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Cheap flights from Massachusetts to the Cayman Islands from $74

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 1/3. 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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0 bags

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Find the cheapest flights from Massachusetts to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:40 am - 12:35 pmBOS-GCM
6h 55m1 stop
Delta Logo
1:52 pm - 9:08 pmGCM-BOS
7h 16m1 stop
$252Delta
Find Deal
Mon, Dec 15 - Mon, Dec 22
Spirit Airlines Logo
5:28 am - 1:53 pmBOS-GCM
8h 25m1 stop
Spirit Airlines Logo
2:49 pm - 11:57 pmGCM-BOS
9h 08m1 stop
$265Spirit Airlines
Find Deal
Thu, Jan 29 - Sun, Feb 1
United Airlines Logo
5:45 am - 4:35 pmBOS-GCM
10h 50m1 stop
United Airlines Logo
2:25 pm - 9:57 pmGCM-BOS
7h 32m1 stop
$270United Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
6:23 pm - 11:26 amBOS-GCM
17h 03m1 stop
American Airlines Logo
1:05 pm - 8:51 pmGCM-BOS
7h 46m1 stop
$274American Airlines
Find Deal
Tue, Jan 20 - Tue, Jan 27
United Airlines Logo
6:00 am - 1:15 pmBOS-GCM
7h 15m1 stop
United Airlines Logo
2:25 pm - 10:36 amGCM-BOS
20h 11m2 stops
$275United Airlines
Find Deal
Fri, Jan 30 - Wed, Feb 4
United Airlines Logo
7:07 pm - 1:15 pmBOS-GCM
18h 08m2 stops
United Airlines Logo
2:50 pm - 10:52 amGCM-BOS
20h 02m1 stop
$277United Airlines
Find Deal
Tue, Jan 20 - Sun, Jan 25
American Airlines Logo
8:40 pm - 12:05 pmBOS-GCM
15h 25m2 stops
American Airlines Logo
1:25 pm - 12:59 amGCM-BOS
11h 34m1 stop
$279American Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
JetBlue Logo
6:00 am - 1:55 pmALB-GCM
7h 55m1 stop
JetBlue Logo
2:55 pm - 9:34 pmGCM-ALB
6h 39m1 stop
$424JetBlue
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Sat, Dec 20 - Sat, Dec 27
Multiple Airlines Logo
10:45 am - 5:50 pmBOS-CYB
31h 05m2 stops
Multiple Airlines Logo
3:40 pm - 11:57 pmCYB-BOS
32h 17m3 stops
$606Multiple Airlines
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Wed, Jan 14 - Wed, Jan 21
Multiple Airlines Logo
3:43 pm - 5:50 pmBOS-CYB
26h 07m3 stops
Multiple Airlines Logo
3:40 pm - 11:57 pmCYB-BOS
32h 17m3 stops
$613Multiple Airlines
Find Deal
Wed, Jan 14 - Wed, Jan 21

Delta flights from Massachusetts to Cayman Islands

Our best Delta deals on Massachusetts to Cayman Islands flight tickets
Delta
Dec 15
BOS5:40 amBoston Logan Intl
6h 55m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Dec 22
GCM1:52 pmGeorge Town Owen Roberts Intl
7h 16m
1 stop
BOS9:08 pmBoston Logan Intl
$252
Find similar
Delta
Jan 23
BOS5:50 amBoston Logan Intl
8h 50m
1 stop
GCM2:40 pmGeorge Town Owen Roberts Intl
Jan 24
GCM3:25 pmGeorge Town Owen Roberts Intl
7h 05m
1 stop
BOS10:30 pmBoston Logan Intl
$286
Find similar
Delta
Jan 22
BOS8:55 pmBoston Logan Intl
17h 45m
2 stops
GCM2:40 pmGeorge Town Owen Roberts Intl
Jan 28
GCM2:05 pmGeorge Town Owen Roberts Intl
10h 59m
1 stop
BOS1:04 amBoston Logan Intl
$291
Find similar

