$11 roundtrip tickets to HAWAII

This morning we bought 3 roundtrip tickets to Hawaii.

Juni is now 2 years old and charged as an adult (laaaame). But for $33 total (yes you read that right) we are all 3 headed out on ROUNDTRIP flights to Hawaii. $11 tickets sound too good to be true?

Here’s the scoop:

  1. Southwest had an insane fare announcing new routes to Maui starting at $49 one-way

  2. We are signed up for an email newsletter that sends alerts about cheap/discounted airfare

  3. We used credit card bonus points to make an already cheap fare become unbelievably cheap

Now we used all 3 of these in conjunction to get this deal and I am going to lay it all out for you about how we did just that.

Lets talk about our credit card and why its perfect for us (and you?):

Some credit cards earn travel points for every dollar spent. We personally don’t use cash because in this day and age, virtually everywhere you go accepts cards and online shopping is now king. So nearly 100% of our spending (gas, phones, food, entertainment, travel, etc) is on the credit card so we can earn points and redeem them for free travel. Our thought process is “we’re spending the money anyway, we might as well earn the points and use the benefits of it” - it’s practically handed to you when you think about it. We primarily use the Chase Sapphire Preferred card (more details below), but have others as well. There are 2 cards we recommend looking into and their pros, cons and differences:

  • Southwest Plus (Good):

    This card has a $69 annual fee. 40,000 point signup bonus (can be up to 60k at times). This card earns 2 points for every dollar spent on Southwest purchases, and 1 point per dollar spent everywhere else. Unless you’re a frequent flyer with southwest, this basically means you’ll be getting a point every time you spend a dollar (gas, food, everything, etc). The points you earn can be redeemed on Southwest for free or discounted flights. We often find cheap airfare (through email alerts) but the departure city is not where we are located. We redeem our points to get from where we are to the departure airport of the cheap flights. Example: Denver to Paris for $240 roundtrip, but we are in Phoenix. Use Southwest points to fly free to Denver and then snag that sweet deal to Europe. PS this card also means you can cancel your flight (full refund) with southwest 10 minutes before departure without penalty. Also 2 free checked bags, always.

    You can apply for this card by clicking Here

  • Chase Sapphire Preferred (Better):

    This card has a $99 annual fee. 50,000 point signup bonus. This card earns 2 points for every dollar spent on Travel and Dining. These categories are even broader than they sound. “Dining” can be Taco Bell. “Travel” includes what you would guess (airfare, hotels, etc) but also includes things like Uber, Airbnb, parking fees in a city you’re visiting, toll roads, ferries, buses, etc etc. So every dollar you spend on food or travel gets you 2 points. So those $240 tickets to Paris earned 480 points if you booked with this card (and pretty much your whole trip over there would be travel costs). See the point (dad joke)? Every other dollar outside of those two categories earns you 1 point. Here’s the kicker though - Southwest is one of Chase’s travel partners. This means that you could use the Sapphire exclusively for all purchases and then if you want to fly on Southwest, you just do a points transfer. This takes literally less than a minute and transfers 1:1 meaning your points are the same value. (you can also transfer to United, British Airways, Korean Air, Hyatt, Marriot, etc). There’s also no foreign transaction fees!

    You can apply for this card by clicking Here

Both of these cards are great on their own, Sapphire being a little better in my opinion, but if you have BOTH of these cards, the benefits are aplenty!

Story time about this morning:

Now that we have some basic information out on those two cards, and which one we prefer and why, here’s how we used it to our advantage this morning:

We received a text from my sister who lives in Oakland (and an email alert from Pomelo Travel around the same time) that flights to Maui and Honolulu were $49 dollars one-way, $98 roundtrip. What the freak??? We logged in to Southwest website (about an hour after the sale was announced), found the cheap dates (by then prices went up to $79 roundtrip), and put in our info to book. In total, with Juniper being an “adult” since she’s already 2 years old, it was $480 roundtrip for our family of 3 to spend 10 days on a gorgeous island. BUT, we are currently low on funds and really probably shouldn’t be spending that money (or going at all, but we’ll figure it out haha) AND the flights are departing out of California in May and we don’t have a clue where we will be in May, but it probably won’t be California. To solve both of those problems we fell back on points. The last 6 months though we haven’t been using our Southwest card, and had previously drained our points. So we were empty. But like I mentioned, using the Chase Sapphire we had a bunch of points saved up from recent travels (and that large sign up bonus). It took us less than 60 seconds to login to the Chase Ultimate Rewards portal and transfer the points needed to our Southwest account. They showed up immediately in our Southwest account and we finished our booking. With rewards travel, you are required to pay a fee/tax per person of $11.20 per booking.

That meant that our $480 booking just got knocked down to $33.60 and 25,000 points!

***Yes, 25k points can take a little bit to rack up, but if you use the Sapphire card you get a 50k point signup bonus. I only used HALF my signup bonus to fly THREE people roundtrip to HAWAII (enough caps?). Since I booked using my Southwest card on their website, I got double the points for that $33 (66 points), I can check 2 free bags per person if I wanted, AND I can cancel my flight day of departure if I changed my mind and still get a full refund and my points back.***


If you’re not intrigued by this point, I am confused. But here ya go - Southwest is also partnered with Booking.com and when you’re logged in to your account, you can book hotels/lodging through this portal to earn bonus points. Some hotels earn you up to 10,000 Southwest points per night.

Super Ultra Mega Bonus Perk:

When booking a hotel through this portal that earns you extra points, you can use your Chase Sapphire card to pay for the booking. This means if my hotel is $100 a night and gives me 500 southwest points (just an example), I can use my Chase Sapphire card to pay for that $100 booking and get 200 points (because its a travel purchase) for a grand total of 700 points - 200 on Chase and 500 on Southwest - and its the same cost per night that it would be normally on booking.com anyway. Its literally a WIN WIN WIN WIN WIN scenario. Its like the movie Inception, it just keeps freaking going… all the dining and transportation we’ll spend in Hawaii will earn double. People say there’s no such thing as a free lunch…maybe not, but there’s perks on perks on perks that make your money stretch further than you thought.

This post isn’t sponsored by anyone or anything I have mentioned above (or not mentioned). It is how we travel and genuinely just wanted to share our tips and tricks so you too can get out there. If using one of the links we provided in this article to apply for a credit card, we do get a small kickback of points if you’re approved. So if you are actually considering getting one of these cards, and you love us, feel free to use the links we’ve provided. Thanks!

Apply for the Southwest Plus card Here

Apply for the Chase Sapphire Preferred Here