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$188+ Cheap flights from the Cayman Islands 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — BOS
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Cayman Islands to Massachusetts

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$280
(American Airlines)

One-way from

$188
(Delta)

Popular in

June

Cheapest in

November

Average price

$283

Good one-way deal

$252 or less
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 Cayman Islands to Massachusetts
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One-way flight from Cayman Islands to Massachusetts
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Highest demand for flights based on searches. 20% potential increase in price ($107 potential increase over avg. RT price).
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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 November 2025
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Price to beat on a one-way flight from Cayman Islands to Massachusetts.
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Find flight deals from Cayman Islands to Massachusetts

Cheapest flights from Cayman Islands to Massachusetts
Explore the most affordable flight options available from Cayman Islands to Massachusetts. 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 12/2012:47 pmGCM - BOS
1 stop9h 50mAmerican Airlines
Sun 1/46:30 pmBOS - GCM
1 stop17h 27mAmerican Airlines
Deal found 11/2$280
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/111:50 pmGCM - BOS
1 stop11h 37mDelta
Sun 12/145:40 amBOS - GCM
1 stop6h 55mDelta
Deal found 11/2$281
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 12/115:45 pmGCM - BOS
1 stop30h 03mUnited Airlines
Sun 12/145:30 amBOS - GCM
2 stops35h 00mUnited Airlines
Deal found 11/2$309
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/185:45 pmGCM - BOS
2 stops17h 22mUnited Airlines
Thu 12/256:01 amBOS - GCM
1 stop7h 44mUnited Airlines
Deal found 11/3$345
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Sun 11/165:45 pmGCM - BOS
2 stops18h 43mUnited Airlines
Fri 11/217:38 pmBOS - GCM
2 stops18h 07mUnited Airlines
Deal found 11/3$359
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:15 pmGCM - BOS
Nonstop4h 10mJetBlue
Sun 1/45:05 pmBOS - GCM
1 stop21h 30mJetBlue
Deal found 11/2$369
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/164:45 pmGCM - BOS
2 stops18h 24mMultiple Airlines
Fri 11/2111:04 pmBOS - GCM
3 stops37h 21mMultiple Airlines
Deal found 11/3$568

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cayman Islands 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 November 3, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Massachusetts that are best for you.

Fly from

Cayman Islands

Fly to

Massachusetts

Route

Depart

Return

Price

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 12/20

12:47 pm-10:37 pm

1 stop9h 50m

Boston Logan Intl

Sun 1/4

6:30 pm-11:57 am

1 stop17h 27m

$280

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 12/11

1:50 pm-1:27 am

1 stop11h 37m

Boston Logan Intl

Sun 12/14

5:40 am-12:35 pm

1 stop6h 55m

$281

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 12/11

5:45 pm-11:48 pm

1 stop30h 03m

Boston Logan Intl

Sun 12/14

5:30 am-4:30 pm

2 stops35h 00m

$309

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 12/18

5:45 pm-11:07 am

2 stops17h 22m

Boston Logan Intl

Thu 12/25

6:01 am-1:45 pm

1 stop7h 44m

$345

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sun 11/16

5:45 pm-12:28 pm

2 stops18h 43m

Boston Logan Intl

Fri 11/21

7:38 pm-1:45 pm

2 stops18h 07m

$359

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sun 1/11

3:40 pm-7:41 am

1 stop16h 01m

Boston Logan Intl

Sun 1/18

7:30 am-2:35 pm

1 stop7h 05m

$404

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 1/31

2:15 pm-10:42 pm

1 stop8h 27m

$188

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 12/20

12:45 pm-11:57 pm

1 stop11h 12m

$188

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Mon 12/29

3:42 pm-11:11 pm

1 stop7h 29m

$188

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Wed 4/29

12:45 pm-1:03 am

1 stop11h 18m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 16 results
1
2

Best time to book a flight from Cayman Islands to Massachusetts

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

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

Currently, April is the cheapest month in which you can book a flight from Cayman Islands to Massachusetts (average of $206). Flying from Cayman Islands to Massachusetts in May is currently the most expensive (average of $460). 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 November 3, 2025.
Read reviews from past customers who have flown American Airlines and JetBlue from the Cayman Islands to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,036 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Boarding

7.5

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
11,036 reviews
American Airlines
7.2
Good
11,036 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Boarding

7.5

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
2,907 reviews
American Airlines
7.2
Good
11,036 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Boarding

7.5

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 Cayman Islands 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 Cayman Islands to Massachusetts?

    A quick flight from Cayman Islands to Massachusetts can take about 9h 50m. American Airlines provides one of the quickest options available for as low as $280. Cayman Islands and Massachusetts are separated by a distance of 1704 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Cayman Islands to Massachusetts (average of $206). Flying from Cayman Islands to Massachusetts in May is currently the most expensive (average of $460). 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 Cayman Islands to Massachusetts

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Top 2 airlines flying from Cayman Islands to Massachusetts

Discover the top 2 airlines that operate flights from Cayman Islands 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$204Average$353FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$288Average$535FlexibilityNo cancel feeOn-time71%

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