7/17/20

education, travel

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How we travel hacked a $10,000 3 week Hawaii dream vacation for free!

I’ve talked a lot about Hawaii the last….well since we decided we were going to go in 2018. I talk about it because I love it and if I love something, I want to share it with others.

couple standing on oahu mountain vow renewal

This isn’t a blog about people or a love story between two individuals, but rather, our journey to Hawaii, how we made it there, what we did, and how you can do it too.

Hawaii is 4294 miles away from where I currently live. That’s quite a hike and stretch. It’s only accessible by airplane (unless you’re a strong kayaker) and requires a little finesse to get there if you don’t want to go broke paying for round trip tickets.

I live in Indiana and that means I have an amazing airport just an hour away, the Indianapolis International Airport. The problem with living in Indiana, however, is that it isn’t quite far enough west OR east to really justify low price points in either direction. The best we can do here are super cheap flights to Florida. Chicago, on the other hand, is a metropolis with easy access and even some direct flights to your final destination. Chicago, also, is home to almost 9 million people and served nearly 85 million people in their airports alone last year. SO it’s safe to say that I’ll be spending the few extra dollars on a flight out of Indianapolis.

Now that we have established that I’m currently not near an ultra-ideal airport but still live near one that is nice–we can begin our journey.

Like I’ve mentioned 10 million times before this post, Hawaii has always been a dream vacation spot. Living in the Midwest Mainland USA, some of the usual haunts of midwesterners such as the Gulf of Mexico, Lake Michigan, and the Southeast get a little old. So, it’s fun to adventure West. Manifest Dream Destiny–head westward! But how to get there? I’d heard horror stories that flying to Hawaii round trip per person was nearly $1000 and for those rates, I might as well travel to Europe. That’s when I first found a handful of news articles about credit card points and travel. Then later, I learned about The Points Guy, Brian Kelly, who founded an entire company based on smart credit card usage and hitting spend amounts in order to qualify for bonuses they were offering. These, along with frequent (and again very smart and responsible uses) of credit cards, earned his team enough travel points to fly all around the world. There are many other point guides out there as well, but Brian was original inspiration and helped me understand how to combine the best deals. 

Not everything is always super black and white in the credit card points industry and it took me dipping my toes in with our trip to The Dominican Republic in March 2019 to really begin to understand it all. I first realized that if I offered to pay for everyone’s trip with my card, I’d earn the 60,000 point bonus on my card. The first of a handful of cards I received was the Chase Sapphire Preferred Card. It’s an amazingly easy and ideal card to use if you’re just beginning the points journey and gets you a really great bonus. The catch is that you have to have the spend on it within a 3 month period of receiving the card. Thankfully, our 5 person trip total was around $8,000 and so I booked it all and with cash in hand, paid the card off a week later. This effectively earned me 68,000 Chase Ultimate Reward Points. A breakdown of the value of this card, before understanding and diving even DEEPER into the practically unlimited power of points was around $1000. I knew that I could use these points and book two economy flights from Indianapolis to Honolulu, saving us $1000+ on flights. Cool! Now we had free flights to Hawaii. We were set, right?

woman sitting in cabana in dominican republic

Not exactly. You see, the Hawaii housing and real estate market is not at what is considered its’ most all time high, but to a Midwesterner who owns a beautiful sprawling ranch in a very nice neighborhood, Hawaii home prices are unattainable. That translates into the cost of staying in Hawaii being high as well. You won’t find many cheap or budget motels in Hawaii–and for good reason. You’re literally staying in paradise. Hawaii has very few bugs, no poisonous snakes or scary creepy crawlies (aside from a few centipedes), and the weather is practically always pleasant. So what am I do to do now that I’m facing down (at minimum) a $1400 hotel bill for a week in Honolulu? Oh, I know! I’ll get another credit card.


I’m a business owner–a photographer in fact if you haven’t guessed that by now. Since I was already accumulating Chase Ultimate Reward Points, I decided I’d keep with the game and applied for Chase Business Ink Preferred card. This card had a point bonus of 80,000 points with a $5,000 spend on it. So, with some savings and cash in hand, I purchased some new business gear and hit the spend on that card and earned myself 85,000 points. (80,000 for the bonus and 5,000 for the spend). Now I had around 150,000 points from Chase. I could easily offset most of my stay in Honolulu with those points and have free flights! Cool, time to stop, right?

