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When I ask someone who hasn’t gotten into the miles and points game where they would like to go if money were no object, Hawaii along with Disney World seem to be the two most common answers.

In this post, I’m going to show you how I would go about booking a nearly free trip to Hawaii for two people.

Step 1 – Figure Out How Many Miles and Points You Need For Flights

First let’s look into flights to Hawaii.  In my example, I’m going to use Washington DC as the person’s home airport.

I always check out first (or  Plugging in a roundtrip economy flight from Washington DC to Honolulu, HI, shows that I need anywhere either:

  • 25,000 SKYPASS miles (Korean Air)
  • 30,000 Flying Blue miles (Air France)
  • 35,000 KrisFlyer miles (Singapore)
  • and many other more expensive options


Scrolling down a bit farther in, I can find the following information and routes:

  • Using SKYPASS miles, I can fly on Delta or Alaska Airlines.
  • Using Flying Blue miles, I can fly on Delta
  • Using Krisflyer miles, I can fly on United or Virgin America

Since both Flying Blue miles and SKYPASS miles both allow travel on Delta, let’s rule out Flying Blue since their award chart is 5K more miles (30K vs 25K) than Korean.

AwardAce also shows me that both SKYPASS and Krisflyer are transfer partners of Chase and SPG.



So for two people to fly roundtrip to Hawaii, it will cost 50K miles using SKYPASS or 70K miles using Krisflyer.  I would definitely prefer to use SKYPASS since it is 20K miles less, but it’s good to have the option to fly United or Virgin America if I can’t find Delta award availability.

So I’ll need between 50K-70K Chase or SPG points for my flights.

Step 2 – Figure Out How Many Points You Need For Hotel Nights

Next I’ll head on over to and search for Honolulu, HI.  Since I’m going to be targeting either Chase or SPG points for my flights, I’ll filter out all hotels except Hyatt (transfer partner with Chase) and Starwood SPG/Marriott (Marriott purchased SPG so you can freely transfer points from SPG to Marriott  at a ratio of 1 SPG = 3 Marriott points and vice-versa).

The results show me that I can use points at the following properties:

  • (2) Hyatts
  • (5) Marriotts
  • (4) Starwood SPG

Let’s say I want to spend a full week in Hawaii – 7 days and 6 nights.  Therefore I’ll need the following points:

  • 72K – 120K Hyatt Points depending on which hotel I chose – Hyatt Place Waikiki Beach or Hyatt Regency Waikiki Beach Resort & Spa
  • 60K – 125K SPG Points (When booking 5 award nights at SPG, the 5th night is free)
  • 150K – 200K Marriott Points (Marriott also gives you the 5th night free on award stays)

So I’ll need between 72K-120K Chase Points for the Hyatt stays or 50K – 125K SPG points for my hotel nights.

Step 3 – Find the Best Credit Card Sign-Up Offers

Currently the Chase Ink Preferred Business card is offering 80,000 Chase points after spending $5000 in the first three months.  I would apply for this card first.  I would also get my spouse/partner to also sign up for their own card in their own name – double up the bonus!

The second card that I would sign up for is Chase Hyatt card which is offering 60,000 Hyatt points after spending $6000 in the first six months.  It allows awards 5,000 Hyatt points for adding an authorized user.  Again I would also get my spouse/partner to also sign up for their own card in their own name to double up the bonus.

Another option would be the Chase Sapphire Reserve – it is offering 50,000 Chase points after spending $4000 in the first three months.

Let’s fast forward a bit – you and your spouse/partner apply for both the Chase Ink Preferred and the Chase Hyatt card and meet the minimum spending requirements for both.  You should have a total of:

  • 170,000 Chase Ultimate Reward points (80,000 bonus + 5,000 spending x 2 cards) and
  • 132,000 Hyatt Points (60,000 bonus + 6,000 spending x 2 cards)

If we end up spending 50,000 Chase points on the flights, that will leave us with 120,000 points.  We can transfer those to Hyatt and have a total of 252,000 Hyatt points.  252,000 points is a heck of a lot – we can book 10 nights at the Hyatt Regency Waikiki Beach Resort & Spa for 200,000 points.

Even if you don’t sign up for the Chase Hyatt card, you would still have 120,000 points which gets you 6 nights at Hyatt Regency Waikiki Beach Resort & Spa or 10 nights at Hyatt Place Waikiki Beach.

Step 4 – Find Airline Availability

Before we transfer any Chase points to either Korean Air or Singapore Airlines – let’s search airline award availability.  With Korean SKYPASS miles we can fly on either Alaska Air or Delta which are both partner airlines.  Delta is a little more complicated to search since they don’t actually publish a set award chart, so let’s search Alaska Air’s website for availability.

Here is a search from BWI to HNL.  Korean Air has access to the low 17.5K mile award seats.  As you can see, there are plenty of options to chose from.



Choosing the September 18th departure date and a September 25th return date gives you a few choices, I like to sort by the shortest duration or least amount of stops.    Below is an example.



But don’t worry, while Alaska is charging 70,000 miles for these two roundtrip tickets.  Korean SKYPASS will only charge 50,000 miles.

While Korean SKYPASS will let you book some award tickets online (i.e. Delta), you have to call to book Alaska.  The Points Guy has a great article on how to actually book the SKYPASS award.  SKYPASS allows you to put the award on hold for a few days while you transfer points from Chase and confirm your hotel reservations.

If we were to book this flight using cash, the lowest roundtrip cost for 2 person is $1452.

So we are getting 2.9¢ per mile value ($1452/50,000 miles)

Step 5 – Find Hotel Availability

Now that we have our airline tickets (or at least have them on hold), let’s check to make sure the hotel we want to stay at has award availability also.  Since we have a bunch of Hyatt points and Chase points that can be transferred to Hyatt, let’s check the nicerHyatt Regency Waikiki Beach Resort & Spa from step 2 above.

Hyatt’s website is much easier to search.  Searching Honolulu, we get the following results:


It looks like needs updating as it didn’t show Hyatt Centric Waikiki (Hyatt Centric’s grand opening was in January 2017).  Let’s select the Hyatt Regency and click on the ‘Show World of Hyatt Points & Awards’ box


We have a few different options:

  • Use 27,000 points per night for a Regency Club room that offers access to the club with a continental breakfast and even hors d’oeuvres
  • Use 20,000 points for a free night in standard room (no club access)
  • Use a combination of 10,000 points and pay $125 for a free night – this allows you to partially pay with points and cash if you are low on points (no club access)
  • Or pay $369 and 3,000 points per night to get access to a Regency Club room


Since we have a bunch of points, let’s just select the free night for 20,000 x 7 nights = 140,000 points.

The cash value of this week long stay is over $2700.

So we are getting 2.0¢ per point value ($2743/140,000 miles)


Need To Knows

This was an abbreviated example of how to put together a free trip to Hawaii.  Check out my free 25 day beginner’s course to learn strategies for applying for different credit cards, tips on meeting spending requirements, and techniques for maximizing and searching for award space.  The course provides you with one short 5-10 lesson each day.

But by opening just 2-3 credit cards and earning their sign-up bonuses, you can take a free week long trip to Hawaii valued at over $4000 too.  It really is that easy!

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