Member Success Story: Jenna’s $19,000 savings on Family Trip to Hawaii
You might remember Jenna as the Travel Freely member who saved $22,000 on a family trip to the Grand Cayman, at a time when every moment together mattered more than ever. During her cancer treatment, those savings weren’t just numbers on a spreadsheet. They became precious time, shared experiences, and memories her family will always hold close.
With thoughtful planning, Jenna opened the door to something she once thought was out of reach: 10 unforgettable nights in Hawaii over Christmas (including 6 nights in Wailea), without paying out of pocket for hotels and only taxes and fees for flights.
From snorkeling with sea turtles to driving the Road to Hana, this trip wasn’t just about free travel. It was about joy, resilience, and creating once-in-a-lifetime memories together.
In this success story, Jenna shares how she made it all happen, the strategies she used, and why Travel Freely has been such an important part of her points-and-miles journey.
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Tell Us About Yourself
I live in Kansas City, MO, and I have been traveling on points and miles for four years. I am married with three kids and love adventuring with my family!
What is extra special right now…I organized our traveling with points and miles very specifically a few years ago, and at the end of year I was diagnosed with cancer. I am so thankful for this hobby and the hours I logged, because making memories and traveling is more special than ever!
Tell Us About Your Trip
By earning companion passes and strategically opening travel cards, my husband and I celebrated Christmas a year ago with 10 unforgettable nights in Hawaii.
Maui at Christmas was pure magic. We snorkeled, hiked to waterfalls, and drove the scenic Road to Hana. Plus, we stayed at stunning spots that would have cost over $13,000, yet we paid nothing out of pocket.
What Kind of Points Did You Use for These Trips?
I used a combination of Southwest Rapid Rewards® and Chase Ultimate Rewards® points to cover every travel expense.
Flights
All of our points for our flights came from Southwest credit cards. So, we used our Southwest points to book our flights. Also, we earned the Companion Pass for the year, which meant that one of us was able to fly for free (+ taxes and fees).
Cards used: Southwest Rapid Rewards® Plus Credit Card, Southwest Rapid Rewards® Priority Credit Card, Southwest Rapid Rewards® Premier Credit Card
Editor’s Note: Chase only allows you to earn the welcome bonus on one Southwest personal card at a time, and the same rule applies per person. In Jenna’s case, she and her husband each held one Southwest personal card, which gave them two personal cards between them. The third card listed here is likely a Southwest business card – a separate product that has its own bonus eligibility. If you’re working toward the Companion Pass, be sure to review the current bonus rules before applying.
Hotels
We booked all of our hotels using Chase Ultimate Rewards and transferred them to Hyatt at a 1:1 ratio. We love Hyatt hotels because we feel like we get the best value from our Chase points.
- First, we stayed 2 nights at the Hana-Maui Resort, a luxury hotel in Hyatt’s portfolio.
- Then, we stayed 6 nights at Grand Champions Wailea. We used our Chase points for this hotel via Hyatt, but Hyatt no longer owns this property.
- To finish out our stay, we stayed at the Hyatt Regency Maui Resort and Spa for 2 nights.
My husband and I each got the 3 Chase Ink Business cards to accrue points quickly. I was able to refer him (and get points for the referral), and vice versa.
Cards used: Chase Ink Business Cash® Credit Card, Chase Ink Business Unlimited® Credit Card, Chase Ink Business Preferred® Credit Card
Editor’s Note – important Ink card updates: The Chase Ink card rules have changed since Jenna earned her points, and there are a few key things to know. These changes don’t make the Ink cards any less valuable – they’re still among the best business cards available – but it’s important to set accurate expectations about what’s currently possible:
- Welcome bonuses: Chase has tightened eligibility on Ink cards, and you may not be able to earn the bonus on all three cards. Check current terms carefully before applying.
- Referral bonuses: The Chase Ink refer-a-friend (RAF) bonus is now only available when referring someone who is new to Chase business cards. This means the multiple referral bonuses Jenna described are no longer possible – you can refer your partner once at the start, but not back and forth after that.
- Referral bonus amount: The Ink RAF bonus has also decreased from 40,000 points to 20,000 points.
How Much Money Did You Save Using Points and Miles for Your Trips?
For our 10-night trip, we saved $19,000!
What Were Some of the Highlights of Your Travel Experiences?
This once-in-a-lifetime trip brought a smile to my face that I can still feel today. Watching the sunset on Christmas Eve, surrounded by the scent of flowers and the beauty of Maui, is a memory I’ll treasure forever. Every hike, splash, and cliff jump with my adventure-loving kids felt like we had stepped right into the Garden of Eden. Snorkeling, hiking, cliff-jumping, and swimming with octopus and sea turtles were highlights for my children and husband.
What Advice Do You Have for Someone Just Starting with Points and Miles?
Take the time! Become a student. Every resource exists to learn this and make it happen. I never thought I would get to visit Hawaii – much less for free!
How Has Travel Freely Helped You Achieve Your Free Travel Goals, and What Do You Like Best About the App?
I stay organized with Travel Freely. The app helps in the present to ensure I don’t make mistakes or miss deadlines. And, it helps when planning for my next card!
Final Thoughts
Jenna’s story shows what’s possible when you stay organized, learn as you go, and build your strategy over time. She and her husband didn’t do this overnight; they planned carefully, earned companion passes, and used the right combination of cards to make 10 nights in Hawaii a reality for their family of five.
The good news? You don’t need to follow Jenna’s exact path to start seeing results. Even one welcome bonus can cover a flight or a few hotel nights. The key is getting started, staying organized, and letting your confidence (and your points) grow from there.
👉Inspired by Jenna’s story? Start tracking your cards with Travel Freely today – it’s free, beginner-friendly, and built to make stories like this possible.
Have a success story you’d like to share with us? We’d love to hear it! Reach out to us at or fill out our form here.
Cards that helped Jenna and her family experience their dream travel experiences:
