Caribbean deal alert: Fly to Puerto Rico and US Virgin Islands from $239 round trip

May 13, 2022

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There’s a killer fare sale happening right now on flights to Caribbean islands that don’t require passports (and yes, I did use “killer” as an adjective because I’m a child of the ’80s). So if you’ve been dreaming of blue skies, white sand beaches and drinks with colorful umbrellas, now’s the time to book your trip.

American Airlines, Delta Air Lines and United Airlines have marked down fares to evergreen tropical destinations such as the U.S. Virgin Islands — particularly St. Croix and St. Thomas — and San Juan, Puerto Rico. We came across some absolutely epic savings as we searched for itineraries.

The best deals are for fall travel between September and November. However, there are also some sweet bargains on early 2023 winter travel. Remember that basic economy fares with JetBlue and United don’t include full-size carry-on bags. It costs between $50 and $80 round trip to upgrade for more overhead bin space. Checked luggage costs around $30 to $35 each way.

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A tip of the travel cap to Scott’s Cheap Flights for alerting travelers of this new deal. Its Premium membership is available for $49 per year. The Elite tier option is available for $199 per year, and it offers access to deals on premium economy, business-class and first-class tickets.

You know what we always say: The more flexible you can be with your travel plans, the better price you’ll find.

Deal basics

Airlines: American, Delta, JetBlue, United.
Routes: Atlanta, Chicago, Fort Lauderdale, Los Angeles, Miami, Newark, New York City, Tuscon to San Juan, St. Croix, St. Thomas.
How to book: Search Google Flights and book directly through the airline.
Travel dates: Best availability September-November 2022 and January-March 2023.

Overlooking Charlotte Amalie, Hassel and Water islands from a Blackbeard’s Castle vantage point on St. Thomas in the U.S. Virgin Islands. (Photo by Nick Heinemann/Getty Images)

Related: US Virgin Islands see surge in tourism

Sample flights

Let’s start out West, where you can fly from Los Angeles International Airport (LAX) to Luis Muñoz Marín International Airport (SJU) in San Juan in February on American for just $321 round trip. American’s basic economy ticket allows for a free carry-on.

screenshot of google flights
(Screenshot from Google Flights)

A nonstop from Hartsfield-Jackson Atlanta International Airport (ATL) to San Juan in January is only $268 on Delta, and this basic economy ticket also comes with a free carry-on.

Screenshot of Google Flights
(Screenshot from Google Flights)

Here’s a fantastic fare we found from Chicago’s O’Hare International Airport (ORD) to San Juan in late October for only $239 round trip on Delta.

(Screenshot from Google Flights)

Chicago to St. Croix’s Henry E. Rohlsen Airport (STX) in late January certainly sounds nice, doesn’t it? You can book that itinerary on American for just $357 round trip.

Screenshot of Google Flights
(Screenshot from Google Flights)

Here’s an excellent end-of-summer deal for Arizona travelers. You can fly from Tucson International Airport (TUS) to Cyril E. King Airport (STT) on St. Thomas for just $291 round trip through Delta. That’s an excellent price for this fare. Please note that the outbound flight includes two stops.

Screenshot of Google Flights
(Screenshot from Google Flights)

If you live in the New York City area, you have plenty of bargain tickets to choose from. JetBlue has Blue Basic fares from JFK to St. Thomas in August for only $274 round trip. That includes a nonstop outbound flight. Carry-on bags are not included, though, so you should consider upgrading a tier for $50, which is cheaper than checking a bag.

Screenshot of Google Flights
(Screenshot from Google Flights)

Nonstop flights from New York City to San Juan in August cost only $276 on JetBlue — a substantial markdown from normal prices. Remember, the Blue Basic fares don’t come with a free full-size carry-on, so plan accordingly.

Screenshot of Google Flights
(Screenshot from Google Flights)

If you live in Music City, here’s a nice deal for you: You can fly from Nashville International Airport (BNA) to San Juan in January for only $235 round trip on American. We found plenty of availability at this great price in early 2023.

Screenshot of Google Flights
(Screenshot from Google Flights)

Related: Cleared for takeoff: A trip to Puerto Rico for a family of four

Maximize your purchase

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 or Chase Sapphire Reserve for 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.

Featured photo by patrickheagney/Getty Images. 

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