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Massachusetts

$187+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — BOS
févr. 28 — mars 71
sam. 2/28
sam. 3/7
1 adult, Economy
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Cheap 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 janvier 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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.
mer. 2/183:35 pm
GCM
-
BOS
1 stop8h 24m
American Airlines
mer. 3/115:47 am
BOS
-
GCM
1 stop6h 23m
American Airlines
Deal found 1/27$285
This American Airlines deal was found by Cheapflights users on 1/26. 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.
ven. 2/133:45 pm
GCM
-
BOS
1 stop9h 14m
American Airlines
mer. 2/185:30 am
BOS
-
GCM
1 stop9h 55m
American Airlines
Deal found 1/26$309
This American Airlines deal was found by Cheapflights users on 1/27. 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.
sam. 4/1812:40 pm
GCM
-
BOS
1 stop18h 46m
American Airlines
sam. 4/256:53 pm
BOS
-
GCM
1 stop17h 39m
American Airlines
Deal found 1/27$316
This United Airlines deal was found by Cheapflights users on 1/26. 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.
ven. 2/132:50 pm
GCM
-
BOS
2 stops23h 22m
United Airlines
mer. 2/1811:48 am
BOS
-
GCM
2 stops25h 57m
United Airlines
Deal found 1/26$319
This United Airlines deal was found by Cheapflights users on 1/27. 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.
ven. 3/131:25 pm
GCM
-
BOS
1 stop7h 16m
United Airlines
ven. 3/206:00 am
BOS
-
GCM
1 stop7h 15m
United Airlines
Deal found 1/27$323
This Delta deal was found by Cheapflights users on 1/26. 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.
sam. 2/141:54 pm
GCM
-
BOS
1 stop8h 49m
Delta
mer. 2/186:45 pm
BOS
-
GCM
1 stop17h 44m
Delta
Deal found 1/26$324
This Delta deal was found by Cheapflights users on 1/28. 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.
sam. 1/313:25 pm
GCM
-
BOS
1 stop7h 05m
Delta
sam. 2/75:35 am
BOS
-
GCM
1 stop7h 05m
Delta
Deal found 1/28$332
This United Airlines deal was found by Cheapflights users on 1/27. 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.
dim. 2/152:50 pm
GCM
-
BOS
1 stop28h 47m
United Airlines
mar. 3/106:00 am
BOS
-
GCM
1 stop7h 15m
United Airlines
Deal found 1/27$344
This United Airlines deal was found by Cheapflights users on 1/27. 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.
dim. 2/152:50 pm
GCM
-
BOS
1 stop21h 56m
United Airlines
dim. 3/87:16 am
BOS
-
GCM
1 stop30h 29m
United Airlines
Deal found 1/27$346

Find 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 janvier 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$285
(American Airlines)

One-way from

$187
(Priceline)

Popular in

May

Cheapest in

January

Average price

$305

Good round-trip deal

$287 or less
Provider with most accurate pricing for George Town Owen Roberts Intl-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for George Town Owen Roberts Intl-Boston Logan Intl flights.
Search Deals
From Cayman Islands to Massachusetts
Search Deals
One-way flight from Cayman Islands 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).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Cayman Islands to Massachusetts.
Search Deals

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 janvier 29, 2026.
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

mer. 2/18

3:35 pm-11:59 pm

1 stop8h 24m

Boston Logan Intl

mer. 3/11

5:47 am-11:10 am

1 stop6h 23m

$285

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

ven. 3/13

1:25 pm-9:41 pm

1 stop7h 16m

Boston Logan Intl

ven. 3/20

6:00 am-12:15 pm

1 stop7h 15m

$323

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

sam. 2/14

1:54 pm-10:43 pm

1 stop8h 49m

Boston Logan Intl

mer. 2/18

6:45 pm-12:29 pm

1 stop17h 44m

$324

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

sam. 4/18

1:40 pm-11:59 pm

1 stop9h 19m

Boston Logan Intl

sam. 4/25

5:40 am-12:43 pm

1 stop8h 03m

$332

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

dim. 2/15

2:50 pm-10:49 am

1 stop19h 59m

Boston Logan Intl

mer. 3/11

6:00 am-12:15 pm

1 stop7h 15m

$344

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

dim. 2/15

2:50 pm-12:46 pm

1 stop21h 56m

Boston Logan Intl

lun. 3/9

6:00 am-12:15 pm

1 stop7h 15m

$344

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

dim. 2/15

2:50 pm-10:49 am

1 stop19h 59m

Boston Logan Intl

ven. 3/13

6:00 am-12:15 pm

1 stop7h 15m

$346

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

dim. 2/15

2:50 pm-12:46 pm

1 stop21h 56m

Boston Logan Intl

dim. 3/8

7:16 am-12:45 pm

1 stop30h 29m

$346

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

dim. 2/15

2:50 pm-10:49 am

1 stop19h 59m

Boston Logan Intl

mar. 3/10

12:07 pm-12:45 pm

2 stops25h 38m

$351

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

mar. 3/3

2:25 pm-9:51 pm

1 stop7h 26m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 $204). Flying from Cayman Islands 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 KY to MA?

Find hourly flight availability from Cayman Islands 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 janvier 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cayman Islands to Massachusetts as you normally would.

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 janvier 29, 2026.
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
11,205 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

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
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

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
2,892 reviews
American Airlines
7.2
Good
11,205 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

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 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 7h 16m. American Airlines provides one of the quickest options available for as low as $323. 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.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $190. Users have also found prices from $194 and $197 on Delta and JetBlue, respectively.

  • 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 $204). Flying from Cayman Islands 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.

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 janvier 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$230Average$327FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$302Average$535FlexibilityNo cancel feeOn-time71%

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