The anticipation of this moment is what originally lead me to the points and miles game. Now, almost two full years after I started this journey, I’ve finally booked our 5th wedding anniversary trip to Hawaii. As planned, I used points and miles for as much as I possibly could, and saved over $9,600! Annie and I will celebrate the anniversary of our marriage with 6 nights in Maui and another 2 in Honolulu. This post explains how we’ll get there, where we’re staying and how we saved over 97% off the retail price of the trip.

Airfare

Prior to booking, I always assumed I’d be flying United because they have so many flight options from Chicago to Hawaii. Plus, United is a transfer partner of Chase Ultimate Rewards. So if I needed a few extra miles to book the flights, I could always transfer some Chase points to my United MileagePlus account. Before booking though, it’s always a good idea to check around in case you can get better flights (i.e. flying direct instead of connecting, getting into a better cabin or redeeming less miles) on other airlines. In my case, after reviewing flight options on American and a few other airlines, United was still my best option.

For 135,000 miles and $22 in taxes and fees, I booked two multi-city award tickets from Chicago to Maui, Maui to Honolulu and Honolulu to Chicago.

Hawaii Trip Award Itinerary (two tickets)

When I was ready to book the trip, I only had 131,000 United miles in my account. So I logged onto Chase and transferred the 4,000 Chase Ultimate Rewards points needed to United. In less than two minutes, the extra miles were in my account and I was able to book the trip.

Paying for these flights would’ve cost around $2,500 which means the value of my miles redemption is around 1.84 cents per point ($2,488 / 135,000 miles). That’s better than the widely considered value of United miles, which is 1.3 cents per point. What makes me even more excited is that around two thirds of the miles used for this trip came from “freebies”. In other words, many miles I earned were not earned through credit card purchases or paying for United flights.

The top three ways I earned miles for free were: 50,000 miles from the sign-up bonus on the United Explorer card, almost 16,000 miles from United’s shopping portal and their MileagePlus X app, and 12,000 miles from taking online surveys.

Chicago (ORD) to Kahului (OGG)

Leg 1: Chicago to Denver on a Boeing 757-300

All flight options from Chicago to Maui included one stopover. While there were a few flights available for 22,500 miles per ticket, they had long layovers that were not ideal. I had to spend 45,000 miles per ticket instead to reduce the overall travel time and ensure that we’ll land in Maui in the afternoon instead of later in the evening.

In choosing seats, I referenced SeatGuru.com and found a quirk in the economy cabin that we could take advantage of. Row 22 is considered standard economy and so United doesn’t charge extra for those seats. However due to an exit row in front, the seats have extra legroom. Even better, there are only two seats on each side of the aisle, so Annie and I get the row to ourselves.

Leg 2: Denver to Kahului on Boeing 777-200

For this long flight, it was worth it to me to pay for upgraded seats in economy plus. Of course, sticking with the theme of this trip, I wasn’t going to pay for the seats in full. At the time of booking, I selected random seats in economy for all legs of the journey. I paid the taxes with my United Explorer card so that we’ll get free checked bags. To save money on the economy plus seats, I then went back into the reservation and purchased the seats with my American Express Hilton Honors Aspire card. That card has $250 in annual airline credits which can offset various fees, including paying for seats. I used some of the credit first for our flight home, so I only had $144 left for this flight. In total, the cost to upgrade both our seats to economy plus on this flight was $238, but after the credit, it came to only $139. Now we have economy plus exit row seats.

Kahului (OGG) to Honolulu (HNL)

This flight is on a Hawaiian Airlines Boeing 717-200. It cost absolutely nothing (no miles or dollars) because of a perk known as the United Excursionist Perk. This perk lets you add a free one-way segment, beginning and ending in the same region, to travelers on round-trip itineraries between two different regions as defined by the United award chart. The travel must end in the same region where it originates.

In this case, our trip begins and ends in the North America region. In addition, the origin and destination of the one-way segment is within a single region, Hawaii. Hence, we get to see a second island and don’t have to pay for the inter-island flight!

Honolulu (HNL) to Chicago (ORD)

Leg 1: Honolulu to Kahului on a Boeing 717-200

United has a non-stop flight from Honolulu to Chicago, but they wanted 43,000 miles per ticket. Instead, we’re going to fly back to Maui and then on to Chicago for only 22,500 miles a ticket. It was worth saving 41,000 total miles to take a quick flight back to Maui and then fly non-stop from there.

Leg 2: Kahului to Chicago on a Boeing 777-200

This is a long red-eye flight, so getting seats in economy plus was my top priority. Hopefully we can get at least a little sleep so we’re not completely wrecked when we land at 5:00 a.m the next day. For these seats, I was able to get them reimbursed entirely by using the annual airline credit perk on two different credit cards. I paid for one seat using my American Express Hilton Honors Aspire card and the other seat using my American Express Gold card. With these card benefits, the cost of upgrading to economy plus was $0 instead of $203. Our seats, once again, are in an economy plus exit row to take advantage of the extra leg room.

