The Challenge: Book a Summer Vacation
After coming back from our trip to New York and Canada last April, I knew that I needed to get my act together and plan a summer vacation with the family. However, it wasn’t that easy. Why? It wasn’t about not having the means. In our case, I have earned a lot of miles and points that could get all of us anywhere in the world.
Ethan and Madison kept asking me if I had booked something for this summer. We make it a point to go to Hawaii every summer with the kids. But with their insanely busy schedule, it was just way too difficult to plan. The ONLY time that all of us could be together? The week of the Fourth of July (it was tough to find awards for that timeframe). Lord knows I tried getting awards with British Airways, Korean Airlines,

Southwest and tried for almost every destination (Maui, Oahu, Kauai, Big Island, Cancun, Belize, Puerto Vallarta, Cabo San Lucas, Punta Cana, Puerto Rico…you name it). I could NOT book a thing. So we decided to just do a local getaway during the 4th (perhaps San Diego or back to San Francisco).
It’s okay to plan at the last-minute
Vacation Plan B – While others plan their vacations way ahead of time, the beauty with earning miles and points, it affords me the flexibility to plan something at the very last minute. And that’s exactly what I did. Since I couldn’t plan a Hawaii trip for all six of us during the week of the 4th of July (that’s Plan A), my next best choice was to go to Hawaii WITHOUT Ethan and Madison. In mid-June, I booked a last-minute trip to Hawaii (Big Island) for four…Nancy and I planned to bring Caitlin and Evan to the Big Island in August. This trip was flying from LAX to Kona (direct flight) roundtrip.
How much? Well, let’s think about this for a second. It was booked for early August (which is still in the heart of the summer (high season in Hawaii). If I paid for the tickets out of pocket, our four roundtrip tickets with Delta would’ve cost us $736 each or $2,945 total for four (see screenshot below). But you know better that I didn’t even spend anything close to that. I used my points that I earned with my Ultimate Rewards earned with cards like the Chase Sapphire Preferred and also the Chase Sapphire Reserve used 25K/person + $11.20 – that’s 100,000 Ultimate Reward points and $44.80 out of pocket!!!! Yes!!!! just $44.80. For details on how I booked this with Korean Airlines….click here.
Imagine that!!! A last-minute trip to Hawaii for four at $44.80. How exactly did I book that? I had to check availability with Korean Airlines (a partner of Delta Airlines). For details on how to get started with doing this, I wrote a blog on How to get $11 flights to Hawaii.
I had a choice….pay $736 per ticket or let my points earned with a credit card like the Chase Sapphire Preferred or the Chase Sapphire Reserve could get us there and only pay $11.20 per person. I chose to pay less.

What about a vacation including Ethan and Madison?
So that’s it, right? Well….not exactly. The whole trip to the Big Island seemed incomplete knowing that Ethan and Madison wouldn’t be joining. So, I kept checking for a chance that something might pop up. Well, lo and behold, it did. Just a few days after I booked our trip to the Big Island for four, availability showed up for ALL six of us to go on the week of the 4th of July. This time, it was with British Airways (partnered with American Airlines). How much? Again….let’s pause for a second. This is not only in the heart of the summer, but it’s around a major US holiday – the Fourth of July. Each ticket if I paid in cash would’ve cost us $967 per person or $5,798. Did I pay anything close to that? You better believe that I did not (see screen shot below)
I paid using points earned with my credit cards, it was 25,000 points per person + $11.20. So with the six of us, that was for 150,000 points + $67.20. Imagine that!!! $67.20 and ALL six of us are bound for Kauai!!! The odds were ever in my favor.
So you might be asking, how could one earn all these points? For starters, sign up for the right credit card….not just any card. This is very possible with cards like the Chase Sapphire Preferred or the Chase Sapphire Reserve.
Just by signing up and meeting the required spend, you get 50,000 bonus points which is good enough for 2 roundtrip tickets to Hawaii. For more details, read this blog entry on how to get started.
How did I book this Kauai trip?
For this booking I did a quick transfer from my Chase Ultimate Rewards account to Korean Airlines. So I had to focus my energy on getting something in August and to those who are in search of a last-minute Hawaii vacation this summer…it can be had with using miles and points! It just happened to me. Flexibility is key!!!
