$98+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Cayman Islands (KY0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.
Round-trip from | $295 (JetBlue) |
|---|---|
One-way from | $98 (JetBlue) |
Good round-trip deal | $295 or less |
Good one-way deal | $89 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 January 21, 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 January 21, 2025.
This United Airlines deal was found by Cheapflights users on 1/20. 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.
This JetBlue Airways deal was found by Cheapflights users on 1/21. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 1/21. 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.
This Delta deal was found by Cheapflights users on 1/20. 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.
This United Airlines deal was found by Cheapflights users on 1/21. 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.
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
This Air Canada deal was found by Cheapflights users on 1/21. 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.
This American Airlines deal was found by Cheapflights users on 1/21. 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.
This American Airlines deal was found by Cheapflights users on 1/21. 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.
This Delta deal was found by Cheapflights users on 1/20. 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.
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Find flights from Massachusetts to Cayman Islands within your budget
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 January 21, 2025.
Fly from
Fly to
Route
Depart
Return
Price
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Mon 3/17
9:47 am-1:16 pm
Nonstop4h 29m
George Town Owen Roberts Intl
Wed 3/26
1:52 pm-6:59 pm
Nonstop4h 07m
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sun 4/6
8:00 am-1:35 pm
1 stop6h 35m
George Town Owen Roberts Intl
Wed 4/9
1:35 pm-11:13 am
2 stops20h 38m
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Fri 2/21
5:24 am-3:00 pm
1 stop9h 36m
George Town Owen Roberts Intl
Thu 2/27
5:20 pm-7:31 am
2 stops14h 11m
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Thu 3/13
5:40 am-11:38 am
1 stop6h 58m
George Town Owen Roberts Intl
Tue 3/18
1:03 pm-1:05 am
1 stop11h 02m
HartfordGeorge Town
BDL - GCM
BDLGCM
Hartford Bradley Intl
Thu 2/27
7:55 pm-1:15 pm
2 stops17h 20m
George Town Owen Roberts Intl
Thu 3/13
4:25 pm-11:56 pm
1 stop6h 31m
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Thu 3/20
7:25 pm-2:00 pm
1 stop19h 35m
George Town Owen Roberts Intl
Sun 3/23
2:40 pm-12:12 pm
1 stop20h 32m
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Tue 2/18
11:33 am-4:10 pm
1 stop28h 37m
George Town Owen Roberts Intl
Thu 2/20
11:30 am-7:14 pm
1 stop7h 44m
HartfordGeorge Town
BDL - GCM
BDLGCM
Hartford Bradley Intl
Fri 2/21
6:07 am-2:20 pm
1 stop8h 13m
George Town Owen Roberts Intl
Wed 2/26
3:20 pm-12:50 am
1 stop9h 30m
AlbanyGeorge Town
ALB - GCM
ALBGCM
Albany Intl
Fri 3/7
5:30 am-12:25 pm
1 stop6h 55m
George Town Owen Roberts Intl
Fri 3/14
4:15 pm-12:01 pm
2 stops18h 46m
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sun 2/16
10:30 pm-12:55 pm
2 stops14h 25m
George Town Owen Roberts Intl
Sun 2/23
1:50 pm-7:55 am
2 stops18h 05m
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.
Travel insights for flights from Massachusetts to Cayman Islands
Get recent, data-driven insights about flights from Massachusetts to Cayman Islands including ideal travel times, pricing trends, and more.
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 January 21, 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 January 21, 2025.
Read reviews from past customers who have flown JetBlue, United Airlines and American Airlines from Massachusetts to Cayman Islands. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Food
Overall
Crew
Comfort
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Food
Overall
Crew
Comfort
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Food
Overall
Crew
Comfort
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Food
Overall
Crew
Comfort
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Food
Overall
Crew
Comfort
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Food
Overall
Crew
Comfort
Entertainment
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Massachusetts to Cayman Islands
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Massachusetts to Cayman Islands
Discover the top 5 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 January 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$514 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$291 | Average$435 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$291 | Average$470 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$307 | Average$501 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$417 | FlexibilityNo cancel fee | On-time67% |