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$176+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — BOS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/252:50 pmGCM - BOS
1 stop9h 55mUnited Airlines
Fri 1/96:00 amBOS - GCM
1 stop7h 45mUnited Airlines
Deal found 12/16$290
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:10 pmGCM - BOS
1 stop6h 44mUnited Airlines
Fri 1/25:20 amBOS - GCM
2 stops35h 00mUnited Airlines
Deal found 12/17$311
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/251:03 pmGCM - BOS
2 stops20h 16mAmerican Airlines
Fri 1/911:10 amBOS - GCM
2 stops9h 10mAmerican Airlines
Deal found 12/15$460

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(Priceline)

One-way from

$176
(Priceline)

Popular in

May

Cheapest in

January

Average price

$377

Good one-way deal

$297 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. 9% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Price to beat on a one-way flight from Cayman Islands to Massachusetts.
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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 December 18, 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 1/31

2:34 pm-11:57 pm

1 stop9h 23m

Boston Logan Intl

Sat 2/7

5:34 am-1:38 pm

1 stop8h 04m

$247

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Fri 1/16

2:25 pm-9:52 pm

1 stop7h 27m

Boston Logan Intl

Mon 1/19

6:00 am-1:15 pm

1 stop7h 15m

$251

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 1/17

5:30 pm-11:49 pm

1 stop6h 19m

Boston Logan Intl

Mon 1/19

7:07 pm-1:15 pm

2 stops18h 08m

$251

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Mon 1/12

2:50 pm-2:17 pm

2 stops23h 27m

Boston Logan Intl

Sun 1/18

6:00 am-1:15 pm

1 stop7h 15m

$251

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 1/31

5:30 pm-11:11 am

2 stops17h 41m

Boston Logan Intl

Sat 2/7

7:22 pm-1:45 pm

2 stops18h 23m

$251

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Mon 1/12

2:50 pm-2:00 pm

1 stop23h 10m

Boston Logan Intl

Thu 1/22

6:00 am-1:45 pm

1 stop7h 45m

$251

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 1/17

5:30 pm-11:49 pm

1 stop6h 19m

Boston Logan Intl

Fri 1/23

7:07 pm-4:35 pm

1 stop21h 28m

$251

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Mon 1/12

2:50 pm-2:00 pm

1 stop23h 10m

Boston Logan Intl

Tue 1/20

6:00 am-1:15 pm

1 stop7h 15m

$251

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Fri 1/16

2:25 pm-11:49 pm

2 stops9h 24m

Boston Logan Intl

Wed 1/21

6:00 am-1:15 pm

1 stop7h 15m

$251

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Mon 1/12

2:50 pm-2:17 pm

2 stops23h 27m

Boston Logan Intl

Fri 1/23

6:00 am-1:45 pm

1 stop7h 45m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 22 results
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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 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 December 18, 2025.

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 December 18, 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
11,054 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
JetBlue
7.2
Good
2,896 reviews
American Airlines
7.2
Good
11,054 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 27m. Spirit Airlines provides one of the quickest options available for as low as $251. 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 JetBlue. According to our data, you can fly for as low as $181. Users have also found prices from $190 and $194 on United Airlines and Delta, 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 $206). 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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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$204Average$364FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$419Average$546FlexibilityNo cancel feeOn-time71%

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