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Deal alert: Roundtrip flights to the Caribbean, most under $200

February 18 2022
5 min read
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It's Friday and what better way to celebrate than with cheap flights to the Caribbean, specifically Puerto Rico and the U.S. Virgin Islands, with roundtrip flights under $300 to both.

New York City has the widest availability to both destinations, and there are flights from various U.S. cities heading to San Juan. You're welcome.

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(Screenshot courtesy of Scott's Cheap Flights)

These discounted fares came from Scott’s Cheap Flights, which sends deals up to 90% off via its Premium membership, which users can try for free for 14 days and then $49 per year. You can also upgrade to the Elite tier for $199 per year and receive all the deals included in Premium membership plus premium economy, business-class and first-class alerts.

Deal #1: Ponce, Puerto Rico

(Screenshot courtesy of Scott's Cheap Flights)

Airline: JetBlue
Routes: JFK/MCO to PSE
How to book: Search Google Flights and book directly through the airline
Travel dates: March — May 2022; September 2022
Price: $192–$230 roundtrip
Book by: 1–2 days

(Screenshot courtesy of Google Flights)

Deal #2: Aguadilla, Puerto Rico

Airline: JetBlue
Routes: ABE/BOS/CLT/CLE/EWR/SFO/TPA/PBI to BQM
How to book: Search Google Flights and book directly through the airline
Travel dates: March–June 2022
Price: $198–$352 roundtrip
Book by: 1–2 days

(Screenshot courtesy of Google Flights)

Related: Reopening guide to the British Virgin Islands for travelers

Deal #3: St. Thomas, USVI

Airline: JetBlue
Routes: EWR/ORD/JFK/LGA/MIA and others to STT
How to book: Search Google Flights and book directly through the airline
Travel dates: March — May 2022
Price: $185–$381 roundtrip
Book by: 1–2 days

(Screenshot courtesy of Google Flights)

These first three deals are for flights in JetBlue's Blue Basic economy class, which only includes one personal item that can fit under the seat in front of you. Any full-size carry-on bag brought to the gate will incur a fee and needs to be checked. The fee is $65 each for the first and second checked bag and $180 for a third bag.

Change and cancel fees apply to basic fares, so consider upgrading for flexibility.

Related: Puerto Rico relaxes entry requirements and expands dining capacity

Deal #4: San Juan, Puerto Rico

Airlines: JetBlue, Delta, United
Routes: ATL/BOS/BWI/CHS/ORD/LAX/MIA/MSP/BNA/EWR and others to SJU
How to book: Search Google Flights and book directly through the airline
Travel dates: March — May 2022; August 2022—January 2023
Price: $134–$360 roundtrip
Book by: 1–2 days

This is the widest-reaching deal of the four, with flights departing from more than 30 U.S. cities to San Juan, including:

  • Fort Lauderdale (FLL), starting at $134
  • Philadelphia (PHL), starting at $155
  • Miami (MIA), starting at $183
  • Columbus (CMH), starting at $195
  • Cleveland (CLE)/Indianapolis (IND), starting at $199
  • Chicago (ORD), starting at $207
  • Newark (EWR), starting at $211
  • Nashville (BNA), starting at $235
  • Atlanta (ATL), starting at $236
  • Chicago (MDW), starting at $239

This deal includes flights on Delta like the one below departing from CLE to SJU flying Delta.

(Screenshot courtesy of Google Flights)

Similar to JetBlue's Blue Basic, flights in this batch are for Delta's basic economy which include a full-size carry-on bag.

(Screenshot courtesy of Google Flights)

Maximize your purchase

Don’t forget to use a card that earns bonus points on airfare purchases, such as The Platinum Card® from American Express (5x on airfare booked directly with the airline or through American Express Travel), on up to $500,000 on these purchases per calendar year, 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 through Amex Travel) or the Chase Sapphire Preferred Card (2x on travel). Check out this post for more on maximizing airfare purchases.

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Bottom line

All of these deals are expected to last just 1–2 days and the widest availability is out of JFK.

Featured photo by Getty Images
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
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6X6x points at hotels participating in the Marriott Bonvoy® program.
4X4x points for purchases made at restaurants worldwide, at U.S. gas stations, on wireless telephone services purchased directly from U.S. service providers and on U.S. purchases for shipping.
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  • Intro Offer
    Limited Time Offer: Earn 100,000 Bonus Marriott Bonvoy Points after spending $4,000 in purchases on your new Card in your first 3 months of Card Membership. Offer expires 11/2/22.

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    75,000 points
  • Annual Fee

    $125
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    670-850
    Excellent/Good

Why We Chose It

The Marriott Bonvoy Business Amex is a stacked card with a rewards rate that will help you earn bonus points on everyday and business-related purchases. You'll earn 15 elite night credits each calendar year, and receive automatic Gold elite status. Finally, the free night award certificate with a redemption level of 35,000 points or less can get you hundreds of dollars in potential value each year.

Pros

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  • 4x points at restaurants worldwide, U.S. gas stations, wireless telephone services purchased directly from U.S. service providers and U.S. shipping
  • 2x points on all other eligible purchases
  • Earn a free-night award each card renewal month (up to 35,000 points)
  • Receive 15 elite night credits to jump-start status
  • Transfer Marriott points to 40+ airlines

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  • Airline points transfer ratios are poor
  • Must spend $60,000 in a year for second free-night award
  • Limited Time Offer: Earn 100,000 Bonus Marriott Bonvoy Points after spending $4,000 in purchases on your new Card in your first 3 months of Card Membership. Offer expires 11/2/22.
  • 6x points at hotels participating in the Marriott Bonvoy® program.
  • 4x points for purchases made at restaurants worldwide, at U.S. gas stations, on wireless telephone services purchased directly from U.S. service providers and on U.S. purchases for shipping.
  • 2x points on all other eligible purchases.
  • Receive a 7% discount off standard rates for reservations of standard guest rooms at hotels that participate in the Marriott Bonvoy program when you book directly. Terms and Conditions Apply.
  • Receive 1 Free Night Award every year after your Card renewal month. Plus, earn an additional Free Night Award after you spend $60K in purchases on your Card in a calendar year. Awards can be used for one night (redemption level at or under 35,000 Marriott Bonvoy® points) at hotels participating in Marriott Bonvoy®. Certain hotels have resort fees.
  • Enjoy Complimentary Marriott Bonvoy Gold Elite Status with your Card.
  • Terms apply.
  • See Rates & Fees