After discussing this with my kids and Nancy, I began the booking process when I found availability, transferred the 150K points from Chase Ultimate Rewards to my British Avios account. Done!
I actually pulled it off….AGAIN!!! I can’t believe it. We all get to go to Hawaii again….we were on Maui last year also during the 4th of July via British Airways (booked it last minute as well). So yes….booking Hawaii last minute is very possible. This is now my 3rd year of booking within 3-6 weeks of travel dates and British Airways came through for me again. Perseverance and patience are a must. Now about the Big Island of Hawaii trip in August….we can still go with our 2 little kids. I booked that with Korean Airlines (Delta) and before I booked our Kauai trip, I checked Korean and their cancellation policy – they allowed me to cancel my Big Island trip with NO PENALTY. All points and fees were refunded to me. Meanwhile….Kauai here we come!!! My whole family…all six of us get to go!!! ALOHA!!!!!
Very interesting! Sounds like something to look into. I’ve had a cc that connects to airline points, but nothing as substantial as you’ve written about!
Thanks, Laura. Prior to this points-earning hobby, I had cc’s too – but never used the rewards. Our travel lives have changed….we went to 10 different places this past year alone. I always advise my friends and family to get the right type to cc – not just any cc. Feel free to inquire and ask questions 🙂
Wow, that’s amazing! I’ll definitely have to look into this credit card- I’m a hardcore AmEx fan, but I might need to reconsider!
Thank you….in this case, Chase Sapphire Preferred is one of those cards that made this possible. Just by signing up for that card, and meeting the required spend, you can use your points and transfer them to an airline partner and get to Hawaii (with 2 roundtrip tickets) and only pay $11 each. Any questions, let me know.
I use my rewards mainly for cosmetics will be saving them for travel from now on…
TFS
Maggie
http://www.cascadeavenue/blog
It will all depend on your credit card and the rewards program. There are programs that are more lucrative than others. Any questions, let me know.
I’ve heard about earning miles etc but I wasn’t aware you can actually save so much money! I love this kind of clever traveling!
I started this miles/points earning hobby 3 years ago. We have NOT paid for airfare and hotel these past 3 years and we’ve gone to many parts of the world 🙂
That took some doing! Great accomplishment. Wonderful vacation too.
Thank you, it was a whole lot of fun.
I wish European credit cards were better at giving points! 🙁
Hawaii is definitely still on my list so points or not, I hope to be able to visit soon!
I wrote quite a few entries on Hawaii….so any questions, please let me know.
Such a great idea to create this post! love it. Now i know how this works! Thanks 😀
Awesome!!!
Air Miles are incredible when they work out like they have for you here. My credit card isn’t attached to any miles programs unfortunately but maybe I should look at switching.
Yes….not all credit cards are created equal. I highly suggest starting with the Chase Sapphire Preferred – this could easily get you 2 roundtrip tickets to Hawaii or anywhere in the US and pay only $11. https://applynow.chase.com/FlexAppWeb/renderApp.do?SPID=FNLC&CELL=63HB&MSC=1543617406
That is quite a detailed post on how best to use your points. Well done with it. I frankly have been too lazy to make these calculations but after seeing this, I am going to so change that. Cheers
Oh cool. I’m here to help so any questions, please let me know.
Awesome job!! Amazing what you can pull with enough points and short notice. We’re headed to the Big Island next month and ended up paying $94.80 for 4 tickets. I wonder if Alaska (who we booked through) has higher taxes and fees somehow?
Hi…did you book online or by phone? I believe you’re assesed the same Sept 11 fees of $5.60 each way….so that’s $11.20 per person x 4 = $44.80…..and then it looks you were charged another $50 on top of that. This is what I found regarding Alaska’s fees “Award travel is subject to applicable taxes and fees. For travel within the United States, this is generally limited to the September 11 security fee of $5.60 per one-way. For international travel, taxes may be significantly more.
Service fees – you may be also be subject to one or more of the following:
$15 nonrefundable call center booking fee — for new awards booked over the phone.
$25 nonrefundable partner award fee — applies to all awards using one of our airline partners.
$125 change/cancellation fee* — applies to changes/cancellation made within 60 days of travel.”
I booked online. Hmm… I wonder if I need to look more closely at what we were charged then.