Travel Hacking Hawaii: How I Booked Four Flights to Maui for $45

How to Fly to Hawaii for Practically Free

Last August I asked my mom if she wanted to go to Hawaii. She quickly shook her head no, “Too expensive.”

“Don’t worry about the money, Mom. I’ll take care of the tickets,” I told her.

A few weeks later, I booked four flights worth $3,800 for only $45. As I’m writing this right now, I’m in Maui, a lush paradise, with my fiancé, mom and uncle in tow. So, as a technically-single person without a baller salary, how did I pull it off?

Two words: travel hacking. In this post, I’ll show you step-by-step how I flew to Hawaii for practically free, PLUS a few other scenarios for how you can do it, too.

Warning: this post is pretty technical and sprinkled with terms that probably sound like gibberish to most people, like “airline partners,” “manufactured spends,” and “point systems.” With that said, this post is aimed for people who have done some travel hacking and are familiar with the concepts. Beginners to travel hacking—don’t worry, I’ll be writing a post just for you in the future. Since I’m in Hawaii right now, and am having a great time, I wanted to share how I did it right away.

How Many Points I Needed

I flew Delta by redeeming points through one of their partner airlines, Airfrance-KLM, who has a frequent flier program called Flying Blue. A roundtrip economy ticket from JFK to Maui cost 30,000 Flying Blue points, plus $11.20 in taxes. For four people, that ended up being 120,000 points and $44.80 total.

PSA: You guys, Hawaii is a “sweet spot” destination, or mega deal, in terms of using points. For those in the US, you can get a roundtrip economy ticket to Hawaii for as little as 25,000 points! Sounds like a deal, right? Well, that’s because it is. Think about it like this: I could use 25,000 points to fly from NYC to Hawaii, saving $950. Or I could use 25,000 points to fly from NYC to Los Angeles, saving $300. Which one do you think is a better value?

How I Earned the Points

I used a combination of two point systems that are both transferrable to Flying Blue: 20,000 Chase Ultimate Rewards points + 100,000 Citi ThankYou points

The credit cards I signed up for:
Chase Sapphire Preferred Card (referral link)
The offer: 50,000 Ultimate Rewards points after spending $3,000 within 3 months (NOTE: The spend minimum has since increased to $4,000 within 3 months)
Opened: July 2014

This is a card I plan to hold for a while, as I’ve found it valuable even after getting the initial sign-on bonus. I use it in tandem with my Chase Freedom card, which has no annual fee. So I earn points on Chase Freedom, then I move them to the Chase Sapphire Preferred when I want to use them.

Citi ThankYou Premier Credit Card
The offer: 50,000 ThankYou points after spending $3,000 within 3 months
Opened: October 2015
Closed: September 2016

I’m always trolling for new credit card offers. Normally, this card offers you 30,000 points but when they had a promo for 50,000 points I pounced. I did the exact thing that I tell people not to do: I signed up for a new credit card without a plan for how to use the points. I always tell people to figure out a destination, then sign up for cards accordingly. But I saw an easy way to earn an extra 20,000 points and couldn’t resist. I’d figure it out later.

CitiBank CitiGold Checking Account (not currently available)
The offer: 50,000 ThankYou points to open a new Citigold Checking Account, spend $1,000 in debit card purchases and 1 qualifying bill payment for 2 consecutive months within 2 statement cycles. Starting in the third month, I’d have to pay $30 a month just to keep this silly account open. Did not want.
Opened: April 2016
Closed: August 2016

I have a frequent flier account with American Airlines, so every now and then they send me email offers. When I saw this offer I perked up: for a relatively low threshold, I could get 50,000 points! So I signed up, transferred $1,000 to the account and linked up one of my bills. Then I set myself up for success: I put in a calendar reminder in my phone so the day the three months came I sent a secure message through the website and asked for my points. To avoid the $30 fee, once the points came through I moved them to my Citi ThankYou Premier account, promptly closed my account, and went on my merry way.

If you add it up, I had to spend $7,000 total to get the bonus points, but notice how I didn’t open up all the accounts at the same time.

How I Booked the Award

1. Signed up for a Flying Blue frequent flier account.
2. Searched for flights one segment at a time: first from NYC to Maui, and then the other direction.
3. Only paid attention to dates that were labelled 15,000 points.
4. Once I found a flight I wanted, I took a screenshot of it.
5. To confirm availability, I called Flying Blue and gave them the flight info from the screenshots.
Tip: Airline websites are NOTORIOUS for being absolute garbage, and I ran into a few website errors when trying to move forward to the next screen.
6. Placed awards on hold for 48 hours and got a confirmation #.
7. Transferred 100,000 Citi ThankYou points to my Flying Blue account (transferred instantly).
8. Transferred 20,000 Ultimate Rewards points to my Flying Blue account (transferred instantly).
9. The next day, I called Flying Blue back and gave them my confirmation # to complete the reservation.

What I Didn’t Do

I didn’t do much manufactured spend. I use my credit cards for EVERYTHING, since Mint is my tool of choice to track my spending. But still, in the worst-case scenario where I might not make the spend for a new card, I’ll grab a grocery store gift card from a place I shop at anyway or time my application for when I’m going to make a big purchase.
I didn’t open up all the cards at the same time. As a single person with relatively fewer expenses, it can be hard enough to swing the minimum spend on just the one card. $4000 in 3 months? Damn. Yeah, I’m super jealous of the families who have higher expenses. Note: If you’d like me to pay for your child’s summer camp and then reimburse me later, let me know.
I didn’t panic over my credit score. I’ve had as many as ten cards at a time, and it stayed steadily in the upper 700s. In fact, in a span of a few weeks, I opened two more cards, and my score has sailed past 800.
I didn’t wait until the last minute to book. Booking awards for four people to a popular destination is no joke, so I locked down the tickets eight months ahead of time. Part of it was because I wanted the best chance to fly there in the season I wanted (spring). Another reason was because I had 50,000 points sitting in my Citi ThankYou Premier account and two months left before I’d have to pay the dreaded annual fee. To avoid the fee I’d have to use the points then cancel the card soon after.

With these three credit cards, I earned a total of 150,000 points. After spending some of them to book the Hawaii tickets, I still had 30,000 Chase Sapphire points left for future trips.

My Top Four Planning Tips

It doesn’t matter how long you’ve been travel hacking, Hawaii can still be a difficult destination to lock down. Here are some tips to increase your chances at grabbing that award:

  • Hawaii is a popular destination, so you can’t expect to have an award waiting for you at the last minute. You need to be scheming as early as a year out. Since I needed four tickets, I booked mine 8 months in advance. The earlier you start the more options you’ll have—you’ll want to remove as many obstacles for yourself as possible. This is important especially for people like teachers and families whose schedules depend on school vacations. Remember the old adage: the early bird gets the worm.
  • For other folks, flexibility is going to be the key. Be prepared to play around with dates. Also, try searching one-ways first, instead of round-trip. It’s easier to piece together an award that way because when you search for a round-trip award, if there isn’t availability for one part of the trip, you’ll run into an error.
  • If you can’t find availability to a smaller island, try plugging in Honolulu as your destination. I find it’s easier to find availability than the other islands. Consider flying to Honolulu then paying out of pocket or using other points to fly to another island.
  • When looking for awards, make sure to plug in the 3-letter airport code. Many times if you enter in the island name there won’t be an airport match, which is confusing.
    • Hawaii (the Big Island) – (KOA) Kailua/Kona
    • Kauai – (LIH) Lihue
    • Oahu – (HNL) Honolulu
    • Maui – (OGG) Kahului

Four Real Ways You Can Do It, Too

I’ve showed you how I booked my award, but it’s not easy to replicate, especially as two of the bonus offers I used are no longer available. You might have different sets of points, fewer points to burn, or want to spend the least amount of time possible on these little schemes. So I’ve done some research and put together four practical scenarios for how you can book awards to Hawaii using various point systems. My hope is that anyone reading this could cobble together their own award right now. Note: there are other ways to redeem awards for Hawaii, like using British Avios or American Airlines, but doing a surface search, I couldn’t find any availability for the times I was checking. Yes, in theory, these awards exist, but if people can’t actually book them then I see no reason to list them here.

