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Cheap flights from Massachusetts to the Cayman Islands from $120

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to the Cayman Islands departing on 9/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Massachusetts to the Cayman Islands

Cheap round-trip flights

JetBlue Logo
7:26 am - 11:54 amBOS-GCM
4h 28mnonstop
JetBlue Logo
1:52 pm - 6:02 pmGCM-BOS
4h 10mnonstop
$315JetBlue
Find Deal
Sat, Nov 15 - Sat, Nov 22
Delta Logo
5:35 am - 11:31 amBOS-GCM
6h 56m1 stop
Delta Logo
12:52 pm - 1:18 amGCM-BOS
11h 26m1 stop
$330Delta
Find Deal
Fri, Sep 5 - Fri, Sep 12
American Airlines Logo
8:37 pm - 11:10 amBOS-GCM
15h 33m2 stops
American Airlines Logo
12:10 pm - 10:50 pmGCM-BOS
9h 40m2 stops
$334American Airlines
Find Deal
Fri, Sep 5 - Thu, Sep 11
American Airlines Logo
7:00 am - 7:20 pmBOS-GCM
13h 20m1 stop
American Airlines Logo
8:25 am - 4:12 pmGCM-BOS
6h 47m1 stop
$335American Airlines
Find Deal
Mon, Oct 13 - Sun, Oct 19
United Airlines Logo
7:00 am - 4:30 pmBOS-GCM
9h 30m1 stop
United Airlines Logo
2:25 pm - 10:47 pmGCM-BOS
8h 22m1 stop
$365United Airlines
Find Deal
Wed, Nov 12 - Sun, Nov 16
Air Canada Logo
6:00 am - 11:55 amBOS-GCM
6h 55m1 stop
Air Canada Logo
12:50 pm - 3:59 pmGCM-BOS
26h 09m1 stop
$373Air Canada
Find Deal
Mon, Oct 13 - Thu, Oct 16
Air Canada Logo
4:45 pm - 11:55 amBOS-GCM
20h 10m1 stop
Air Canada Logo
12:50 pm - 11:29 amGCM-BOS
21h 39m1 stop
$376Air Canada
Find Deal
Sun, Oct 12 - Thu, Oct 16
Logo
7:55 pm - 12:20 pmBOS-GCM
16h 25m1 stop
Logo
11:55 am - 12:40 amGCM-BOS
12h 45m1 stop
$379
Find Deal
Wed, Nov 26 - Sat, Dec 6
Logo
3:40 pm - 12:20 pmBOS-GCM
20h 40m2 stops
Logo
11:55 am - 12:40 amGCM-BOS
12h 45m1 stop
$401
Find Deal
Wed, Nov 26 - Sat, Dec 6
United Airlines Logo
8:30 pm - 4:30 pmBOS-GCM
20h 00m2 stops
United Airlines Logo
5:45 pm - 6:32 pmGCM-BOS
24h 47m3 stops
$416United Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17

JetBlue flights from Massachusetts to Cayman Islands

Our best JetBlue deals on Massachusetts to Cayman Islands flight tickets
JetBlue
Nov 15
BOS7:26 amBoston Logan Intl
4h 28m
GCM11:54 amGeorge Town Owen Roberts Intl
Nov 22
GCM1:52 pmGeorge Town Owen Roberts Intl
4h 10m
BOS6:02 pmBoston Logan Intl
$315
Find similar
JetBlue
Oct 25
BOS5:15 amBoston Logan Intl
6h 30m
1 stop
GCM10:45 amGeorge Town Owen Roberts Intl
Nov 1
GCM11:50 amGeorge Town Owen Roberts Intl
4h 09m
BOS4:59 pmBoston Logan Intl
$388
Find similar
JetBlue
Nov 29
BOS8:19 amBoston Logan Intl
4h 28m
GCM12:47 pmGeorge Town Owen Roberts Intl
Dec 7
GCM3:40 pmGeorge Town Owen Roberts Intl
8h 07m
1 stop
BOS11:47 pmBoston Logan Intl
$395
Find similar

United Airlines flights from Massachusetts to Cayman Islands

Our best United Airlines deals on Massachusetts to Cayman Islands flight tickets
United Airlines
Nov 12
BOS7:00 amBoston Logan Intl
9h 30m
1 stop
GCM4:30 pmGeorge Town Owen Roberts Intl
Nov 16
GCM2:25 pmGeorge Town Owen Roberts Intl
8h 22m
1 stop
BOS10:47 pmBoston Logan Intl
$365
Find similar
United Airlines
Nov 13
BOS8:30 pmBoston Logan Intl
20h 00m
2 stops
GCM4:30 pmGeorge Town Owen Roberts Intl
Nov 17
GCM5:45 pmGeorge Town Owen Roberts Intl
24h 47m
3 stops
BOS6:32 pmBoston Logan Intl
$416
Find similar
United Airlines
Sep 5
BOS1:00 pmBoston Logan Intl
24h 30m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Sep 13
GCM1:35 pmGeorge Town Owen Roberts Intl
8h 53m
1 stop
BOS11:28 pmBoston Logan Intl
$426
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated August 12, 2025.
Use the filters below to find and compare flights from Massachusetts to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/15

