Chasing Hilton points: Transfer with a bonus, or apply for Hilton cards?

Over the past year, we’ve become increasingly excited about Hilton redemptions. That’s driven in large part due to Hilton’s partnership with Small Luxury Hotels of the World (SLH). I now find myself very much in the market for more Hilton points and I’m trying to decide whether I want to replenish my Hilton points by applying for new Hilton cards or to chase more Membership Rewards points and hope to transfer to Hilton with a bonus down the road.

Loving SLH

When Hyatt first partnered with Small Luxury Hotels of the World (SLH), I wasn’t immediately excited. In fact, at first, I was downright skeptical. One of the things I appreciate about staying in chain hotels is a reliable (or what you may call “predictable”) experience: a brand name often indicates what to expect from a property in terms of quality, cleanliness, customer service, etc.

However, my first couple of SLH experiences (like the castle I stayed at in Germany and of course the Grand Hotel Victoria on Lake Como) really changed my perspective. While I’m sure that, as is the case with any chain, SLH will have its share of both standouts and disappointments, I’ve been very pleased so far.

As I plan my 2025 trips, I’ve run into a couple of situations where SLH has the hands-down best award option for my situation (which, as a side note, is re-highlighting for me the magnitude of the loss of SLH for Hyatt!). The problem is that I’ve already purchased a large stash of Hilton points this year (and almost completely cleaned them out). I need more Hilton points ASAP, so I’m now considering how to best go about getting them….

Want: More Hilton points

I’m eyeing two situations for next year where I’ll need multiple rooms and nights where an SLH property would be an ideal or near-ideal fit. I’m basically out of Hilton points, so if I want to book SLH properties, I need to consider one of three options: pursue Hilton cards, take up the next transfer bonus, or purchase more Hilton points. A 30% transfer bonus from Amex Membership Rewards to Hilton ended earlier this week on 9/30/24, but we tend to see those come around a couple of times each year (see our current point transfer bonuses to see both current offers and search the “expired” offers section to see how often bonuses have run in the past). We’ve already seen two transfer bonuses to Hilton in 2024, so we probably won’t see another one until 2025 (though you never know).

I’m eyeing a couple of redemptions at properties that cost 120,000 points per night. I’d need a total of 720,000 Hilton points for the nights I’d theoretically like to book.

As I see things, we have a few possibilities to earn about that many points:

1. American Express has been offering 30% transfer bonuses from U.S. Membership Rewards accounts to Hilton Honors a couple of times each year. We would need to transfer 277,000 Membership Rewards points to Hilton to get the 720,000 Hilton Honors points that I’d like to have.
2. We could open new Hilton cards to earn some combination of points and free night certificates.
3. We could focus on cash back and buy Hilton points with cash.

I’d rather save cash right now, so I’m least excited about option #3. I’m not as flush with Amex points as I’d like to be, so whether I transfer from Amex or we pursue more Hilton cards, I’d be looking to earn the points anew (or replace the points I use) rather than drain my existing points balance further.

Strategy 1: Earn at least 260K Amex Membership Rewards points & transfer to Hilton during the next transfer bonus

I would only consider a transfer from Amex Membership Rewards points to Hilton Honors during a transfer bonus of 30% or more. Luckily, since such a bonus just ended a few days ago, I likely have time to build up some new points before the next transfer bonus hits (which is of course assuming that we’ll see one again, which we never know for sure but we can reasonably guess will happen).

As it so happens, my wife and I have a few cards that are eligible for an upgrade to a Business Platinum card for a bonus of 120,000 points after $10,000 in purchases in 3 months (that’s a targeted offer that we wrote about here). If I could meet the spend to upgrade two of those cards, we would end up with a total of at least 260,000 Membership Rewards points (that’s because we’ll earn 120K bonus points x 2 plus at least 10K points on each card for the $10K spent to earn the bonus). That’s pretty close to our target of 277K Amex points. If I simultaneously spent $4,250 in a 4x category on either my Gold card or Business Gold card (or combination thereof), that would make up the 17K point gap. Alternatively, I have a couple of cards where I can earn a bonus of 30,000 points per referral to a new Amex card.

This plan would require spending at least $20,000 (or more if I generate the extra 17K points through spend). It wouldn’t require opening any new credit cards, though it would require paying the $695 annual fee x 2. That sounds steep, but when you consider the fact that I could earn each card’s $200 airline incidental fee rebate in 2024 and again in 2025 plus $120 in rebates for wireless purchases over the first year, up to $200 in credits for Dell purchases this year, and whatever they add in credits next year if the Dell credits end on 12/31/24 as is currently expected. Obviously, I’ll need to maximize my use of the airline fee credits and I’d probably look to use all three Business Platinum credits on a single large purchase since Dell allows you to split tender over up to 3 payment methods on a single order.

When all is said and done, I expect to receive at least $720 in statement credits on each Business Platinum card (more if the Dell credit gets extended or replaced with something useful next year). I don’t value those statement credits at “face value”, but nor do I find the card to feel as expensive as the sticker price suggests.

Strategy 2: Open Hilton cards

My wife has the Hilton Aspire card, but she has never had a Hilton Honors Surpass card. The current introductory bonus offer on the Surpass card would yield 165K Hilton points plus at least 9,000 points from meeting the minimum spend requirement.

However, if she were to open the Surpass card, she would likely do it intending to spend $15,000 on it this calendar year and $15,000 on it as early as possible in 2025 so that she would earn a free night certificate in each calendar year (that could hopefully be applied to our intended stay).

Even if all of the spend were done at the base level of 3x, that means she would have earned at least 90,000 points from spend (45K points from spending $15K this year and 45K points from spending $15K next year). Add that to the 165K points from the intro offer and that’s 255,000 points two free night certificates. That covers a total of at least 4 nights at a property where standard rooms cost 120K per night (2 nights with free night certificates + 2 nights with points).

However, the true story would likely be a bit better yet. We don’t generally recommend putting spend on a Hilton card at the base earning rate of 3x because, based on our Reasonable Redemption Value for Hilton points and the priced at which Hilton frequently sells the points, it’s like a return on spend of just 1.5%. If she focused all of the spend in the card’s 6x categories, she would earn 180K points from spend (90K from $15K spend at 6x this year + 90K from $15K spend at 6x next year). Added with 165K from the card’s intro bonus, she would have a total of 345,000 points plus two free night certificates. That would be very close to covering 5 rooms nights at a property where standard rooms are 120K per night.

That said, the spending requirement is high and that plan requires waiting until after the new year to meet half of the spend. While it probably won’t be difficult to meet spend over the next few months as we head into the holiday shopping period, it may be harder to meet the spending requirements in early January. Furthermore, this process is a little slow — the hotel I want could book up before we finished earning the points and free night certificates.

A slightly different option would be for her to open that Surpass card and meet the $15K spend to earn both the introductory bonus and earn a free night certificate this calendar year. She could then also ask to downgrade her Hilton Aspire card to a second Surpass card. That strategy would mean that she could also spend $15K on that newly-downgraded Surpass card this calendar year to earn a second free night certificate. Essentially, this would enable her to get the same result as the first strategy outlines (earning two free night certificates and 255K to 345K points), but accomplish that end result entirely within this year (taking advantage of holiday shopping / resale opportunities). If she could also meet $15K or $30K in purchases in early 2025, she might be able to earn another free night certificate (or two) between the two Surpasses and more points.

Personally, I haven’t had a Surpass card in a long time, so another option yet would be for both of us to get a Surpass card. While there was a time when I had the card, I haven’t had it in long enough that I would probably be eligible for the introductory offer. However, I’d rather not open a new personal account right now. I’m trying to get back under 5 new accounts opened within the past 24 months to go for a second household Southwest Companion Pass. I don’t value that so much that I would turn away from a monster offer on a consumer card, but in this case, we could get most of the way to the goal without affecting my 5/24 status, so I’d rather not open a Surpass card myself.

