Get Started

Learn more about Credit Cards, Travel Programs, Deals, and more.

Planning My Wife’s Birthday Maui Trip: Turning A $9,000+ Trip Into $300 Out Of Pocket Cost

This post may contain affiliate links - Advertiser Disclosure. As an Amazon Associate, we earn from qualifying purchases.
Travel Hacking Maui
Hyatt Regency Maui

Travel Hacking Maui

I don’t think my wife would like me talking about how old she is, but let’s just say it is a bigger birthday. You could say she is celebrating turning 30…for a second time, ha! We have been going back and forth on destinations too. Originally the plan was to go to Europe for the Christmas Markets since her birthday is in December. With the current covid rules in place, and me getting it for a second time last month, potentially both being stuck overseas didn’t seem prudent. Especially with it likely rolling into the holidays if it should happen. Our back up plan was Maui. Easy, right? Not so much! I’ll share with you how I ended up travel hacking Maui and turned an $9000 trip into a few hundred dollars out of pocket.

Award Flights To Maui

The goal was to book lie flat, if possible, for at least some of our flights. It takes us longer to get to Hawaii than it does to get to Europe after all.  We have a pretty great guide on the site showing which routes have lie flat seats.

Non Stop From Detroit To Honolulu

One such route is starting up service again in November, Detroit to Honolulu. That was where I started my search. The plan was to spend a few days in Waikiki and then jump a short flight to Maui after.  There was space but it was costly.  Delta wanted 130,000 Skymiles per person one way, ouch! They earned the skypesos moniker right there. I searched partners Virgin and Flying Blue but nothing showed there either.  That seemed like a tough pill to swallow and would require me transferring most of the miles in from Amex Membership Rewards, not something I wanted to do.

Checking Flights to Maui Instead

I have been sitting on a stash of American Airlines miles for several years now and had used them to book our 15 year anniversary trip to Maui. We ended up having to cancel that booking because of covid but I figured that was a good place to check. I was even able to get lie flat through Dallas (DFW) back in 2020 for 67,000 miles (I think) a person one way.  Could lightning strike twice? Nope!

American Flights

I did find some decent award pricing coming back from Maui. We would connect through Phoenix and it was 50K a person one way plus the $5.60 in taxes and fees. That seemed like a deal these days, especially with domestic travel, so I booked it. We weren’t getting our desired lie flat seats, but the times of the flights were good, and regular first class is good enough for us.

Travel Hacking Maui
Hyatt Regency Maui

Searching High An Low For A Flight Out

I really wanted to get her in a lie flat bed for her birthday, if I could, so I searched high and low for the flights out. I started searching all of the west coast gateway cities for decent award space. Seattle, San Francisco, Los Angeles were all on the docket. I would then try to tack on a positioning flight if possible or book it separately.

The plan was to focus on miles I already had in my accounts versus needing to transfer. That included searching British Airways Avios for American flights, Lifemiles for United Flights and more Virgin Atlantic for any Delta options from the West Coast. Nothing was coming up in any partner searches.

I then tried United miles, which we had a nice stash of from the United Quest card. The best thing I could find was 60K a piece from San Francisco and in the dreaded 2-4-2 business class cabin. At that price, for those seats, no thanks.

United seats

I did find a decent price out of Seattle on Delta. It was 43,000 Skymiles per person in domestic first class, but was a 8AM flight, which meant flying in the night before. That wouldn’t work unless it had to.

Travel Hacking Maui

American didn’t have any great options to Maui or Honolulu from the west coast either.  I even tried Alaska Airlines but they want 60K-80K per person one way for first class.  The one spot I didn’t try was Hawaiian Airlines since I didn’t have any of their miles and nothing was coming up on Virgin.

Circling Back To American Airlines As A Stop Gap

That left me slinking back to American Airlines. Luckily enough, I was able to find a flight out to Maui through Phoenix for 50K per person. With the ability to cancel award flights without having to pay a fee I decided to lock it up. This gives me the best deal now and then I can continue to check for something that may work better up until we leave in December.

  • Airfare Cost: 200,000 American Airlines Miles & $22.40
  • Cash Price: $4,704


Travel Hacking Maui: Booking A Hotel

After my marathon flight search session I figured Hotels would be a bit easier.  Well they were and they weren’t.  There wasn’t a lot of options available, which made the decision easier to make I guess.

Waldorf Astoria Grand Wailea

I first pulled up Hilton to see if I could burn any free night certificates at the Waldorf Astoria Grand Wailea. On our previous booking I was able to snag a couple of standard award nights here. This time around the lowest priced room was over 500K a night. It looked like a standard room they were playing games with. I searched their award chart for the rest of the year and saw probably less than 10 nights where a standard 110,000 point room was available. I’ll keep checking from time to time up until we go and see if I can snag a few nights.

Andaz Maui

The Andaz Maui was another bust. They didn’t have any award rooms available the entire time we were there in December. Not surprising since this hotel is notorious for playing games with award space. Plus, with it being a 35K a night property now I wasn’t overly sad about it. The cash rates were like $1,200+ a night, pass!

Hyatt pricing

Hyatt Regency Maui

I was starting to sweat a bit at this point. Did I just waste all that time finding flights only to strike out with hotels? That is when the Hyatt Regency Maui came to the rescue! I was able to find award space here and the really nice thing was it was pricing out as off peak. So I only paid 21,000 Hyatt points a night for this category 6 Hyatt. Score! The cash prices were $500-$600 a night.

To Road To Hana Or To Not Road To Hana?

After reading Jim’s amazing guide on the Road to Hana I was thinking about throwing this into the mix. There is a Hyatt in Hana that had award space. It was also pricing out as off peak. Zack at TPG did a good review on the hotel too.  The place looks like an amazing spot to unplug and get away from a night or two. I mean it doesn’t even have TVs or air conditioning. The problem was with us going in December it would get dark so early, what the heck would we do at night? That plus this being a shorter trip, only 5 nights, we decided this just wasn’t a great fit for us this time. If you are planning on doing the Road to Hana this would be a cool way to break it up. The resort also looks like such a pretty and secluded place to spend a night or two as well.

  • Hotel Cost: 105,000 World of Hyatt Points
  • Hotel Cash Price: $3568.52

Travel Hacking Maui

Car Rental

Carmaggedon here we come! This is a cost I was fearing since prices in Hawaii have been sky high since the pandemic.  National was pricing out at $800 for the 5 day rental which was more than I wanted to spend. Luckily, we some free days to use and got the price down to under $300.

  • Car Rental Cost: $279.95
  • Car Rental Original Cost: $800

Locking In Now But Room For Adjustments

One of the main things I wanted to do while travel hacking Maui, besides save money, was have flexibility. Everything we booked can be canceled without penalty, and that is important. Plans change, now more than ever, so we need to be able to be fluid without having money tied up in vouchers etc. This also allows us to pivot to Christmas Markets (my wife’s first choice) should rules change by December. But, it also allows me to continue to search for other hotels and flights so I can switch it up if we want. These days standard operating procedure should be to book what is the best option NOW since you can always improve on it later. Assuming you book flexible options of course. That is what makes award booking so valuable to me.

Travel Hacking Maui – Final Thoughts

There you have it, that is how we turned a $9000+ trip into $300 out of pocket. I know it isn’t sexy, because it is a domestic trip, but the prices in Hawaii right now are probably as high as pretty much anywhere in the world. It is just nuts out there right now. That is where miles and points can make a huge difference.

I am pretty happy with our flight bookings. Spending 200,000 miles isn’t as good of a deal as I may have been able to get 3-4 years ago, but it is better than most of the options out there right now. The big 3 just aren’t releasing space to partner airlines like they used to. Thanks dynamic pricing (sarcasm font)!

I was very happy to see a hotel in Hawaii pricing out as off peak. I will take that 20,000 World of Hyatt points savings every day and twice on Sunday. That wouldn’t have been the case a few years ago. So, I guess peak and non peak worked in my favor this time around. The non peak pricing is a savings of around $300 in points for me alone.

The hardest thing to hack is car rentals for sure. Booking through a bank travel portal and wiping off the charge with points is probably the best option for most. That or use a travel credit on your credit card on it like you have with the Capital One Venture X or the Chase Sapphire Reserve.

Has anyone else booked a trip to Hawaii recently? How did you end up faring?

Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers.

Increased Offer! - Chase Sapphire Preferred® Card 75K!

Chase Sapphire Preferred® Card is the old king of travel rewards cards. Right now earn 75K Chase Ultimate Rewards points after $4K spend in the first 3 months with a $95 annual fee. That's over $900 when you redeem through Chase Travel℠.

Learn more about this card and its features!

Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
Mark Ostermann
Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. That sounds like a great trip. And you did well with points. It’s tough right now. Hana is really wonderful/relaxing/scenic and as noted shortness of day is less of an issue in Hawaii. Funniest part of the post: trip for just the two of you, and you say ‘what the heck would we do at night?’

  2. We did an overnight at the then Hotel Hana Maui. Free iPrefer upgrade got us into an ocean cottage. The adults only pool was deserted and amazing. Once the sun went down everything shut down and it rained for 4 hours, it was incredibly dark. Sunrise was amazing and having Hamoa Beach all to ourselves for hours was great.

    But .. We’ve done it once, i doubt we’ll do it again

  3. I object to the stated cash value of the flights. If you had spent $2300 in cash per ticket I presume you could have gotten a better routing and timing of flights, as it is very unlikely you found optimal flights via awards. How much the inconvenience is worth is up to you, but it definitely isn’t $2300 in value.

    I’m unclear why you still had to pay with National free days? Didn’t have enough? You can use up to 7.

    • The times were actually what I wanted and good for the flights so no complaints there. Yeah I didn’t have enough free days

  4. 200k AA points – if you used purchases on a card = lost cash 2.5c; if you signed up for cards = 0.3-0.5c each I am putting down an average of 0.5c overall
    e.g., 60k AA miles for 5k spend = 99$ fee + 100$ lost cash = 200$ for 60k = 0.33c each
    100k Hyatt – even if you did 5X office stores = cost 1c each = 1000$
    e.g., 200$ staples fee free card = 1k points = lost cash 200$ = 5$ –
    Now you have a card that you have to use for spend (unlike a check that you can deposit in to your account) so when you use it you lose cash back again = lost cash back 2.5% = 5$
    total loss in lost cash = 10$ for 1k points = 1c each

    My point is your real cost was between 1500$ – 3000$ in lost cash along with all the time and effort you spent on getting the miles – so it was never just a 300$ cost.
    Yes, you saved a bundle, but don’t fool yourself too much – it was less than you advertise

  5. Hawaii has been our go-to vacation spot for decades now. We can just book NoCal to HNL for as low as 45,000 United points round-trip.

    We then go to the United Club Lounge in SFO and inquiry about first class upgrades. They always tell us, “not available since you used miles instead of cash to purchase your tickets.”

    So we then ask the price for a cash upgrade on Polaris lie-flat first class seats. We’ve been able to purchase these for as low as $350 per person (one-way) for a $1,350 Polaris seat.

    Alaska Air offers the same game 24 hours in advance for $99 per person to upgrade to first class, although not lie-flat seats.

    • I am jealous of how easy west coasters have it for Hawaii. But I guess you feel the same about Europe so it is a wash 🙂

  6. WA was terrible. I stayed with free night certs a couple of times. Not impressed. Front desk staff was like a robot, cold faces. Room was dated. Glad not to have to pay with cash.

  7. My family and I recently stayed for a night at the Hyatt in Hana. We loved the property. The pool was was great f and the food trucks next door had great options for a take out dinner. Burned 35K hyatt points, which I think was worth it.

    • I wanna check it out for sure one of these times. Looks like an awesome experience. Just don’t think we have enough time to do it this trip.

  8. FYI, the length of daylight here on Maui doesn’t change nearly as much from Summer to Winter as it does for people living as far north as you. Not a ton of difference between December and June.

    • I came here to point that out. The closer you get to the equator, the less variation in day length.

      We live in MN, go somewhere warm, usually Zihua, every January. The fact that the sunsets are after 6 pm feels like a blessing.

  9. We spent 5 nights at the Hyatt residence a few years ago and then ended the trip with two nights at the Hyatt Regency (which is next door). Gotta say, I was NOT impressed with the Hyatt Regency. At the time the room rates were closer to $300/night. We were able to use a Club upgrade…and then at the hotel they upgraded us to a suite. Even with the two upgrades I wouldn’t pay $300/night again to stay there. It’s too far to travel to stay at a mediocre property. I was not a fan of the beach. The pool situation was an absolute zoo….and we went during an off week at the end of October. The only saving grace is we could use the pool area of the Hyatt Residence…which was dead.

    I don’t know if they are still doing timeshare offers at the Hyatt Residence…but I’d see if that was an option. They advertised for 2BR units but i was able to get a reduced price for a 1BR unit…which was plenty of space for 2 of us.

  10. I’m heading to Honolulu on Friday. I wasn’t so lucky with points and miles. However, I would say that you should always keep checking car rental prices. When I originally booked via Costco last October, it was $965 for a SVU for the week, now the price is $465. I did pay $1300 for LGA-ATL-HNL, frist/delta one.

    • For sure – I check everything I book now since prices are so dynamic and you can cancel. Car rentals is a great one to do that with for sure. You should enjoy that D1 🙂

  11. Did you consider any of the “Destination Residences by Hyatt” properties, like Wailea Elua Village? I understand its more of a condo than a hotel, but have been considering it for an upcoming trip instead of the Hyatt Regency (on which I’ve read mixed reviews).

    • Not really. If the kids were going then we would have but wanted more of the resort experience for this trip.

  12. I recently just did Hawaii as a pivot to a Japan trip in April 2022. Like you stated so much flexibility and being able to cancel/re-book was crucial for us. We originally had Hilton Maui and Hyatt Centric Waikiki but pivoted that to being Andaz Maui and Grand Hyatt Kauai instead.

    RDU-SFO-HNL in United Polaris using UA travelbank that we had stashed away from the past 2-3 years.
    OGG-SLC-RDU in D1 using miles (70K Delta miles for each of us).
    Andaz Maui 5 nights at 30K/night before the change and was able to add our suite upgrade and confirm it. The Andaz Suite was amazing. Grand Hyatt Kauai for 3 nights at 25K/night which we winded up booking 2 weeks before our trip was scheduled to depart. Rental with national for $150 in Kauai and $275 in Maui. My company has corporate codes that can be used for personal use and ability to use executive elite status got us upgraded to a jeep and a mustang.
    Paid for inter-island flights via HA and WN with cash. Before any excursions or anything it this would have priced out at about $10K for just the flights/hotels/rental car. Thankful for this hobby.

    • Sounds like an awesome trip Paul. Awesome that you were able to find space later on an pivot to those hotels.


Please enter your comment!
Please enter your name here