Hilton Honors: Advanced Reward Optimization

May 7, 2020

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The Hilton rewards program offers a lot of value to travelers, especially if you can fully utilize perks such as the fifth night free on award stays and free weekend night certificates. Extracting the most from these benefits requires a little creativity, so follow along as we share what you need to know to maximize your Hilton Honors points.

Hilton is one of the most widely recognized brands in the hotel industry. In recent years, Hilton has taken a lot of flack for eliminating award charts and generally not having the strongest award redemption options. However, a lot of value still exists in its loyalty program. Combined with how easy it is to earn Hilton points, this is a program that shouldn’t be quickly dismissed. Before digging in, you may want to get familiar with the basics of redeeming Hilton points.

In this article, we will focus on strategies to help you maximize the value of your Hilton points. NerdWallet values Hilton points at 0.5 cent per point, which isn’t a lot. Generally speaking, if you can find a redemption that exceeds that value, you’re in the optimal zone. Let's take a look at some ways that allow you to derive a value that’s significantly above 0.5 cent per point.

Fifth night free on award stays

When you book a five-night stay using Hilton Honors points, you get the fifth night free. This benefit is available to any Hilton elite (Silver and above) — and don’t worry, elite status is really easy to get with Hilton (more on that below).

By taking advantage of the fifth night free perk, you are spending 20% less points on an award stay. For example, if an award night costs 30,000 points, a four-night stay and a five-night stay will both cost 120,000 points. By taking advantage of the fifth night free, you’re effectively paying 24,000 points per night instead of 30,000.

For example, take a look at this five-night hotel stay at the Hilton Garden Inn Brussels City Centre in September 2020.

Although each night is priced at 30,000 points, when you book five nights, the last night is free — so the entire stay will cost only 120,000 points. Those points used for the stay are worth $600 given NerdWallet's valuation of 0.5 cent per point.

Now, if you look at the hotel price in cash, you will see that you’re being charged for the fifth night. That's because fifth night free perk is not available on stays paid in cash.

This five-night stay will set you back over $900. By using points, you’re getting a value in excess of 0.75 cent per point, which is above what the points are worth based on our valuation.

By using points on a five-night stay, you’re not only spending fewer points but also saving more cash. As long as you book a five-night stay, this perk will let you meaningfully increase the value of your points. As a general rule, you should avoid four-night award stays and always add on the fifth night.

As mentioned before, to take advantage of this benefit, you’ll need to at least have Silver status. Luckily, Hilton makes it pretty simple to reach Silver...

Getting Silver elite status

Hilton has three elite status levels: Silver, Gold and Diamond. Once you sign up for a loyalty account and get a Hilton Honors account number, you reach the Member level. As a Member, you still get some perks like no resort fees on award stays and free Wi-Fi.

To get the fifth night free award, you’ll need to reach Silver elite status, which can be achieved by staying 10 nights at Hilton properties. However, a much faster way to attain Silver status is to get approved for a Hilton credit card (even one without a fee).

For example, the Hilton Honors American Express Card does not charge an annual fee. In addition to automatic Silver status, the card offers the following perks:

  • 7 points per $1 spent on eligible purchases at Hilton hotels or resorts.

  • 5 points per $1 spent on eligible purchases at U.S. restaurants, U.S. supermarkets and U.S. gas stations.

  • 3 points per $1 spent on all other eligible purchases.

  • No foreign transaction fees. Terms apply.

Unlike many other cards without annual fees, this card does not charge foreign transaction fees. If you’re a Hilton loyalist and you’re looking to add a hotel card to your portfolio, this is a solid option. Not only can you use it when traveling internationally, but you can also earn 7x Hilton points when you swipe the card at Hilton properties. Most importantly though, you get Silver status, which gets you the fifth night free on award bookings.

Free weekend night certificates

While the fifth night award is great, the free weekend night certificate is also a great perk and provides you with a lot more flexibility for shorter stays. These certificates can only be earned by those who have Hilton co-branded credit cards that charge an annual fee. Before we get into the eligible credit cards, here are a few important facts about these weekend certificates:

  • Can only be used on Fridays, Saturdays or Sundays.

  • Valid only on standard room bookings.

  • Expire one year from the date they are issued. The stay must be completed within that year. For example, if you receive the certificate on May 15, 2020, you need to use it on a hotel stay that is completed by May 14, 2021.

The best thing about these certificates is that they must be used on weekends, which are usually the most expensive nights of the week. The certificate can be used at almost any Hilton property as long as there is a standard room available. Hilton hotels are priced from as low as 5,000 points per night to upwards of 120,000 for a standard room — generally, you’d be extracting the most value from a certificate by using it at a higher-end property.

