Last Year’s Sweepstakes Winner Dishes on How He Redeemed His Points

Jun 17, 2019

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Last week, we announced our largest-ever sweepstakes with a massive grand prize — the trip of a lifetime planned by The Points Guy with 1 million Chase Ultimate Rewards Points. That’s right, Brian Kelly himself will help you put your winnings to good use.

So what does it cost you to get in on this?

A $10 minimum donation — that’s it! (Though the more you donate, the more opportunities you have to win.) Proceeds go to support Rainbow Railroad, a LGBTQI organization helping those facing state-enabled persecution.

In honor of the sweepstakes — and to show our readers what it looks like to win — we caught up with Patrick Kavanagh, the 2018 recipient of our 500,000-point grand prize. He spent his points on a month-long trip around Asia, flying in style with some of our favorite airlines, including Emirates and Singapore.

ENTER NOW for a chance to win 1 million Chase points

First, however, he had to meet with TPG and staff at our New York City headquarters, where they broke down where he wanted to go and helped him figure out how to get there. The best part, according to Patrick? “Letting them book it was so efficient, and they got such a better value (from the points) than doing it myself.”

The Trip

Patrick’s journey started in Newark, where he was picked up by Emirates’ chauffeur service.

He was then driven (luxuriously) to the airport, where he boarded his fifth-freedom Emirates flight to Athens, complete with his very own first-class suite.

He took advantage of the layover and spent a week in Athens, visiting all the top sites.

(Photo courtesy of Patrick Kavanagh)

After a quick overnight in Zurich, his next stop was Singapore via Singapore Airlines’ famous A380 suites, which — according to Patrick — was the best flight of his trip, “The flight attendant-to-passenger ratio is very low, so I got to know the crew very well,” he said. “They waited on me hand and foot.”

(Photo by Zach Honig/The Points Guy)

He also mentioned that the Krug and Dom Perignon were free-flowing, which is a must for the discerning traveler.

(Photo courtesy of Patrick Kavanagh)

The following three weeks were spent traveling throughout Asia, from the Mongolian steppes to the Forbidden City in Beijing.

(Photo courtesy of Patrick Kavanagh)

(Photos courtesy of Patrick Kavanagh)

All told, he visited nine cities in six countries, using the points he won to fly first class — with the exception of a few intra-China flights — the whole way.

Alas, all good things must come to an end, so when his vacation ran out, he boarded his Asiana flight …

(Photo courtesy of Patrick Kavanagh)

… and settled in for the long journey back home.

His Advice

So what does last year’s winner have to say to those hoping to take home this year’s haul of points? Quite a lot, actually. While there’s nothing he would change about his own trip, Patrick had these words to offer:

  • Travel for as long as you can.
  • Go as many places as you want.
  • Figure out where you want to go early on, so TPG can help you redeem your points for maximum value.
  • Leverage your existing status, if you have any. [Patrick is a Hilton Diamond member, and used his executive lounge access extensively throughout the trip.]
  • Enjoy yourself!

Will you be this year’s winner? All it takes is a $10 donation for the chance to win the trip of a lifetime!

All photos courtesy of Patrick Kavanagh unless otherwise noted.

Chase Sapphire Preferred® Card

WELCOME OFFER: 80,000 Points


CARD HIGHLIGHTS: 3X points on dining and 2x points on travel, points transferrable to over a dozen travel partners

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

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More Things to Know
  • Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,000 when you redeem through Chase Ultimate Rewards®.
  • Enjoy benefits such as a $50 annual Ultimate Rewards Hotel Credit, 5x on travel purchased through Chase Ultimate Rewards®, 3x on dining and 2x on all other travel purchases, plus more.
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards®. For example, 80,000 points are worth $1,000 toward travel.
  • With Pay Yourself Back℠, your points are worth 25% more during the current offer when you redeem them for statement credits against existing purchases in select, rotating categories
  • Count on Trip Cancellation/Interruption Insurance, Auto Rental Collision Damage Waiver, Lost Luggage Insurance and more.
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