Seattle Trip Planning – How I Booked Josh’s Birthday Trip For A Song

My husband Josh and I have known each other since the fourth grade. Of course we haven’t been together that long – we reconnected at our tenth year high school reunion. He had no idea who I was. We were married five months later.

At the time of the reunion, Josh was living in Seattle, and I was living in New York. After a whirlwind long-distance relationship (which lasted all of three months), I quite my job at Lancome cosmetics (the best job I ever had!) packed up all of my belongings into a U-Haul, and drove across the country to be with him. We lived in Seattle together for the next year, before we sold all of our stuff and backpacked through Africa for four months.

Yeah, I know.

Anyway, Josh’s birthday is coming up, and I thought it would be fun to spend it in Seattle. Since many of you have expressed an interest in how I plan our family trips, I’m going to share some of my strategies, tips, and tricks with you.


We are planning on staying at the Hyatt at Olive 8.  We are actually paying cash for the room (gasp!) because Josh is in the middle of a Hyatt Diamond challenge. He needs to stay a total of 12 nights in order to achieve Diamond status; because he started the challenge after June 1, it will be good through February 2015! So this is a very valuable perk for us. We booked a King room for $259/night, then used a Diamond “suite upgrade award” to book a confirmed suite upgrade for our entire 3-night stay. So, for about $1000, we will be in a suite for 3 nights. Not cheap, but totally worth it because of our Hyatt Diamond goal. (We are planning on using the heck out of this status for the next year and a half!)

Tip: if you wanted to stay at this hotel for free, you could either use Hyatt points, or you could transfer Chase Ultimate Rewards points to Hyatt. Since this is a category 4 hotel, cost is 15,000 points/night for a standard room, or 23,000 points/night for a suite.

For those of you who are not familiar with the Diamond challenge, it is basically a status match with teeth. First, you need to prove that you have status with another hotel chain (they currently accept Hilton Gold, Hilton Diamond, Marriott Gold, Marriott Platinum, Starwood Platinum, or Priority Club Platinum). Then, you need to stay  12 paid nights within 60 days. (This is a great offer, because the normal route to earning Diamond status is either 25 stays or 50 nights).

What do you get if you earn Hyatt Diamond status? A lot. Here are the highlights (according to me):

  • Achieve rewards even faster with a 30% point bonus when choosing points
  • Enjoy the best room available upon arrival, excluding suites
  • Receive exclusive access to the Regency Club or Grand Club lounge featuring complimentary continental breakfast and evening hors d’oeuvres. Enjoy daily complimentary full breakfast in hotels without a club lounge
  • Treat yourself to a suite upgrade at the time of reservation four times annually on paid room nights
  • Receive a special welcome point bonus or food and beverage amenity during each stay
  • Stay connected with complimentary in-room Internet access
  • Extend your stay until 4:00 p.m. with a late check out request

For family travel, some of the above perks are worth a ton. Specifically, the complimentary breakfast (huge money saver), the evening hors d’oeuvres (this can be dinner for little ones!), the suite upgrades, and the late check out.

If you apply for a Diamond Challenge (and they confirm that you are eligible), you are recognized as a Diamond member from the moment you start the challenge. In other words, even if you don’t make the challenge, you can enjoy all the benefits of being a Diamond for two glorious months – including the suite upgrades. AND, any suite upgrades you make while you are a Diamond member (ie, during your challenge period) will stick with the reservations even if you are no longer a Diamond member at the time of your stay. For example, if you are a trial Diamond member during July and August, and you make a reservation using a suite upgrade for November, you will still be able to enjoy the suite, even if your status changes back to Gold in September.

(Does that make sense? It totally makes sense to me, but I live and breathe this stuff, so tell me if you are confused and I will try to do a better job explaining it).


In February, I earned a Southwest Companion Pass, and chose my daughter Bird as my companion. This means that whenever I travel on Southwest, she can accompany me for free. It doesn’t matter if I am traveling on points or on cash, she is in like Flynn. So I used 19,319 points for my ticket, and got hers for free.

Josh doesn’t have a Companion Pass, so we converted some Chase Ultimate Rewards points into Southwest points, and bought two more tickets that way, one for Josh, and one for my son Bear.

Our total cost: 57,957 points. If we had purchased the flights (with cash), our total would have rung in at $1,600!! Even with their least expensive “Wanna Get Away” fares! Totally scandalous. This is exactly the reason why I got into this hobby of Points and Miles collecting in the first place. We could never afford to take these kinds of trips unless we were traveling for free (or almost free).

Car Rental

I followed my own advice here and started on I found an Intermediate car for a whopping, expensive $191 (for 3 days). Then I submitted this information to AutoSlash. Within several days, I got an email notifying me that they had found a rate of $79 for the same class of car with Avis. Did I want it? What do you think? 😉


So far we’re spending a little over $1000 for our flights, 3 nights in a suite, free breakfasts and other goodies at the hotel, and a rental car. Before I learned how to earn points (and use them wisely!), this trip would have cost us more than 3x that amount.

You Can Do It, Too!

If you’ve got a destination in mind, you can do a little backwards planning. Think about the hotel you’d like to stay in and the airline you’d like to fly to get there. Then you can plot out how to earn the points it will take to achieve your goal. To take this exact trip, you could use:

  • 69,000 Hyatt and/or Chase Ultimate Rewards points (for 3 nights in a suite)
  • 57,957 Southwest and/or Chase Ultimate Rewards points (for 4 round-trip flights from SFO-SEA)
  • $79

One strategy for earning this amount of points would be to mix and match the following cards:

  • Chase Sapphire for 40,000 points
  • Chase Ink Bold for 50,000 points
  • Hyatt Visa (good for 2 free nights)
  • Southwest Visa (good for 50,000 Southwest points)

As with any trip, it does take some advance planning, but it is totally worth it!

Next Up…

I’ll share some of my resources for how I plan activities and fun things to do. (Have you heard of Hot Tub Boats?)


  1. Bucket List says

    I thoroughly enjoyed reading this (detailed) planning trip. I am not a novice at this game, but I still appreciate a good report of how trips are made by being knowledgeable about miles and points, determination, and planning. I wish you and your family lots of fun!

  2. Points Pixie says

    Bucket List – So glad you enjoyed the post. Thank you for the wishes of fun – I will definitely write about what happens as it unfolds.

  3. pinkisnice says

    It totally makes sense. You do such an amazing job at explaining – one of the reasons I LOVE your blog! (Bring on the hot tub boats, please.)

  4. Points Pixie says

    pinkisnice – Glad it makes sense, and thank you! Hot tub boats…coming soon!!

  5. Wow. #thatisall

  6. Points Pixie says

    ElleX – I can always count on you for a good comment.

  7. I just got back from attending a conference in Seattle and stayed at the Hyatt OLIVE 8! It was a nice hotel, and a very short walk to the convention center (where my conference was). I didn’t stay in a suite, but my king bed room was decent. I can’t say it was any more spectacular than a Westin or Hilton, but it was clean, modern and I had no issues. There was a gym on the 2nd floor including an indoor pool I didn’t get to use. The room service menu had good veg options that were good sized (not skimpy like some hotels) and served until midnight if I recall correctly. I liked that they had small portions as an option on many items. There is only valet parking, as well as a parking lot across the street I noticed (but didn’t investigate). It was really nearby lots of activity. Good choice!

  8. Points Pixie says

    Rebecca – Great mini hotel review! Love it. Thanks for the heads up about parking – I will investigate nearby options because I am annoyed by “only valet.”


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