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

Do you dream of beaches with white sand and clear blue water? You can book a flight to gorgeous Grand Cayman for less than $300 round trip from a number of US cities, including Boston, Miami, and New York. Good discounts are also available from West Coast.

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

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Many thanks to Scott 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 provides access to deals on Premium Economy Class, Business and First Class tickets.

If you are flexible with your travel plan, you will usually find better rates.

Deal Basics

Airlines: American Airlines, Cayman Airlines, JetBlue Airways, United Airlines.
ways: Boston, Hartford, Los Angeles, Miami and New York to Grand Cayman.
How to book: Search for flights on Google and book directly with the airline.
Travel dates: September 2022; November 2022 – February 2023.

Georgetown, Cayman Islands. (Rose Massingham AIM/Getty Images)

Sample flights

Let’s start with JetBlue’s $295 non-stop fares from 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 handbag. A bag check will cost $60 round-trip. Here’s one example we found a week before Thanksgiving.

(screenshot from google.com/flights)

There is good availability at this price in January and February, which is a good time to head south and escape the freezing temperatures of New York.

(screenshot from google.com/flights)

Want to free yourself from the stress of the holidays? A trip to the Cayman Islands can do the trick. You can book a ticket with Cayman Airlines from Miami International Airport (MIA) to Grand Cayman and spend Christmas week there. Grand Cayman is a great family beach destination.

(screenshot from google.com/flights)

United has flights from Boston Logan International Airport (BOS) to the Cayman Islands after New Years Eve for $309 one way. This itinerary has a stop in Newark each way, and a bag check will cost $65.

(screenshot from google.com/flights)

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

(screenshot from google.com/flights)

American has a basic economy ticket from Los Angeles to the Cayman Islands in February for $380, which is another good price for this route.

(screenshot from google.com/flights)

Maximize your purchase

Don’t forget to pay for your flight with a credit card that earns extra points for travel, like Platinum® Card from American Express for 5 points per dollar on an airline ticket booked directly with the airline or through American Express Travel (up to $500,000 on such purchases per calendar year), a Citi Prestige® Card for 5 points per dollar on an airline ticket, Citi Premier® Card or Chase Sapphire Reserve For 3 points per dollar on air travel, The American Express® Gold Card For 3 points for every dollar on a flight ticket when booking directly with the airline or through Amex Travel or Chase Sapphire Favorite Card For two points per dollar for travel.

The information for the Citi Prestige card was collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

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There is plenty to enjoy on Grand Cayman, from the legendary Seven Mile Beach to the charming town of Stingray. Whether you haven’t visited yet or are thinking of returning, book your flight now and get a huge discount.

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