Using Points and Miles for a Trip To San Diego

It’s hard to believe that summer is almost over. Monday was the first day of school for my kids, and now it’s back to our routine of homework and lunches and nightly reading logs. Sigh.

But not so fast, summer! I just put the finishing touches on a weekend trip designed to soak up every last drop of the season. In a few weeks, we’re headed to San Diego for a final hurrah before fall sets in. I’m excited about this trip, but the best part is that we’re traveling for free.

You can do it, too. In fact, I hope that by the end of this post, you feel inspired to plan an end-of-summer trip of your own!

Fly to San Diego Using Miles

I booked our flights on Southwest, because that was the least expensive and most convenient option.

  • First, I got two of our flights for the “price” of one (with points). I’m flying with points, and because I have a Companion Pass for my daughter Bird, she can fly for free. How did I get the Companion Pass? At the beginning of this year, I applied for 2 Southwest Visa cards (one personal card and one business card) when the signup bonus was 50,000 points per card, for a total of 100,000 Southwest points. I was able to earn or transfer the remaining 10,000 points, for a grand total of 110,000 points, which is the amount you need to earn the pass. (In case you are interested in exactly how I did this, you can read more details here).
  • For the remaining two flights, I waited for a fare sale, then booked with points. This method ensures that you spend the least amount of points possible!

If you want Southwest points, there are several ways to get them:

  • Apply for the Southwest Visa card(s). These cards regularly have 50,000 point signup bonuses, so it is possible to earn 100,000 Southwest points by applying for both the personal and business version of the Visa.
  • Transfer Chase Ultimate Rewards points to Southwest. There transfer at a 1:1 ratio, so if you’re flush with UR points, this could be a good option for you.
  • Fly Southwest 😉

Stay for Free – Use Points for Hotels

Originally, I had planned for us to stay at the Andaz San Diego. However, after reading a few reviews of this hotel, I quickly realized that this was not the hotel we were looking for. (You can read my post titled “Why I’m Switching My Andaz Reservation To Homewood Suites” here.) Basically, the Andaz is more of a sleek, snazzy hotspot than a family-friendly chill zone. So instead we’ll be chilling at the Homewood Suites.

As the name implies, every room at this property is a suite.  This setup is perfect for our family because of my dynamic no-sleep duo (AKA my kids).  On the property, there are rolling lawns, a bike/walking path, and a swimming pool with a big patio area.  Rooms feature kitchens, and many rooms are bay view, some with balconies.


View of the pool at the Homewood Suites

Each night at this property costs 40,000 Hilton points.

I’m going to use 2 weekend night certificates (the signup bonus from my Citi Hilton Reserve card), plus 40,000 points for another night, so our 3-night stay will be free. Normally, rooms at this hotel average $200/night, so we will be saving $600.

If you want free Hilton nights, here are some ways you can earn them:

  • Sign up for the Citi Hilton Reserve Card. This will earn you two weekend night certificates. The Citi Hilton Reserve Card will also earn you an anniversary bonus of one weekend night when you spend $10,000 or more on eligible purchases each cardmembership year.

Here is a big tip to double your points:

  • Transfer Hilton points from Amex Membership Rewards to Hawaiian Airlines or Virgin Atlantic (at a 1:1 ratio), then transfer your airline points to Hilton (at a 1:2 ratio).

Here are all of the various sign up bonuses you can earn through credit card applications:

  • The Bank of America Virgin Atlantic Card will earn you 50,000 Virgin Atlantic Miles (which you can transfer at a 1:2 ratio to earn 100,000 Hilton points)
  • The Bank of American Hawaiian Airlines Visa will earn you 35,000 Hawaiian Miles (which you can transfer at a 1:2 ratio to earn 70,000 Hilton points)
  • The Citi Hilton HHonors Visa will earn you 50,000 Hilton points
  • The American Express Hilton Surpass will earn you 60,000 Hilton points
  • The American Express Hilton HHonors card will earn you 50,000 points

While we are in San Diego, we plan to hit Sea World, the San Diego Zoo, and Legoland. If you’ve seen the admission price for these hot spots, you know they can be more expensive than a flight or a hotel room! I’ll share my tips on how to lower your costs for these fun attractions in a future post.

Now it’s your turn – where will you go for your last trip of the summer?


  1. Thanks for a great break down on the knots and bolts of yet another great trip! I’m from San Diego (SD ) and miss SD tremendously. I have a specific question about the Southwest companion ticket. We are a family of four, like yours, is it a good idea trying to get two companion passes at the same time when the 50,000 pts sign up bonus gets promoted again? Like I sign up for personal and business and my husband sign up for both business and personal, granted we’ll reach the spending requirement? Thanks!

  2. Points Pixie says:

    Sandy – I think that is a great idea! That was my original plan, but Josh’s credit card application schedule was off so we missed the window. My thought was that we could each apply for different versions of the 2 cards (one of us would get 2 Plus cards, while the other would get 2 Premier cards). Then we would each cancel the cards after a year or so and repeat the process in 2 years. (Granted the deal was still alive – you never know what will happen in the crazy world of points and miles) 😉

    • Thanks for you input…. Crossing my fingers that the deal will be alive towards the end of the year. Good luck with Josh’s applications if your going for another companion pass!

      • Points Pixie says:

        Sandy – The deal is usually pretty cyclical, so I think it’s a good bet that it will return in 2-3 months. I think Josh will definitely dive in this time, so thanks!

        Keep me posted and let me know if you have any more questions.

  3. Wow, what a timely piece. I’m struggling to get the last 6,000 miles to get the companion pass this year. Better late than never. I have enough in UR points but SW won’t take them towards the pass. Do I just open a Hyatt hotels account and funnel them through there?

    Pixie – fun thing. Go to the clothing catalogue On the opening page is a woman who looks like your sister. I first saw her in the paper catalogue where she looks even more like you.

  4. Points Pixie says:

    Anne – Hi!

    You could open a Hyatt account (which I totally think you should do anyway because I’m realizing more and more how great Hyatt is), and then do a transfer.

    5,000 Hyatt points will transfer into 2,400 Southwest Airline points, but note that you have to transfer in increments of 1,250 points and start off with a transfer of 5,000 Hyatt points.

    For readers who don’t have any points to transfer, the least expensive way to get 6,000 Southwest points is to buy 18,000 Choice hotel points for $198. These will transfer at a 3:1 ratio, so you will end up with 6,000 Southwest points.

    And…I just checked out I see what you mean!! Especially since I now have hair that length…my very sensitive hair snapped off because of all my beach time in Hawaii 🙁
    It’s fun to see Doppelgangers out there.

    • oh no! Hawaii made your hair break??? That is awful! Most ppl say how the humidity helps skin/hair. I wonder if salt water didn’t get rinsed soon enough? bummer!

  5. Points Pixie says:

    Rebecca – Exactly. It was the salt water 🙁

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