7:26 am-11:54 am

Nonstop4h 28m

George Town Owen Roberts Intl

Sat 11/22

1:52 pm-6:02 pm

Nonstop4h 10m

$315

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

Fri 9/12

12:52 pm-1:18 am

1 stop11h 26m

$330

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 9/5

8:37 pm-11:10 am

2 stops15h 33m

George Town Owen Roberts Intl

Thu 9/11

12:10 pm-10:50 pm

2 stops9h 40m

$334

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 10/13

7:00 am-7:20 pm

1 stop13h 20m

George Town Owen Roberts Intl

Sun 10/19

8:25 am-4:12 pm

1 stop6h 47m

$335

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 11/12

7:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Sun 11/16

2:25 pm-10:47 pm

1 stop8h 22m

$365

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 10/13

6:00 am-11:55 am

1 stop6h 55m

George Town Owen Roberts Intl

Thu 10/16

12:50 pm-3:59 pm

1 stop26h 09m

$373

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 10/12

4:45 pm-11:55 am

1 stop20h 10m

George Town Owen Roberts Intl

Thu 10/16

12:50 pm-11:29 am

1 stop21h 39m

$376

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 11/26

7:55 pm-12:20 pm

1 stop16h 25m

George Town Owen Roberts Intl

Sat 12/6

11:55 am-12:40 am

1 stop12h 45m

$379

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 11/26

3:40 pm-12:20 pm

2 stops20h 40m

George Town Owen Roberts Intl

Sat 12/6

11:55 am-12:40 am

1 stop12h 45m

$401

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 11/13

8:30 pm-4:30 pm

2 stops20h 00m

George Town Owen Roberts Intl

Mon 11/17

5:45 pm-6:32 pm

3 stops24h 47m

$416

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Massachusetts to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of January, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $406.

What is the cheapest day to depart on your flight to Cayman Islands?

Our data shows that Tuesday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $295. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Saturday is $542.

What is the cheapest time of day to depart on your flight to Cayman Islands?

According to our data, the cheapest time of day to fly to Cayman Islands is in the afternoon. momondo users have found flights departing from Massachusetts to Cayman Islands in the afternoon for as low as $305. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $455 on average. Flights to Cayman Islands from Massachusetts in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Massachusetts to Cayman Islands flight route?

Fly from Boston Logan Intl to George Town Owen Roberts Intl for the best Massachusetts - Cayman Islands flight prices

How far in advance should I book a flight to Cayman Islands?

You are more likely to see cheaper flights to Cayman Islands from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $495 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cayman Islands from Massachusetts for as low as $377 on momondo.

What cabin class options are available on Massachusetts to Cayman Islands flights?

There are 1 cabin classes available to choose from on Massachusetts to Cayman Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Massachusetts to Cayman Islands flights?

No. A direct flight is the cheapest option for a flight between Massachusetts to Cayman Islands.

Cheap Massachusetts to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Cayman Islands

Best Price Found

$120

Fastest flight time

4h 28m

Direct flights

Sun

Airports in Cayman Islands

1 airport
The best one-way flight to Cayman Islands from Massachusetts in the past 72 hours is $120. The best round-trip flight deal from Massachusetts to Cayman Islands found on momondo in the last 72 hours is $315.
The fastest flight from Massachusetts to Cayman Islands takes 4h 28m
Direct flights go from Massachusetts to Cayman Islands on Sunday. The only airline offering direct flights is JetBlue.
There is 1 airport near Cayman Islands: George Town Owen Roberts Intl (GCM)
Search flight deals

  • When did momondo last update prices for flights from Massachusetts to Cayman Islands?

    Prices for flights from Massachusetts to Cayman Islands refresh daily.

  • How many operators does momondo search for flights from Massachusetts to Cayman Islands?

  • How old do you have to be to fly from Massachusetts to Cayman Islands?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The travel and health documents required for your trip to Cayman Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Cayman Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Massachusetts to Cayman Islands?

Best airlines flying from Massachusetts to Cayman Islands

Compare and see reviews for airlines that fly from Massachusetts to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $214Free CancellationRating
8.0
7,979 reviews
Search Delta flights
JetBluePriceFrom $261Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights
United AirlinesPriceFrom $270Free CancellationRating
7.4
8,920 reviews
Search United Airlines flights
American AirlinesPriceFrom $318Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Air CanadaPriceFrom $457Free CancellationRating
7.1
9,943 reviews
Search Air Canada flights
SouthwestPriceFrom $469Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Cayman Islands?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Cayman Islands from Massachusetts.

Can I find flights from Massachusetts to Cayman Islands with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Massachusetts to Cayman Islands flights to just show those with flexible booking policies.

How can momondo help me find flights from Massachusetts to Cayman Islands?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Massachusetts to Cayman Islands.

I’m not ready to book a flight from Massachusetts to Cayman Islands right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Cayman Islands from Massachusetts. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Cayman Islands trip

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Find better results for your trip to the Cayman Islands

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Popular flights according to clicks in the last 7 days on momondo
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