3 Hilton Aspire = Free Vaycay Every AD Year

Each Hilton Honors card costs $450 a year, but this annual fee is waived for Active Duty. It has been over one year with my Hilton Aspire Card, and my only regret is to have closed my Hilton Honors Surpass Card in order to get it. What a fool I was to not have closed anything else in order to keep my Surpass and to upgrade to another Aspire. First off, my anniversary was rewarded today with another one of these free weekend nights at any Hilton Worldwide (excluding these properties).

I realized now how valuable the Hilton Honors Aspire from AmEx really is, and how it’s a perpetual free vacation machine. Now that we know each card can generate a $250 Southwest gift card, as well as give $250 for a resort credit for room rate & incidentals.

You can easily squeeze out thousands of dollars in value every year if you hit all three Hilton Products:

In one year you would upgrade the Honors and Ascend both to Aspire for 3 free weekend nights every year. You would then get 400,000 Hilton Honors points to book free rooms. I would then use the free nights at pricey hotels like The Waldorf Astoria Beverly Hills:

I would book individually a Friday, Saturday, and Sunday Night and then combine the three reservations at check in. Remember that these have to be weekend nights per the terms and conditions. In the case of the Beverly Hills Waldorf we are looking at $926 a night for a total of $2,778 not counting taxes and fees. This benefit is perpetual with the card, so I am ready to have 3 of my 5 card be strictly Hilton Honors Aspire cards!

Regarding flights, the three cards would mean $750 in Southwest airfare every January. I looked at taking a flight from MKE (Closest Southwest airport to Great Lakes) to LAX:

You can use up to three payment methods per transaction, so that means you can get up to a $750 ticket over the three gift cards. Southwest won’t let you pay any overages over three Gift Cards with a credit card, but you can use two gift cards and then the rest on credit.

The best part of the trio of Aspires is your getting fed at these places for free. With the Hilton Diamond status from the card you can get breakfast if there is a lounge or restaurant (Most Hilton) or some other means. For example I was given a credit at the Chicago Waldorf Astoria for Breakfast since there was no lounge.

Even better usage would be for a Hilton Resort such as the Orlando Waldorf Astoria:

Here you would be able to charge up to $750 in incidentals and then at the end of the stay split charge over my three Hilton Honors Aspire cards for the $250 resort credits each. Remember the $250 resort credit only resets on the anniversary of the card along with the free night. Now I got to get to a more stable AmEx card portfolio!


16 thoughts on “3 Hilton Aspire = Free Vaycay Every AD Year

  1. Community Player says:

    Derp, just a tip to get around the 3 payment limit is to split the round trip ticket into 2 tickets. This allows for 6 payment sources if you have a lot of gift cards. I’ve used this a couple times. Just need to ask the representative and they are happy to do it. Southwest has incredible customer service!

  2. YoniPDX says:

    @Derp –

    Don’t forget the “$100 HILTON ON-PROPERTY CREDIT” on the Aspire card when you book two nights.

    Don’t have the card but was looking over the Benefits – not sure if you have to book and pay with Aspire card to get the credit.

    • ArmyGrunt07 says:

      TL/DR: (1) You MUST use the reference code in the fine print for the extra Waldorf/Conrad $100 property to apply. (2) The CSR who books your free room reservation (it must be done over the phone) should be able to just combine multiple free nights codes for one stay. (3) Not sure how you could get more than 1 Aspire’s $250 credit because only once you checkout you then get the final bill for the overall stay that actually charges your card for everything that you spent while at the hotel.

      Data point from last month: I recently used my Aspire at the Boca Raton Beach Club (Waldorf property). I used the annual free night credit and the signup bonus points for a free 4 day/3 night stay from a Thursday – Sunday. The CSR was able to book the whole trip over the phone and said it could potentially be an issue if I booked both parts (the free night and the points) separately and then attempted to combine at check in. There wasn’t anything that seemed to suggest she wouldn’t be able to book a multiple night stay with multiple free nights since all I needed to provide her was the code for the free night, no card or account info was necessary until the end when the room reservation itself needed one to be on file.

