(Free Nights Awarded ) Why I paid over $1000 to upgrade 3 no-fee Hilton cards without a bonus offer


Update 5/15 – I wanted to do a follow-up to this original post as there were some questions about whether not upgrading to the Aspire would trigger a free night award without having to wait for the next cardholder anniversary.

I upgraded all three cards at the same time at the end of March. All three of them had different anniversary dates, but were in the middle of the membership year (not just before the anniversary date). All of them received the resort credit immediately upon upgrading. All three of them were charged a pro-rated annual fee (ranging from $200ish-$400ish) in the statement period AFTER the statement period in which I upgraded. And we have now recieved three free night awards, 2-3 weeks after being charged the pro-rated annual fee and 6-7 weeks after upgrading.

American Express is famous for providing very lucrative targeted upgrade offers from the no-fee Hilton Honors card to the premium Hilton Surpass and the super-premium Hilton Aspire.  These upgrade offers usually occur after a no-fee card has been active for at least a year and will often provide 100,000-150,000 Hilton Honors points, but without a hard pull or a new account on a credit report.

Because of this, common procedure is to avoid cancelling an Aspire or Surpass and instead to downgrade them to the no-fee card.  After a year or so, there will frequently be upgrade offers to tempt you back.

My wife and I had three no-fee cards between us that were all over a year out from a downgrade.  I’ve been eyeing our accounts for awhile, waiting for that upgrade to appear.  But instead, I upgraded all three of them last week, paying 3 annual fees in the process…all without any bonus points on offer.  And I think it was a great decision.

Zemi Beach House, Anguilla

Details of Relevant Cards

Card Offer
Hilton Honors American Express Business Card
130K points + up to $130
Limited Time Offer: Earn 130K points after $3K spend in 3 months + earn up to $130 in statement credits on purchases at any Hilton family hotel in first 12 months. Terms apply. (Rates & Fees)
(Offer Expires 7/6/2022)

$95 Annual Fee

Why we downgraded our Aspires

The Hilton Aspire might be the single best hotel card on the market and can be a revenue-positive annual proposition. As a refresher, here’s the schwag:

  • No foreign transaction fees
  • Hilton Diamond status
  • $250 Hilton Resort Credit per membership year.
  • $250 Airline Incidental Fee Credit per calendar year.
  • One Weekend Night Reward at almost any hotel or resort in the Hilton portfolio with your new card and each year of Card Membership (currently usable any night of the week).
  • Priority Pass
  • Annual Fee: $450

Assuming you can take advantage of the full value of the two credits, you’re $50 up each year, with a free night valuable up to 120,000 points each AND Diamond status (that never seems to go away, even after you downgrade the card). That’s a good deal.

So why did we downgrade both of our Aspires in the first place?  COVID, that’s why.  Amex has been great about extending the “weekend” night certs, but we ended up at the beginning of last year having seven certificates that we’d have to use throughout 2022 (and that’s not counting our Hyatt, Marriott and IHG certs). With no Hilton resort stays planned for last year, we decided to downgrade and wait for an upgrade offer sometime this year.

lunch at the new gwen's
Gwen’s Reggae Beach bar…a walk down the beach from Zemi.  Photo courtesy of Anguilla-beaches.com

Ok makes sense, but then you did what?!?

We’ve been wanting to spend some time on the Caribbean island of Anguilla for some time now and got much more interested when Zemi Beach House joined the Hilton Portfolio as an LXR property.  The resort is right on Anguilla’s dreamy Shoal Bay East and gets rave reviews.  It looks awesome.  Standard rooms start at 95,000 points per night, making it a perfect candidate for the Hilton Free Night cert.  The problem is that, traditionally, it’s difficult to find more than a couple standard nights in a row. It’s bit of a time gauntlet to get to the island, especially from the West Coast where we live, so a short stay isn’t desireable.

We were originally supposed to be at a conference in Germany the last week of March over my wife’s Spring Break, but that was postponed, leaving us with an open week.  And what would you know, Zemi Beach House was wide open.  We booked a 6-night stay using free night certs.

We’ll get free breakfast at the resort and there’s a plethora of fun beachside grills/bars to check out on the island, but I assumed that we’d want to eat at least once at the resort. Also, while we’re not big resort spa folks (primarily because of the often exhorbitant cost), the Thai House Spa looks pretty incredible.  What a perfect place to have a few hundred bucks of Aspire resort credit, right?  I thought so too.

Thai House Spa at Zemi Beach House. Photo courtesy of elitetraveler.com

But wait. We have a lot of math-aware folks who read this site and all of them are saying…you spent $1350 to upgrade three cards in order to get $750 of resort credit?  What kind of fool are you?  Well, a big one, but that’s another story…

Here’s my reasoning:

  • I can always use the full value of the airline credits by paying a seat fee to upgrade cheap Alaska tickets (without logging into my account).  After 24 hours (so the charge isn’t refunded to the card), I can log in to my account, cancel the ticket for no fee and place the entire balance in my Alaska wallet for future travel.  The airline credits reset on the calendar year, so I’ll get a total of $1500 in Alaska credit before I have to pay another annual fee.
  • Stephen (who saves us all money) confirmed that when he upgraded his no-fee HH card to the Aspire last year, he got a free night on the front end and another one on his first anniversary.  After researching it, I found that others have found this to be the case as well.  I dont know whether or not this is official policy and so it could end at any time.  But it seems as though, even without a points bonus, upgrading to the Aspire triggers an immediate free night cert.
  • Officially you can’t keep your anniversary free night if you downgrade to a no-fee card, but in practice if you wait for it to deposit into your Hilton account and then downgrade, it will stay there.  Since Amex will prorate annual fees throughout the year (as opposed to the 30 or 60 day limit on most issuers), it might cost an extra $30-50 dollars depending on how quickly the cert is deposited.  But you’ll have a free cert valid almost anywhere.

So, in the first year, for my $1350-$1500 investment I’m expecting:

  • $1500 in Alaska wallet funds
  • $750 in credit at Zemi Beach House
  • 6 Free Night certs good for up to 120,000 points each (completely replenishing what we used for Zemi, but valid until into 2023)

It felt a little yucky to have to waste the opportunity at an incentivized upgrade.  That said, the bird-in-the-hand of 6 certs and $750 to spend (at a resort that we’re going to be at already) seemed too good to pass up.

Nick at the Conrad Bora Bora…one of his favorite places to burn a Hilton free night cert

Final Thoughts

I wanted to talk through this whole process as a follow-up to my earlier posts about trying to tailor our points and miles earning/burning towards both enjoyment and value…and how personal a proposition that is. (See The Myth of One Size Fits All and Chase Sapphire Reserve: Why .25 cents is worth $250 (for me)).

This was another example in which I hesitated to make decisions that ran counter to how I perceived “conventional wisdom.” Burning 6 free night certs when I could utilize a 5th Night Free and one cert and upgrading the no-fee Hilton cards to the Aspire without waiting for a bonus points offer aren’t intuitive for me. I think it’s undoubtedly the right call in this situation, but I really had to think through it, as my first impulse was to say, “no way.” I don’t think everyone should run out and upgrade their no-annual fee Hilton cards without a good reason.  But, for me, the immediate utility outweighed the theoretical future value of a possible points upgrade.

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John T

I upgraded two no fee cards to Aspire on April 1, 2022 and still no free night. My anniversary dates are around August/September

Paul Davis

I’m always amazed with things you guys do thinking outside the box. I’m confused about the value you put on the free night cert of 120000. I thought it was 95000. Did I miss something?


I was going to downgrade my Aspire (get PriorityPass through Venture X and already used 2022 airline credit) to no-fee and hope to get upgrade offer later. You suggest I can pay the AF and cancel after receiving the free night certificate, receiving a prorated AF refund (guessing 9 months worth)? If so, probably will hold off for few months. Thanks for any guidance


Related to Stephen’s DP in the article, the first time you upgrade an account to Aspire you may get tat bonus free night. Subsequent upgrades (if you downgrade and upgrade again in late years) do not get the bonus free night.

Always be sure to upgrade before your anniversary date. The anniversary night will only trigger if your card is at the Aspire level before the anniversary date hits.

Biggie F

Not trying to be facetious here, but isn’t any date always before your anniversary date? By which I mean: how long before is optimal? Once you blow through your anniversary date and are, say, 11.5 months from the next one, how long does one want to wait?


Yes, I’m just trying to say if you upgrade after your anniversary date has passed you won’t get a certificate until after your next anniversary date.


Opposite experience as Tim, same experience as Slim. Cards that had previously been upgraded / downgraded do not receive free nights until the following anniversary (even if it’s been more than 12 months since downgrading)

Zach E

If I upgrade my Surpass and my current renewal date is in July for my card, if I upgrade will the annual fee be prorated till July than renew at full in July?

Will I get the annual resort credit $250 resort credit to use till July and again in July?


Hi Tim: wondering about the Amex travel credit. So after you book an alaska ticket, you pay for seat assignment upgrade separately ( heard it won’t trigger if it’s on the same fare)? Then you go into your account, enter the reservation number and then cancel ? Didn’t know the seat assignment is so expensive.


Thanks for the reply! Not an elite so cannot use the method 🙁


Tim: I tried this, but the seat selection cost was refunded to my credit card. I was told I could not have it deposited into my award wallet. Not true?


Was not aware of this and good to know as I don’t fly United much and prefer Alaska (and in case TravelBank dries up). However, with your plan you only have 1 year after ticket cancelation to use the AS wallet refund, correct? Or is there a longer period to use the funds?


Thanks! How do you get $250 in seat assignment fees though, multiple tickets? I looked at a $39 sale fare and fee to pick a seat is only $40.


Read their terms, travel wallet only for future flights. I don’t fly with them but do book award tickets, guess my plan won’t work. Always helps to read their T&C 🙁



Had you not downgraded the Aspire during Covid, you would have very likely even made out better because the 3 Aspire cards that my wife and I share amongst ourselves were each accorded the $20 dining bonus that commenced in 2/21 and ended 12/21; therefore, each yielding another $220 in dining savings per card!

And we were able to use our free nights along with our resort credit at a resort near us on simultaneous stays plus the United airline credit, as well, so we made out like bandits.

Will drop one of those cards to no fee card soon as se already have received the United credit on all card for this year.

Question for you.

I recently cancelled my Hilton Biz card and not more than 1 week later, I received an e-mail from Amex for the very same card with a bonus offer.

What do I make of this?

Are they really offering me a bonus on a card I recently cancelled not more than 2 weeks ago, as of this date?

Should I wait longer and if so, when should I respond to the e-mail as I would love to earn more bonus points for just opening the card!!!


Wow, this was very clever on your part. I am really impressed. I’m too scared of Amex to push the buttons like that, but wow, just wow.


That was great that you still got the $20 back per month as a no fee card — thought that would not occur, but such offers must stay with the card once selected, even though the card has been downgraded and the offer was only available on the previously higher level card.

With respect to getting the free night after upgrading the card, may I ask, when did they upgrade in their billing cycle?

I, too, plan to do this maneuver and have done this on occasion but I was informed by an AMEX rep once — and it held true — that one should look to upgrade the no annual fee card about 3 weeks prior your anniversary date (of the original card even if it was only a no fee card) so that the systems will recognize you as a high level card member when you anniversary date occurs — then ~ 2 months later the free night should hit your account.

Your reports that the free night was issued after upgrading requires that they report to you exactly when was the upgrade processed and when was their anniversary date and when did the free night first hit their account.

I find it hard to fathom that AMEX would automatically issue a free night upon the upgrade when their Modus Operandi is to have you wait 2 months to receive it.

Could you provide more information on the dates of the above?

Thanks for the response on the Biz card — I don’t really expect them to honor it, but I’ll wait a couple of weeks and see what happens.


Love this post!
Juggling the variables.

Sue T

Thank you for the great info. How did you get 6 certificates in the 1st year with only paying the AF’s for 1st year with only 3 cards?

Sue T

Thank you! We have 2 Aspire cards. I’ve thought about signing up for the no fee card to get the points and then upgrading to the Aspire card to get the extra free night. I haven’t been able to get the benefit out of the airline credit. We fly out of DTW so Alaska Airlines doesn’t usually have good flights for us. We usually use Delta or United. I also have the Amex Platinum which gets us into the lounges. Are there any tricks to get use out of the $250 credit for either Delta or United, preferably Delta?

Biggie F

Check out the DL and/or UA-specific threads on Flyertalk, under Amex.

Joe Y

It most certainly does! 2 years running and before that — Jetblue under $150!


One trick that works for Delta is to pay for a part of a ticket cost with a gift card. Then whatever goes on the credit card will be coded as ancillary fees on the Amex side trigerring the credit.

Zach E

Can you hold two of the same hilton amex cards such as two personal no annual fee cards or two aspire cards etc?

Zach E

How do you use all three cards resort credit at the same time at the same property on the same reservation?


Easy answer for the Hilton resort credit as well as Hilton and Marriott AMEX Offers as well as Marriott $100 gift cards that you can pick up occasionally for $80 and the gift cards you can earn through nights at Hyatt. Just stop by the front desk during (not at the end of) your stay and prepay what you need to get the benefit. Avoids the issue of the hotel charging your credit card the night before checkout and then having to undo it at checkout. I have done this many, many, many times.


I’m sorry, I don’t understand this. Why would you prepay with your hilton card during your paid stay when you’re at a hilton and they will charge your Hilton card anyway?


Simple–because I didn’t want to charge the whole stay to my Hilton card. In each of those cases, I wanted to put part of the stay on a different card with an AMEX Offer (like $35 off $250 for example), or use a gift card for part of the stay. By prepaying during the stay, the final bill was less and the entire amount was automatically charged to my Hilton card, and checkout took less time and was much simpler.


I’ve had trouble at many hotels with them charging the card on file very early in the morning and then fixing it is a PITA. So, DSK I’m with your method. Just did that at the Hyatt Kauai last night. Charged $250 to my CSR for a 15% credit and the rest will go on my Hyatt Visa on file.

Biggie F

Thanks for the incredibly timely post. I too downgraded my Aspire card (as well as an Ascend) during the first year of the pandemic and have been patiently waiting for an upgrade offer that has yet to arrive.

This left me ruminating about the value of just thinking about the last year-plus as a pause, i.e., like you, upgrading without points. I appreciate your confirmation of the positive benefits of doing so, especially when one has an eye on stays outside of the U.S., where Diamond status can actually mean some good breakfasts.

Your news about the potential two free night certificates is, I think, going to be the clincher for me. A consequence of the recent stealth devaluation by Hilton of points at high-end properties is to (in comparative perspective) raise the value of the free night awards and lower the value of points (hence the rationale of waiting around for a points-included upgrade offer.)