Deal Alert: Flights to Caribbean Islands From $153 Round-Trip

Aug 23, 2019

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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 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.

Delta SkyMiles® Platinum American Express Card

Earn 90,000 bonus miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new card in the first three months of card membership. Offer ends 11/10/2021.

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More Things to Know
  • Limited Time Offer: Earn 90,000 Bonus Miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new Card in your first 3 months. Offer expires 11/10/2021.
  • Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
  • Earn 3X Miles on Delta purchases and purchases made directly with hotels.
  • Earn 2X Miles at restaurants worldwide, including takeout and delivery and at U.S. supermarkets.
  • Earn 1X Miles on all other eligible purchases.
  • Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. *Payment of the government imposed taxes and fees of no more than $75 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
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Regular APR
15.74%-24.74% Variable
Annual Fee
$250
Balance Transfer Fee
N/A
Recommended Credit
Excellent/Good
Terms and restrictions apply. See rates & fees.

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