How I Got $3000 of Free Travel and Used it to Propose to my Best Friend

The whole point of travel hacking for me is to use those accrued miles and points to create memorable experiences. Well, over the holiday break, I spent under $500 for over $3000 worth of travel so that I could ask my girlfriend to spend the rest of her life with me in New York during the beautiful holiday season. Let’s break down how I did that.

First let me show you the things I got for “free” and what they are valued at:

  1. 2 one-way AA flights from DFW–> JFK: $250
  2. 2 one-way Delta flights from LGA–> DFW: $320
  3. 4th night free at Renaissance Hotel 57: $225
  4. 2 free nights at the Park Hyatt New York: $2000
  5. Ride from JFK to hotel: $60
  6. Admirals Club access for two at two separate airports: $240

Now let me show you HOW I got them for free:

  1. Citi Prestige Airfare credit
  2. 25,000 Delta Skymiles
  3. Citi Prestige 4th night free benefit
  4. Sign-up bonus for Chase Hyatt credit card
  5. Uber American Express promotion
  6. Citi Prestige Admirals Club access (when flying American)

This is probably one of the more basic examples of “travel hacking” as there is really not much to it. There’s no doubt I could have made this trip completely free, but I wanted to stash some points and hard pulls for future trips.

Money saved on travel can lead to AWESOME experiences like seeing a musical on Broadway!
… Or dining at a Michelin Star restaurant. Gotham Bar and Grill

If I had paid with cash even by staying in hotels outside of Manhattan, I still would not have been able to afford this trip. Instead, credit card benefits and bonuses allowed me to give my SO a truly luxurious and unforgettable experience. It allowed us to spend money on other things like tickets to Matilda on Broadway and the Nutcracker at the Lincoln Center. On our flight there, we experienced airport lounges (Admirals Club) for the very first time which meant free food, silence, and… COMFORT. Both of our hotels were right in Midtown, so we were able to walk or use the subway to anywhere with ease. The day I proposed, we were staying at the most beautiful and opulent hotel room either one of us had ever stepped into.

Park Hyatt New York
Beautiful bathrooms with a TV IN the mirror

Of course, the cash that I spent on the trip didn’t come from nowhere. With travel hacking there should always be budgeting and saving involved, and I did just that in the preceding 6 months. I’ve had many people tell me how skinny I’ve gotten. Well, there’s a reason for that… Just kidding!!! 🙂 I always ask myself this question: Would I rather spend my money on buying nice clothes and eating out? Or would I rather save up as much money as I can, pay back my loans, and have a little bit to spare to go somewhere I haven’t been, to create memories that will last forever? I think it’s safe to say that this trip will be one that I will remember for the rest of my life.



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