Deal alert: Roundtrip flights to the Caribbean, most under $200
Quick summary
Update: Some offers mentioned below are no longer available. View the current offers here.
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.
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
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
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
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
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.
Similar to JetBlue's Blue Basic, flights in this batch are for Delta's basic economy which include a full-size carry-on bag.
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 (see rates and fees), 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.