I’m So Excited! I Just Planned My Amazing Trip To Hawaii and Saved ~$7000

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A few days ago, I posted an article with details about how I booked business class tickets to Hawaii (for my entire family) for less than $20. I don’t often have the opportunity to travel with my wife and daughter as much as I would like so I’m pretty excited about this trip. I thought it would be interesting to walk you through the booking process and provide a “trip report” after the trip to give a glimpse into how I saved money.


As I said in my previous post, my wife had expressed her desire to go to Hawaii several years ago for our honeymoon. Unfortunately, I had visited Honolulu a decade ago and was underwhelmed so I did what every loving and caring husband would do…promise that we would go, stealthily move the idea to the bottom of my “to do list,” and picked a better honeymoon destination. Hey…stop judging me! At least, I added it to the list.


I am amazed at what I have been able to pull together over the course of a weekend. At the end of last week, I had only purchased one-way business class tickets to Hawaii. I had also determined, based on my previous experience in Hawaii, that it would be a great idea to visit more than one island so let’s talk details…


Business class award availability has the potential to appear and disappear overnight. The key is to be flexible. I already had a ticket to Hawaii and typically, my next step would be to determine the return flight and then fill in the details. However, I have the Southwest Companion Pass and had planned to use it to return home. The great thing about the companion pass is as long as there is a seat on the SWA flight, it can be booked as an award so I was not worried about award availability.

I decided that 8 days would be sufficient for Hawaii. Our routing would take us non-stop from Detroit (DTW) to Honolulu (HNL) where we would stay for 4 days. We would then fly from Honolulu (HNL) to Maui (OGG) where we would spend the remaining 4 days. Finally, we would fly from Maui (OGG) to Atlanta (ATL) via Oakland (OAK).

  • Step 1 – DTW-HNL: Non-stop, Business Class on Delta
  • Step 2 – Honolulu Hotel: 4 nights (& Rent Car?)
  • Step 3 – HNL-OGG: Book Southwest Flight (Companion Pass 3-for-1)
  • Step 4 – Maui Hotel: 4 nights (& Rent Car?)
  • Step 5- OGG-OAK: Book Southwest Flight (Companion Pass 3-for-1)
  • Step 6- OAK Hotel: 1 night
  • Step 7 – OAK-ATL: Book Southwest Flight (Companion Pass 3-for-1)

My wife and I had such a pleasurable experience at the Hyatt Centric in Miami a few weeks ago that we decided to try it again. The price fluctuated quite a bit for the nights we planned to stay in Waikiki but were about $260 / night. That’s far above my budget so I redeemed a free-night certificate and paid Hyatt 45,000 points (15k/night) to cover the 4 nights.

Note: In addition to the room rate, there is a $40/night resort fee that you do not have to pay if you’re redeeming points. Otherwise, I would’ve been paying approximately $300 / night.

STEP 3: BOOK A SOUTHWEST Inter-Island Flight (HNL-OGG)

Depending on where you stay (Waikiki in our case), it can be extremely walkable so we decided not to rent a car and utilize a ride-sharing service to/from the airport.

Additionally, Southwest began flying inter-island recently with fares about $30 one-way (or ~1379 points one-way), so I went ahead and booked that too.


We decided that we would splurge a bit and use our points for a very very nice hotel in Maui so we picked the Fairmont Kea Lani. Using my Chase Sapphire Reserve (CSR), we redeemed points through the Chase portal (1.5 points per dollar).

Just for clarification, I logged into the Chase portal using my Chase Sapphire Preferred (CSP) for the screenshot above. Using CSP requires 39,120 points per night (1.25pts/dollar). Using CSR, requires you only redeem 32,600 points per night (1.5pts/dollar). I used CSR so we paid 32,600.

However, with taxes and resort fees the rates climb a bit higher…

STEP 5: Book Southwest Flight (OGG-OAK)

I have the Southwest Companion Pass that I obtained from credit cards. My wife is my companion so she flies for free. My daughter is less than 2 years old, so she flies for free also. Therefore, all of us fly for the price of one ticket.


There are a number of cheap hotels around the OAK airport. I will likely choose the Courtyard Marriott which has a rate of $122 total (taxes included). I could use points to stay for free but the value of the points required exceed the cash rate so I’m fine paying cash.


Again, I have the Southwest Companion Pass so 3-for-1.



  • DTW-HNL (Business Class): $1058.48 x 2 adults = $2116.96
  • Honolulu Hotel: Hyatt Centric; ~ $300 x 4 nights = $1200
  • HNL-OGG: $39 x 2 adults = $80
  • Maui Hotel: Fairmont Kea Lani; $638.45 x 4 nights = $2553.80
  • OGG-OAK: $212 x 2 adults = $424
  • OAK Hotel: Courtyard Marriott = $122
  • OAK-ATL: $167 x 2 adults = $334
  • TOTAL = $6830.76


  • DTW-HNL: [37,500 miles +$5.60 (me)] + [37,500 miles +$5.60 (wife)] + [5,000 miles +$5.60 (Daughter)] = 80,000 + $16.80
    • Note: I took advantage of a 30% Amex transfer bonus to Virgin for a different redemption that did not pan out so I only redeemed 62,000 miles (80,000/1.3) for this trip
  • Honolulu Hotel: Hyatt Centric – 45,000 pts + 1 FNC
    • (15k pts/nt & 1 free night certificate)
  • HNL-OGG: SWA Companion Pass (3-for-1) = 1379 points +$11.20
  • Maui Hotel: Fairmont Kea Lani – 130,400 points
  • OGG-OAK: SWA Companion Pass (3-for-1) = 14,035 points + $11.20
  • OAK Hotel: Courtyard Marriott = $122
  • OAK-ATL: SWA Companion Pass (3-for-1) = 9,772 points +$11.20
  • TOTAL = $172.40


Obviously, this list is not an exhaustive list of our trip expenses. For example, we have yet to determine if we will rent a car or budget how much we plan to spend on food. But hopefully, this example gives you a visual of the money that can be saved when planning a trip using miles and points.

Was it free? No, but had we paid cash, the cost of the booking would have amounted to, at least, $6830.76. That’s certainly well outside of our budget and means. Our out-of-pocket expenses for an 8-day trip that includes a 10-hour business class flight, two different islands (Oahu and Maui), and a 5-star hotel are costing us cents on the dollar and that makes me excited.

Unfortunately (or fortunately depending on your perspective), the number of posted daily blogs decreased over this past week/weekend because I spent a considerable amount of time planning this trip.

Hopefully, this trip yields a spectacular trip report and you will be inspired to plan your next vacation using points.

Have you traveled to Hawaii before? What was your experience? Any suggestions for my trip?


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