Every points collector has that one unforgettable redemption — the booking that reminds you why you play the game. Over the years, I’ve scored some incredible ones, from luxury flights halfway around the world to hotels during major events that would’ve cost a fortune in cash.
Sure, people say the days of “amazing” redemptions are gone. Award charts have disappeared, availability is tougher, and dynamic pricing has made things unpredictable. But I don’t buy it. Those great values are still out there — you have to reset your expectations and look a little harder.
Classic Wins From Back in the Day
Back when festival tickets were cheaper and hotel points stretched further, I used 20,000 IHG points for a Holiday Inn Express during Desert Trip — a three-day concert in California featuring Bob Dylan, The Who, The Rolling Stones, Paul McCartney, Neil Young, and Roger Waters. Rooms in the area were going for over $400 a night, but my redemption put me right across from the shuttle stop.
Then there was the time I booked an open-jaw itinerary from Thailand to Bali and home on EVA and ANA for 136,000 Amex Membership Rewards points — a $10,000 itinerary that remains one of my proudest award bookings.
And one of our personal favorites: staying right along the Macy’s Thanksgiving Day Parade route in Manhattan using Marriott points instead of paying thousands in cash. (Here’s that story if you missed it.)
Yes, Great Redemptions Still Happen
Fast-forward to today, and even with all the changes, those “wow” moments aren’t gone — they’ve just shifted.
One of my recent favorites was flying to Vietnam on Singapore Airlines using points. It was one of those redemptions that felt like a throwback — a long-haul premium flight that would’ve cost thousands of dollars, but thanks to points and good timing, I got it for a fraction of the cost. That experience reminded me that aspirational travel isn’t dead; it just takes more creativity to find.
But not every win has to be glamorous. Sometimes it’s about practicality — like using points to book a hotel in Fort Worth during a busy weekend when cash rates were sky-high. It wasn’t a bucket-list trip, but it still saved hundreds of dollars, which is a win in my book.
Why I Still Collect Points
Award programs evolve, prices change, and “sweet spots” come and go. But the core idea stays the same — points are a hedge against high travel costs. Even if I’m not getting 7¢ per point anymore, getting 1¢ or better for a redemption I actually want to use still feels like value.
That’s why I keep collecting. Not every redemption needs to be once-in-a-lifetime — sometimes it’s just about saving real money on the trips that matter most.
Cover photo by Ish Consul on Unsplash.
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