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$190+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — BOS
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheap 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 September 19, 2025.

Round-trip from

$301
(United Airlines)

One-way from

$190
(Delta)

Popular in

May

Cheapest in

November

Average price

$369
From Grand Cayman to Massachusetts
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One-way flight from Grand Cayman to Massachusetts
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Highest demand for flights based on searches. 10% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 19, 2025.

This United Airlines deal was found by Cheapflights users on 9/16. 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 11/85:30 pmGCM - BOS
1 stop6h 12mUnited Airlines
Thu 11/277:50 amBOS - GCM
2 stops32h 40mUnited Airlines
Deal found 9/16$301
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/83:18 pmGCM - BOS
1 stop7h 35mAmerican Airlines
Wed 11/265:36 amBOS - GCM
1 stop14h 52mAmerican Airlines
Deal found 9/16$380
This Priceline deal was found by Cheapflights users on 9/16. 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 11/812:54 pmGCM - BOS
Nonstop4h 11mJetBlue
Thu 11/2710:50 amBOS - GCM
1 stop27h 41mJetBlue
Deal found 9/16$381
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/84:01 pmGCM - BOS
1 stop17h 28mAmerican Airlines
Thu 11/278:16 pmBOS - GCM
1 stop16h 08mAmerican Airlines
Deal found 9/16$385
This Priceline deal was found by Cheapflights users on 9/16. 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 11/812:54 pmGCM - BOS
Nonstop4h 11mJetBlue
Wed 11/262:55 pmBOS - GCM
1 stop23h 36mJetBlue
Deal found 9/16$435
This Delta deal was found by Cheapflights users on 9/17. 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.
Sun 9/2112:52 pmGCM - BOS
1 stop11h 26mDelta
Sun 9/285:35 amBOS - GCM
1 stop7h 01mDelta
Deal found 9/17$454
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:10 pmGCM - BOS
1 stop11h 49mAmerican Airlines
Thu 10/97:30 amBOS - GCM
2 stops12h 50mAmerican Airlines
Deal found 9/18$525
This American Airlines deal was found by Cheapflights users on 9/17. 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 9/2112:28 pmGCM - BOS
2 stops17h 46mAmerican Airlines
Sun 9/285:47 amBOS - GCM
1 stop6h 23mAmerican Airlines
Deal found 9/17$535

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 September 19, 2025.
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

Sat 11/8

5:30 pm-9:30 am

2 stops16h 00m

Boston Logan Intl

Thu 11/27

7:50 am-4:30 pm

2 stops32h 40m

$301

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 11/8

3:18 pm-10:53 pm

1 stop7h 35m

Boston Logan Intl

Wed 11/26

5:36 am-8:28 pm

1 stop14h 52m

$380

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 11/8

12:54 pm-5:05 pm

Nonstop4h 11m

Boston Logan Intl

Thu 11/27

10:50 am-2:31 pm

1 stop27h 41m

$381

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 11/8

4:01 pm-9:29 am

1 stop17h 28m

Boston Logan Intl

Thu 11/27

8:16 pm-12:24 pm

1 stop16h 08m

$385

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 11/8

12:54 pm-5:05 pm

Nonstop4h 11m

Boston Logan Intl

Wed 11/26

2:55 pm-2:31 pm

1 stop23h 36m

$435

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Tue 3/17

2:10 pm-12:14 am

1 stop9h 04m

Boston Logan Intl

Wed 3/18

5:30 am-1:02 pm

1 stop8h 32m

$470

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Fri 10/3

12:10 pm-12:59 am

1 stop11h 49m

Boston Logan Intl

Thu 10/9

7:30 am-7:20 pm

2 stops12h 50m

$525

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 3/14

1:15 pm-7:24 am

1 stop17h 09m

$190

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Fri 12/19

1:50 pm-1:22 am

1 stop11h 32m

$190

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Wed 11/12

1:50 pm-1:22 am

1 stop11h 32m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 14 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, January is the cheapest month in which you can book a flight from Grand Cayman to Massachusetts (average of $218). Flying from Grand Cayman to Massachusetts in July is currently the most expensive (average of $311). 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.

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 September 19, 2025.
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
10,000 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
JetBlue
7.2
Good
2,911 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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 4h 11m. Grand Cayman and Massachusetts are separated by a distance of 1704 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, January is the cheapest month in which you can book a flight from Grand Cayman to Massachusetts (average of $218). Flying from Grand Cayman to Massachusetts in July is currently the most expensive (average of $311). 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

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Alternative routes for Grand Cayman to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$182Average$326FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$288Average$469FlexibilityNo cancel feeOn-time71%

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