All in all, our flights cost 135,000 miles plus $161 in taxes, fees and non-reimbursed seat upgrades. That’s a savings of $2,813!

Note: Since I wrote this article, I changed our Chicago to Maui segment in order to get back 45,000 United miles. United charged me $150 to do this and it dropped the total miles used for airfare to 90,000 (from 135,000). The value of the redemption is now 2.76 cents per point ($2,488 / 90,000 miles), up from 1.84. For more details on what I did and why, see how a flight change put 45,000 miles back in my United account.

Hotel

Grand Wailea Maui

When I first had the idea to celebrate our anniversary in Hawaii, I knew that we’d stay at the Grand Wailea Maui, a Waldorf Astoria resort. It’s a beautiful hotel and even though I had no Hilton Honors points at the time, they are notoriously easy to earn. Within a mere nine months, I already had enough points for a 5-night stay, mostly from the welcome bonuses on two new Hilton Honors credit cards (one for me, one for Annie). However, earning Hilton Honors points isn’t just about credit card bonuses and everyday spending. Over the past two years, I’ve earned over 160,000 points from online surveys, 60,000 points from Hilton promotions and 54,000 from hotel stays.

The Grand Wailea is a 5-star resort and prices can range from $600 to over $1,000 per night. For award night redemptions, they charge 95,000 Hilton Honors points a night. As a cardholder of the American Express Hilton Honors Aspire card, I get automatic Hilton Honors Diamond status. One of the perks of having Diamond status is getting the 5^th night free when redeeming points for four nights. So for 380,000 points (95,000 x 4), we get a 5 night stay. In addition, another perk of the being a cardholder is an annual free weekend night certificate to use at any Hilton property. Using the award certificate allowed me to add a 6^th night to our stay. If I had paid for a standard room for 6 nights, it would’ve cost $5,426. Instead we get it for absolutely nothing!

From a valuation standpoint, this redemption, excluding the free night, is worth 1.18 cents per Hilton Honors point ($4,516 / 380,000 points). This is about two times the commonly held value of a Hilton Honors point, which is 0.5 to 0.6 cents per point.

Hyatt Regency Waikiki Beach

In Honolulu, we decided to stay at the Hyatt Regency Waikiki Beach Resort and Spa because the Hilton Waikiki Beach was sold out. The Hyatt Regency is actually closer to the beach anyways and still right in the heart of the city. Normally, it would go for $856 for the two nights, but I used points to get it for free. Hyatt is a transfer partner of Chase Ultimate Rewards, so I transferred 35,000 Chase points to Hyatt to bring my Hyatt balance to 40,000 points. I then booked the hotel for 40,000 Hyatt points. In total, I saved $855!

The value of this redemption is 2.14 cents per Hyatt point ($855 / 40,000 Hyatt points). The commonly held value of Hyatt points is 1.7 cents per point, so I did well again.

Rental Car

A car is pretty much a necessity on Maui if you want to be able to get around to various parts of the island. From the very beginning, I planned to rent a car from Hertz because one can earn Hertz points by taking surveys on E-rewards.com. When you take enough surveys, you can transfer the survey points earned to various partners, including Hertz. There are no similar programs available for the other major rental car companies, so it was Hertz or bust! I was able to amass enough points for a free weekly rental. Those points were earned entirely through survey taking which means I didn’t spend anything to earn the free rental.

To rent a convertible for a week would normally cost $680. Instead I used 7,500 Hertz points to get a free weekly rental. This made it so the only money I would pay would be to cover certain taxes and fees. This came to $89 for a total savings of $591.

Maui Redemption Table

Bottom Line

Using points and miles allowed us to take a dream vacation celebrating our wedding anniversary for pennies on the dollar. A trip that would’ve cost just under $10,000 will only cost me $250! Annie and I are so excited to go on this trip and I’ll have lots more once we get back. Look for flight and hotel reviews, as well as posts about things to do in Maui and Oahu. Aloha!

Trip Report Index

1. Introduction and Planning
2. Using Points and Miles to get to Hawaii
3. How a Flight Change Put 45,000 Miles Back in My United Account
4. Postponing Hawaii Due to a Pandemic
5. Flight from Chicago to Maui
6. Grand Wailea Maui, A Waldorf Astoria Resort
7. Activities in Maui
8. Flight from Kahului to Honolulu
9. Hyatt Regency Waikiki Beach Resort And Spa
10. Activities in Honolulu
11. Flight from Honolulu to Chicago