Not exactly.

Like I mentioned earlier, Hawaii is over 4,000 miles away and it takes a LONG flight to get there. Since it’s a long flight there and a long flight home, I really wanted to make sure that I spent as much time as possible in Hawaii to make my time there count. So, I looked into more cards and found two Southwest cards and two Alaskan Airline cards. The long story made short for these cards is that they offer a special bonus on top of just their normal points that no other airline cards offer. With Southwest, if you earn 120,000 (as of 2019, now 125,000 points in 2020+) you also earn a Companion Pass. The Southwest Companion Pass is EASILY the most valuable asset you can get from a credit card outside of cash or points because it allows you to choose a companion–whether it be a spouse, a best friend, or even a business colleague, and they can fly for just the cost of tax which usually is around $10-$20 round trip. 

It’s an outstanding benefit that can save you hundreds or thousands of dollars over the course of it’s lifetime. The best part about the benefit is that you can earn it through credit card points and not just by flying 100 one way flights in a year. So, my credit card spend on two Southwest cards–a business card and a normal one allowed me to earn the bonuses on them PLUS with the dollar spend, put me over the amount needed for the coveted companion pass. Now I could use all 120,000 points I had for my flights alone and my wife could join me for essentially free. (about $11 round trip–no extra points needed).

I mentioned that I also had two other cards through Alaska Airlines. Both of these cards had a lower spend and a much lower bonus sign up. But the bonus was enough for us to earn first class tickets (one way) from the West Coast to Honolulu which equals about 5 hours in first class. Now, Alaska Air doesn’t have a traditional first class cabin. It’s more like a really cushy business class with large seats, unlimited top shelf liquor, and a pretty excellent meal served. So, we used our points to book our passage to Honolulu. 

On the way home, we flew Premium Economy which is an economy seat with 4 extra inches of legroom. Standing around 6’4” inches, this was a necessity for me and made the long flight home much more enjoyable. Finally, Alaska also offers a companion pass once a year which allows you to book a ticket and then pay taxes on a second “free” flight which is around $100. It’s quite a cost savings. 

My only complaint about Alaska is that when you’re trying to utilize points OR their once a year companion pass, they black out a lot of dates and options for you. I wasn’t able to find the same flights with the companion pass on the way home and rates seemed to be higher for the “single ticket” with companion pass option versus not using the coupon code for the pass. This was my biggest complaint and I felt like Alaska Air was misleading. Southwest allows you to book their lowest cost seat the “Gotta Get Away” option which can come in at hundreds of dollars or 10s of thousands of points less for the same flight (you just earn more points when flying and sometimes get a priority spot when boarding) without blackouts. Southwest also only offers a certain amount of these types of “gotta get away” seats but even if I had purchased the last one with points, I could still add my companion on for free without an premium being accrued. Alaska Air was not that way.

ANYWAY, with all of these points, you must be wondering how we spent them?

I’ll break it down for you–but before I do–I have to tell you about something that is even better than JUST getting Chase Ultimate Reward Points. These points through Chase (not Southwest or Alaskan) can be used in three ways. The first, cash back. Have you ever seen a card that says a percentage of your spend is cash back? Well, through Chase, those are just points that they’ve turned into cash. Usually it’s 1 point = 1 cent. It’s not a very high value and points used elsewhere are more valuable. 

The second way is to use the Chase points through their travel portal.

Once you receive your card, you’ll get a log in to pay your bill and also access the amount of points. This takes you into the Chase Travel Portal *insert futuristic space sounds*. It’s really an awesome way to spend your points. It allows you to book flights DIRECTLY from this portal with points, rent cars, and even book hotel stays! All through the portal. On average, most of the vendors that you can purchase from use the points as cash. 1 point = 1 cent. That’s not always the case–especially with rental cars. I found that I was able to use both vehicles we rented in Hawaii through points. I chose the location, the dates needed, and it gave me a list of vehicles from every vendor from Enterprise to Budget and Dollar–pretty much every car rental option is available. 

What’s even better is that points usually go farther with booking car rentals through the travel portal. An example would be I want to book a Prius for Maui and the cost on the Hertz or Enterprise website is $200 for the week (which translated into points = 20,000 points. In the travel portal, you can book the same car through the same vendor for 14,000 points. That saves you $60 worth of points which goes a long way with points. We booked all our car rentals through the portal and got great deals on them. 

The LAST way, which is the trickiest but can be the MOST valuable way to use Chase Ultimate Reward points are through travel partners.

Travel partners are companies that have teamed up with Chase to accept their points as cash. You don’t have to worry about paying anyone, simply, you transfer the points (in the Travel Portal) to your specific company you want to book through, and then use those points to book on the company’s website. My real life example is Hyatt Rewards. Hyatt is an amazing hotel chain that has different hotels all over the world including some very NICE places such as Maui and even Maldives. (Where’s Maldives? Well, if you look out in the middle of the Pacific Ocean, surrounded by nothing but gorgeous clear blue water, it’s there. It’s where they have those over water hotel bungalows you see on Instagram and dream about staying at. That’s where Maldives is). 

I could book my hotel directly through the Chase portal for the Hyatt Place in Waikiki Beach–which is a lovely hotel by the way, for $200-$300 a night. This is also one of the cheaper hotels in Waikiki so that’s not a bad deal, right? That’s why we got these cards, to offset the cost of our stay as long as possible. But using points directly through the portal would be a waste. Instead–Hyatt is a Chase travel partner. So, I signed up for free Hyatt membership. Within minutes, I had a user ID number and was able to enter that information into the Chase Portal because on Hyatt’s website for the Hyatt Place Waikiki (or whichever Hyatt location you choose) you can check the the cost of of the room in cash or points for the dates you travel. I recommend doing this BEFORE anything else because sometimes “award stays” (travel booked with points) aren’t always available during certain times of the year. Thankfully, our January and February travel allowed us to book room at the Hyatt Place Waikiki for 12,000 points a night.

WAIT, HOLD UP! You mean it’s actually cheaper to book direct with the hotel? YES! Since Chase and Hyatt are partners, I was able to figure that I could stay 8 days at this hotel for 96,000 points. Point cost of the room equals around $960. If we would have booked the room through the travel portal or without points, we would have paid $1680 for 8 days. Instead, we paid 0 dollars and 0 cents AND had the resort fee waived. (Oh don’t get me started on THOSE).

The final reason we chose to stay at the Hyatt Place Waikiki is because they offer a FREE continental breakfast every day to their patrons. It didn’t cost us anything to eat every morning and with the cost of food and snacks being higher than the mainland and with us trying to stretch as much out of this vacation as we could, we ate their breakfast every morning. The selection was good and even included an area that catered to more to Asian dining culture.

hawaii couple on beach

Not everything was always cooked the best and the pancakes and waffles were a little bit of a let down, but I could easily forgo those to get some delicious homemade monkey bread, fresh eggs, bacon, sausage, different juices, rice, tofu, cereal, and potatoes. Seriously, the daily savings of eating “in” at the hotel with the included breakfast probably saved us around $40 a day–maybe more if we had gone somewhere a little swankier. The breakfast savings and paying with points (which waives the resort fees and taxes) equals $760 for 8 days. Our total savings by booking the Hyatt Place Waikiki $2,440. That’s a lot of savings!

You might be wondering what we did the rest of the time in Hawaii because we spent ALMOST 3 weeks there. Well, we traveled around Oahu about 4 times, renewed our wedding vows, had our portraits and a video taken of us, took a guided tour around the island, visited the north shore, ate at MANY amazing restaurants, and met new friends along the way. All of these experiences are PRICELESS–but if you had to put a price on it–Oahu could have been treacherously expensive. Instead, it wasn’t, which made our trip all the more enjoyable knowing we didn’t have to worry about money and how much the hotel cost. 

After our stint in Honolulu, we flew to the Big Island of Hawaii. There aren’t many hotel options on this island as it’s the biggest and newest island. It’s the only Hawaiian island to currently have a live volcano on it. I did my due diligence and looked through the travel portal and for any hotel options that we could transfer points to while on the big island. Unfortunately, there weren’t many options so we decided to use AirBnB to book two different stays on two different sides of the island. 

These were then paid for with points as cash (I used my card to pay for the stays and then paid the card off with points which turned into cash). While there may have been better ways to use those points, my research for the islands showed me that there really weren’t too many more options for the limited amount of points I had left. We were able to book both our Jeep on the big island with points through the portal and enjoyed 5 days on the big Island in Kona and in Volcano. 

