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The Hilton Honors program has become quite formidable in recent years. While the program no longer publishes award charts and causes frequent heartburn with its seasonal pricing, there are plenty of ways to extract solid value.

One of Hilton’s strong suits is its breadth. It’s doubling-down on luxury properties with over two dozen new Conrad and Walford-Astoria properties on the roadmap, opening up a broader portfolio for those who adore aspirational stays. On the other end of the spectrum, Hampton Inn and Hilton Garden Inn allow road-trippers to cash in points on satisfactory stays where the property itself takes a back seat to the journey.

While we’ve covered the basics of earning Hilton points and how to redeem those points, today I’ll get a bit more strategic and highlight my favorite ways to make the most of my awards with the Hilton Honors program.

In This Post

Automatic Diamond Elite Status

As with any loyalty program, maximization comes easier to those with elite status. That’s true at Hilton as well, where Diamond members earn more on stays and are offered added perks like complimentary breakfast and room upgrades.

Hilton offers an incredible shortcut to its highest elite tier (Diamond). By simply signing up for and holding the Hilton Honors Aspire Card from American Express, you’ll keep Diamond status for as long as you retain the card. Said another way, you can come into the Hilton Honors program having never spent a single night in a participating property, and this card will rocket you to its highest elite tier.

Not only does this card roll out the red carpet for anyone interested in maximizing their stays with Hilton, but it also nets you 14x Hilton bonus points at participating hotels or resorts within the Hilton portfolio. It’ll also unlock the fifth night free on award stays (see below), a perk that is only extended to members with any level of elite status in the Hilton Honors program.

While the $450 annual fee (See Rates & Fees) may seem steep, we value Diamond status at over $3,000. If that’s not enough, here are 7 more reasons why you should have the Amex Hilton Aspire in your wallet.

Standard Room Rewards

Standard (base level) room rewards are generally capped at certain amounts (e.g. 50,000 points per night). When you see these in multiples of 5,000 or 10,000 points, that generally means revenue rates are high, like in this example of an Embassy Suites in Midtown Manhattan on New Year’s Eve.

With taxes and fees, your Honors Discount rate comes to $748.48.

However, award rates are variable as paid rates drop. This same room falls to 47,000 points literally the next night ($214.76 with taxes and fees).

What’s important to note here is that fewer points for a room isn’t always the best value for a room. In the above example, it’s not difficult to see that 70,000 points is higher than the 47,000 points charged the next day. However, due to the cash rate being so high on New Year’s Eve, you could extract over 1 cent per Hilton point by paying for that room with points rather than cash. TPG values Hilton Honors points at 0.6 cents apiece, so you’d be getting nearly double the value compared to what we typically see from Hilton redemptions.

In the cheaper example, it’s a worse value to use points compared to cash. Redeeming 47,000 Honors points for a ~$214 room nets you just 0.46 cents per point in value. In that scenario, you’re better off paying cash, earning points on the stay and pocketing those points for a later date when cash rates are through the roof.

Long story short: try to look for award stays where the Standard Room Rewards are in an increment of 10,000 points. That’s a likely indicator that you’ll be getting solid value for your points.

Premium Room Rewards

Hilton Moorea Lagoon Resort and Spa - canonball from porch
Not too many rooms where jumping from the back porch is encouraged (Photo by Darren Murph / The Points Guy)

While some hotel chains reserve premium rooms for cash purchasers, Hilton opens up its premium rooms and suites for redemption via Honors points. You’ll find premium room rewards at virtually any Hilton property, even the ultra-luxe Waldorf Astoria Maldives Ithaafushi (which briefly stopped showing award availability on Feb. 23 due to a technical issue that was resolved the next day).

The only issue? Hilton charges accordingly. Given that there’s no award chart, this allows Hilton to price its premium room rewards dynamically (and indeed, stratospherically).

Looking to use points to secure a king panoramic overwater bungalow at the Hilton Moorea Lagoon Resort & Spa? You can do it, but you may want to have a seat before parting ways with 341,000 Honors points per night.

Still, deals can be spotted if looking at off-peak times, and it’s useful to have the option when you absolutely need to confirm a special room or spacious suite. This can be an especially appealing option for families when a standard hotel room just won’t cut it.

Fifth Night Free

As noted above, Hilton allows all of its elite members to get the fifth night free on award stays. This isn’t just available to upper-tier elite members; Silver, Gold and Diamond Hilton Honors travelers can utilize this perk. Remember that you can achieve Hilton’s lowest status tier, Silver, simply by holding the no-annual fee Hilton Honors American Express Card (See Rates & Fees).

And if you don’t have a Hilton cobranded card, see below for welcome offers currently available:

Bear in mind that you can also snag Hilton Gold status by adding The Platinum Card® from American Express to your wallet, while Diamond status is given with the Hilton Honors Aspire Card from American Express.

When you have this status and are logged into your account, you’ll see this discount automatically reflected in the reservation.

The fifth-night-free perk applies to every fifth night on up to a 20-night stay, and it can be used an unlimited number of times per year. Unfortunately, the perk only applies to Standard Room Rewards.

Given this information, you should do your best to never book four-night, standard award stays with Hilton Honors. After all, since the fifth night is free, you can extend your trip by 25% for no additional points, so why not add another night?

Points & Money

If you’re an infrequent traveler and won’t be able to earn enough points for multiple free nights, consider Points & Money. When booking online, you can use a slider to select any combination of points (in increments of 1,000) and cash.

Just be aware that a Points & Money selection is final once booked. You can’t go back and create partial cash refunds by applying newly earned points later on. You’ll also need to redeem a minimum of 5,000 points, though any cash amount will earn you Hilton points.

The program generally gives you around 0.5 cents per Honors point when factoring your Points & Money discount. That’s not a great value, but it’s better than letting your points collect dust indefinitely.

Bottom Line

Hilton Moorea Lagoon Resort and Spa - beach view from restaurant
What’s better than four nights here? A fifth one for free. (Photo by Darren Murph / The Points Guy)

Hilton Honors isn’t as easy to maximize as programs like Hyatt, but its incredible range of properties makes it one worth checking out. You can redeem for simple Hampton Inn stays as well as aspirational holidays at a Waldorf-Astoria, and the fifth night free perk is ideal for those able to unplug for long weekends.

Perhaps the best use of Honors points is to redeem when cash rates are through the roof. If there’s a convention or major sporting event in town, Hilton tends to jack up the cash rates. Award stays usually tick higher as well, but rarely in proportion, thereby creating a better value for exchanging points for a stay.

Those seeking to truly maximize the program would be wise to check out one of its cobranded American Express cards. The ability to secure top-tier Diamond status simply by holding the Aspire Amex is tremendous, and it allows those new to the brand to enter as if they were a seasoned VIP.

Related video:

Featured image by the author.

For rates and fees of the Hilton Aspire Card, please click here.
For rates and fees of the Hilton Amex Card, please click here.

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