The Global Slowmad

Ok, the headline is cringe-worthy. But the tips below are real.

Earning Hilton free nights with the AmEx Hilton Surpass card

There are several Hilton-branded credit cards that offer nice signup bonuses from time to time. Stuart signed up for the Hilton Surpass American Express card in mid-2024. We earned 130,000 Hilton Honors points plus a free night award certificate for completing the minimum spend ($2,000 within 3 months) toward the primary sign-up bonus (SUB) and a second free night award certificate for completing the annual large-spend bonus ($15,000 total spend in any calendar year, including the initial $2,000 toward the SUB) thanks to a couple of college tuition payments.

We ended up keeping the card for a second year because the $50 quarterly Hilton credit more than offsets the $150 annual fee if you have a good way to use it (we have either been using them for incidental expenses or meals at Hilton properties — like Side Hustle and the Pot Luck Club pop-up in London — since the Hilton gift card website “temporarily” ran out of inventory more than a year ago). The card also includes Hilton Honors Gold status, which seems to (slightly) improve our chances of a room upgrade at check-in and typically includes a free breakfast the next morning.

We completed another large-spend bonus in early 2025 thanks to more college tuition and an income tax payment to earn a third free night award certificate.

Pro Tip: Websites like Plastiq and Melio allow you to indirectly use a credit card to pay a variety of bills that normally cannot be paid with a credit card in exchange for a modest transaction fee. You can do the same thing with federal income taxes. The key is to do the math on each transaction to determine if the reward points you earn will outweigh the transaction fee.

The value of Hilton free night certificates

Many co-branded hotel credit cards (e.g., Chase World of Hyatt, IHG Premier, Marriott Boundless) offer a free night each year as a benefit. It’s almost always worth more than the annual fee if you have a reason to stay at that particular hotel brand. Hilton free nights are more valuable than most, for a few different reasons. First, they may be used at any Hilton property worldwide that has a “standard award” night available — i.e., most Hilton and Small Luxury Hotels (SLH) properties. Second, they are uncapped, meaning there are no pesky rules limiting you to low-end hotels and don’t require you to burn additional points to stay at a premium property. And third, they include most applicable taxes and resort fees so you aren’t getting nickled and dimed onsite. Naturally, the optimizer in us wanted to extract maximum value from our three Hilton free night certificates during our European excursion.

Pro Tip: While Hilton free night certificates are perhaps the most valuable free night awards offered by any hotel chain, Hilton Honors points are perhaps the least valuable hotel currency — worth about half a penny per point, or roughly a quarter of its Hyatt counterpart.

Redeeming our Hilton free night certificates

We spent our first night upon arrival in Portugal at a hotel to make life easier in the event of any unforeseen travel delays. Our thinking was that a nice hotel with a 24/7 staffed front desk will be more flexible with arrival time than an AirBNB host. We didn’t want to be standing around for extended period outside an apartment at night with our luggage in a new city waiting for someone we don’t know to show up and let us in if we are running late or have issues with a keybox.

After a little research comparing our options on the Hilton website, we decided to book a one-bedroom suite at the Lumiares Hotel and Spa in Lisbon. The Lumiares is a highly rated property in a trendy part of the city that happened to be within a short walk of the AirBNB where we were living for the rest of our Lisbon stay. The property was all we had hoped for and more, with an amazing view of the castle and the Tagus from the rooftop terrace, a comfortable bed and plenty of room to spread out. We were too tired from the overnight flight and taxi ride to think about taking pictures of the room itself but did snap a few shots of the view after breakfast.

Here’s how much it would have cost me to book the same room with cash:

We initially had planned to use a second free night in Edinburgh to avoid an early morning train the morning of Alex’s arrival during the middle of the Fringe Festival, but we were able to upgrade his flight to lie-flat business class arriving at a more reasonable hour in Glasgow and cancelled the redemption. (That’s another nice feature of free night awards and hotel point redemptions in general — they are almost always fully refundable as late as 24-48 hours before arrival.) This meant we still had not used the other two certificates by the time Darla returned to Tulsa in early October, and one was set to expire in November since our free night award certificates were only good for 12 months after they were earned.

Stuart had already decided that six days in Athens might be more than he really needed, so why not take a bucket list side trip from Athens to Santorini? He could redeem some miles to pay for a flight out there, use two Hilton free night certificates to stay for free and then take a scenic ferry back to Athens through the Greek Isles before flying on to his next destination. After a little research, he settled on a superior suite at the Canaves Oia Suites, a lovely property featuring an ocean view and a private plunge pool. It’s a bummer that Darla was not be able to enjoy this little taste of luxury, but sometimes you have to take one for the team.

Here’s how much it would have cost per night to pay cash for the same room. (Of course, there’s no way we’d ever pay this much for any room.)

Pro Tip: As you may have noticed, neither of the properties we booked with our Hilton free night award certificates were branded as “Hilton” properties. That’s no coincidence. All of the major hotel chains have a number of different brands targeting different market segments. Some also have relationships with curated collections of luxury boutique hotels. Hilton’s partnership with Small Luxury Hotels (SLH) is one such example. SLH properties present a particularly good value for Hilton free nights, as they are consistently great hotels in highly desirable locations and have a lot more character than the mainstream corporate brands.

How It Works

To use a Hilton free night certificate, you have to call the Hilton reservation line (800-446-6677). Sorry, there’s no online booking option. If you want to stay for more nights than you have award certificates, the phone agent can help you redeem points for additional nights. They also will help you find the best room available at a given hotel. Fortunately, it is a simple process, and there has been no wait any of the times we have called to book, cancel or reschedule a free night.

Pro tip: Make sure you have added your cell phone number to your online Hilton Honors profile because you will have to provide an identity verification code sent through text while on the phone with the Hilton representative.

Bottom Line

Even though we would not have booked either of these hotels without the free night certificates, we would have happily paid well more than $300 (the cost to keep the Hilton Surpass card open for two years) for the same three nights of lodging. The $50 quarterly Hilton credits that come with the card also outweigh the $150 annual fee on an ongoing basis if you use them well. And don’t forget about the initial 130,000 Hilton points from the SUB or the additional points we earned from spending, most of which Alex and Stuart will be using for a trip to Washington DC later this spring. All told, the card has provided an excellent return on our investment.

Sadly, Hilton seems to have recognized that it made its rewards program a little too generous. They quietly phased out the ability to use quarterly credits to purchase Hilton gift cards in late 2024. They also have been quietly increasing standard award pricing for high-value properties over the last year. It feels like it’s only a matter of time before they cap the maximum value of free night certificates, but we’re going to collect all the golden eggs we can find from the Hilton goose in the meantime.