While we were there, my wife was able to visit with friends from her high school days and we ate the most amazing poke out of three islands we visited at Kona Brewing Company and Da Poke Shack in Kona. We booked surf lessons through the AirBnB experiences and had an amazing private surf lesson. We also got to see our first volcano and learn about the newest Hawaiian island that will one day appear in a few thousand years.

We left the big island and flew Southwest to Maui. (All our interisland flights were booked through Southwest and were super low in point costs and made even cheaper because of our Southwest Companion Pass). Our stay in Maui was hosted by friends who live in Lahaina, on the western side of Maui. It’s the drier side of the island but home to hundreds or thousands of humpback whales who swim for weeks to get to Hawaii in the cold months to breed, give birth, and enjoy the warmth of the Hawaiian sun! We rented another car with points through the travel portal and saved money by staying with our friends. As payment to them, I photographed them on two different occasions and also took a few shots of her wedding dove release business. (Seriously, so cool!)

hawaii maui couple sitting on beach

After it was all said and done, we flew home on Alaskan airlines through one paid ticket and noe companion pass booked in Premium Economy. We stayed the night in a Hyatt in Los Angeles and then flew home via Alaska as well with a short stop in Seattle. 

The total cost of our trip would equal out to around $10,000 give or take a bit. Our total out of pocket cost was around $3000 which includes cash we had on the island for souvenirs, food, and fun excursions as well as a little travel paid for out of pocket such as our flight home from Hawaii.

My dream vacation to Hawaii is complete and we loved every single minute of it. Our favorite place to stay was Maui because we felt it was the best mix of the western world but with the charm of the Hawaiian islands. It has beautiful mountains, clear water, and a far less touristy feel. Each island was unique and special to us and we have memories for our entire lifetime and goals to go back soon.

Now you know that travelling to Hawaii doesn’t have to cost a small fortune. If you have time, start your plan to get there and decide on how much you want to spend and how much you DON’T want to spend. Everything you don’t want to spend money on, such as accommodations or travel, can easily be taken care of with the right travel cards and perks. The key, as I’ve stated before, is to use them responsibly and to have cash in hand to pay them off before you accrue interest payments. If you’re paying more than you spend on them, you might want to consider just saving up for Hawaii. If you can use them in a smart way, you can find yourself on your dream vacation!

Here are a few links to the cards that I used with referral codes if you want to sign up for them.

Did I mention that the Southwest Companion Pass, when earned is good for not only the year you earn it but for the following year as well? So the ideal time to earn the Companion Pass is earlier in the year so that you can travel for free more! *edit* because of Covid they’ve extended the Companion Pass for those whose would expire in December 2020 to June 2021. 

couple kissing in jean roach dry lake bed las vegas

Maybe Hawaii isn’t your dream vacation. Maybe it’s Mexico, Europe, or anywhere else in the world. The point is, you can do it. Travel doesn’t have to be expensive. Some places might be more difficult to reach than others but there are ways to offset that cost. The familiar phrase of you only live once” comes to mind here. Cliches aside, some travel opportunities are once in a lifetime and I’d hate to think that on my deathbed I was wishing I took that trip with my wife to some far off location. 

If you want to learn more about “travel hacking” as it’s affectionately called or if you want to hear more about my travels, send me an email. I’m always looking for new places to travel.

Currently, I’m hoping to visit Iceland, Ireland, France, Spain, Morocco, Thailand, Fiji, Maldives, and Bali. While some might have to wait or strategically be planned, I plan on making it to these places eventually! I hope that this information is something that can help you get where you want to go with your favorite person!

Here are some referral links for the Southwest Cards I recommend:

The Southwest Rapid Rewards Card – 40,000 points when you sign up and hit the minimum spend ($1000 in 90 days)

The Southwest Premier Business Card – 60,000 points when you sign up and spend $3000 in 90 days.

You’ll still be short about 25K in points but there are other business cards that Southwest offers as well that have an 80,000 point sign up bonus. Check the links above and you’ll see them. You also get points for each dollar spent. Just be smart with spending and ensure you have that cash in HAND when making purchases!

Happy adventuring!