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Travel is awesome but travel with family is even better – being able to share those special moments with your loved ones means the world. I love taking trips with friends and family and sharing the world with them – whether we are flying First Class or in a middle Economy Class seat; flying and traveling with someone you care about really makes the trip more memorable and special. We highlight success stories from our community to share with everyone how our readers were able to redeem their miles and points for nearly free trips and how you can do the same. Note that availability and mileage prices change frequently so they may not be current at the time of writing, but were accurate when the trip was booked. Today we highlight Hawaii for nearly free for a family from Seattle.

Planning a Quick Family Trip

My good friend Harry and his family from Seattle wanted a getaway somewhere warm for a week or so during February (a rather ugly time in Seattle). We took a look at his miles and points and at availability and narrowed it down to a few destinations in North America – since this trip was only going to be a week or so, it doesn’t make sense to go anywhere outside of this region.

Naturally, Hawaii and Mexico were at the top of the list, but so was Costa Rica and several Caribbean countries – all of these places offer great weather and stunning beaches with plenty of activities for the whole family. Another factor was the price – how much out of pocket would they be paying for this trip, did it make sense to fly somewhere for just a week if they were going to still pay a few hundred dollars in addition to the miles and points?

We took a look at availability and found that we could easily make the flights happen using miles and points to Hawaii and Mexico on Alaska Airlines. The Caribbean was possible, too, but it was more expensive both in miles and taxes/fees – and furthermore, we weren’t able to find great hotel availability using points that matched up with the flight award availability.

There was flight availability to the Hawaiian islands of O’ahu and Maui, and there was also availability to both Los Cabos and Puerto Vallarta. Mexico’s hotels are significantly cheaper than Hawaii’s are, but flying to Mexico on an award ticket comes with about a $100 in taxes and fees – whereas Hawaii is just $11.20 round-trip. Depending on the number of family members traveling, this could add up quickly.

fly to Hawaii using miles and points

fly to Hawaii using miles and points

Success Story: Free Trip to Hawaii

Harry and his family ended up selecting Hawaii as their getaway – mainly because of the much lower taxes and fees on the award ticket and because there was hotel availability that lined up nicely with the flights – which meant that their flights and hotels really would be close to free.

Looking at award availability from Seattle, Alaska Airlines flies to both Honolulu, O’ahu (HNL) and Kahului, Maui (OGG), and flights from Seattle were easily available to Honolulu but there was nothing decent on the way back – with Maui, there were no flights there but there was award availability on the way back. Since flights within Hawaii are relatively cheap, Harry decided to take his family to both and split time between the islands.

Harry’s points balance was 170k Chase Ultimate Rewards points and his wife’s balance was 120k Marriott Bonvoy points. When they signed up for credit cards, they agreed one person would get a flexible and transferable points credit card and the other would get a hotel card so they could balance out their miles and points.

Redeeming Chase Points for Free Flights to Hawaii

There was award availability from Seattle to Honolulu and back from Kahului to Seattle on Alaska Airlines for the whole family. Alaska is a member of the oneworld alliance, which means you can earn and redeem miles from any oneworld airline on Alaska. Since Harry had Chase points, we transferred them to British Airways Executive Club and booked those Alaska flights for just 13k Avios points + $5.60 per person, per direction. The short Hawaiian Airlines flight from O’ahu to Maui was just $44.

The flights priced out and were booked as follows:

  • Seattle – Honolulu: 13k Avios points + $5.60 per person in Economy Class
  • Honolulu – Kahului: $44 in Economy Class (but we booked through the Chase portal and instead redeemed around 2,933 points)
  • Kahului – Seattle: 13k Avios points + $5.60 per person in Economy Class

The cost for all flights per person in Economy was: 28,933 Chase points + $11.20. Because Harry has the Chase Sapphire Reserve, his points are worth 1.5 cents each when redeeming for travel through the Chase portal – which is what we decided to do for that short inter-island flight.

Booking Free Hotel Stays with Chase and Marriott Points

Harry and his family were in Hawaii for 4 nights in Honolulu and 3 nights in Maui and they needed a place to sleep. Harry explained to me he didn’t really care where they stayed as long as they could do it on points and because they would be renting a car and traveling around the islands from beach to beach, a beach-front hotel was not necessary.

Hotels in Hawaii are outrageously expensive in some cases both in cash and in points, and some of them don’t even offer good value. We took a look at Marriott, Hyatt, and Hilton options and compared all of the available hotels, and in the end we redeemed points as follows:

  • Night 1 and 2 in Honolulu: Hyatt Place Waikiki Beach – 12k Hyatt points per night
  • Night 3 and 4 in Honolulu: Hyatt Centric Waikiki Beach – 15k Hyatt points per night
  • Night 1 and 2 in Maui: AC Hotel by Marriott Maui Wailea – 53k Marriott points per night
  • Night 3 in Maui: Courtyard by Marriott Maui Kahului Airport – 44k Marriott points (35k free night certificate + 9k Marriott points)

We transferred some of Harry’s points from Chase to Hyatt and then used up his wife’s Marriott Bonvoy points and a free night certificate that came with her Bonvoy credit card. In total, we redeemed 54k Hyatt points and 115k Marriott points plus a free night certificate – not bad for 7 nights in Hawaii with the family. Hyatt publishes an award chart while Marriott doesn’t and therefore you will find Bonvoy prices are dynamic.

Hotels in Hawaii are overpriced and it shows – a Courtyard by Maui airport is 44k points or $380 a night, that’s insane. I really don’t understand why Hawaii hotels are so expensive (and the quality isn’t that amazing). It is important to note that it took us some time to find award availability of the hotels and match it up with the flights – while in writing it doesn’t seem that hard, it definitely took quite a bit of searching and different flight and date combinations.

say Aloha to paradise with miles and points

say Aloha to paradise with miles and points

All in All

Harry and his family really didn’t have to pay that much in dollars for their trip to Hawaii – by using their miles and points, they were able to save thousands of dollars and escape cold Seattle in February for a nice week-long family getaway. We did book this trip quite a bit in advance and perhaps that’s why we were so lucky with availability, but Hawaii is generally tough when it comes to finding decent prices for hotels (both in cash and points).

Flights to Hawaii are fairly easy to book as long as you aren’t traveling over peak times – airlines tend to publish low fares between the islands and the West Coast of the US if you are booking in advance and have a bit of flexibility. If you can travel off-peak and in the middle of the week, you too, can find award availability for the whole family if you are flexible and have the right miles and points.

Travel Miles 101 has partnered with CardRatings for our coverage of credit card products. Travel Miles 101 and CardRatings may receive a commission from card issuers.