HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Islands

$70+ Cheap flights from Massachusetts to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Cayman Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Massachusetts to Cayman Islands

Cheapest flights from Massachusetts to Cayman Islands
Explore the most affordable flight options available from Massachusetts to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amBOS - GCM
1 stop9h 09mAmerican Airlines
Sat 12/131:01 pmGCM - BOS
1 stop9h 42mAmerican Airlines
Deal found 11/2$280
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:00 amBOS - GCM
2 stops10h 35mUnited Airlines
Sat 11/225:30 pmGCM - BOS
1 stop6h 12mUnited Airlines
Deal found 11/1$284
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/295:40 amBOS - GCM
1 stop5h 54mAmerican Airlines
Sat 12/61:25 pmGCM - BOS
2 stops9h 19mAmerican Airlines
Deal found 11/2$285
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amBOS - GCM
1 stop7h 15mUnited Airlines
Sat 12/135:30 pmGCM - BOS
2 stops17h 28mUnited Airlines
Deal found 11/1$289
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:15 pmBDL - GCM
1 stop19h 30mUnited Airlines
Sun 12/285:10 pmGCM - BDL
1 stop6h 48mUnited Airlines
Deal found 11/1$303
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:02 amBOS - GCM
1 stop7h 13mUnited Airlines
Sat 11/155:30 pmGCM - BOS
1 stop6h 12mUnited Airlines
Deal found 11/2$310
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:00 amBOS - GCM
2 stops10h 30mUnited Airlines
Sat 12/202:25 pmGCM - BOS
1 stop8h 23mUnited Airlines
Deal found 11/2$313
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amALB - GCM
1 stop7h 45mUnited Airlines
Fri 12/125:45 pmGCM - ALB
2 stops27h 29mUnited Airlines
Deal found 11/2$315
This Priceline deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:19 amBOS - GCM
Nonstop4h 28mJetBlue
Sat 12/612:54 pmGCM - BOS
Nonstop4h 11mJetBlue
Deal found 11/2$316
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:20 pmALB - GCM
1 stop18h 40mAmerican Airlines
Thu 12/113:14 pmGCM - ALB
1 stop7h 30mAmerican Airlines
Deal found 11/2$317
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:20 amBOS - GCM
1 stop11h 15mUnited Airlines
Sat 12/205:30 pmGCM - BOS
1 stop6h 24mUnited Airlines
Deal found 11/2$317
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:09 amBDL - GCM
1 stop5h 48mAmerican Airlines
Thu 11/1312:55 pmGCM - BDL
1 stop11h 32mAmerican Airlines
Deal found 11/2$328

Cheap flight deals from Massachusetts to Cayman Islands

Keep the following information in mind while searching for Massachusetts to Cayman Islands flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$277
(United Airlines)

One-way from

$70
(Priceline)

Popular in

December

Cheapest in

January

Average price

$448

Good round-trip deal

$385 or less

Good one-way deal

$118 or less
Provider with most accurate pricing for Boston Logan Intl-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-George Town Owen Roberts Intl flights.
Search Deals
From Massachusetts to Cayman Islands
Search Deals
One-way flight from Massachusetts to Cayman Islands
Search Deals
High demand for flights, 5% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Cayman Islands.
Search Deals
Price to beat on a one-way flight from Massachusetts to Cayman Islands.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 3, 2025.
Use the filters below to find and compare flights from Massachusetts to the Cayman Islands that are best for you.