So with that said, let’s take a look at a two-night weekend stay at Hilton’s fanciest, most aspirational property in the Maldives.

Situated across three islands in the Maldives, including one private island, this Waldorf Astoria is Hilton’s most expensive property with rates starting at $1,800 per night. The hotel was opened in July 2019, and reward nights start at 120,000 points for a standard room.

In the chart below, we’ve priced out a one-night and a two-night stay in August 2020. For the one-night stay, we assumed a booking for Friday night using 120,000 points. The two-night booking includes Friday and Saturday nights using 120,000 points and a free weekend certificate.

Waldorf Astoria Maldives

Waldorf Astoria Maldives


8/7 - 8/8

8/7 - 8/9

Nightly cost in points



8/7/2020 - 8/8/2020



8/8/2020 - 8/9/2020



Cost in dollars



Cent per point



NerdWallet valuation



What are points worth



Extra value gained



For the one night stay, the cash cost is a whopping $2,850. By applying 120,000 points instead, you’re extracting a value of 2.4 cents per point. Given that NerdWallet values Hilton points at 0.5 cent per point ($600 total for this redemption), you’re essentially gaining $2,250 over the NerdWallet valuation.

For the two-night stay, we’ve assumed that the free night certificate is valued at 120,000 points, so the total stay is valued at 240,000 points. Based on the NerdWallet valuation, those 240,000 points are worth $1,200. However, if you paid in cash, that weekend would set you back an astronomical $5,700. By using your points and a free weekend night certificate, you’d gain $4,500 in excess of the valuation.

Although this property is an outlier, it demonstrates the high-end value that you could derive from your Hilton points and free weekend night certificate.

Eligible Hilton credit cards for earning a weekend night certificate

You can earn the certificate on any Hilton credit card that charges an annual fee. The lowest annual fee on a card is $95, which in most cases is below the cost of any weekend night at a Hilton hotel.

Annual fee





Free weekend night certificate


Certificate can be earned after spending $15,000 in a calendar year.

Certificate can be earned after spending $15,000 in a calendar year.

Second certificate can be earned after spending an additional $45,000, for a total of $60,000 spent in a calendar year.

Initial certificate received when you are approved for the card.

Second certificate can be earned after spending $60,000 in a calendar year.

Hilton Honors status





The Hilton Honors American Express Surpass® Card and the The Hilton Honors American Express Business Card allow you to earn a free night certificate after you spend $15,000 in a calendar year. If you have monthly chargeable expenses of $1,250, the certificate is easy to earn over the course of a year.

The Hilton Honors American Express Aspire Card comes with the free weekend night certificate upon approval. You can earn a second certificate after you spend a steep $60,000 per calendar year. Although this card has a high annual fee, it provides Hilton loyalists with a lot of value. In addition to the free weekend night certificate, the card offers a $250 Hilton resort credit and a $250 airline fee credit. If you’re a frequent traveler and will have at least one stay per year at a Hilton resort, these two perks can more than offset the annual fee. Terms apply.

So now that you know all about the fifth free night award and free weekend night certificates, what can you do to improve your chances of getting the best redemption for the least amount of points?

Look for value in up-and-coming places

One way you can maximize your redemption is to explore properties in up-and-coming tourist destinations or at hotels that are slightly farther away from all the tourist attractions.

DoubleTree by Hilton Hotel Istanbul - Piyalepasa

If you want to visit Istanbul, consider this DoubleTree, which is only 3km away from Taksim Square. We’ve priced out a five-night stay in August 2020 to use in our example.

Four of the room types cost only 20,000 points per night. If you book a five-night stay and take advantage of the fifth night free, you will only pay 80,000 points for the entire trip.

If you paid in cash, the five-night stay would cost almost $1,000. By using points, you’d be able to extract a value of around 1.1-1.2 cents per point, which is more than double the NerdWallet valuation of 0.5 cent per point. This is an example of an excellent redemption.

The bottom line

Hilton Honors points can be quite valuable, especially if you can take advantage of the fifth night free on award stays and the free weekend night certificates. Have you taken advantage of any of these benefits? Any other ways you’ve gotten the most out of your Hilton points? Let us know in the comments.

To view rates and fees of the Hilton Honors American Express Card, see this page. To view rates and fees of the Hilton Honors American Express Surpass® Card, see this page. To view rates and fees of The Hilton Honors American Express Business Card, see this page. All information about the Hilton Honors American Express Aspire Card has been collected independently by NerdWallet. The Hilton Honors American Express Aspire Card is no longer available through NerdWallet.

How to maximize your rewards

You want a travel credit card that prioritizes what’s important to you. Here are our picks for the best travel credit cards of 2021, including those best for:

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