stuck in a different era entirely.

Allowing members to redeem Free Night Rewards through the standard online booking flow just like any other award stay would remove unnecessary friction from what is otherwise one of the most rewarding credit card benefits in the travel space. It's not a complex ask. In fact, it seems like the kind of update that could be implemented without reinventing anything.

The Bottom Line

Free Night Rewards of Hilton Honors are one of the most elastic and, literally, worthwhile benefits that a hotel credit card offers. The size of the eligible properties, the fee cover and the possibility of combining certificates with paid or award nights all make these certificates worth chasing regardless of whether you are a casual traveller or a points expert.

All one needs to do is be ready to waste some minutes on hold when it comes to utilizing one. The phone remains the sole means of entry until Hilton manages to keep up with the rest of the digital world. And until that time, there will be happy but impatient dialing by Hilton loyal fans.