There’s still so many places that I want to visit in the world: Hawaii, Bora Bora, Australia, Europe, Turks and Caicos.

The list goes on and on.

What appeals to me more when I read these amazing travel hacking stories of people touring the globe while paying little fees because they were able to use frequent flyer miles.

This is commonly referred to as “travel hacking” and I’m all about it.

As most people know, traveling can get expensive.

Traveling with 3 kids can get REALLY expensive. When Geoff from contacted me about a guest post I immediately bit….kinda.

My requirement for the guest post was to show me (and my readers) how I could take my entire family to Hawaii for basically free.

How’s that for a tall order for a guest post? :)

Let’s see what Geoff has to say….

free hawaii vacation

When Jeff Rose asked me to demonstrate how his family could travel somewhere exotic using rewards points, I was like “no biggie” – until he dropped the bomb that he had a family of 5.


My household family consists of three members, and one of those is a spoiled dog. Still, I pulled myself together and accepted this assignment. I always enjoy a good challenge.

Below is the result of me digging me heels in on this family travel stuff. I hope you’ll use these tips to get your family (of 5!) to Hawaii – one of the most sought out destinations in the world.

Reward Yourself

Over at my blog, Noobtraveler, I educate readers on how to travel with reward miles & points. “Traveling classy for pennies” is our motto. A big way this is achieved is through rewards credit cards, which happen to be the quickest and easiest strategy for accruing lots of miles & points, and fast. First, let me cover the bases.

You shouldn’t apply for any credit cards if you:

  • can’t manage your spending
  • don’t have a good credit score
  • can’t pay your bills on time
  • are looking to apply for a loan soon

But, if you have a good credit score and are responsible with your spending and payments, you can reap the benefits of rewards credit cards – MEGA sign-up bonuses and a mile or point for EVERY single dollar you spend.

And if you’re worried about managing your credit cards, check out Card Watchdog. It’s free.

Trust me, the rewards you can pile up and use for virtually free travel are tremendous. I now fly first and business class internationally with my wife, and there’s nothing special about us. Believe me on that.

Lufthansa Business Class
Lufthansa Business Class

Going to Europe used to be a big dream for us, but now through rewards loyalty programs, it’s become a reality. I love rewards points because I work hard for my money, so it feels good to be earning something back on every dollar I spend. My mortgage and auto loan payments, charitable giving, groceries, gas, and other everyday expenses – it all adds up, and it’s nice knowing I’m getting up to 5x points per $1 on many of those purchases.

It’s worth noting that business rewards cards play a big part in maximizing my rewards for travel.

Note: Anyone who has an explainable business can apply for a business rewards card. You don’t have to be incorporated to apply. This allows you to reap benefits beyond your personal spending – your business spending will pile on the rewards too!

Ok, so there’s value in rewards loyalty programs. Here’s how you can leverage the rewards for family travel to Hawaii. Let’s go.

Getting to Hawaii

There are many ways to get to Hawaii from the landlocked States, especially from the West Coast. However, Jeff will be leaving from St. Louis, so I searched from there for flights to Honolulu. I also assumed that Jeff’s three kids are too old to fly for free.

I have many readers who split up their reservations when traveling with more than two people to make booking easier.

Also, the further out you can plan, the better, especially when kids are involved because of school. That means looking for award travel in June/July, which is pretty competitive. You may have better luck looking in early December/January around the holidays.

Of course, during the school year is better when looking for award space, but I’m not sure taking your kids out of school for 2 weeks is an option (although I don’t think they would mind).

TIP: when searching for award flights, search segment by segment or city by city. You’ll see better results this way. Then, once you find the flights you want, do a multi-city search and, voila!

Let’s get our hands dirty and figure out the best routes for a family of 5 from mid-America.


Starting Feb. 1, it will cost 45,000 each or 225,000 United miles total for 5 round-trip tickets in economy to Hawaii. Currently it’s 40,000, but United has made certain changes to their award chart starting Feb. 1, this being one.

I was able to find 5 seats from St. Louis to Denver to Honolulu (one-way). Boom. The damage is 100,000 (going to be 112,500) United miles and $25. Or you could pay $5,883.50. You choose.

United Family of 5
United Family of 5

Alright, so it’s 225,000 United miles for a family of 5 to fly round-trip to Hawaii. That may sound like a lot, but it’s actually pretty doable with a couple of credit card applications.

Since United is a transfer partner of Chase’s Ultimate Rewards program, you have a lot of options when it comes to earning points for United flights.

There are often sign-up bonuses of 50,000 miles on the United personal and business cards. And then there are the Ultimate Rewards cards: Sapphire Preferred, Ink Bold, and Ink Plus. The Sapphire Preferred currently comes with a bonus of up to 45,000 points, and the Ink cards have a 50,000 point sign-up bonus.

So, Jeff and his wife could each apply for a personal credit card that earns 50,000 points, and then both sign up for a business card with a sign-up bonus of 50,000 points, and they would be sitting on 200,000 points. (This is obviously the fast track. You can always be more conservative with your applications and earn points over time with your spending.)

The 200,000 points they would have would be from the sign-up bonuses alone, and doesn’t include any spending done on the cards. And there are some great spending bonuses of up to 5x points per $1 with these cards, so it wouldn’t be hard to get the additional points needed for the airfare. We’re looking at over $11,000 in value! I told you, there’s crazy value in rewards cards.

British Airways (AA) 

Ok, so this wouldn’t necessarily apply to Jeff, unless he found himself wandering around the West Coast, but getting to Hawaii with British Airways Avios points can be a steal from the West Coast. This is because British Airways has a distanced-based award chart, meaning short-haul flights are cheap.

And I know you might be thinking, “British Airways doesn’t fly to Hawaii from America.” True, but their partner American Airlines does, and you can redeem Avios for American Airlines flights. 

Here’s an example:

British Airways to Hawaii
British Airways to Hawaii

As you can see, there are (7) open seats on this flight from LAX – HNL, and it’s only 12,500 Avios one-way (25,000 roundtrip) and $11. So for a family of 5, it would cost 125,000 Avios.

It’s easy to earn 125,000 Avios since there’s a co-branded British Airways card that’s currently coming with a 50,000 sign-up bonus. And British Airways is a transfer partner of Chase’s Ultimate Rewards and American Express’ Membership Rewards programs. There are plenty of great cards that earn those points (see first example). So, yes, it’s easy to build a big Avios balance.

American Airlines – US Airways

You may not know this, but American Airlines and US Airways are in the process of merging. This means you can now burn AAdvantage miles on US Airways flights, and US Airways Dividend miles on American Airlines flights. Make sense?

With American Airlines, it’s only 17.5k AAdvantage miles one-way or 35,000 round-trip to Hawaii. Plus, if you hold the Citi AAdvantagePlatinum Select card, you will get 10% back on your redemption. Smoking deal.

5 AA to Hawaii
5 AA to Hawaii

It was challenging to find 5 award seats searching, but I did it just in time to get away before the Christmas holidays. All in, it’s 175,000AAdvantage miles round-trip for a family of 5 to fly to Hawaii. That’s excluding the 10% discount you will receive if you hold the Citi AA card.

You could also book this same exact flight on US with Dividend miles for 40,000 miles and $60 per person. And you’d receive an additional 5,000 miles discount if you hold the US Airways co-branded rewards card. See, these cards have perks beyond the sign-up bonuses.

One annoying thing about US Airways award bookings is that they will price out the same if they’re a one-way or round-trip booking. I don’t like that at all.

The good news is, there are plenty of cards to earn miles to fly on US Airways or American Airlines metal. There’s currently an offer to earn 40,000 Dividend miles on the US Airways co-branded card, and there are regularly 50,000 miles offers on the Citi personal and business rewards cards. Between a couple, it would be very easy to earn close to 300,000 AAdvantage and Dividend miles just through applying and meeting the minimum spending requirements.


If you’re completely new to rewards travel, this may overwhelm you. And I won’t lie, booking award tickets for a family of five to Hawaii will take work. But the value is worth the work if you’re up for it! Believe me. And if you start early enough with your award booking, it can definitely be done. It’s not a stretch to earn enough miles within a few months through rewards credit cards to make this trip (or another dream trip) happen. You can find the rewards credit cards mentioned in this post here.

If you’re unable to pay off your credit card bills in full each month, or you have a less than good credit score, rewards cards aren’t for you. The interest you’ll pay will most likely negate the rewards you’ll earn, and you’ll need good to excellent credit to be approved for these cards. But if you’re in the other boat, the value is incredible.

Maximizing rewards points in this manner will save you over $10,000 easy on the trip. And we didn’t even discuss hotels yet. But this has gone on long enough, so that will have to wait for another day.

Happy Travels!

Geoff Whitmore is lead traveler/writer at, a blog dedicated to educating its readers on reward travel, travel tips, and cost-saving travel techniques. The blog particularly focuses on new travelers (or as they like to call them, “Noobs”), and it teaches its readers how to save BIG. All the while, the site maintains a humorous writing style that is both fun and informative.


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