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

Aug. 22, 2022
4 min read
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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.

George Town, Cayman Islands. (Rose MassinghamEyeEm/Getty Images)

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.

(Screenshot from google.com/flights)

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.

(Screenshot from google.com/flights)

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.

(Screenshot from google.com/flights)

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.

(Screenshot from google.com/flights)

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.

(Screenshot from google.com/flights)

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

(Screenshot from google.com/flights)

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.

Featured image by Getty Images/iStockphoto
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
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Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases
Best starter travel card
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

3XEarn 3 Points per $1 spent at Restaurants and Supermarkets
3XEarn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
1XEarn 1 Point per $1 spent on all other purchases
  • Intro Offer
    For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening

    Earn 80,000 ThankYou® points
    60,000 points
  • Annual Fee

    $95
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    670-850
    Excellent, Good

Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
  • World Elite Mastercard benefits, extended warranty, damage and theft protection.

Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases