Guest Post: A perfect Orlando Birthday Weekend. How my husband and I took a $3200 trip for less than $500!!

The following post is from an O-3 AD Navy Dental Corps Spouse. They just got back from Harry Potter World at Universal Studios in Orlando. All while staying at the Waldorf Astoria and flying on United out and American Airlines back. They agreed to post this trip report in exchange for hosting their AmEx Hilton Honors Aspire Link here, Ascend Here and Honors Here. Also their AmEx Platinum Link here. Please let me know if you want to write and I can host your links as well. Here is her post:

The Writer is a AD Spouse that has all three Hilton Honors Cards (all waived)

By maximizing the benefits of credit card points and perks, my husband and I treated ourselves to a luxury weekend at the Waldorf Astoria in Orlando. Using welcome bonus points we acquired from the Chase United Explorer Club card, we flew for free on United from Chicago to Orlando.  That same card granted us access to the United Club at O’Hare, where we enjoyed free food and drinks in a comfortable lounge.

After landing in Orlando, we took an Uber from the airport to the Waldorf Astoria for free using a portion of the $250 annual travel credit on my husband’s Citi Bank Prestige credit card. Side note, you can buy $100 worth of Uber cash for only $95.  That is an instantaneous 5% return on your money, which is almost unheard of. It’s free money!

We chose to stay at the Waldorf Astoria Orlando because it is a Hilton Resort property.  My husband and I both have the American Express Hilton Aspire credit card, which carries the benefit of annual free weekend night at almost any Hilton hotel. So between our two aspire cards, we got both nights free! 

When making the reservation over the phone, the Hilton agent combined the two reservations so we were able to stay in the same room both nights and didn’t have to check out and recheck in Saturday.  I found there was an added benefit by booking over the phone; the agent asked why we were traveling, so I said we were going to celebrate my birthday. The representative attached a note to the reservation and informed us to except a welcome gift! 

We arrived at the Waldorf Friday night and were upgraded to a king suite with a balcony on the Hilton Honors floor. See pics below. Upon entering the room, we were greeted with balloons and a box of fancy chocolates. And it only got better from there.

Another benefit of the Hilton Aspire card is an annual $250 resort credit. This credit has to be used at a “resort property” and the credit only counts for things charged to the room. So in our case, when we checked in, we attached both our aspire cards to the room. Now for the fun part, we had $500 of free money to spend at the hotel!!! 💸 Normally the hotel has a resort fee of $45 a day plus tax, but if using the free night award, there is no fee.  So that left us with a full $500 to have fun with. After checking in, we spent $125 on dinner and a bottle of wine at the lobby bar…$375 of totally free money left :). 

We spent most of Saturday at Universal Studios, but prior to taking an Uber to the park (again for free via the Citi Prestige travel credit) we had the continental breakfast at the hotel. Thanks to our Amex Hilton Aspire cards, my husband and I are both have Hilton Diamond status, which comes with the benefit of free breakfast daily. After a day of Harry Potter world (which I HIGHLY recommend), we Uber’d back to the hotel (free of course!) and had a few hours to kill before our 8:30 dinner reservation so we soaked up some sun and drinks by the pool. $75 worth of drinks actually, and I know that’s pricey, but remember, it’s all free! So that left of us with $300 left, all of which we spent on an amazing steak and wine dinner at Bull and Bear Restaurant at the hotel where the waiter treated us to free dessert.

Our flight on Sunday didn’t leave until 4:30 pm, so we requested a late check out, which the concierge happily granted us because of our Hilton Diamond status. We grabbed some free breakfast then spent a few more hours at the pool before heading to the airport. Unfortunately, we had maximized our $500 resort credit, so we had to shell out our own hard earned money for poolside drinks but it was worth it!

At check out, we asked for a split charge with our two Amex Hilton aspire cards. We had the concierge charge $250 on one card and the remaining balance on the other, that way we only had a balance on one card to pay off. 

We took another free Uber (thanks Citi Prestige!) to the airport to catch our American Airlines flight home. We paid for the flights home with yet another Hilton Aspire benefit. The card comes with an annual $250 airline benefit. This benefit is meant for flight incidentals such as bag fees, seat upgrades, or in-flight snacks, but we worked around this by buying American Airlines gift cards. Unfortunately, AA got wise to this work around and it no longer works. However, the $250 credit still works for gift cards to Southwest Airlines, so if you get an Aspire card be sure to select Southwest for your airline of choice. 

Orlando’s airport has an American Airlines Admirals Club where they let active duty military members and their families into for free if they are flying with American. So of course we took advantage of this and got free lunch and refreshments before boarding our flight and heading home.

All in all, it was an amazing weekend getaway. We paid $450 for $3,167 worth of travel, and we can’t wait to do it again!

  • Cost of flight for two from ORD to MCL: $400 
  • Cost of 4 drinks and snacks at ORD United lounge: $75 
  • Cost of Uber from MCL to hotel: $51
  • Cost of two nights in king suite with balcony with daily breakfast at Waldorf Astoria Orlando: $1238
  • Cost of drinks and dinner at lobby bar: $125
  • Cost of Uber to universal studios: $19
  • Cost of 2 universal studios passes: $350 (military rate)
  • Cost of Uber from universal to hotel: $20
  • Cost of poolside drinks: $75
  • Cost of dinner: $250 ($50 over $500 freebie)
  • Cost of poolside drinks: $50
  • Cost of Uber to airport: $39
  • Cost of food and drinks at Admirals Lounge: $75
  • Cost of two flights from Orlando to Chicago: $400

Total cost of trip: $3,167

Total amount actually paid for trip: $450

Thanks for posting! A few take away data points:

  • You can split a $500 Hilton Hotel bill over multiple cards to take advantage of the $250 benefit
  • You can combine points with free weekend night stays with Hilton Honors
  • Uber counts for the $250 travel credit for Citi Prestige
  • Diamond status give you resort fee waivers

4 thoughts on “Guest Post: A perfect Orlando Birthday Weekend. How my husband and I took a $3200 trip for less than $500!!

  1. Jason says:

    Hello,
    Army reserve soldier here that is about to deploy in less than two months. First of all, thank you so much for doing this and writing, sharing and helping! Wonderful stuff. So glad that I found it via Reddit.

    I wanted to maximize my benefits but while I was on ADOS three years ago, I was able to get my AMEX plat waived. I currently have the Hilton Aspire, AMEX Gold and AMEX Plat. Only my plat is waived and I paid the annual fee for the hilton aspire and the amex rose gold. My deployment starts in July and ends around end of April. Do you think I should get the Amex Green and the basic amex hilton card without any annual fees so that I can product change and upgrade? What is the best way to maximize this Hilton card like you?

    What about the Marriot card?

    Your help on this is GREATLY appreciated and I cannot thank you enough.

    • uiucderp2011 says:

      The name of the game id to max out all 5 AmEx slots with these cards: 3x Hilton, 2x Marriott

      If you haven’t gotten the Marriott Bonvoy Brilliant, that is the best one to get to enjoy a free night as well as $300 each year. Get the Hilton Aspire and Hilton Basic to upgrade to another after a year, and then a green to upgrade to plat in one year as well:

      http://refer.amex.us/JERRYCgAla

      With the three Hiltons, call in and book a weekend every year using your three free nights, then spend $750 at the hotel stay to split at the end, use all three to buy 3x southwest gift cards to fly to your destination for free as well.

      Use you platniums for southwest gift cards as well, when you upgrade your green and rose gold use that to buy a $200 gift card from SW. Boom! free vacation every year!

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