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

Feb. 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.

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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 image 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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Our points-obsessed staff uses a plethora of credit cards on a daily basis. If anyone on our team wouldn’t recommend it to a friend or a family member, we wouldn’t recommend it on The Points Guy either. Our opinions are our own, and have not been reviewed, approved, or endorsed by our advertising partners.
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TPG featured card

Best for the well-traveled foodie
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review
Apply for American Express® Gold Card
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Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of Card Membership.

Annual Fee

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Recommended Credit

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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.

Why We Chose It

There's a lot to love about the Amex Gold card. It's been a fan favorite during the pandemic because of its fantastic rewards rate on restaurants (that includes takeout and delivery in the U.S.!) and U.S. supermarkets. If you're hitting the skies soon, you'll also earn bonus points on travel. Paired with up to $120 in Uber Cash (for U.S. Uber rides or Uber Eats orders) and up to $120 in annual dining statement credits at eligible partners, there's no reason that the foodie shouldn't add this card to their wallet. Enrollment required.

Pros

  • 4x on dining at restaurants and U.S. supermarkets (on the first $25,000 in purchases per calendar year; then 1x)
  • 3x on flights booked directly with the airline or with Amex Travel
  • Welcome bonus of 60,000 points after spending $4,000 in the first six months

Cons

  • Weak on travel outside of flights and everyday spending bonus categories
  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber/food credits
  • Few travel perks and protections
  • Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of Card Membership.
  • Earn 4X Membership Rewards® Points at Restaurants, plus takeout and delivery in the U.S., and earn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per calendar year in purchases, then 1X).
  • Earn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and each month automatically get $10 in Uber Cash for Uber Eats orders or Uber rides in the U.S., totaling up to $120 per year.
  • $120 Dining Credit: Satisfy your cravings and earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, Milk Bar and select Shake Shack locations. Enrollment required.
  • Choose the color that suits your style. Gold or Rose Gold.
  • No Foreign Transaction Fees.
  • Annual Fee is $250.
  • Terms Apply.
  • See Rates & Fees
Apply for American Express® Gold Card
at American Express's secure site
Terms & restrictions apply. See rates & fees
Best for the well-traveled foodie
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

4XEarn 4X Membership Rewards® Points at Restaurants, plus takeout and delivery in the U.S.
4XEarn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per calendar year in purchases, then 1X).
3XEarn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.
  • Intro Offer
    Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of Card Membership.

    60,000 bonus points
  • Annual Fee

    $250
  • 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

There's a lot to love about the Amex Gold card. It's been a fan favorite during the pandemic because of its fantastic rewards rate on restaurants (that includes takeout and delivery in the U.S.!) and U.S. supermarkets. If you're hitting the skies soon, you'll also earn bonus points on travel. Paired with up to $120 in Uber Cash (for U.S. Uber rides or Uber Eats orders) and up to $120 in annual dining statement credits at eligible partners, there's no reason that the foodie shouldn't add this card to their wallet. Enrollment required.

Pros

  • 4x on dining at restaurants and U.S. supermarkets (on the first $25,000 in purchases per calendar year; then 1x)
  • 3x on flights booked directly with the airline or with Amex Travel
  • Welcome bonus of 60,000 points after spending $4,000 in the first six months

Cons

  • Weak on travel outside of flights and everyday spending bonus categories
  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber/food credits
  • Few travel perks and protections
  • Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of Card Membership.
  • Earn 4X Membership Rewards® Points at Restaurants, plus takeout and delivery in the U.S., and earn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per calendar year in purchases, then 1X).
  • Earn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and each month automatically get $10 in Uber Cash for Uber Eats orders or Uber rides in the U.S., totaling up to $120 per year.
  • $120 Dining Credit: Satisfy your cravings and earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, Milk Bar and select Shake Shack locations. Enrollment required.
  • Choose the color that suits your style. Gold or Rose Gold.
  • No Foreign Transaction Fees.
  • Annual Fee is $250.
  • Terms Apply.
  • See Rates & Fees