$123+ Cheap flights from Massachusetts to the Cayman Islands
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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Aug 6 — Aug 131
1 adult, Economy
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Find cheap flights from Massachusetts to Cayman Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Massachusetts to Cayman Islands
Keep the following information in mind while searching for Massachusetts to Cayman Islands flight deals. Data was last updated August 1, 2025.
Round-trip from | $327 (American Airlines) |
|---|---|
One-way from | $123 (Delta) |
Popular in | February |
Cheapest in | January |
Average price | $459 |
Good round-trip deal | $380 or less |
Find flight deals from Massachusetts to Cayman Islands
Cheapest flights from Massachusetts to Cayman IslandsExplore the most affordable flight options available from Massachusetts to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2025.
Explore the most affordable flight options available from Massachusetts to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2025.
This American Airlines deal was found by Cheapflights users on 7/30. 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 11/86:00 amBOS - GCM
1 stop6h 06mAmerican Airlines
Tue 11/113:14 pmGCM - BOS
1 stop7h 32mAmerican Airlines
Deal found 7/30![American Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 7/31. 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.
Fri 9/55:35 amBOS - GCM
1 stop6h 56mDelta
Sat 9/2012:52 pmGCM - BOS
1 stop11h 26mDelta
Deal found 7/31![Delta logo]()
$330
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/126:30 pmBOS - GCM
2 stops18h 25mAir Canada
Thu 10/1612:50 pmGCM - BOS
2 stops19h 40mAir Canada
Deal found 7/31![Air Canada logo]()
$370
This Priceline deal was found by Cheapflights users on 8/1. 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.
Sun 11/305:11 amBOS - GCM
1 stop9h 19mJetBlue
Sat 12/612:48 pmGCM - BOS
Nonstop4h 04mJetBlue
Deal found 8/1![JetBlue logo]()
$390
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 8/265:27 pmALB - GCM
2 stops18h 43mAmerican Airlines
Fri 8/292:10 pmGCM - ALB
2 stops21h 17mAmerican Airlines
Deal found 7/30![American Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 8/1. 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 11/17:00 amBOS - GCM
1 stop9h 00mUnited Airlines
Sat 11/152:25 pmGCM - BOS
1 stop7h 34mUnited Airlines
Deal found 8/1![United Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 7/31. 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 9/146:07 amALB - GCM
1 stop6h 29mDelta
Sun 9/2112:52 pmGCM - ALB
1 stop9h 41mDelta
Deal found 7/31![Delta logo]()
$466
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/296:00 amBDL - GCM
1 stop6h 31mDelta
Fri 9/512:50 pmGCM - BDL
1 stop6h 38mDelta
Deal found 7/30![Delta logo]()
$466
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/296:12 amBDL - GCM
1 stop5h 58mAmerican Airlines
Fri 9/512:25 pmGCM - BDL
2 stops22h 07mAmerican Airlines
Deal found 7/30![American Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/283:25 pmBOS - GCM
1 stop21h 15mMultiple Airlines
Fri 9/54:45 pmGCM - BOS
1 stop19h 38mMultiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/293:20 pmORH - GCM
2 stops45h 05mAmerican Airlines
Wed 9/312:10 pmGCM - ORH
2 stops26h 49mAmerican Airlines
Deal found 7/31![American Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:00 amBDL - GCM
1 stop11h 00mMultiple Airlines
Sun 9/2812:40 pmGCM - BDL
1 stop23h 05mMultiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$509
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Cayman Islands 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 August 1, 2025.
Use the filters below to find and compare flights from Massachusetts to the Cayman Islands that are best for you.
Fly from
Massachusetts
Fly to
Cayman Islands
Route
Depart
Return
Price
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 11/8
6:00 am-12:06 pm
1 stop6h 06m
George Town Owen Roberts Intl
Tue 11/11
3:14 pm-10:46 pm
1 stop7h 32m
$327
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Fri 9/5
5:35 am-11:31 am
1 stop6h 56m
George Town Owen Roberts Intl
Sat 9/20
12:52 pm-1:18 am
1 stop11h 26m
$330
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sun 10/12
6:30 pm-11:55 am
2 stops18h 25m
George Town Owen Roberts Intl
Thu 10/16
12:50 pm-9:30 am
2 stops19h 40m
$370
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sun 11/30
5:11 am-2:30 pm
1 stop9h 19m
George Town Owen Roberts Intl
Sat 12/6
12:48 pm-4:52 pm
Nonstop4h 04m
$390
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 1/3
7:44 pm-1:15 pm
2 stops17h 31m
George Town Owen Roberts Intl
Sat 1/10
5:30 pm-11:54 pm
1 stop6h 24m
$400
AlbanyGeorge Town
ALB - GCM
ALBGCM
Albany Intl
Tue 8/26
5:27 pm-11:10 am
2 stops18h 43m
George Town Owen Roberts Intl
Fri 8/29
2:10 pm-12:27 pm
2 stops21h 17m
$400
AlbanyGeorge Town
ALB - GCM
ALBGCM
Albany Intl
Sun 9/14
6:07 am-11:36 am
1 stop6h 29m
George Town Owen Roberts Intl
Sun 9/21
12:52 pm-11:33 pm
1 stop9h 41m
$466
HartfordGeorge Town
BDL - GCM
BDLGCM
Hartford Bradley Intl
Fri 8/29
6:00 am-11:31 am
1 stop6h 31m
George Town Owen Roberts Intl
Fri 9/5
12:50 pm-8:28 pm
1 stop6h 38m
$466
HartfordGeorge Town
BDL - GCM
BDLGCM
Hartford Bradley Intl
Fri 8/29
6:12 am-11:10 am
1 stop5h 58m
George Town Owen Roberts Intl
Fri 9/5
12:25 pm-11:32 am
2 stops22h 07m
$470
WorcesterGeorge Town
ORH - GCM
ORHGCM
Worcester
Fri 8/29
3:20 pm-11:25 am
2 stops45h 05m
George Town Owen Roberts Intl
Wed 9/3
12:10 pm-3:59 pm
2 stops26h 49m
$504
Showing 1-10 of 26 results
Best time to book a flight from Massachusetts to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Massachusetts 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 Massachusetts to the Cayman Islands
What is the cheapest month to book a flight from Massachusetts to Cayman Islands?
Currently, January is the cheapest month in which you can book a flight from Massachusetts to Cayman Islands (average of $467). Flying from Massachusetts to Cayman Islands in March is currently the most expensive (average of $594). 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 MA to KY?
Find hourly flight availability from Massachusetts to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 1, 2025.
When flying from Massachusetts to Cayman Islands, 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 Cayman Islands
Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated August 1, 2025.
See what other customers who have flown with Delta, United Airlines, and JetBlue from Massachusetts to the Cayman Islands have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
7.9
Crew
8.5
Boarding
8.2
Food
7.3
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Comfort
7.9
Crew
8.5
Boarding
8.2
Food
7.3
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Comfort
7.9
Crew
8.5
Boarding
8.2
Food
7.3
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Comfort
7.9
Crew
8.5
Boarding
8.2
Food
7.3
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Comfort
7.9
Crew
8.5
Boarding
8.2
Food
7.3
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Overall
8.0
Comfort
7.9
Crew
8.5
Boarding
8.2
Food
7.3
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentKim,May 2025
PIH - SLC
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Massachusetts to Cayman Islands
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Massachusetts to Cayman Islands
Discover the top 6 airlines that operate flights from Massachusetts to Cayman Islands. 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 August 1, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$214 | Average$474 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$458 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$270 | Average$440 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$529 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$457 | Average$559 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$469 | Average$868 | FlexibilityNo cancel fee | On-time63% |