Member Success Story: Jenna’s $22,000+ Savings on Family Trips to Grand Cayman

by Zac Hood | Oct 27, 2025 | Member Success Stories
A family of six wearing life jackets sits on a catamaran in clear blue water. Text reads: Travel Freely. Success story for member Jenna: $22,000 saved! On two family trips to Grand Cayman. An airplane icon is also shown.

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Most of us get into points and miles because we love to see new places, make memories, and share those adventures with the people we love.

But sometimes, travel becomes something even bigger. It can offer hope, joy, and a reminder of what really matters.

That’s exactly what happened for Jenna, a mom of three from Kansas City who loves adventure. Even while dealing with serious health challenges, she turned to travel as a source of joy and strength, and created amazing family memories, all thanks to points and miles.

Since learning how to maximize her rewards through Chase Ultimate Rewards®, IHG® One Rewards, and Southwest Airlines Rapid Rewards®, her family has traveled to destinations including Nicaragua, Mexico, Jamaica, New Hampshire/Maine, and Grand Cayman. They even pulled off a 10-night Christmas trip to Hawaii completely on points. Incredible!

Today, she’s sharing one of her family’s favorite destinations: Grand Cayman. Her family loves it so much, they’ve actually been there twice.

Here’s a look at what they did, and how they saved $22,000 on 2 incredible trips!

👉 New to points and miles? Read our beginner-friendly guide: How to Get Started with Free Travel

A family of five stands with their bicycles on a sandy path near the beach, surrounded by palm trees. The ocean and a blue sky with scattered clouds are in the background.

Jenna and her family in Grand Cayman

Tell Us About Yourself

Hi! I’m Jenna from Kansas City, MO. I’m married with 3 kids, and we love adventuring together as a family of 5. I’ve been using points and miles for about 4 years now. I’ve always loved to travel, but my desire to see the world didn’t exactly fit my budget. That’s when I discovered the world of points and miles and I started digging in. I learned about card bonuses, flight deals, and all the little tricks that help regular families stretch their travel dollars.

When I was diagnosed with cancer in 2023, I assumed travel would have to stop. But, my doctors saw it differently. They knew travel wasn’t just a hobby for me – it was life-giving.

Tell Us About Your Trip

Grand Cayman quickly became one of our family’s favorite destinations – and we’ve been lucky enough to visit twice using points and miles! Between snorkeling in crystal-clear water, relaxing on Seven Mile Beach, and soaking up island sunsets, every moment felt like a dream.

A group of six people wearing life jackets sit on a white Hobie catamaran at the edge of a sandy beach. The boat is in shallow, clear water under a sunny sky with light clouds.
Jenna and her family in Grand Cayman

What Kind of Points Did You Use for These Trips?

Trip 1

For our first trip to Grand Cayman, my family and I estimate the trip would have cost us $10,000! Here’s what we actually spent using points:

  • Flights:
    • American Airlines®: Booked using 20,000 AA miles plus $120 in taxes and fees per person (100,000 AA miles total + $600 in taxes and fees) for 5 people with AA miles earned from the Barclays AAdvantage® Aviator Mastercard® and CitiBusiness® / AAdvantage® Platinum Select® Mastercard®
  • Hotels:
    • Kimpton Seafire Resort and Spa: 4 nights, paid 70,000 IHG® points per night with the 4th night free IHG cardholder benefit
    • Holiday Inn Resort Grand Cayman: 4 nights, paid 30,000 IHG® points per night with the 4th night free IHG cardholder benefit

Trip 2

Our second trip to Grand Cayman should’ve cost us $12,000. Instead, points turned it into an almost-free vacation. Here’s how we did it:

  • Flights:
    • Southwest Airlines®: Booked using 51,000 Southwest points +$120 in taxes and fees per person for 3 people and 2 people free with 2 Southwest Companion Passes + $5.60 in taxes and fees per person (total 153,000 points + $371.20 in taxes and fees)
  • Hotel:
    • Hotel Indigo Grand Cayman: 8 nights in a spacious family suite (6 booked with points, 2 nights free using the 4th night free IHG cardholder benefit)

Both Grand Cayman trips were made possible with IHG points earned through the Chase IHG One Rewards Premier Business Credit Card and the Chase IHG One Rewards Premier Credit Card. As an IHG cardholder, I was able to take advantage of the 4th night free benefit when you redeem your points for a consecutive 4-night stay at IHG hotels.

We love IHG properties because the 4th night free benefit makes it easy to stretch our points. The Kimpton Seafire was absolutely stunning, and staying there on points felt like a dream come true.

My spouse and I also both opened the Chase Southwest Rapid Rewards® Plus Credit Card and the Chase Southwest Rapid Rewards® Performance Business Credit Card to earn Southwest Companion Passes for 2 years. Since we’re a family of 5, this enables us to fly 2 of our kids nearly free every time we fly together.

👉 That’s a massive savings and a great reminder of what’s possible with a little planning. Check out strategy for earning the Southwest Companion Pass for 2-for-1 travel here.

Jenna’s Tip: IHG points can’t be combined or transferred for free (unless you have top tier Diamond status), so we keep all IHG cards under one account. The free annual night and 5x earnings make it worth it! Sometimes, we’ll purchase IHG points during 100% bonus points promotions. We once bought 35,000 for $350 and received 70,000 total. It’s worth it for the value we get back.

How Much Money Did You Save Using Points and Miles for Your Trips?

For our trips to Grand Cayman, it’s safe to say we’ve saved over $22,000 in travel costs.

But, that’s just the start! Though our calculations prove we’ve saved over $58,000 between Hawaii, Grand Cayman, and other family adventures, I estimate that we’ve saved more like $85,000+ over the course of the last several years using points and miles.

Three smiling children stand barefoot on a sandy beach at sunset, with the ocean and a partly cloudy sky in the background. Two boys and a girl, all wearing blue, pose together near the water’s edge.
Jenna’s kids enjoying Seven Mile Beach

What Were Some of the Highlights of Your Travel Experiences?

My journey with points and miles took on even deeper meaning in 2023. After years of planning trips with precision, I was diagnosed with cancer.

I’m so thankful I had already logged the hours to learn this hobby. My doctors actually scheduled treatments around our trips because making memories together became even more special.

What Advice Do You Have for Someone Just Starting with Points and Miles?

For anyone curious about getting started with points and miles, my advice is simple: Take the time! Become a student. Every resource exists to learn this and make it happen.

How Has Travel Freely Helped You Achieve Your Free Travel Goals, and What Do You Like Best About the App?

I don’t miss a detail and always have a plan. Organization is key, and that’s where Travel Freely helps me stay on top of everything.

Final Thoughts

Through every challenge, travel has been a source of hope, joy, and purpose. This hobby truly changed my life. It gave me something to look forward to, even in hard seasons.

Note from the Travel Freely team: Thank you for sharing your incredible story with us, Jenna. And we hope it inspires others to share theirs!

👉 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.

Cards that helped Jenna and her family experience their dream travel experiences: