Travel Hacking: How I Booked Four Flights to Hawaii 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 Reserved – 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)

1. Search on 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 Reserved – Earn 50,000 points after spending $4,000 in the first 3 months ($450 annual fee not waived the first year)
  • Starwood Preferred Guest – Earn 25,000 points after spending $3,000 in the first 3 months ($95 annual fee waived the first year)
  • Starwood Preferred Business – Earn 25,000 points after spending $5,000 in the first 3 months ($95 annual fee 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)

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 Reserved – Earn 50,000 points after spending $4,000 in the first 3 months ($450 annual fee not waived the first year)
  • Starwood Preferred Guest – Earn 25,000 points after spending $3,000 in the first 3 months ($95 annual fee waived the first year)
  • Starwood Preferred Business – Earn 25,000 points after spending $5,000 in the first 3 months ($95 annual fee waived the first year)
  • SKYPASS Visa Signature Card – Earn 15,000 points after your first purchase ($80 annual fee not waived the first year)


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 Reserved – Earn 50,000 points after spending $4,000 in the first 3 months ($450 annual fee not waived the first year)
  • Starwood Preferred Guest – Earn 25,000 points after spending $3,000 in the first 3 months ($95 annual fee waived the first year)
  • Starwood Preferred Business – Earn 25,000 points after spending $5,000 in the first 3 months ($95 annual fee 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)


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.


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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  • Finance Patriot

    Thanks so much for posting this. I was curious how you got to HI on so few points. The face that you even took 3 with you makes it all the more impressive. We (wife and me) only started travel hacking in November, but in addition to our already booked trip to Puerto Rico, we have 185,000 chase UR points in reserve, 114,000 Marriott points, and am now working on an AmEx biz platinum 100,000 points targeted offer (still can book flights for a year with 50% points refund!). So ya, I’m all in.

    The good thing about you getting married is travel hacking is actually EASIER as a married couple. Want to stay under 5/24 for Chase? No problem, way easy for one spouse to stay under and the other one to go on a application spree. We don’t manufacture spend. We simply apply one card after another.

    A tip about the business Ink preferred, right now they have a “referral” bonus of 20,000 points, so you could refer your fiance, he can get 80,000 points and you will get 20,000 points once he meets the minimum spend bonus. As a couple, or perhaps even the same household, you can transfer points to each other back and forth or just use your points seperate. My single brother always jokes to me that he wishes he had a “points wife.”

    When or if we decide to go to Hawaii, I will definitely consider Flying Blue. Thanks for this article, I will reference it.

    • Sounds like you caught on quick to the points game!

      Grrrrrrr, I’m already way over 5/24 with Chase so I CANNOT maximize that Ink referral deal. Super bummed.

      LOL at “points wife”. I used to wish that too when I was single. For me, sharing my points with someone else was a gauge for how serious I feel about them. Example: when my fiance (then boyfriend) and I were planning our first trip together to Paris, I had to think long and hard. He was an an “unaware” of the points game and I had to decide: do I want to share my hard-earned points with this fool? Well, turns out yes, and obviously, I make him sign up for credit cards now. He says he’s my “points mule” and he’s not wrong, hehe…The plus side of him signing up for credit cards is his credit score has greatly improved.

      So I just got back from Hawaii, and had a pretty great experience on the Delta flight (they are the partner for Flying Blue). We had 4 legs total and there were absolutely no issues with delays, nasty flight attendants, etc. The last leg, the flight was full so somehow they put us in Delta Comfort plus, which was a nice treat. I would definitely recommend using Flying Blue or Korean points for a Delta flight to Hawaii if you can.

      What’s the minimum spend for the Amex offer? And the 50% rebate sounds sweet–do you have to book a biz or first class flight, though? Also remember Singapore is a transfer parter for membership rewards and some deals can be had there, as well.

      • Finance Patriot

        So my offer was targeted via snail mail. It was 100,000 MR points after a 5k spend in 3 months. It sounds like a lot but we are a family of 4 and it’s no problem for us to meet that spend.

        So the rebate for the Amex Biz applies to ANY first class flight (on any airline) or any coach flight on your selected airline of choice. So if I choose Southwest or Delta, for example, I am stuck with them until January 1 for the points rebate. You can change airlines once a year in January.