United Airlines flights from Massachusetts to Cayman Islands

Our best United Airlines deals on Massachusetts to Cayman Islands flight tickets
United Airlines
Jan 10
BOS5:45 amBoston Logan Intl
10h 50m
1 stop
GCM4:35 pmGeorge Town Owen Roberts Intl
Jan 17
GCM2:25 pmGeorge Town Owen Roberts Intl
7h 32m
1 stop
BOS9:57 pmBoston Logan Intl
$270
Find similar
United Airlines
Jan 30
BOS6:00 amBoston Logan Intl
7h 15m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Feb 4
GCM2:25 pmGeorge Town Owen Roberts Intl
20h 11m
2 stops
BOS10:36 amBoston Logan Intl
$275
Find similar
United Airlines
Jan 20
BOS7:07 pmBoston Logan Intl
18h 08m
2 stops
GCM1:15 pmGeorge Town Owen Roberts Intl
Jan 25
GCM2:50 pmGeorge Town Owen Roberts Intl
20h 02m
1 stop
BOS10:52 amBoston Logan Intl
$277
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 November 18, 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

Mon 12/15

5:40 am-12:35 pm

1 stop6h 55m

George Town Owen Roberts Intl

Mon 12/22

1:52 pm-9:08 pm

1 stop7h 16m

$252

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 1/29

5:28 am-1:53 pm

1 stop8h 25m

George Town Owen Roberts Intl

Sun 2/1

2:49 pm-11:57 pm

1 stop9h 08m

$265

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/10

5:45 am-4:35 pm

1 stop10h 50m

George Town Owen Roberts Intl

Sat 1/17

2:25 pm-9:57 pm

1 stop7h 32m

$270

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 1/20

6:23 pm-11:26 am

1 stop17h 03m

George Town Owen Roberts Intl

Tue 1/27

1:05 pm-8:51 pm

1 stop7h 46m

$274

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 1/30

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Wed 2/4

2:25 pm-10:36 am

2 stops20h 11m

$275

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 1/20

7:07 pm-1:15 pm

2 stops18h 08m

George Town Owen Roberts Intl

Sun 1/25

2:50 pm-10:52 am

1 stop20h 02m

$277

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 12/9

8:40 pm-12:05 pm

2 stops15h 25m

George Town Owen Roberts Intl

Tue 12/16

1:25 pm-12:59 am

1 stop11h 34m

$279

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sat 12/20

6:00 am-1:55 pm

1 stop7h 55m

George Town Owen Roberts Intl

Sat 12/27

2:55 pm-9:34 pm

1 stop6h 39m

$424

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Wed 1/14

10:45 am-5:50 pm

2 stops31h 05m

Cayman Brac Gerrard-Smith

Wed 1/21

3:40 pm-11:57 pm

3 stops32h 17m

$606

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Wed 1/14

3:43 pm-5:50 pm

3 stops26h 07m

Cayman Brac Gerrard-Smith

Wed 1/21

3:40 pm-11:57 pm

3 stops32h 17m

$613

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 March, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $404.

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

Our data shows that Wednesday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $373. 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 $544.

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 $484 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 $505 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 $369 on momondo.

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

There is only 1 cabin class 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?

You could potentially save up to 24% on your flight if you consider stops on a Massachusetts to Cayman Islands flight.

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

$118

Fastest flight time

4h 22m

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 $118. The best round-trip flight deal from Massachusetts to Cayman Islands found on momondo in the last 72 hours is $385.
The fastest flight from Massachusetts to Cayman Islands takes 4h 22m
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
7.9
8,003 reviews
Search Delta flights
United AirlinesPriceFrom $270Free CancellationRating
7.4
9,020 reviews
Search United Airlines flights
JetBluePriceFrom $278Free CancellationRating
7.2
2,903 reviews
Search JetBlue flights
American AirlinesPriceFrom $333Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
Air CanadaPriceFrom $457Free CancellationRating
7.1
10,462 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.

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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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