Deal alert: Winter getaways to Puerto Rico, US Virgin Islands from $199 round-trip

Jan 8, 2022

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You can leave the passport at home with this new deal alert. There are great sales available for quick weekend winter getaways to Caribbean hotspots like Puerto Rico and the U.S. Virgin Islands from a number of American cities. We found round-trip fares as low as $199 for Economy seats.

Note: The cheapest fares with JetBlue and United do not include a full-size carry-on bag. Expect to pay at least $80 roundtrip to upgrade to regular economy on those airlines. So if you need to pack a bit more for your beach vacation, keep in mind that a checked bag costs $30-$35 each way.

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This deal hit our radar thanks to our friends at Scott’s Cheap Flights in a deal first sent to their premium subscribers and is available from January to March 2022. Their premium subscription is $49 per year, and the elite membership costs $199 annually.

Nonmembers can find sale prices by using Google Flights to search for desired routes and dates.

Condado Ocean Club San Juan, Puerto Rico May 2021. (Photo by Clint Henderson:The Points Guy)

Deal basics

Airlines: American, Delta JetBlue, United.
Routes: ATL/BUF/CLE/DEN/JFK/MIA/ORD and others to Aguadilla, Puerto Rico (BQN), San Juan (SJU), St. Croix (STX) and St. Thomas (STT).
Cost: Flights available from $199; some nonstop routes available.
Dates: January-March 2022; Some routes available April/May and between August-November 2022.

Pay with: The Platinum Card® from American Express for 5 points per dollar on airfare booked directly with the airline or through American Express Travel (on up to $500,000 on these purchases per calendar year); the Citi Prestige® Card for 5 points per dollar on airfare; the Citi Premier® Card (3 points per dollar on air travel); Chase Sapphire Reserve (3 points per dollar on air travel); the American Express® Gold Card for 3 points per dollar on airfare when booked directly with the airline or through Amex Travel or the Chase Sapphire Preferred Card for 2 points per dollar on travel.

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.

(Photo by Glow Images/Getty Images)

Here’s one of the best bargains we found: New York City (JFK) to St. Croix (STX) on American for just $199. That’s about as low as you’ll find for a February respite from the east coast winter. It’s Basic Economy so you don’t get a seat selection, but you do get a free carry-on.

(Screenshot courtesy of Google Flights)

New Yorkers can also fly in February from JFK to San Juan (SJU) for only $200 nonstop on JetBlue. This is a Blue Basic fare, so note that carry-on bags aren’t allowed for passengers flying in this tier. Checking a bag will cost you $60, or you can upgrade to Blue tier for $40, which not only gives you a free carry-on for your weekend getaway, but also an assigned seat.

(Screenshot courtesy of Google Flights)

Flights from NYC to the city of Aguadilla, part of the Porta del Sol region of Puerto Rico, are also available at a great price in late January and into February. JetBlue has $226 nonstop Blue Basic fares. That’s a low enough price that either choosing to pay the $60 fee for a checked bag, or upgrading for $80, is still worth it.

(Screenshot courtesy of Google Flights)

We found some rock-bottom fares from Los Angeles (LAX) to San Juan (SJU) in late February. JetBlue has Blue Basic itineraries for only $249. That’s well more than 50% off what that fare usually goes for. Keep in mind that it’s JetBlue’s bare-bones tier, so no full-size carry-on bag is allowed. Unless you can pack everything you need for a long weekend into a backpack, we want to let you know that a checked bag will set you back $60.

(Screenshot courtesy of Google Flights)

We like to spotlight the best deals from those parts of the U.S. that get the full winter experience because a Caribbean escape just means a bit more when you have to shovel your driveway and always remember your gloves to go to work.

That’s why this fare from Cleveland (CLE) to San Juan is so appealing. American has it for just $199 round-trip for an end-of-January trip. We also saw $199 fares in March, too, but don’t wait too long. This is roughly half what this fare usually costs.

(Screenshot courtesy of Google Flights)

Related: A beginner’s guide to visiting Puerto Rico

Atlanta (ATL) to St. Thomas (STT) at the end of January is just $258 round-trip on American. You have some extended layovers in Miami both ways, but It’s too good to pass up at that discounted price.

(Screenshot courtesy of Google Flights)

 

Maximize your purchase

Don’t forget to use a card that earns points on airfare purchases, like The Platinum Card® from American Express for 5 points per dollar on airfare booked directly with the airline or through American Express Travel (on up to $500,000 on these purchases per calendar year); the Citi Prestige® Card for 5 points per dollar on airfare; the Citi Premier® Card (3 points per dollar on air travel); Chase Sapphire Reserve (3 points per dollar on air travel); the American Express® Gold Card for 3 points per dollar on airfare when booked directly with the airline or through Amex Travel or the Chase Sapphire Preferred Card for 2 points per dollar on travel.

Bottom line

Whether you plan to kick back and relax with your feet in the sand and your hands on a frosty beverage by the beach in St. Croix, or want to try out some of the great golf and water sports available in Aguadilla, this great deal will help get you there at some excellent prices.

Featured photo by John Bilyou/500px/Getty Images.

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More Things to Know
  • Earn 50,000 Bonus Miles and 5,000 Medallion® Qualification Miles (MQMs) after you spend $2,000 in purchases on your new Card in your first 3 months.
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