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.
Top offers from our partners
How we chose these cards
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| 3X | Earn 3X Miles on Delta purchases and purchases made directly with hotels. |
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Intro offer
Annual Fee
Recommended Credit
Why We Chose It
Build your loyalty to Delta by applying for the carrier's mid-tier card option, the Delta SkyMiles Platinum card. The annual fee is quickly recouped by the card's travel perks, such as an application credit to Global Entry or TSA Precheck, annual companion certificate and so much more. Plus you can fast-track to elite status simply through card spend.Pros
- Earn bonus Medallion® Qualification Miles (MQMs) and an Medallion Qualifying Dollar (MQD) waiver when you hit specific spending thresholds with your card within a calendar year
- Receive a Domestic Main Cabin round-trip companion certificate each year
- Statement credit for TSA PreCheck/Global Entry fee (up to $100)
- First checked bag free
Cons
- Doesn't make sense if you don't fly Delta
- SkyMiles aren't the most valuable airline currency
- Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.
- Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
- Enjoy your first checked bag free on Delta flights. Plus enjoy Main Cabin 1 Priority Boarding and settle into your seat sooner.
- New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
- Earn 3X Miles on Delta purchases and purchases made directly with hotels.
- Earn 2X Miles at restaurants worldwide including takeout and delivery in the U.S., and at U.S. supermarkets.
- Earn 1X Mile on all other eligible purchases.
- Enjoy a per-visit rate of $50 per person for Card Members and up to two guests to enter the Delta Sky Club when traveling on a Delta flight.
- Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
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- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees
Rewards Rate
| 3X | Earn 3X Miles on Delta purchases and purchases made directly with hotels. |
| 2X | Earn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets. |
| 1X | Earn 1X Miles on all other eligible purchases. |
Intro Offer
Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.Earn 90,000 Bonus Miles50,000 Bonus MilesAnnual Fee
$250Recommended 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.670-850Excellent/Good
Why We Chose It
Build your loyalty to Delta by applying for the carrier's mid-tier card option, the Delta SkyMiles Platinum card. The annual fee is quickly recouped by the card's travel perks, such as an application credit to Global Entry or TSA Precheck, annual companion certificate and so much more. Plus you can fast-track to elite status simply through card spend.Pros
- Earn bonus Medallion® Qualification Miles (MQMs) and an Medallion Qualifying Dollar (MQD) waiver when you hit specific spending thresholds with your card within a calendar year
- Receive a Domestic Main Cabin round-trip companion certificate each year
- Statement credit for TSA PreCheck/Global Entry fee (up to $100)
- First checked bag free
Cons
- Doesn't make sense if you don't fly Delta
- SkyMiles aren't the most valuable airline currency
- Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.
- Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
- Enjoy your first checked bag free on Delta flights. Plus enjoy Main Cabin 1 Priority Boarding and settle into your seat sooner.
- New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
- Earn 3X Miles on Delta purchases and purchases made directly with hotels.
- Earn 2X Miles at restaurants worldwide including takeout and delivery in the U.S., and at U.S. supermarkets.
- Earn 1X Mile on all other eligible purchases.
- Enjoy a per-visit rate of $50 per person for Card Members and up to two guests to enter the Delta Sky Club when traveling on a Delta flight.
- Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
- Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs up to two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees