HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$89+ Cheap flights from Massachusetts to Grand Cayman

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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Grand Cayman 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.

Cheap flight deals from Massachusetts to Grand Cayman

Keep the following information in mind while searching for Massachusetts to Grand Cayman flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$294
(United Airlines)

One-way from

$89
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$598
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 Grand Cayman
Search Deals
One-way flight from Massachusetts to Grand Cayman
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

Find flight deals from Massachusetts to Grand Cayman

Cheapest flights from Massachusetts to Grand Cayman
Explore the most affordable flight options available from Massachusetts to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/127:36 pmBOS - GCM
2 stops17h 39mUnited Airlines
Tue 3/184:25 pmGCM - BOS
2 stops17h 34mUnited Airlines
Deal found 2/19$294
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/197:11 amBOS - GCM
1 stop8h 23mAmerican Airlines
Wed 3/2612:45 pmGCM - BOS
2 stops8h 58mAmerican Airlines
Deal found 2/19$296
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/205:40 amBOS - GCM
1 stop6h 58mDelta
Mon 3/241:03 pmGCM - BOS
1 stop11h 02mDelta
Deal found 2/19$330
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/125:20 amBOS - GCM
1 stop6h 50mJetBlue
Wed 3/191:52 pmGCM - BOS
Nonstop4h 07mJetBlue
Deal found 2/19$331
This Air Canada deal was found by Cheapflights users on 2/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/16:00 amBOS - GCM
1 stop6h 55mAir Canada
Mon 5/512:50 pmGCM - BOS
2 stops24h 42mAir Canada
Deal found 2/18$425
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/411:33 amBOS - GCM
1 stop28h 37mMultiple Airlines
Sun 3/92:00 pmGCM - BOS
1 stop17h 52mMultiple Airlines
Deal found 2/18$451
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 4/302:56 pmBDL - GCM
2 stops22h 34mUnited Airlines
Sat 5/34:15 pmGCM - BDL
1 stop16h 20mUnited Airlines
Deal found 2/20$524
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 4/305:02 amBDL - GCM
2 stops8h 57mAmerican Airlines
Sat 5/312:25 pmGCM - BDL
2 stops19h 37mAmerican Airlines
Deal found 2/20$528
This United Airlines deal was found by Cheapflights users on 2/19. 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 4/56:00 amALB - GCM
1 stop10h 10mUnited Airlines
Sat 4/124:15 pmGCM - ALB
1 stop16h 50mUnited Airlines
Deal found 2/19$538
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 7/177:47 pmALB - GCM
1 stop16h 18mAmerican Airlines
Thu 7/313:50 pmGCM - ALB
2 stops18h 01mAmerican Airlines
Deal found 2/20$553
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/277:05 amBDL - GCM
1 stop5h 45mSouthwest
Sun 6/112:45 pmGCM - BDL
2 stops10h 20mSouthwest
Deal found 2/20$576
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 3/172:12 pmORH - GCM
2 stops22h 33mAmerican Airlines
Tue 3/2512:45 pmGCM - ORH
2 stops23h 55mAmerican Airlines
Deal found 2/19$580

Find flights from Massachusetts to Grand Cayman within your budget

Customize your flight search to find flights from Massachusetts to Grand Cayman 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 February 20, 2025.

Fly from

Massachusetts

Fly to

Grand Cayman

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 3/12

7:36 pm-12:15 pm

2 stops17h 39m

George Town Owen Roberts Intl

Tue 3/18

4:25 pm-10:59 am

2 stops17h 34m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 3/19

7:11 am-2:34 pm

1 stop8h 23m

George Town Owen Roberts Intl

Wed 3/26

12:45 pm-10:43 pm

2 stops8h 58m

$296

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 3/10

9:47 am-1:16 pm

Nonstop4h 29m

George Town Owen Roberts Intl

Wed 3/19

1:52 pm-6:59 pm

Nonstop4h 07m

$316

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 3/20

5:40 am-11:38 am

1 stop6h 58m

George Town Owen Roberts Intl

Tue 3/25

1:03 pm-1:05 am

1 stop11h 02m

$330

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 5/1

6:00 am-11:55 am

1 stop6h 55m

George Town Owen Roberts Intl

Mon 5/5

12:50 pm-10:03 am

1 stop20h 13m

$425

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 3/4

11:33 am-4:10 pm

1 stop28h 37m

George Town Owen Roberts Intl

Sun 3/9

2:00 pm-8:52 am

1 stop17h 52m

$451

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Wed 4/30

2:56 pm-12:30 pm

2 stops22h 34m

George Town Owen Roberts Intl

Sat 5/3

4:15 pm-9:35 am

1 stop16h 20m

$524

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Wed 4/30

5:02 am-12:59 pm

2 stops8h 57m

George Town Owen Roberts Intl

Sat 5/3

12:25 pm-9:02 am

2 stops19h 37m

$528

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sat 4/5

6:00 am-3:10 pm

1 stop10h 10m

George Town Owen Roberts Intl

Sat 4/12

4:15 pm-10:05 am

1 stop16h 50m

$538

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Mon 3/17

2:12 pm-11:45 am

2 stops22h 33m

George Town Owen Roberts Intl

Tue 3/25

12:45 pm-1:40 pm

2 stops23h 55m

$580

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 23 results
1
2
3

Best time to book a flight from Massachusetts to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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.

Travel insights for flights from Massachusetts to Grand Cayman

Get recent, data-driven insights about flights from Massachusetts to Grand Cayman including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Grand Cayman (average of $467). Flying from Massachusetts to Grand Cayman in March is currently the most expensive (average of $594). 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 LAW?

Find hourly flight availability from Massachusetts to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

When flying from Massachusetts to Grand Cayman, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Grand Cayman. Reviews last updated February 20, 2025.
To help decide which airline to fly from Massachusetts to Grand Cayman, see what other customers have to say about Southwest, Delta and JetBlue. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

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

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

    $89 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $94 and $104, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts to Grand Cayman 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 Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Grand Cayman (average of $467). Flying from Massachusetts to Grand Cayman in March is currently the most expensive (average of $594). 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 Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
Newark to George Town flights
John F Kennedy Intl to George Town flights
LaGuardia to George Town flights
O'Hare Intl to George Town flights
Boston to George Town flights
Dallas/Fort Worth to George Town flights
Miami to George Town flights
Baltimore to George Town flights
Dulles Intl to George Town flights
Reagan-National to George Town flights
Atlanta to George Town flights
Charlotte to George Town flights
Philadelphia to George Town flights
Minneapolis to George Town flights
Los Angeles to George Town flights
Denver to George Town flights
Seattle to George Town flights
Tampa to George Town flights
Orlando to George Town flights
Pittsburgh to George Town flights
Cleveland to George Town flights
St. Louis to George Town flights
George Bush Intcntl to George Town flights
Hobby to George Town flights
Indianapolis to George Town flights
Midway to George Town flights
Cincinnati to George Town flights
Sky Harbor Intl to George Town flights
Raleigh to George Town flights
Columbus to George Town flights
San Francisco to George Town flights
Fort Lauderdale to George Town flights
Detroit to George Town flights
Kansas City to George Town flights
Love Field to George Town flights
Richmond to George Town flights
Austin to George Town flights
Ontario to George Town flights
Milwaukee to George Town flights
Little Rock to George Town flights
Omaha to George Town flights
Hartford to George Town flights
Portland to George Town flights
Lexington to George Town flights
Nashville to George Town flights
West Palm Beach to George Town flights
Albuquerque to George Town flights
White Plains to George Town flights
Providence to George Town flights
Louisville to George Town flights

Top 6 airlines flying from Massachusetts to Grand Cayman

Discover the top 6 airlines that operate flights from Massachusetts to Grand Cayman. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$234Average$559FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$261Average$487FlexibilityNo cancel feeOn-time62%
DeltaCheapest$288Average$435FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$291Average$464FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$325Average$508FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$618Average$934FlexibilityNo 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.