Covering all 6 nights that we currently want with a Surpass card strategy would require not only spending $30,000 this year but also another $15,000 as early as possible in 2025. That’s a lot of spend in a short window of time, especially when compared to the 676,000 Hilton points that I could have with $20,000 in purchases on the Business Platinum upgrades.

Strategy 3: Focus on cash back and buy Hilton points

I’ve long said that one can look at cash back as an opportunity to buy points and get a reasonable return on spend. For instance, if you used a card that earns 2% cash back on everyday purchases and used the cash to buy Hilton points on sale, it would be like having earned 4 Hilton points per dollar spent. That’s not as good as the return on the Hilton Business card, but it beats the unbonused return on the other Hilton cards. And if you have Platinum Honors with Bank of America, you could be earning 2.625% back everywhere or if you got the Robinhood Gold card you could earn 3% back everywhere, yielding more Hilton points yet when you use that cash to buy points.

I’ve also mentioned in the past that I look at new checking account bonuses as something of a slush fund for buying points. I’ve gotten kind of lazy on this front — after earning quite a bit in 2020 and in 2021, I slowed down a bit over the past couple of years. I really ought to get back into that game and if I did, I could use the cash earned from those new account bonuses to buy Hilton points without feeling like I’m dipping into my savings.

That said, I’m currently less keen on buying more Hilton points. I’m actively trying to put some more cash aside for a future purpose and so if I did pursue more bank bonuses or cash back bonuses, I’d rather keep that as cash for now. Of course, you could argue that my Membership Rewards points bonuses could be viewed as cash-like since there are ways to redeem the points for cash at a value of 1c per point or better. You’re not necessarily wrong, but I have an easier time considering those like “monopoly money” than actual cash.

Are Membership Rewards points really the way to go?

As I outline my options, I can’t help but feel like earning more Membership Rewards points seems like a better strategy than opening Hilton cards, though of course that is only true if I expect to see another 30% transfer bonus in the future (I do) and if that transfer bonus comes in time for me to book a couple of hotels I want for a trip next year (I don’t know whether or not this will happen). Therein lies the big difference: if I pursue the Surpass card strategy, I’ll end up with the vast majority of points and free night certificates this year, presumably with plenty of time to still book the stays I want. The Membership Rewards strategy is much more of a gamble.

Still, after two Business Platinum upgrades and $20K spend, I would end up with 260,000 total Membership Rewards points. Even without a transfer bonus, that would translate to 520,000 Hilton points at the ordinary 1:2 transfer ratio from Amex points to Hilton (I do not recommend transferring at that rate, I’m just illustrating the number). That would cover 4.5 room nights for the 120K properties I’m considering even without a transfer bonus. If I do manage to hit the next 30% transfer bonus, that $20K in spend that yielded 260,000 Amex points would turn into 676,000 Hilton points. That’s far better than I could achieve with my wife’s Surpass card strategy unless she spent $45,000 in total ($30K this year + $15K next year).

After years of being a naysayer on transfers from Amex to Hilton, I may finally be coming around to the idea that it’s the best way to generate Hilton points.

To be clear, I still don’t find transfers to Hilton to be among the best uses of Membership Rewards points. I want Hilton points because of some very outsized redemptions that I’m eyeing, but I think it’s worth mentioning that I still don’t think of those scenarios as yielding more than half a cent per Hilton point.

As an example, one property I’m considering costs about $1,000 per night or 120,000 Hilton Honors points. Some will say that I’d be getting 0.833 cents per point with that redemption. And I’ll certainly concede that the ratio of cash savings-per-point-spent is what makes a redemption like that attractive. However, that comparison is based on the assumption that you have two choices: A) Use $1,000 in cash or B) Use 120,000 points. In reality, there’s frequently a third option: C) Buy 120,000 points from Hilton for $600. I have often argued that redeeming 120,000 points is saving me $600 no matter what the cash price of the property may have been, so I look at Hilton points as always being a 0.5c per point redemption.