Fly from

Massachusetts

Fly to

Cayman Islands

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 2/7

7:22 pm-1:45 pm

2 stops18h 23m

George Town Owen Roberts Intl

Sat 2/14

5:30 pm-11:57 pm

1 stop6h 27m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/3

6:45 am-1:15 pm

1 stop6h 30m

George Town Owen Roberts Intl

Sat 1/10

5:30 pm-11:49 pm

1 stop6h 19m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 12/6

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 12/13

5:30 pm-10:58 am

2 stops17h 28m

$289

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Mon 12/22

6:15 pm-1:45 pm

1 stop19h 30m

George Town Owen Roberts Intl

Sun 12/28

5:10 pm-11:58 pm

1 stop6h 48m

$303

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Tue 1/6

3:00 pm-1:15 pm

2 stops22h 15m

George Town Owen Roberts Intl

Sat 1/10

5:30 pm-11:44 pm

1 stop6h 14m

$308

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Tue 1/6

6:00 am-12:40 pm

1 stop6h 40m

George Town Owen Roberts Intl

Sat 1/10

12:15 pm-10:34 pm

1 stop10h 19m

$310

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sat 12/6

6:00 am-4:35 pm

2 stops10h 35m

George Town Owen Roberts Intl

Fri 12/12

5:45 pm-2:20 pm

2 stops20h 35m

$315

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sat 12/6

6:00 am-1:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Thu 12/11

5:45 pm-5:27 pm

2 stops23h 42m

$315

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sat 12/6

5:20 pm-12:00 pm

1 stop18h 40m

George Town Owen Roberts Intl

Thu 12/11

3:14 pm-10:44 pm

1 stop7h 30m

$317

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Tue 1/6

5:03 pm-12:05 pm

2 stops19h 02m

George Town Owen Roberts Intl

Sat 1/10

12:35 pm-10:34 pm

1 stop9h 59m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 38 results
1
2
3
4

Best time to book a flight from Massachusetts to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to the Cayman Islands

What is the cheapest month to book a flight from Massachusetts to Cayman Islands?

Currently, November is the cheapest month in which you can book a flight from Massachusetts to Cayman Islands (average of $235). Flying from Massachusetts to Cayman Islands in June is currently the most expensive (average of $419). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MA to KY?

Find hourly flight availability from Massachusetts to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

It’s typically best to fly out from Massachusetts to Cayman Islands in the afternoon. Doing so could potentially save you 55% on the flight price compared to flying at noon, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Massachusetts to Cayman Islands?

    United Airlines, Delta, and American Airlines can get you from Massachusetts to Cayman Islands in just under 6h 40m. Your travel time can differ by up to 12h. The distance from Massachusetts to Cayman Islands is about 1644 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Massachusetts to Cayman Islands one-way?

    One-way options have recently been found by users for as low as $83 on United Airlines. Other airlines that offer cheap prices include Delta from $88 and JetBlue from $146 one-way.

  • Can I find deals for flights from Massachusetts to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Cayman Islands.

  • Can I find deals for business class flights from Massachusetts to Cayman Islands?

    Yes. Cheapflights offers flight deals from Massachusetts to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Cayman Islands?

    Currently, November is the cheapest month in which you can book a flight from Massachusetts to Cayman Islands (average of $235). Flying from Massachusetts to Cayman Islands in June is currently the most expensive (average of $419). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
Orlando to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
John F Kennedy Intl to Santo Domingo flights
Dulles Intl to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
Philadelphia to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Baltimore to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Boston to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Newark to Oranjestad flights
John F Kennedy Intl to Montego Bay flights
Boston to Oranjestad flights
LaGuardia to Punta Cana flights
Hartford to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
Newark to Montego Bay flights
Tampa to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Boston to Santo Domingo flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
John F Kennedy Intl to Port of Spain flights
Raleigh to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
Newark to Nassau flights
O'Hare Intl to Punta Cana flights
Minneapolis to Luis Munoz Marin Intl flights
Newark to Saint Thomas Island flights
George Bush Intcntl to Luis Munoz Marin Intl flights
LaGuardia to Oranjestad flights
Dulles Intl to Punta Cana flights
John F Kennedy Intl to Nassau flights
Miami to Santo Domingo flights
Fort Lauderdale to Santo Domingo flights
John F Kennedy Intl to Simpson Bay flights
John F Kennedy Intl to Kingston flights
Detroit to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
Orlando to Punta Cana flights
LaGuardia to Montego Bay flights
John F Kennedy Intl to Saint Thomas Island flights

Top 6 airlines flying from Massachusetts to Cayman Islands

Discover the top 6 airlines that operate flights from Massachusetts to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$489FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$460FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$270Average$412FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$330Average$541FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$457Average$559FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.