I had my doubts about travel hacking.

As someone with credentials under their name, “hacking” doesn’t sound all to professional.

But reading stories from people like Chris Guillebeau, who travel hacked his way to every country in the world had me intrigued.

Nearly a decade ago, I purchased his eBook: Frequent Flyer Master (now Upgrade Unlocked). Since I made the small investment, I’ve saved well over $10,000 in travel expenses.

I guess that makes me a faithful travel hacker.

One of my most memorable travel hacks was spending three weeks in Hawaii in 2015.

The timing was perfect. My oldest daughter was over two years old (old enough to watch Frozen on repeat for the long flight but young enough not to have to deal with school). My wife was 5 months pregnant (flying with one kid is a lot easier than two).

We had so much fun on the trip, we booked another long-term trip in 2018.

With the logistics fresh in my mind, I wanted to write a beginners guide on how you can do something similar.

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The Beginner’s Guide to Travel Hacking Hawaii

What Is Travel Hacking?

By utilizing strategies such as earning points through credit card and hotel loyalty programs, one can get flights, hotels, and upgrades for free or a fraction of the price.

For example, I booked four seats from Chicago to Honolulu for $22.40 and 90,000 United Miles.

Here’s my confirmation:

hawaii travel hacking

Paying retail, this would cost over $ 1,500 for the four seats.

When you hear about travel hacking, the most talked about strategy is earning points for maximizing credit card spend. Then, turning those points into flights.

This is the easiest way to earn points for most.

How exactly is this done?

There are many ways you can go about doing this. But in it’s simplest form it looks like this:

Sign Up For Credit Card >Maximize Card Benefits > Get Points > Book Flight

Why do credit card companies do this?

They understand the long-term value of a customer. They’re willing to lose money upfront, to get a customer long-term.

Which brings me to the most important thing I’ll say about travel hacking.

Credit card companies are very smart. They build very large buildings for a reason. 

Most individuals who take out a credit card carry a balance. Credit card companies make a lot of money when you do this. So, don’t even think about travel hacking if you don’t pay your bill in full every month and don’t have an emergency fund. 

Now that we have that out of the way, how can you travel hack your way to Hawaii?

Let’s dive in…


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The Beginner’s Guide to Travel Hacking Hawaii: Flights

Priority # 1 is to find a way to get a decent flight, for as cheap as possible.

Again, in it’s simplest form, travel hacking looks like:

Sign Up For Credit Card >Maximize Card Benefits > Get Points > Book Flight

Let’s fill in the holes:

Sign Up For Credit Card

Step # 1 is finding the right credit card offer.

There are a few things we’re looking for here:

  • What credit cards are currently offering large signup bonuses?
  • What are the minimum spend requirements of these credit cards?
  • How many points are needed to book a trip to your Hawaii destination of choice?
  • What is the availability of the flights?
  • What is the annual fee of the credit card?
  • What other benefits does the card have and how does this fit into your spending i.e. earn 3X points on all dining purchases

Let’s look at two real world options:

A few things to keep in mind:

  • Availability will change by your location
  • Availability will change based on what time of year you go
  • The top offers will change depending on the time you’re reading this

Option # 1 – Chase Sapphire Preferred Card

How It Works: AwardHacker is a handy tool that allows you to see award options for flying to your destination of choice.

When I enter Chicago to Honolulu, here’s the top three results:

The Beginner's Guide to Travel Hacking Hawaii

One thing that stands out is that Chase Ultimate Rewards points can be transferred to each airline’s loyalty program.

With that in mind, a card like the Chase Sapphire Preferred, with its generous welcome bonus and lower minimum spend, is on top of my list.

Compare this card to other top travel credit cards

What’s nice about the Chase Sapphire Preferred is that you earn 2X points on travel. This is quite handy for anyone who has travel expenses for their job, they get reimbursed for.

Also worth mentioning is that Inter-island flights can be booked with United, a transfer partner of Chase’s,  for 6,000 points. Inter-island flights can get pretty pricey (around $300 for a round trip). So, if you’re wanting to island hop, United Miles come in handy.

The Chase Sapphire Preferred happens to be my top recommendation for beginning travel hackers. 

