Travel Hacking Case Studies: My 6 Best Award Points Redemptions

Travel Hacking Case Studies - Featured
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If you’re new to the world of travel hacking, the possibilities can be hard to fathom. Can points and miles really take you to luxury resorts, or score you first-class tickets for you and your family? 

The answer is a resounding “yes.” 

In this post, I’ll share some of my most rewarding travel experiences to show you what’s truly possible when you strategically redeem points and miles.

If you’re just starting your journey into travel hacking, understanding the potential rewards can be both inspiring and instructive. So let this article serve as your roadmap to what’s possible.

#1. First-Class Tickets from Chicago to Buenos Aires

  • Type of redemption: Airline booking with British Airways (flown on American Airlines).
  • Points used: 50,000 per ticket.
  • Travel date: 2011.
  • Estimated value: $3,000 per ticket. (Note: Current prices are around $5,000, when adjusted for inflation.)

In 2011, my foray into travel hacking began with a first-class flight from Chicago to Buenos Aires, thanks to a now-expired 100,000-point bonus offer from a British Airways credit card. 

The trip was not only luxurious but also life-changing, as it was on this vacation that we learned we were expecting our first child. This experience ignited my passion for travel hacking and marked the beginning of a new chapter in my life.

The value of this redemption was one of the highest I’ve ever booked. Similar tickets today run for $5,000. Of course, this was over a decade ago, so my best estimate is that the cash value of this fare would have been $3,000 to $4,000 per ticket. 

While the specific British Airways card offer I used for my Buenos Aires trip is no longer available, there are plenty of other ways to earn points for your dream trip. Check out my tips on earning points and miles for the latest strategies.

Beyond the numbers, Buenos Aires was quite memorable. We spent just $1,500 for a month-long rental and enjoyed fine dining almost every night that cost a fraction of what we’d pay in the U.S.

The city and the trip hold a special place in our hearts, forever linked to a pivotal life moment.

Initially, I was hesitant to dive into the points and miles game, fearing it would negatively impact my credit score. However, a deeper understanding of how credit scoring actually works not only alleviated my concerns but also paved the way for what’s now been more than a decade-long hobby. For more insights, check out my article on the impact of travel hacking on your credit score.

#2. The Phoenician Resort in Scottsdale

  • Type of redemption: Hotel booking with Starwood Preferred Rewards (which has since merged with Marriott Bonvoy.
  • Points used: Just over 60,000 for five nights.
  • Estimated value: $600 per night.
  • Travel date: 2016.

In 2016, my wife and I enjoyed our first getaway after the birth of our second child, thanks to 60,000 points accumulated on the Starwood Preferred Rewards credit card. This card used to be a go-to option before the landscape of rewards programs changed (Marriott and Starwood merged).

We stayed at the Phoenician, a five-star resort in Scottsdale, Arizona. The experience was further enhanced by a Marriott perk that’s still available: book four nights and get the fifth night free, bringing our total to just over 60,000 points for five nights.

While the specific redemption for the Phoenician Resort at 12,000 points per night is no longer available due to program changes, don’t be discouraged. There are still plenty of opportunities to book luxurious stays with points. 

For instance, some exceptional Hyatt hotels start at just 20,000 points per night. 

For a deeper dive into maximizing value on hotel bookings, check out my article on booking hotels with points.

#3. Family Trip to Switzerland and Italy

View of the Dolomites captured during our Plose hike, just a short drive from our cozy stay in Brixen, a charming northern Italian town.
View of the Dolomites captured during our Plose hike, just a short drive from our cozy stay in Brixen, a charming northern Italian town.
  • Type of redemption: Airline bookings using Aeroplan and LifeMiles.
  • Points used: 40,000 per ticket (Aeroplan, Chicago to Zurich), 30,000 per ticket (LifeMiles, Rome to Chicago).
  • Estimated value: Roughly $2,500 per ticket round trip.
  • Travel date: 2023.

For our family’s first European adventure, we managed to book a direct flight from Chicago to Zurich for 40,000 points in economy class per ticket. The flight was through Air Canada’s Aeroplan program and flown on Swiss Air.

Then we booked a return flight from Rome to Chicago, on a direct flight with United Airlines, for 30,000 points per ticket via LifeMiles. 

This reward booking made what could have been an expensive peak-season journey surprisingly affordable.

The value of this redemption is hard to overstate. United has priced the one-way tickets at $1,413 from Rome to Chicago (totaling over $7,000 in cash) for the summer of 2024.

One-way direct flights from Chicago to Zurich are priced over $1,000. So, the cash value here is roughly $2,500 per ticket (multiplied by five people in our family). 

Thanks to our strategic use of points, we were able to allocate our budget to exploring Italy, with our itinerary including the Lake Como region, the Dolomites and Tuscany. We found affordable Airbnbs in remote areas and opted to pay cash for our stays, making our three-week Italian adventure incredibly cost-effective.

For tips on maximizing your points, see my article on tips for finding award airfare

#4.Family Trips to Florida

  • Type of redemption: Airline Booking with British Airways Avios (flown on American Airlines).
  • Points used: 7,500 per one-way ticket.
  • Estimated value: Varies depending on the trip.
  • Travel date: Multiple.

Our trips to Florida may not be luxurious (we stay with my parents), but they’re invaluable for the simple joy of spending time with family. After all, it’s not always about five-star hotels or first-class flights; sometimes it’s about using travel rewards to make frequent visits to see family more attainable.

Unlike many carriers that price their tickets based on cash value, British Airways operates differently, using a distance-based award chart. This chart outlines how many points you’ll need for flights based on their distance. 

The unique advantage here is that the cost in points is fixed and not influenced by the cash price of the ticket.

American Airlines and British Airways are part of an airline alliance, which is a partnership that allows airlines to share resources and benefits. This alliance allows you to book flights on American Airlines using the British Airways rewards program. 

When American Airlines releases what’s known as “saver availability,” discounted seats can be booked via the British Airways loyalty program. In such instances, we can secure one-way tickets from Chicago to Fort Myers for just 7,500 points each.

This strategy has saved us thousands of dollars over multiple trips, and has even been extended to other destinations like Denver on multiple occasions (where we have more family).

What makes this redemption even more versatile is that it’s not limited to economy class. I’ve personally used this sweet spot to fly domestic first class on American Airlines for just 15,000 points (finding five tickets in first-class is difficult).

#5. Vacasa Vacation Rental in Kauai

Pool deck of the four-bedroom Vacasa rental in Kauai we booked for 2024.
 Pool deck of the four-bedroom Vacasa rental in Kauai that we booked for 2024.
  • Type of redemption: Vacation rental booking with Wyndham Rewards (Vacasa).
  • Points used: 54,000 per night for a four-bedroom rental.
  • Estimated value: $7,477.85 for the entire stay.
  • Travel date: 2024.

One of my newest favorite sweet spots in travel hacking is booking vacation rentals through Wyndham Rewards, thanks to their acquisition of Vacasa. This has been a game-changer for family travel. 

With Vacasa rentals, the cost is calculated at 15,000 points for each bedroom per night. For example, if you’re interested in a four-bedroom home, you would multiply 15,000 points by four bedrooms, resulting in a total of 60,000 points per night. 

If you have one of the Wyndham credit cards, you’re eligible for a 10% discount on this point total. So, for a four-bedroom luxurious house in Kauai, the cost after applying the 10% Wyndham card discount would be 54,000 points per night.

Here’s where it gets interesting: I bought most of these points during a sale for just under 1 cent per point. 

Combined with a sign-up bonus on the Wyndham business card, which also gave a 10% discount, the value became extraordinary. 

The total cash cost for this luxurious stay would have been $7,477.85. However, by sharing the cost with another family and using purchased points, our cost came down to under $200 per night per family.

#6. Family Flight to St. Lucia

View of the Pitons from the road in St. Lucia, where hiking these iconic peaks was a trip highlight.
View of the Pitons from the road in St. Lucia, where hiking these iconic peaks was a trip highlight.
  • Type of redemption: Airline booking with British Airways Avios (flown on American Airlines).
  • Points used: 202,500 total for round-trip tickets.
  • Estimated value: $1,500 per ticket.
  • Travel date: Spring break 2022

Our Spring Break trip to St. Lucia in 2022 was a milestone for our family, as it was our first time traveling out of the country together. 

We used a total of 202,500 points for round-trip tickets from Chicago via British Airways Avios, flying on American Airlines. Considering that tickets for spring break tend to be priced around $1,500 each, the value of this redemption was significant.

But the trip was memorable for more than just the flights. We rented a house in the middle of the St. Lucian rainforest, complete with a butler, driver, and maid, for around $700 per night. 

The cost was split between two families, making it an affordable luxury. Although the location was a bit off the beaten path, having a driver made it convenient and allowed us to fully enjoy this unique experience.

Final Thoughts

I hope that seeing a glimpse into my incredible travel experiences serves as inspiration for you to embark on rewarding adventures of your own.

The fact that most of these can be earned through welcome bonuses on credit cards makes them doable for any one person or family. To set yourself up for success, don’t miss this guide on the best travel rewards credit cards for beginners

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R.J. Weiss
R.J. Weiss, founder of The Ways To Wealth, has been a CERTIFIED FINANCIAL PLANNER™ since 2010. Holding a B.A. in finance and having completed the CFP® certification curriculum at The American College, R.J. combines formal education with a deep commitment to providing unbiased financial insights. Recognized as a trusted authority in the financial realm, his expertise is highlighted in major publications like Business Insider, New York Times, and Forbes.

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