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Airfare deals are typically only available on limited dates. We recommend you use Google Flights to find dates to fly, then book through an online travel agency such as Orbitz or Expedia, which allows you to cancel flights without penalty by 11pm Eastern Time within one day of booking. However, if you’re using The Platinum Card® from American Express, you’ll need to book directly with the airline or through the Amex Travel portal to get 5x MR points. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz or Expedia’s courtesy cancellation if you’re unable to get the time away from work or family.

It’s drizzling here in New York City and TPG staffers are already searching for ways to escape the weather.

If you’re looking for an immediate Caribbean escape like me then you’re in luck because flights to various islands have dropped as low as $153 round-trip — with a plenty of availability to Puerto Rico. One of the best parts about vacationing in Puerto Rico as a US citizen is that you don’t need a passport for the island escape.

Buildings on the coast of San Juan, Puerto Rico (Image by dbvirago/iStock/Getty Images)
Buildings on the coast of San Juan, Puerto Rico (Image by dbvirago/iStock/Getty Images)

To search, head to Google Flights and enter your origin and destination cities. Scroll through the calendar function to find dates and prices that work for you. Finally, click through to book directly with the airline or through an OTA like Priceline or Expedia.

Airline JetBlue, American, Delta, United
Routes: JFK/EWR/PHL/BOS/MCO/MIA/DCA to SJU/BQN/PSE/HAV/STT/AUA/NAS/SDQ
Cost: $153 round-trip in basic economy
Travel Dates: 
September 2019 – February 2020
Pay With: 
The Platinum Card® from American Express (5x on airfare booked directly with the airline), Citi Prestige® Card (5x on airfare), Citi Premier℠ CardChase Sapphire Reserve, (3x on airfare), American Express® Gold Card (3x on airfare when booked directly with the airline) or Chase Sapphire Preferred Card (2x on travel)

Here are a few examples of what you can book:

Orlando (MCO) to Aguadilla (BQN) for $153 round-trip on JetBlue:

Miami (MIA) to Saint Thomas (STT) for $168 round-trip on American:Miami (MIA) to San Juan (SJU) for $178 round-trip on American: Boston (BOS) to Havana (HAV) for $204 round-trip on JetBlue: Miami (MIA) to Havana (HAV) for $204 round-trip on Delta: Philadelphia (PHL) to San Juan (SJU) for $209 round-trip on American:

Newark (EWR) to Santo Domingo (SDQ) for $214 round-trip on United:

New York (JFK) to Aguadilla (BQN) for $223 round-trip on JetBlue: New York (JFK) to San Juan (SJU) for $227 round-trip on JetBlue:

Miami (MIA) to Aruba (AUA) for $229 round-trip on American:

Washington DC (DCA) to Ponce (PSE) for $234 round-trip on JetBlue:

Miami (MIA) to Nassau (NAS) for $235 round-trip on American:

Maximize Your Purchase

Don’t forget to use a credit card that earns additional points on airfare purchases, such as The Platinum Card® from American Express (5x on flights booked directly with airlines or American Express Travel), Citi Prestige Card (5x on airfare), Chase Sapphire ReserveAmerican Express® Gold CardCiti Premier Card (3x on airfare) or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.

Featured photo by Liz Hund/TPG.

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The Platinum Card® from American Express

WELCOME OFFER: 60,000 Points Terms Apply.

TPG'S BONUS VALUATION*: $1,200

CARD HIGHLIGHTS: Delta Sky Club and Centurion lounge access, $200 annual airline fee credit and up to $200 in Uber credits annually

*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 60,000 Membership Rewards® points after you use your new Card to make $5,000 in purchases in your first 3 months.
  • Enjoy Uber VIP status and free rides in the U.S. up to $15 each month, plus a bonus $20 in December. That can be up to $200 in annual Uber savings.
  • 5X Membership Rewards® points on flights booked directly with airlines or with American Express Travel.
  • 5X Membership Rewards points on prepaid hotels booked on amextravel.com.
  • Enjoy access to the Global Lounge Collection, the only credit card airport lounge access program that includes proprietary lounge locations around the world.
  • Receive complimentary benefits with an average total value of $550 with Fine Hotels & Resorts. Learn More.
  • $200 Airline Fee Credit, up to $200 per calendar year in baggage fees and more at one qualifying airline.
  • Get up to $100 in statement credits annually for purchases at Saks Fifth Avenue on your Platinum Card®. Enrollment required.
  • $550 annual fee.
  • Terms Apply.
  • See Rates & Fees
Intro APR on Purchases
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Regular APR
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Annual Fee
$550
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Recommended Credit
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