        Nominally, the points are only worth 1 cent each. However, with the 50% points refund, they become worth 2 cents each, or $2,000 total if the offer is maxed out properly. These points are ideal for wanting to chose a specific flight, as you can buy them through the Amex mall at normal flight rates and not have to worry about award seats.

        Another small advantage to using the Amex points for flights is you still earn frequent flyer miles from that airline, for those flights. The airlines treat those flights, booked via Amex, as “revenue flights.” In future value, that’s worth perhaps an additional 5-10% of the flight points.

        Amex has some cool offers, though most are whack. I accepted an offer for a $25 statement credit for spending $65 at (38% discount). That offer was definitely worthwhile.

        • That explains why when I Googled it the MS was 15k in 3 months. I thought, damn, is Finance Patriot secretly ballin’? I would avoid using Delta as the airline of choice; their mile values really suck.

          I’ve taken advantage of some of the Amex offers, too. It has come to a point where I won’t let my fiance buy anything online without checking the portals.

          • Finance Patriot

            I think I was targeted due to my website registration. Anyway, you can always call Amex to see if you qualify “for a higher offer.”

  • Your Average Dough

    LOVE this post! So so helpful!

    My husband and I started with the Chase Sapphire Preferred and upgraded to the Reserve to get the 3% over the 2%. We also use it with my Chase Freedom to combine rewards! I definitely think this is the best way. We also use our cards for absolutely everything and just pay in full every month so we just get the rewards.

    It’s funny you mention you’re a frequent flyer with American because so are we.

    We’re planning to go to Hawaii around a year from now, so I’m really happy I read this post now. I am totally using your tips! We’ve got enough points to cover our flights and hotel, so we’re thinking about booking everything through Chase if possible!

    Thank you 🙂

    • Yay, thanks!

      Oh man, the full suite of Chase credit cards is a deadly combination. I also have all three, and have them segmented for different uses. Even though the Freedom one seems kinda useless, I’ve been able to rack up thousands of points by strategically using their 5% rotating categories. For example, through June you get 5% cashback at groceries and drugstores, so you bet I’m moseying into stores now to get gift cards and stuff for future use. I also booked our car rental through the Chase portal and got 10% cashback!

      Nice you’ll be able to essentially make your whole vacation free by redeeming for both airfare and hotel. For our lodging we used the Chase Reserve credit twice ($600) in both calendar years to reduce the cost of an Airbnb. Late in 2016 we bought an Airbnb gift card, then once 2017 rolled around, we bought another gift card. Then added both cards to my Airbnb account as credits. Because we had 4 ppl we would have been cramped in one room. I had enough Starwood points to book a hotel but decided against it for the previous reason, plus I hella value the Starwood points and want to save them for aspirational things like biz class seats to faraway places.

      Did you see the latest deal for American where you can get 10k points by shopping through their portal 4 times? With Mother’s Day coming up and people buying flowers online (the AA portal has several flower partners), it’s pretty low barrier to entry in terms of earning points.

      Let me know if you have any more questions on hacking Hawaii–I’d be happy to help!

      • Your Average Dough

        I did not see the American deal! Thanks for the heads up. Also, I never thought about buying gift cards from grocery stores to make sure I take full advantage of the 5% cash back with Chase Freedom. That’s so smart! We also have American Express Blue Cash Preferred which offers 6% cash back at grocery stores, so that one usually takes precedence, but gift cards is a great idea because we can buy them in advance for birthdays or Christmas!

        Since our trip to Hawaii will just be my husband and I, we definitely prefer doing a hotel. I love rentals for group vacations, though. We’re just really bad as being loyal to the same hotel chain because we always find something more appealing at different chains or choose destinations that don’t have the chain we’ve been accumulating points for. I’m trying to get better with it, but we also have our hearts set on the Four Seasons in Maui, so eeeeeek haha.

        Thanks so much for all the valuable input and the offer to help! I will definitely keep you posted! 🙂

  • Jax

    This is so awesome. Thanks for all the detail in this post. I am still a novice at travel hacking. My only experience was getting a Southwest credit card to put our new roof on, so that we could use the points to fly to California to see my family. I was pretty pleased with myself. Now my sights are set a little higher!

    • Hey, everyone has to start somewhere, right? My first award flight I spent way too many points than I needed to, but sometimes it’s about just getting from point A to B.

      I see a lot of PF bloggers have the Southwest card and it def has flown under my radar until recently. I was like, what is this card? I always forgot Southwest existed since they advertise very little, but it really seems people have been able to get amazing deals. And now that they fly outside of the continental US, it’s even better.

