How I Traveled to Hawaii with a Family of Four for Nearly Free

Join me as I show you how I traveled to Hawaii on credit card points and miles for nearly free. I was able to book this travel to Hawaii for our family of four using points and miles earned through credit card sign up bonuses and my every day spend.

Finding Flights

We are home-based out of California, so flying to Hawaii from the West Coast naturally has some advantages. We have multiple options for direct flights to several of the islands. In addition, we have multiple airlines to choose from. Alaska Airlines, Hawaiian Airlines, United and Southwest all have decent cash prices at various times throughout the year.

We were limited on our travel dates due to our kids’ school calendar and our own work schedules and had settled on traveling over the Thanksgiving break. This holiday was, of course, not a friendly week to travel on the wallet. Both my husband and I had earned the Southwest Companion Pass this year, making traveling on Southwest Airlines the most desirable option for us.

Southwest typically opens their calendar for booking six to eight months in advance. If you are trying to book on heavily traveled weeks, such as holidays, it is a good idea to keep an eye on when the airlines will release their availability.

Rebooking Flights

I booked our original flights (each direction one-way) as soon as they were released about six months out from San Diego to Honolulu on Thanksgiving Day, returning the Monday after Thanksgiving. Our original return flight cost 53,520 Southwest Rapid Reward points per person. This was a lot of points! But I felt fairly certain that over the course of six months, the cost of the flight would drop. My gamble paid off! Ultimately, our flights ended up costing 15,932/person Rapid Reward points from San Diego to Honolulu and 28,627 Rapid Reward points/person from Honolulu to San Diego. In total, we paid $44.80 in taxes and fees for all four of us to fly ($5.60/person for each leg).

Rebooking flights with Southwest is not difficult but can be cumbersome, especially if you have a companion ticket linked. The extra steps to regain some points back that can be used for future travels is well worth it.

Finding a Hotel

We traveled to Oahu for this trip, where there is definitely no shortage of hotel options. We opted to stay near Waikiki beach to be within walking distance to the beach, restaurants and shopping. Most major hotel chains are represented in/near Waikiki and there are plenty of private hotel options as well. One of our favorite hotel chains for traveling with points is Hyatt due to the outsized value we can get.

In the Waikiki are, there are three Hyatt hotels to choose from. Hyatt Centric, Hyatt Place and Hyatt Regency all have a presence near Waikiki beach. The Hyatt Centric Waikiki is a Category 5 situated about a 5-7 minute walk from the beach. Hyatt Place Waikiki is a Category 4 also situated around a 5 minute walk from the beach. The Hyatt Place offers a complimentary breakfast for all guests. Hyatt Regency Waikiki is a Category 5 and is the closest of the three properties, located directly across the street from the beach. If you are a Globalist, the Hyatt Regency has a Club Lounge offering breakfast and snacks during the day.

We opted for the Hyatt Regency, primarily for the close proximity to the beach. We stayed four nights at the standard reward pricing of 20,000 points/night for a total of 80,000 Hyatt points. To redeem these points, I transferred Chase Ultimate Rewards points earned through credit card sign up bonuses and my every day spend to my Hyatt account. Although we could have stayed for fewer points at the Hyatt Place, we were very happy with the Hyatt Regency and would likely stay here again if we travel back to Oahu.

Earning Points and Miles for Travel

If you are new to the points and miles game, visit our Travel on Points and Miles page for an introduction on how to start earning!