How I Booked an 8 Night Hawaiian Vacation for $153.52

Hawaii has always been on my travel bucket list! From the bright blue ocean water, to the tropical drinks & the amazing views… not to mention you don’t need a passport to get there, it sounds like the perfect recipe for a fun, relaxing and eye-opening vacation!

Years ago, I thought the flights to Hawaii and the hotels at the various islands would result in thousands of dollars out of my pocket. I now know that if you do spend that much on plane tickets or hotel nights, you are not traveling smart and you must love to throw your money away! :) You don't need to be a millionaire or anywhere close to that to fulfill your dreams of a five-star Hawaiian vacation! All you need is dedication to planning your trip, some flexibility and hotel points & miles! Using points & miles saves you a TON of money and is completely worth it in the end. So, here’s how I booked 8 nights in Hawaii and saved myself almost $5,400:

The Flights

The flight is the first thing on my to-do list when planning a vacation. We booked our flights on using United miles. James (my husband) and I both signed up for the United Mileage Plus credit card a while back which earned us each 50,000 miles after spending the minimum amount required. Since we earned these miles separately, we booked our reservations separately and just selected seats next to each other on the flights.

Our flights cost us 51,000 miles plus $11.20 in taxes each. Typically, you can get a round trip ticket to Hawaii for 45K miles on United; however we booked an extra flight between Oahu & Maui for an additional 6K miles. Without using miles, our flights would have cost over $1200 each, yikes!

Our Flight Schedule:
Orlando to Honolulu (22.5K miles)
Honolulu to Maui (6K miles)
Maui to Orlando (22.5K miles)
Total: 51K miles

TIP: If you book your flights using your United MileagePlus credit card to pay for the taxes (or paid flights) you get two free checked bags and free priority boarding. Something to keep in mind, because otherwise it's $25 for your first checked bag and $35 for your 2nd checked bag. Eeek! Now that we have the flights covered, we need to find amazing resorts to stay at...

The Hotels

There are so many beautiful resorts in Hawaii; however it was really easy to pick the ones we were going to stay at since we had free hotel nights at certain chains.

Three Nights in Oahu on Waikiki Beach:

I earned two free weekend nights at essentially any Hilton property (with the exception of a few high-end resorts) from my Citi Hilton Reserve Credit Card I had signed up for last year. We decided to book two nights at the Hilton Hawaiian Village Resort on Waikiki Beach located on the island of Oahu. I also had 36,888 Hilton points from various purchases from the Citi Hilton card that I knew I would probably never use since Hilton’s redemptions for free nights using points is super high. The Hawaiian Village costs 50,000 Hilton points for a free night, so I decided to purchase an additional 13,122 points for $131.12 to get one more free night at the resort. Since I have the Citi Hilton Reserve card, it automatically gives me Hilton Gold status which includes free Wi-Fi, free bottled water, an upgrade to the best available room on the day of arrival, and at this resort we'll get a $10 daily credit voucher for food & beverage at the resort. The credit is for me and one additional guest so since we are staying three nights, we get $60 in free food & beverage... not bad, huh? We would have spent $1040 for three nights if we didn't use points/free night certificates!

Five Nights in Maui:

Maui was super simple to book. We decided to stay at the Hyatt Regency Maui as it comes highly recommended by friends and family and it only costs 20K points per night. James signed up for the Hyatt Chase credit card which gave us two free nights and we transferred 60K Chase points to Hyatt for the other three nights. Having the Hyatt Credit card automatically gives us Platinum status which gives you late checkout, free Wi-Fi, and a few other perks. We earned the 40K Chase points through a combo of credit card sign-up bonuses from the Chase Ink Card (60K points) and various purchases. The 5 night stay would have cost us roughly $1900 if we didn't use points!


We booked a Sunset Dinner Cruise in Maui for 16,488 Chase points (which normally would have cost $206) It’s a great way to use your Chase points since you get 20% discount for using your points and booking through the Chase Ultimate Rewards portal.  I love to use my points for activities that include a meal & drinks since you get more bang for your buck (in this case points).  

  • We booked our flights for 51K miles plus $11.20 each. We earned the miles from each signing up for the United MileagePlus Explorer Credit Card (however, the current sign-up bonus is only 30K points right now). I would recommend signing-up for the Chase Sapphire Preferred credit card for the current 55K sign-up bonus or the Chase Ink Credit Card for the current 60K sign-up bonus and transferring your Chase Ultimate Rewards points to United miles at a 1:1 ratio. 
  • We booked three nights at the Hilton Hawaiian Village in Oahu using our two free weekend night certificates we earned from the Citi Hilton Reserve credit card and one extra night using points (36,888 points earned plus 13,112 points purchased). 
  • We booked 5 nights at the Hyatt Regency Maui using our two free Hyatt nights earned by signing up for the Hyatt Chase Credit Card. For the other three nights, we transferred 60K Chase Ultimate Rewards points to Hyatt at 1:1 ratio. We earned the 60K points by signing up for the Chase Ink Credit Card
  • We booked a Sunset Dinner Cruise in Maui for 16,488 points using the Chase Ultimate Rewards portal. 
Total we WOULD HAVE spent:
$2400 on flights + $2940 on hotels +$206 on dinner cruise = $5546

Totals we actually spent:
$22.40 flight taxes + $131.12 hotel points = $153.52

We saved $5392.50!

So, there you have it everyone! Now... I need to go pack for our tropical trip of a lifetime! Check back for my next post which is going to be all about packing essentials for your next trip! For more Travel posts, check out the Travel section on my site!

 Do you have any travel advice for Hawaii? What are your favorite activities to do on the islands? Let me know in the comments. 

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