Grand Cayman from Boston, Los Angeles and New York City from $288 round-trip

Dreaming of white-sand beaches and crystal-clear blue waters? You can book a flight to glorious Grand Cayman for under $300 round-trip from a number of U.S. cities, including Boston, Miami and New York. There are also good discounts available from the West Coast.

This deal is for travel in the fall and into early 2023. These are economy fares, so checking a bag will likely cost you between $30 and $35 each way.

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Big thanks to Scott’s Cheap Flights for alerting us to this deal. Its Premium membership is available for $49 per year, while the Elite option is available for $199 per year. The latter offers access to deals on premium economy, business- and first-class tickets.

If you're flexible with your travel plan, you'll typically find better prices.

Deal basics

Airlines: American Airlines, Cayman Airways, JetBlue Airways and United Airlines.
Routes: Boston, Hartford, Los Angeles, Miami and New York to Grand Cayman.
How to book: Search Google Flights and book directly with the airline.
Travel dates: September 2022; also November 2022-February 2023.

Sample flights

Let's start with JetBlue's $295 nonstop fares out of New York City's John F. Kennedy International Airport (JFK) to Owen Roberts International Airport (GCM) in Grand Cayman. This is JetBlue's most restrictive fare, so you don't even get a full-size carry-on bag. Checking a bag will cost $60 round-trip. Here's one example we found the week before Thanksgiving.

There's good availability at this price in January and February, which is a good time to head south and escape New York's frigid temperatures.

Want to free yourself from the pressures of the holidays? A trip to the Caymans could do the trick. You can book a ticket via Cayman Airways from Miami International Airport (MIA) to Grand Cayman and spend Christmas week there. Grand Cayman is a fantastic family beach destination.

United has flights from Boston Logan International Airport (BOS) to the Caymans after New Year's for $309 round-trip. This itinerary has a layover in Newark each way, and checking a bag will cost $65.

We promised you some discount fares from the West Coast, so here's a United Airlines itinerary from Los Angeles International Airport (LAX) to Grand Cayman in November for $383 round-trip.

American has a basic economy ticket from Los Angeles to the Caymans in February for $380, another nice price for this route.

Maximize your purchase

Don't forget to pay for your trip with a credit card that earns extra points for travel, such as 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.

Bottom line

There is much to enjoy in Grand Cayman, from the legendary Seven Mile Beach to enchanting Stingray City. Whether you haven't visited yet or you're pondering a return, book your trip now and lock in a solid discount.