Compare this card to other top travel credit cards

Here’s what I like about the card:

  • The lower annual fee makes it easier to keep the card open, which helps your credit history
  • Earning transferable points e.g. Chase Ultimate Rewards, American Express Membership Rewards (compared to points directly with airlines, e.g. United) expands your options both short and long-term
  • Chase’s airline and hotel transfer partners cover just about every travel goal imaginable

Option # 2 – CITI® / AADVANTAGE® Platinum Select® World Elite™ MASTERCARD®

How It Works: With this card you’ll earn points with AAdvantage, American Airlines’ miles program. These can’t be transferred, so you’ll want to make sure of the availability from your destination and desired travel time.

Other benefits of this card include:

  • Earn 2 miles for every $1 spent on eligible American Airlines purchases
  • First checked bag free on domestic American Airlines itineraries
  • No foreign transaction fees

For those who travel with American Airlines throughout the year, this card makes a lot of sense.

Picking the Right Card to Book Your Flight

Once you pick a card that’s right for you, it’s time to maximize the card’s benefits.

What exactly does that mean?

You want to make sure to:

  • Hit the minimum spend requirements to get the bonus
  • Take advantage of bonus category spending, e.g. 2X points for every dollar spent on travel
  • Review any other benefits of ways to earn points, e.g. adding an authorized user

Compare the top travel reward credit cards

The Beginner’s Guide to Travel Hacking Hawaii: Hotels

Let’s now look into ways to save on hotels.

Everyone has different preferences here.

For some a place to sleep and store their luggage is all that’s required. Others might prefer high-end hotels.

Let’s look at a low, middle, and high-end option.

Option # 1 – AirBNB/HomeAway

If you’re traveling with kids or a large group, this is my preferred way to stay. There are plenty of options all over the island.

For our 2015 trip, we had a two-story Villa right outside St. Regis Hotel in Princeville for $143 a night.

There’s all sorts of price ranges here but if you’re looking for a cheap place start with AirBNB and Homeaway.

Option # 2 – Priceline / HotWire

If you’d like to stay in a hotel, one way is through Priceline or HotWire.

With HotWire, you’re booking a hotel based on features and location. With Priceline you’re actually putting in a bid.

You don’t know which hotel you’re staying at until you actually book.

The key with both of these websites is to use BetterBidding. This is a forum where users go in and insert their successful/failed bids and the hotel they’re staying at.

So, if someone says they booked a 5-Star Hotel in Princeville for $200 a night, you can then try and bid lower or have some more certainty about the hotel you’ll be staying at.

Option # 3 – Points

Just as with flights, there are ways to book hotels for free or next-to-nothing.

You’re first step is finding out which hotel loyalty programs allow you to book reward stays.

To see my options, I like to use a site called Hotel Hustle.

With Hotel Hustle, I enter in my destination and it tells me which hotels in the area are available for booking with points.

Once I know my options, I can backtrack to see how to accumulate enough points to stay at a hotel.

Let’s look at an example.

Say my goal is to stay at a minimum four star hotel on Honolulu for five-nights.

I’d start by entering the trip details into hotel hustle.

One option that caught my eye was the Hyatt Place Waikiki Beach. This is a category 3 hotel within Hyatt, which means I can book it for 12,000 points a night. In other words, I’ll need to accumulate 60,000 Hyatt points to book the hotel.

Again, Chase Ultimate Rewards is a transfer parter of Hyatt. That means I’d probably be looking at ways to earn more Chase Ultimate Rewards.

A few options:

  1. I can apply for another Chase card, such as the Chase Sapphire Reserve to earn the points.
  2. I can look into flight options, which don’t require a Chase card, e.g. earning points through American Express Membership Rewards and transferring them to an airline like Hawaiian Airlines.
  3. If I have a spouse, we can combine points within our accounts

Whatever option I choose, I know what I have to do and can plan how to accomplish the feat depending on my financial situation.

The Beginner’s Guide to Travel Hacking Hawaii: Conclusion

One last tip for those new to travel hacking–think long-term. A popular destination like Hawaii, award flights book up quickly. So, be ready to plan your stay well in advance.

But it’s possible to book both your flight and hotel using a basic points strategy.

Good luck!

 

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