Deal alert: Winter fares to Puerto Rico from various US cities for under $300 round trip

A winter escape to the sunnier climes is a cherished tradition. Savvy travelers know to plan these trips well in advance, especially this year since deals are harder to come by.

Right now, there are quality discount airfares to Puerto Rico, with several sub-$300 round-trip tickets available. San Juan is a particularly attractive destination for those who live in cities that are often frigid in winter, such as Buffalo, Chicago, Cleveland, New York City and Washington, D.C., all of which are part of this sale. That's even more true now that all COVID-19 travel restrictions have been removed for visitors.

This fare sale is for economy tickets, so expect to pay at least $60 to check a bag if you need to do so. The majority of the sale fares we found were for travel between September and March 2023.

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Thanks to Scott’s Cheap Flights for first alerting us to this deal. Its Premium membership is available for $49 per year, while the Elite tier option is available for $199 per year. The latter offers access to deals on premium economy, business- and first-class tickets. As always, try to be as flexible with your travel plans as possible, as it'll typically help you find better prices.

Deal basics

Airlines: American, Delta, JetBlue.
Routes: Akron, Ohio; Baltimore; Chicago; Cleveland; Newark; New York City; Washington, D.C.; and more to San Juan, Puerto Rico.
How to book: Search Google Flights and book directly through the airline.
Travel dates: From September through March 2023.

Sample flights

Once football season ends and the winter weather really kicks in in cities like Buffalo, a trip south may be just what you need. Consider heading to sunny San Juan, where average daytime highs rarely fall below 85 degrees year-round. Delta has round-trip fares from Buffalo Niagara International Airport (BUF) for just $305, a nice markdown from regular prices.

You can fly American out of Cleveland Hopkins International Airport (CLE) to Puerto Rico in March for only $297 round trip. It's a basic economy fare, so keep in mind that you only get a free carry-on bag. If you wish to check a bag, it will cost you $60.

You can fly Delta out of Chicago's O'Hare International Airport (ORD) to Puerto Rico in January and February for as low as $309 round trip. We found lots of availability at this price in early 2023.

Indianapolis International Airport (IND) to Puerto Rico is also available in January for just $261 round trip on American.

Additionally, you can fly nonstop on JetBlue out of New York City's John F. Kennedy International Airport (JFK) to San Juan for only $296 in early December. That's a great price for this route during the holiday travel season, and we saw quite a bit of availability at this price.

JetBlue has excellent fares out of Washington, D.C.'s Ronald Reagan Washington National Airport (DCA) to San Juan just before Christmas, too. You can fly nonstop for only $304, a huge savings from what this route normally costs during the holiday season.

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.