Deal Alert: Flights to Caribbean Islands From $153 Round-Trip
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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.
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℠ Card, Chase 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 Reserve, American Express® Gold Card, Citi 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.
- Earn up to 70,000 bonus miles. Earn 60,000 bonus miles after you spend $2,000 in purchases on your new Card in your first 3 months. Plus, earn an additional 10,000 bonus miles after your first anniversary of Card Membership. Offer Expires 4/1/2020.
- Enjoy your first checked bag free and Main Cabin 1 Priority Boarding on Delta flights.
- New! Get ready for your next trip - spend $10,000 in purchases on your card in a calendar year and receive a $100 Delta Flight Credit to get you there sooner.
- Earn 2X Miles on Delta purchases, at restaurants worldwide and at U.S. supermarkets.
- Earn 1X Mile on all other eligible purchases.
- Receive a 20% savings in the form of a statement credit after you use your Card on eligible Delta in-flight purchases of food, beverages, and audio headsets.
- Enjoy a $0 introductory annual fee for the first year, then $99.
- Terms Apply.
- See Rates & Fees