1. The No-BS Executive.

You want to lock down the trip with as little hassle as possible—so what if you have to spend more points to do so? Time is money.

Total Cost: 90,000 miles and $22.40
What You Get: Two roundtrip economy tickets from New York City to Maui on United Airlines
Points to Use: United Airlines
Time: 30 minutes
Pros: You can literally book this award in one lunch break.
Cons: You have to pay more points than you need to, an extra 20,000 points per ticket…
Ways to Get the Points:

  • Chase Ink Business Preferred – Earn 80,000 points after spending $5,000 in the first 3 months ($95 annual fee not waived the first year)
  • Chase Sapphire Preferred (referral link) – Earn 50,000 points after spending $4,000 in the first 3 months ($95 annual fee waived the first year)
  • Chase Sapphire Reserve (referral link) – Earn 50,000 points after spending $4,000 in the first 3 months ($450 annual fee not waived the first year)
  • United Mileage Plus Explorer – Earn 50,000 points after spending $3,000 in the first 3 months ($95 annual fee not waived the first year)
  • United Mileage Plus Explorer Business – Earn 50,000 points after spending $3,000 in the first 3 months ($95 annual fee  waived the first year)

Steps:
1. Search on United.com for one-way flights, making sure the ‘Search for award travel’ box is checked. For max flexibility, check off  ‘My dates are flexible’.

2. On the results screen, pay attention to only the Saver Award Economy dates on the calendar (the ones with the solid blue lines marked). Look at how much availability there is.

3. If you don’t have the 90,000 points in your account already, transfer them from Chase Ultimate Rewards. They should transfer instantly.

4. Complete the reservation. The final screen before you pay should look like this. It’s that simple with United!

2. The Optimizer.

You liked how easy it is to find awards on United, but you don’t mind putting in a little bit of extra work if it means saving points. You can get the same exact United flight for fewer points by booking through their partner Singapore Krisflyer instead. Taking a good thing and then making it even better? That’s the definition of optimization.

Total Cost: 60,000 points
What You Get: Two roundtrip economy tickets from New York City to Maui on United Airlines
Points to Use: Singapore KrisFlyer (they’re a United partner)
Time: 1 hour
Pros: You could get the same United flights from Scenario #1 AND save 15,000 points per ticket!
Cons: By the time the points transfer the award could be gone…
Ways to Get the Points:

  • Chase Ink Business Preferred – Earn 80,000 points after spending $5,000 in the first 3 months ($95 annual fee not waived the first year)
  • Chase Sapphire Preferred (referral link) – Earn 50,000 points after spending $4,000 in the first 3 months ($95 annual fee waived the first year)
  • Chase Sapphire Reserve (referral link) – Earn 50,000 points after spending $4,000 in the first 3 months ($450 annual fee not waived the first year)
  • Citi ThankYou Premier – Earn 30,000 points after spending $3,000 in the first 3 months ($95 annual fee waived the first year)
  • Citi ThankYou Preferred – Earn 15,000 points after spending $1,000 in the first 3 months (No annual fee)

Steps:
1. Follow steps 1 and 2 from Scenario #1 above, only paying attention to Saver Economy Awards.

2. Double check the KrisFlyer partner award chart again.

2. Take screenshots of the flights you want.

3. Transfer points to your KrisFlyer account (could take a few days).

4. With your screenshots pulled up, call KrisFlyer to book: 1-800-742-3333.

3. The Frugalist.

You’re super choosy about how you use your points, or you don’t have a ton to burn. Either way, you want to use the least amount of points possible.

