Jul 30, 2024

get one of these certificates each year, while holders of the Hilton Honors American Express Surpass® Card can earn one by spending $15,000 on the card in a calendar year. My husband and I each carry both the Aspire and the Surpass, allowing us to rack up four certificates each year. When I spotted three consecutive nights available at standard rates at Pedregal this past May, I quickly applied three certificates to maximize their value. Doing so allowed me to hang onto 360,000 Hilton points — which I figured I could use in part for two more nights at a less-expensive Hilton property — and book a room that would have cost over $5,700 for three nights in cash. Instead of going ahead and locking in the last two nights elsewhere, though, I took a gamble. Knowing that many Hilton hotels — Pedregal included — tend to make rooms available at standard rates at the last minute, I decided to hold off on booking anything and instead checked Pedregal's availability daily. My persistence paid off: On the flight to Mexico, the last two nights finally opened up at standard rates, and I was able to use our last certificate and 120,000 points to grab them. By the time we arrived at the hotel, we were all set for a free five-night stay. 2. We used credits to cover airfare, taxes and fees We chose United flights to and from Mexico, and in order to pay as little for them out of pocket as possible, we got creative. For the way down, we chose to use 20,000 United MileagePlus miles — discounted from 24,900 because I hold United Premier Gold status — and pay $48 in taxes for award tickets instead of paying $304 for revenue tickets. Advertisement I already had 10,000 MileagePlus miles in my account. To get to 20,000 for my husband's ticket, we transferred 10,000 Bilt Rewards points earned with the  Bilt Mastercard® to my United account so that I could book at the reduced rate. I then transferred 20,000 Chase Ultimate Rewards points earned through a combination of spending on the Chase Sapphire Preferred® Card and Ink Business Preferred® Credit Card to United to book my own ticket. The Hilton Honors Aspire has a great new perk that helped us cover the $48 per person in award ticket fees. Each quarter, cardholders receive up to $50 in statement credits for eligible flight purchases made directly with an airline or through amextravel.com, so we each used our own card to trigger the credit. After running down our points balances for the outbound flight, I decided to leverage other credits for the $334-per-person return leg, also on United. I'm a Capital One Venture X Rewards cardholder, meaning I get a $300 annual credit for bookings made through Capital One Travel. The credit covered all but $34 of the ticket price, but since it was a travel charge, it was eligible for removal with Capital One's "Purchase Eraser" feature; I used 3,400 Capital One miles to wipe the remaining balance off my statement. My husband had about $130 in travel credits with United already from a previously canceled ticket, so he applied those toward his ticket home from Cabo. I charged the remaining balance to my United Quest℠ Card to earn three miles per dollar; at the time, I was also working toward a spending bonus on the card to earn extra Premier Qualifying Points, which help secure elite status for the following year. Business Insider's Pick for the Best travel credit card Chase Sapphire Preferred® Card Carly Helfand is a points and miles blogger and coach who's been using points to travel to 52 cities in every calendar year since 2011. She’s also a full-time financial journalist who got her start in the business reporting world while earning her master's at Northwestern University's Medill School of Journalism. In 2017, she founded a blog and online course devoted to sharing the strategies she’s used to see the cherry blossoms in Tokyo, trek to Machu Picchu, sundown in the Maldives and more without spending a dime on airfare.When not traveling, Carly prefers watching pro hockey to nearly everything. She also plays the Irish fiddle. You can connect with her at 52citiesblog.com or on Instagram at @carlyhelfand. Read more Read less My husband and I both have two Hilton cards, which we used to get free nights at a resort. I took a gamble on standard rate rooms opening up last minute at the resort, and it paid off. By transferring points and being strategic about how we paid, our flights were also covered. Sign up to get the inside scoop on today’s biggest stories in markets, tech, and business — delivered daily. Read preview Thanks for signing up!