In this success story, find out how Denise’s family of four traveled to Maui for a dream vacation without paying for flights or a hotel room on the last night, thanks to savvy points and miles strategies. Here’s how they made it happen:

Flying to Maui for Free with Southwest Points

We were relatively new to using points and miles, but with the help of points, we were able to fly to Maui without spending a dime on our Southwest Airlines flights. We used Chase Ultimate Rewards points to book four round-trip tickets, which was a huge win for us!

Here’s how:

1. Chase Ultimate Rewards: We transferred our Chase points to Southwest Airlines Rapid Rewards, which is one of Chase’s best transfer partners.
2. Booking: Once the points were transferred, booking our flights was simple. Southwest’s easy-to-use website made it clear how many points were needed for our flights, and we were able to book four tickets without having to dip into our savings.

The beauty of Southwest is that they allow you to book using points for free-checked bags, which saved us more money. Plus, we could cancel or change the flight if needed, and we love the flexibility Southwest offers.

Free Last Night’s Stay with Wyndham and Capital One Points

After booking the flights, our next task was to find a place to stay. We chose an Airbnb for most of our stay, but we wanted something a little extra special for the last night. That’s where Wyndham Hotels came into play. Thanks to Capital One points, we were able to book two rooms for free on our last night in Maui!

Here’s the breakdown:

1. Capital One Travel: Capital One’s Venture Miles is a fantastic tool for booking hotels through their travel portal, which offers the ability to transfer points to hotel chains like Wyndham.
2. Booking with Points: Using Venture Miles, I found a Wyndham property in Maui that was available. I transferred enough points to cover both rooms for our final night, eliminating the need for hotel expenses.

Using Southwest’s Drop-in Points Feature

After booking the flights, I wanted to make sure I was optimizing every aspect of the trip. One feature I love about Southwest Airlines is the ability to earn points back if the price of your flight drops after booking. Here’s how it works:

• Checking Flight Prices: Once we booked our flights with points, I kept a close eye on the prices in case they dropped.
• Drop-in Points: If the flight price went down after booking, Southwest allows you to get points refunded for the difference. For example, if our flight initially cost 20,000 points per person, but a few weeks later the same flight was available for 18,000 points, I could request a refund of 2,000 points per ticket.
• Easy Process: I love that Southwest makes it so easy to check and request points back for any fare reductions. It’s a simple process, and the points go straight back into my Rapid Rewards account.

Our family vacation to Maui was not only memorable but also affordable, thanks to the points we earned through Chase and Capital One.

Final thought

The ability to book free flights with Southwest and free hotel nights with Capital One points made this trip even more special. As newcomers to using points, they were amazed at how easy it was to use these points to save money while enjoying a great family vacation.

If you’re looking to get started with using points and miles for your next trip, Chase Ultimate Rewards and Capital One Venture Miles are excellent programs to use. They provide an easy entry point into the world of points, and with a little strategy, you can enjoy trips like this family—for free!

So, whether you want to take a dream vacation to Hawaii, explore Europe, or book your next adventure, using points and miles is a game-changer. Don’t be afraid to dive into this rewarding world—it’s not as complicated as it seems, and the benefits are worth it!