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$187+ Cheap flights from Grand Cayman to Massachusetts

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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — BOS
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap flight deals from Grand Cayman to Massachusetts

Cheapest flights from Grand Cayman to Massachusetts
Explore the most affordable flight options available from Grand Cayman to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.

This American Airlines deal was found by Cheapflights users on 2/2. 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.
Wed 3/112:44 pm
GCM
-
BOS
1 stop8h 21m
American Airlines
Wed 3/186:30 am
BOS
-
GCM
1 stop8h 14m
American Airlines
Deal found 2/2$285
This American Airlines deal was found by Cheapflights users on 2/3. 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 4/1812:40 pm
GCM
-
BOS
1 stop9h 50m
American Airlines
Sat 4/256:53 pm
BOS
-
GCM
1 stop17h 40m
American Airlines
Deal found 2/3$310
This United Airlines deal was found by Cheapflights users on 2/3. 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 4/181:35 pm
GCM
-
BOS
2 stops18h 50m
United Airlines
Sat 4/257:30 pm
BOS
-
GCM
2 stops18h 00m
United Airlines
Deal found 2/3$330
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/52:25 pm
GCM
-
BOS
2 stops9h 24m
United Airlines
Sat 2/79:30 am
BOS
-
GCM
2 stops28h 15m
United Airlines
Deal found 2/3$332
This United Airlines deal was found by Cheapflights users on 2/4. 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.
Fri 2/62:25 pm
GCM
-
BOS
1 stop7h 27m
United Airlines
Sun 2/86:00 am
BOS
-
GCM
1 stop7h 45m
United Airlines
Deal found 2/4$341
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/42:25 pm
GCM
-
BOS
2 stops20h 11m
United Airlines
Sat 2/72:27 pm
BOS
-
GCM
2 stops23h 18m
United Airlines
Deal found 2/3$388
This JetBlue deal was found by Cheapflights users on 2/3. 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.
Sat 4/182:10 pm
GCM
-
BOS
1 stop9h 04m
JetBlue
Sat 4/2512:20 pm
BOS
-
GCM
Nonstop4h 20m
JetBlue
Deal found 2/3$423
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/122:49 pm
GCM
-
BOS
1 stop8h 55m
Multiple Airlines
Sun 2/156:55 pm
BOS
-
GCM
1 stop17h 30m
Multiple Airlines
Deal found 2/2$436

Find flight deals from Grand Cayman to Massachusetts

Keep the following information in mind while searching for Grand Cayman to Massachusetts flight deals. Data was last updated February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$285
(American Airlines)

One-way from

$187
(Cheapflightsfares)

Popular in

May

Cheapest in

January

Average price

$311
Provider with most accurate pricing for George Town Owen Roberts Intl-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for George Town Owen Roberts Intl-Boston Logan Intl flights.
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From Grand Cayman to Massachusetts
Search Deals
One-way flight from Grand Cayman to Massachusetts
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Grand Cayman to Massachusetts 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 5, 2026.
Use the filters below to find and compare flights from Grand Cayman to Massachusetts that are best for you.

Fly from

Grand Cayman

Fly to

Massachusetts

Route

Depart

Return

Price

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Wed 3/11

2:44 pm-12:05 am

1 stop8h 21m

Boston Logan Intl

Wed 3/18

6:30 am-1:44 pm

1 stop8h 14m

$285

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 4/18

12:40 pm-11:30 pm

1 stop9h 50m

Boston Logan Intl

Sat 4/25

6:53 pm-11:33 am

1 stop17h 40m

$310

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 4/18

1:35 pm-9:25 am

2 stops18h 50m

Boston Logan Intl

Sat 4/25

7:30 pm-12:30 pm

2 stops18h 00m

$330

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 4/18

2:10 pm-12:14 am

1 stop9h 04m

Boston Logan Intl

Sat 4/25

12:20 pm-3:40 pm

Nonstop4h 20m

$423

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 5/7

1:40 pm-11:59 pm

1 stop9h 19m

$204

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 2/26

2:50 pm-9:51 pm

2 stops31h 01m

$206

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Fri 2/27

2:25 pm-9:51 pm

1 stop7h 26m

$206

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 2/28

2:50 pm-10:49 am

1 stop19h 59m

$206

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 2/26

2:49 pm-11:44 pm

1 stop8h 55m

$207

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Tue 5/5

1:25 pm-1:15 am

1 stop10h 50m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 13 results
1
2

Best time to book a flight from Grand Cayman to Massachusetts

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

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

Currently, April is the cheapest month in which you can book a flight from Grand Cayman to Massachusetts (average of $204). Flying from Grand Cayman to Massachusetts in November is currently the most expensive (average of $504). 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 LAW to MA?

Find hourly flight availability from Grand Cayman to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 5, 2026.

When flying from Grand Cayman to Massachusetts, 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 Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated February 5, 2026.
Peruse reviews from past customers who have flown with American Airlines and JetBlue from Grand Cayman to Massachusetts to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,237 reviews

Food

6.4

Comfort

7.2

Crew

8.0

Overall

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,237 reviews
American Airlines
7.2
Good
11,237 reviews

Food

6.4

Comfort

7.2

Crew

8.0

Overall

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
JetBlue
7.2
Good
2,894 reviews
American Airlines
7.2
Good
11,237 reviews

Food

6.4

Comfort

7.2

Crew

8.0

Overall

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Grand Cayman to Massachusetts. 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 Grand Cayman to Massachusetts?

    Departing from Grand Cayman to Massachusetts will take you 8h 21m. Grand Cayman and Massachusetts are separated by a distance of 1704 mi.

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

    One-way options have recently been found by users for as low as $190 on United Airlines. Other airlines that offer cheap prices include Delta from $194 and JetBlue from $197 one-way.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Grand Cayman to Massachusetts (average of $204). Flying from Grand Cayman to Massachusetts in November is currently the most expensive (average of $504). 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.

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Top 2 airlines flying from Grand Cayman to Massachusetts

Discover the top 2 airlines that operate flights from Grand Cayman to Massachusetts. 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 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$265Average$330FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$302Average$499FlexibilityNo cancel feeOn-time71%

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