By being flexible with staying at multiple hotels and getting a separate return flight, I was able to save thousands on my trip to Hawaii.
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Courtesy of Carly Helfand
When you're looking to use points and miles on flights and hotel stays, booking as far out as possible is often the best bet for finding award availability, especially if you're looking to fly business class. But if you've already missed the boat, booking at the last minute can sometimes work just as well.
That's the strategy I employed for a trip to Maui last Memorial Day weekend. Prices tend to skyrocket for Memorial Day, and availability can be scarce. Here's how I combined rewards credit card points, benefits, and a free night certificate to take a $7,000 trip for less than $350 per person.
Late last April, I was searching for a place for my husband and me to spend our first wedding anniversary. Given that I was looking over peak travel dates, I knew I'd want to use points to dodge surging cash prices for both flights and hotels. With my expectations low, I casually checked availability at the Andaz Maui, a World of Hyatt property that's not exactly known for making it easy to redeem your points.
To my amazement, I happened to find three consecutive nights open at 40,000 points apiece — over a holiday weekend, no less — and knew I had to pounce. With 2,000 points already in my World of Hyatt account, I quickly transferred the remaining 118,000 from my Chase Sapphire Preferred® Card account to lock in a stay that would have cost over $3,000 had I been paying in cash.
But while my home in Portland, Oregon, is closer to Hawaii than many other US cities are, it's still far enough away that I knew I'd want to add a fourth night in order to make the most of our travel time. With the Andaz all booked up and my Chase balance depleted, I turned to Hilton, parent of the Waldorf Astoria Grand Wailea (the Andaz Maui's next-door neighbor).
Both my husband and I have the Hilton Honors American Express Aspire Card from American Express, and we had each gotten a free night certificate with that card. Hilton is generous with these certificates, allowing holders to redeem them at nearly any property in the world if standard rates are available. Once again, we lucked out. We applied a certificate to our final night on the island for a stay that would have otherwise cost over $1,000, and we were set.
With flights, we wanted to arrive as early as possible to make the most of our first day, and that meant booking a nonstop flight. Between Portland and Hawaii, Alaska Airlines is usually our go-to; while Alaska's miles are difficult to rack up through credit card spending, its flights are often easier to book with British Airways Avios, a currency that's much easier to amass.
Sure enough, I found space for two people in business class for 77,500 Avios and $11.20, which would have cost over $2,500 if paying cash. While Alaska economy tickets from the West Coast to Hawaii can often help you extract more value from your points on a cost-per-point basis, I was more than happy to drop the extra miles to sit in business for the six-hour flight. I transferred some American Express Membership Rewards points to British Airways to complete the transaction.
On the way home, we didn't mind adding a connection, so we purchased tickets on United through San Francisco for $324. At the time, I had United PlusPoints — the airline's upgrade currency — in my account as a MileagePlus Platinum member, so I applied those to the tickets so we could move into business class.
Our flight to San Francisco was a redeye, which left us several hours between checkout at the Waldorf Astoria and when we needed to head to the airport. Wanting to spend them at the pool — and needing a place to shower afterward — we opted to pay extra to extend checkout until the evening.
The main reason was that our Aspire card came with up to $400 in resort credits a year, meaning our Waldorf charges were ultimately reimbursed. Our credits covered not only the late checkout but food and drinks on the property throughout the course of our stay.