Total Cost: 50,000 points + $22.40 (The screenshots below only show steps for ONE ticket. You need to fill out paperwork to book a ticket for family members.)
What You Get: Two roundtrip economy tickets from New York City to Maui on Delta Airlines
Points to Use: Korean Air Skypass (they’re a Delta partner)
Time: 2 hours
Pros: These are relatively easy to book, if you can find availability. Also, Korean Air lets you hold reservations for about 5 days. This will give you time to complete any paperwork or transfer miles safely.
Cons: Unless you’re booking an award for just yourself, there is some surprisingly old-school paperwork involved if you want to book for other using one points pool. Also, you can’t book one-ways.
Ways to Get the Points:

  • Chase Ink Business Preferred – Earn 80,000 points after spending $5,000 in the first 3 months ($95 annual fee not waived the first year)
  • Chase Sapphire Preferred (referral link) – Earn 50,000 points after spending $4,000 in the first 3 months ($95 annual fee waived the first year)
  • Chase Sapphire Reserve (referral link) – Earn 50,000 points after spending $4,000 in the first 3 months ($450 annual fee not waived the first year)
  • SKYPASS Visa Signature Card – Earn 15,000 points after your first purchase ($80 annual fee not waived the first year)

Steps:

1. To book this flight using Korean points, it’s easier to first check availability on Delta’s website. For economy flights, make sure you pay attention to only the ones that say 45,000 points. These are how you identify the awards you can book with Korean. Note: you will NOT have to actually pay 45,000 points. This step is simply to identify availability.

2. Once you find dates, log onto your Korean SKYPASS account and confirm the same flight prices out to 25,000 points, like below.

3. If so, proceed to book online.

4. If you are booking a ticket for yourself and family members, you’ll need to set up a SKYPASS account for each person, upload proof with a marriage record or birth certificate, and then link them to your account.

5. If you are booking with someone you’re not related too, they’ll have to set up their own SKYPASS account and book their ticket separately.

4. The Families.

The name says it all: you’re travelling in a group of some kind, usually in packs of 4. You want the option that tends to have the most amount of availability.
Total Cost: 120,000 + $44.80
What You Get: Four roundtrip economy tickets from NYC to Maui on Delta Airlines
Points to Use: Airfrance-KLM Flying Blue (they’re a Delta partner)
Time: 3 hours
Pros: If you look early enough, there tends to be lots of availability. The flights also tend to be pretty good, in terms of flying time and stopovers.
Cons: The Flying Blue website can be total garbage, and it’s likely you’ll run into a technical error when trying to book. Be persistent.
Ways to Get the Points:

  • Chase Ink Business Preferred – Earn 80,000 points after spending $5,000 in the first 3 months ($95 annual fee not waived the first year)
  • Chase Sapphire Preferred (referral link) – Earn 50,000 points after spending $4,000 in the first 3 months ($95 annual fee waived the first year)
  • Chase Sapphire Reserve (referral link) – Earn 50,000 points after spending $4,000 in the first 3 months ($450 annual fee not waived the first year)
  • Citi ThankYou Premier – Earn 30,000 points after spending $3,000 in the first 3 months ($95 annual fee waived the first year)
  • Citi ThankYou Preferred – Earn 15,000 points after spending $1,000 in the first 3 months (No annual fee)

Steps:

1. Log into your Flying Blue account and start searching segment by segment. To use the least amount of points possible, pay attention only to dates marked as 15,000 points on the calendar.

You can confirm the total points needed by clicking through a few screens until you get something like these.


2. Once you find flights you like, if you have enough points in your Flying Blue account already, proceed to try booking online.

3. If you don’t have the points in your account yet, take screenshots of each segment.

4. Call Flying Blue to confirm availability: 1-866-434-0320.

5. Once availability is confirmed, ask to place a hold on the reservation, writing down the reservation #.

6. Transfer the necessary points to your Flying Blue account.

7. Once the points have arrived, call Flying Blue back, give them your reservation # and complete the booking.

Takeaways

As you can see, just by signing up for one credit card and redeeming as little as 25,000 points, you can book a flight to Hawaii for basically free. And I know tons of folks signed up for the Chase Reserve card when the bonus offer was 100,000 points. Looking at the four scenarios above, do you see what you can do? That’s right: you can book FOUR roundtrip tickets to Hawaii with just the ONE card. If not, there are lots of ways to mix and match different points systems. And using partner airlines, you can get the most valuable redemptions.

With a little bit of elbow grease and creativity, a vacation to Hawaii no longer has to be a pipe dream.

Have you travel hacked Hawaii or are you planning to? Let me know your tips!

Image: The Luxe Strategist

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