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A Bucket List Trip to the Kentucky Derby — Reader Success Story

Dec. 26, 2017
4 min read
A Bucket List Trip to the Kentucky Derby — Reader Success Story
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Today I want to share a story from TPG reader Lauren, who used points to save a bundle on hotels. Here's what she had to say:

Like millions of other Americans, the first weekend in May I turn on the TV, fix myself a drink and watch the pageantry of the Kentucky Derby. Since my birthday is in late May, going to the Derby has been on my bucket list for as long as I can remember. As a child I can remember telling my mother that one day I was going to wear the dress and the hat while singing along with the rest in the stands.

Next year is finally the year. My husband and I will be in Kentucky the weekend after the Derby for another event, so it made sense to take the week off and do the Derby first. We booked flights with our recently opened Ink Business Preferred Credit Card to help us meet the spending requirements, and then started looking at hotels.

I had some points leftover from the sign-up bonus on my Chase Sapphire Reserve card, which came to mind after I saw the $1,000+ per night price tag for hotels on Derby weekend. I transferred 28,000 points from Chase to Hyatt (since they have no blackout dates), and bought 7,000 more from Hyatt with a 20% bonus for $168. I then redeemed 36,000 points for a three-night stay during the Derby at the Hyatt Regency in Louisville, where the going rate was $1,300 per night.

I received slightly better than 10 cents per point by transferring from Chase to Hyatt. Even if I didn't have those points to begin with, it would have been worth buying whatever balance I needed from Hyatt in order to book the room. This was definitely a good lesson on the value of transferable points. Thanks for helping my bucket list trip become a reality!

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Photo courtesy of Hyatt.
Lauren stayed at the Hyatt Regency Louisville for 12,000 points per night over Derby weekend. Photo courtesy of Hyatt.

Lauren made good use of her Ultimate Rewards points, but her story also illustrates that award travel strategies can be profitable even when you don't already have points on hand. She paid 2 cents for each point she purchased, but she got five times as much in return when she redeemed them. If she had started from zero, she still could have purchased 36,400 points (28,000 with a 30% bonus) for $672. That's a substantial out-of-pocket cost, but it's a massive discount from the cash rate.

Buying rewards doesn't always make sense, so learning to differentiate between good and bad deals is important. Airlines and hotels routinely offer promotional bonuses that make buying points and miles worthwhile, but you should always compare the cost to buy them with your expected redemption value. When you see an opportunity to buy low and redeem high, take it.

I love this story and I want to hear more like it! To thank Lauren for sharing her experience (and for allowing me to post it online), I’m sending her a $200 airline gift card to enjoy on future travels, and I’d like to do the same for you. Please email your own award travel success stories to; be sure to include details about how you earned and redeemed your rewards, and put “Reader Success Story” in the subject line. Feel free to also submit your most woeful travel mistakes. If your story is published in either case, I’ll send you a gift to jump-start your next adventure.

Safe and happy travels to all, and I look forward to hearing from you!

Featured image by Getty Images