      Unfortunately, I DID NOT get the $100 Waldorf/Conrad credit. If you read the fine print there is a reference code that is supposed to be used when booking for that extra $100 credit to apply during your stay. I’m attempting to get it applied retroactively but so far no luck. I WAS able to get the $250 credit applied to my account and that posted within 3 days of checkout.

      At this specific property instead of an actual “free” breakfast I got 2x $15 coupons for breakfast for each day booked. While it could have been doable to make that $15 cover the each of our breakfasts, my guest really needed an $8 latte each morning and any other non-included items (water, coffee, juice, made-to-order foods) quickly add up. There was an “express” option as well that didn’t have much (bagels, coffee, etc.) that was much cheaper, but not very ideal when 15 feet away people are devouring smoked salmon, tropical fruit, and made to order omelettes.

      Looking forward to adding two more Hilton Aspires through product changes over the next couple years to have a free yearly vacation, and excited to hear if anybody has luck getting $750 in room credit, but i’m not sure how they would bill you at checkout on three separate cards after your stay is complete. I received a final bill that was the total, and all the expenses on the actual card day-to-day were just holds that disappeared after the checkout amount reflected on my card statement. In the future i’ll probably use a free night plus points for a two-night weekend vacation at either Waldorf or Conrad property so that each Aspire can be used for its own weekend and apply the $250 & $100 credits

      • Ryan says:

        I’ve tried before and was told the $100 credit is only good on paid stays.

      • Mike says:

        I’ve been able to split charges across multiple cards at check out. I just tell them to run x dollars to card 1, y dollars to card 2, etc.

      • uiucderp2011 says:

        Army Grunt 07,

        Hey thanks for the information. I have yet to use the $100 property credit because the Conrad and Waldorf Astoria are so pricey in North America. It’s my understanding that they must be paid stays for the credit to work. On top of that it must be a certian rate and the Military rate would not count. I posted earlier on some properties in South America that are around $116 a night, making this $100 credit reasonable: http://www.derpreport.com/2018/01/23/maximizing-the-hilton-aspire/

        Also kudos on suggesting just making one phone call with three free night codes, that makes a lot more sense this way. Now my O-3 friend just went to Park City Waldorf Astoria and was able to spit the $500 bills from Spa and dining over two Aspire cards and it worked without a problem.

        Thank you for all the data points, I went out to the Hilton Resort on Oak Brook and charged lunch, golfballs, and a snack from the front desk to see if the charges would come off of the Resort credit without charging to a room. It does not look good so far as the charges on the statement show up as each respective store and not the resort. Next time I am just going to book a room with points or the military rate with all intentions to charge the expenses to the room rate.

        Thanks for reading,


  3. bc says:

    Hey Derp, what’s the latest info on how many AmEx personal credit cards you can have at any given time? I have three Plats, Delta Reserve, Hilton Aspire, Hilton Ascend, and Bonvoy. With 4 credit cards, I should be able to add the regular Hilton Honors card, right? Because last time I opened to the Ascend, they made me close one of my cards (closed the Everyday). Is there a special method to adding a 5th? Thanks!

    • uiucderp2011 says:

      It is a solid 5 CREDIT cards (both biz and personal) per person. Charge cards like the AmEx Plat, Gold, Green do not count towards these 5. You should have been able to open a 5th card no problem. Are you sure you are not counting a business card in your mix?

      • bc says:

        No biz cards here. When I opened my last card, it went to pending status and I ended up closing my Everyday in the interim because I thought that would help my chances of getting it approved. Maybe I was just a little too cautious and would have had the 5th card approved if I’d waited a little longer. I’ll try the Hilton card once I finish my Ascend minimum spend. Thanks!

  4. Pfrank says:

    Hey Derp. Newbie question: When applying for multiple Amex Hilton cards, do you use the same Hilton Honors Members number or establish new ones?
    Currently have the Aspire card, and wondering if the adding non-Aspire cards would affect my current Diamond status.

    • uiucderp2011 says:

      use the same number to pool points nad nights. your Diamond status will remain even with the new cards.

  5. Steve says:

    If you already have an Amex Hilton Aspire card, can you just apply for another Aspire card instead of getting non Aspire card and upgrade to Aspire after a year?

    • Mike says:

      You can, but you’d be forgoing the sign up bonus of the Ascend and/or regular Hilton honors card.

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