By the way, if you’re wondering whether I’m exaggerating my claim about Hilton points nearly always being on sale, consider that in 2024, Hilton points have been on sale for 0.5c per point on 188 of the 275 days we’ve had so far in 2024. That means that points have been on sale at that rate on more than 68% of the days in 2024. I guess that’s not quite “all the time”, but it isn’t hard to buy Hilton points for half a cent per point. And since you can pool points with up to 10 members, you can effectively buy millions of points per year.

Based on my “always 0.5cpp” perspective, transferring from Amex to Hilton with a 30% transfer bonus yields 1.3c per Amex Membership Rewards point (if 1 Hilton point becomes 2.6 Hilton points, which is what happens with a 30% bonus, I’m getting 1.5c worth of Hilton points per Amex point). That’s less than our Reasonable Redemption Value for Amex points and it is far less than I’m accustomed to getting in value when redeeming points for premium cabin flights. I thought about transferring during the most recent transfer bonus but hesitated because I don’t love the idea of getting only 1.3c out of each Amex point.

However, I think a major factor for me in accepting that less-than-ideal value for Amex points is the relative ease of replacing the points. We’ve often referred to what has felt like an Amex Point Parade over the past three or four years whereby we’ve seen one offer outdo another as Amex has offered a multitude of opportunities to juice one’s Membership Rewards points balance. My wife and I have been earning plenty of Membership Rewards points each year. The speed with which we’re replacing the points we use greatly factors into our willingness to use them. If it were harder to earn more Amex points, I would be far more hesitant to consider transferring to Hilton.

But given the relative ease of replacement of Membership Rewards points and some of the exciting redemption opportunities we’ve seen with SLH, I’ve been more excited than ever about Hilton points. Even though I don’t mentally account for redemptions as yielding more than 0.5cpp, there’s no denying that I find it exciting to redeem points in those situations where the going rate would otherwise be far more than I’d be willing to spend.

But I still struggle a bit over whether or not I love the idea of redeeming Amex/Hilton points this way. When a 30% transfer bonus is in effect, a night that would cost 120,000 Hilton points requires transferring 47,000 Membership Rewards points. On the one hand, I have long struggled with the notion of parting with nearly enough points for a business class flight to Europe in exchange for a single hotel night. On the other hand, if I would trade that many points (or more) for 6 or 8 hours in a flat-bed seat on the way to Europe, is it crazy to spend that many points on a night in a luxury hotel where I may spend 20 hours or more between check-in and check-out and enjoy free breakfast for two? Maybe that isn’t as crazy as I’ve considered it to be in the past.

In my own defense, the reason I’ve had trouble parting with so many points for a hotel stay and not for a business class flight is because the heart of a hotel stay is a clean and comfortable place to sleep. I know that I have options to do that for a couple hundred bucks almost anywhere I go in the world. On the flip side, it is generally impossible to get a flat bed business class seat on a flight of 6 or 8 hours for a couple hundred bucks. Sure, I could get an economy class ticket to Europe for a couple hundred bucks, but in my mind that’s far less comparable to the business class experience than a room at a couple-hundred-bucks-per-night hotel (your mileage, and certainly your opinion, may vary).

Still, if I want more Hilton points, I think I’m more likely than not to pursue them from an Amex transfer bonus. That’s not something I’d have said a year ago, so kudos to Hilton for turning the tide on me.

What will I do?

Ultimately, I think I’ll upgrade at least two cards to Business Platinum cards right now. One of my upgrade-eligible cards is a Business Green that renewed 3 months ago, so I expect to get a prorated refund of the annual fee on that card and to pay a prorated amount of the Business Platinum card’s annual fee, which will make it even easier for me to justify the first-year cost of that card. I’ll then hope for the convergence of a transfer bonus and the availability I want and re-evaluate whether I want to accept the ~1.3c per point that a 30% bonus yields. I think I’ll be more excited if we see a 40% bonus return. In the meantime, I do want to get back into the checking account bonus game and I’ll consider using some of that cash to buy points on sale. I don’t think we’ll take the Surpass card route for now because, as things stand, I can earn enough Hilton points with similar spent to yield as many or more Hilton nights while retaining the flexibility to instead use my points for premium cabin flights. I think that gamble will pay off, but check back with me when the next transfer bonus rolls around.

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