Booking a Last Minute Hawaii Trip on Points

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Hawaii is probably one of the destinations to get the most bang for your buck in terms of points and miles.  Airfare to Hawaii from Los Angeles has been quite high for the summer at about $700 per roundtrip ticket.  Booking a last minute Hawaii trip on points can be a great use of points.

My normal and most cost effective way to book Hawaii is using Avios.  However, recently the availability on American Airlines has been absolutely terrible.

Not a single seat in the next month.

Not a single seat in the next month.

My alternate go to method is using 15,000 Flying Blue miles to book Delta flights.  You can transfer American Express Membership Rewards of Chase Ultimate Rewards to Flying Blue.  I looked for a few dates, but nothing worked for me.

My third best option is using Singapore Krisflyer miles on United.  It costs 17.5K one-way to Hawaii and there’s no close in booking fee (when you book under 21 days, AA and United charge extra $75).

I could not find availability to Honolulu and back (our target destination), so I looked at other islands.  I found an itinerary that finally worked, which was one-way to Kauai and then one-way back to LA from Honolulu.  For the inter-island flight I used Chase UR to book the $70 flights, which ended up being 5,600 Chase UR using the Chase Ink Plus card (it would be 4,666 using Chase Sapphire Reserve).

To book United flights on Krisflyer, you would do the following:

  1. Search and look for saver availability.

    Use 17.5K Krisflyer for this flight, and no $75 close-in booking fee.

    Use 17.5K Krisflyer for this flight, and no $75 close-in booking fee.

  2. Once you see a flight for 22.5K one-way, transfer miles to Krisflyer through Chase UR or AMEX MR.
  3. Call Krisflyer at 1 (800) 742-3333 and feed the phone agent the exact flight on
  4. Pay with your no foreign transaction fee credit card $5.60 one-way for taxes.
  5. Get the Confirmation number in your email shortly after and go to to pick your seats.

Although I would have liked to have paid 25K roundtrip per ticket, 35K isn’t a bad deal especially when flights are near $700.  I consider getting 2 cents per point still a great deal.  In case you’re wondering what I did for hotels, here is how I paid for them.

  • 1 Night at Kauai Palms Hotel AirBnB – $87 (flew in at night and went to hike the Kalalau trail the next day)
  • 1 Night at the Grand Hyatt Kauai – 25,000 Hyatt points with 10% rebate
  • 3 Nights at Wyndham Royal Garden Waikiki – 45,000 Wyndham points from Wyndham Credit Card
  • 2 Nights Courtyard Marriott North Shore – 70,000 Marriott points, transferred from AMEX SPG
  • 2 Nights Car Rental Advantage with 1 free night coupon – $58
  • 3 Nights Car Rental National through – 9,400 Chase UR points
  • 1 Night parking at Wyndham – $32
  • Total spent on Hotels, Airfare, and Car Rentals = $177 + 22.40 for flights = $199.40

For a 7 night vacation, spending under $200 for the above definitely saves a ton of money and makes Hawaii affordable.  We spent 2 nights carless in Waikiki, so just had to pay 1 night of overpriced parking.  We also saved some money by using a free club upgrade at the Grand Hyatt Kauai for free breakfast and dinner.

Points for the win!  The main cards we used were Chase Sapphire Preferred, Chase Ink, and AMEX Starwood Preferred Guest.  Booking a last minute trip to Hawaii on points was a bit challenging, but it paid off!

Grand Hyatt Kauai on Points!

Grand Hyatt Kauai on Points!


3 comments for “Booking a Last Minute Hawaii Trip on Points

  1. Maury
    June 27, 2017 at 10:28 am

    Did you do the whole entire Kalalau hike? Did you camp? How did you get the permit? Went alone?

    • July 6, 2017 at 9:59 pm

      Just 4 mile roundtrip, didn’t camp. It was an awesome and strenuous hike! Highly Recommended. Went with Mrs. Romsdeals 🙂

      • Maury
        July 16, 2017 at 9:20 am

        I did that four mile roundtrip hike before. I was thinking that you did the entire hike. You need a permit for that.

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