      And yes, I wanted to show that a place that many people would consider to be “fancy” is actually within reach! I definitely think Hawaii is a great use of points for the value you get. All you need is 25,000 points for one ticket!

  • This is a great overview and really appreciate the detail! I’m a newbie trying to figure out the whole travel hacking world so being able to see exactly how it’s done is amazing. I did my first travel hack for my honeymoon, getting our flights for free through a sign up bonus – about $1,000 worth of flights between the two of us. (nice thing was card was a no annual fee card too, so didn’t take much work since I also never have to close the card). Will definitely be bookmarking this for later use.

    One thing, I haven’t noticed too many travel hackers talk about Citi Thank You Points. Typically I only hear about the Chase points or the Starwood points.

    • Thanks for appreciating the detail! I spent a lot of time on this post, especially the real scenarios, because I wanted to make sure it was practical, and not just me bragging, ya know? It makes my day to know that the detail helped, because there’s a ton to process in travel hacking and it’s easy to get overwhelmed.

      Nice job on the honeymoon travel hack. That’s basically what this game is all about. Having nice experiences without paying as much for them. If you’re looking for another card that doesn’t have an annual fee and can complement the Sapphire card, definitely consider the Chase Freedom card. At first glance, the signup bonus is meh, but where it shines are the rotating categories where you can get 5% cash back. See the calendar here:

      So from now until June, I’m probably going to pick up a couple gift cards from my grocery store, and Amazon gift cards from drugstores. Last year, when the category was drugstores, I bought a couple Amazon gift cards and we bought a $500 TV from there. So at 5 pts per dollar we got 2,500 points for almost no effort. I’ve been able to rack up thousands of points by using this card solely for the 5% categories. And since you’re married now, you can transfer Chase points to your wife, and vice versa, and also move them to pad your Sapphire account for redeeming awards.

      The Citi card I only got because I already had the Chase and Starwood cards, and I was looking to diversify my points portfolio. I would only recommend getting Citi if you’ve already gone through the Chase and Starwood cards first. Citi doesn’t get a lot of action because they don’t have nearly as many transfer partners. To be honest, at first, I thought I made a mistake getting the card because it wasn’t obvious how to use them on these obscure airlines. But with some digging I figured out how to make it work.

  • Luxe,

    This is a bad ass overview of how to do this. My wife and I always think we could do it but never want to open cards and deal with the hassle. You make it seem reasonable that we could manage this with ease!

    I typically just use my venture card for everything to earn travel points. I use it for absolutely everything and it saves us a lot for travel every year. I will have to look into this Chase idea.

    As you were on a beach in Hawaii I was in your neck of the woods (Manhattan). Great weather in NYC but hopefully the beach was awesome! Thanks for this post!

    • Nice to hear from you. Next time you’re in the city, hit me up! Deals abound in NYC.

      I had the Venture card too, but I totally failed on bonus points by not paying attention to the 3 month deadline. Experienced travel hackers–they mess up, too.

      I totally get the “hassle” part of it. But that’s why I included several scenarios, because I know some people just want to get in and out, and some are OK with doing more work to get the best deal. I’m glad I made it seem manageable. If you only open 1 or 2 cards, you can still get some great scores. Once you do it once, it’s pretty addicting.

      If you decide to get Chase Sapphire Preferred feel free to use my application link 🙂

  • Loved this overview! I feel like a lot of guides don’t go into full end-to-end descriptions of how to travel hack. This is a perfect introduction with examples to boot! Imma send any friends with travel hacking questions your way for sure. <3

    My only quibble would be saying the additional price was only $45. To me, the alternative to travel hacking like this would be to just use cash back credit cards, where you get 2% or more back, meaning at least $140 you didn't get back for the total $7000 of minimum spends. Still a screaming deal for four to Hawaii!!! (and literally every other person writing about travel hacking discounts it too, so I totally understand)

    • Hey Felicity,

      Thanks for checking this out. I spent a lot of time looking at other travel hack posts to see how I could make mine more detailed, so love that you noticed the *werk* I put into it, haha. Not sure I’m understanding the point about the cost. Do you mean I have to factor in the annual fee of the credit cards? In theory, you’d be spending how you normally would, and the points are just a nice byproduct.

      • Yeah, of course!

        So I’m not talking about annual fees (though I guess those should also be considered), more looking at the opportunity cost of using travel cards for the minimum spend vs. straight cash back credit cards. Though, now that I’m thinking about it, you’re usually getting 1-3% back in points on travel cards (that you still accrue when working up towards the minimum spend), so my original point might be moot anyway. I guess technically the $1k on the debit card would still apply though, meaning a measly $20 in opportunity costs.

        I originally was super confused about travel hacking and thought it was just obtaining points through credit cards purchases (as opposed to curbing through cards), so I was really confused when people would talk about “free” vacations, when they could have been accruing that vacation money with cash back (and especially considering those points could potentially disappear in a year). And…apparently I’m still not the clearest on the finer points of travel hacking XD

        • Oh, I see! Hmm, I never thought about using cash-back cards for flights. I use them too, but for other stuff like ground travel, etc. The way I calculate the value is by taking the out-of-pocket cost and then dividing that over the # of points used. So in my case, it’s about 3.16 cents (3800/120000). If you use a cash-back travel card like Barclays, you’ll get 40k points bonus after completing the minimum spend. Say, with your normal spend you’ve not accrued a total of 50k points. The most you’ll be able to redeem with those points is about $500 worth of travel. Nice, but not $3,800. Anyway, travel hacking is confusing af, like you said. I’ve held off on writing about it until I can wrap my head around doing it in a way that’s clear and easy to understand.

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  • Woot, love how you broke this down into details. I do something similar (different credit cards of course as I’m from tropical Asia) but I just flew to Toronto on awards tickets, and it really IS a great way to travel. It’s often been difficult for me to explain to people exactly how I do it on my like-you-not-baller salary; guess I’ll just forward them here next time someone asks!

    • Thanks! Some of my posts I’m not sure how I managed to put them together. I’m pretty sure I wrote this one while I was on the vacation, actually! Yeah, I don’t see why you would pay for travel if you don’t have to! But yes, it’s definitely complicated and all of these rules are easy to overwhelm someone who’s new to this stuff. But very well worth it to me, especially for premium experiences. Thanks for sending folks this way!

  • randomizationme

    I love the breakdown !

    Quick question: is it worth it to keep the credit card that charges annual fee such as the Chase Sapphire Credit Card after the first year? Or is it better to just close the card and open a new one when we need them in order to avoid the annual fee?

    *I am not a frequent traveler so I will not always be utilizing travel points.

    • Hi, thanks for stopping by!

      I personally don’t mind annual fees, because what I can get out of the credit cards is WAY more. So I’m always trying to rack up the points. If you aren’t going to be using travel points in the future, I think you’d want to cancel the card if you don’t like fees. Keep in mind you have to wait 24 months to reapply again and get the bonus. The other option is to downgrade your account to the Chase Freedom card. No annual fee and you can keep earning points for cashback or to transfer back to the Chase Sapphire Preferred when you reapply.

      Hope that helps!

      • randomizationme

        That’s a smart idea!! I didn’t think of transferring points from different Chase cards, thanks!

        • Yep, you can combine points from your Chase accounts!

          Just make sure you strategize because Chase has a rule where you will be rejected if you’ve signed up for more than 5 credit cards within the past 2 years. So, it’s smart to start with the Chase cards first, if you’re trying to use points.

          You have two no annual fee options:
          Chase Freedom (what I’ve used forever): if you use this link (referral) you’ll get $150 bonus if you spend $500 in the first three months:
          Pro: they have 5% rotating calendars, which I use. This month you can get 5% on Walmart and department stores. Since I shop online a lot, I can really boost my points this way.

          Chase Freedom Unlimited: you get $150 bonus if you spend $500 in the first three months.
          Pro: you get a flat 1.5% per dollar in case you don’t feel like keeping up with categories, etc.

  • Man Overseas

    Thank you for the detailed travel hack post. You’ve gotta be the hardest working woman in the blogosphere! Bookmarking this because Kauai is our favorite island in the world. We’d go more often if we could find a way to do it cheaper. Thank you!

    • Hiya! Glad you found this post useful. And yeah, I wrote this WHILE I was on the vacation, so appreciate the hard work note!

      I really wanted to go to Kauai, but couldn’t find the tickets. Maui was lovely, though, and had a nice mix of activities for the whole family.

      Travel hacking Hawaii is such a good deal in terms of points, so hope you can make it happen!

  • kyle

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