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Cheap flights from Massachusetts to Grand Cayman from $90

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 Grand Cayman departing on 3/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Massachusetts to Grand Cayman

Cheap round-trip flights

United Airlines Logo
6:00 am - 1:15 pmBOS-GCM
7h 15m1 stop
United Airlines Logo
5:45 pm - 12:21 pmGCM-BOS
18h 36m1 stop
$270United Airlines
Find Deal
Sat, Nov 29 - Tue, Dec 9
United Airlines Logo
6:00 am - 1:15 pmBOS-GCM
7h 15m1 stop
United Airlines Logo
5:30 pm - 10:49 amGCM-BOS
17h 19m2 stops
$274United Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
United Airlines Logo
7:00 am - 4:20 pmBOS-GCM
9h 20m1 stop
United Airlines Logo
2:25 pm - 10:48 pmGCM-BOS
8h 23m1 stop
$294United Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
JetBlue Logo
7:22 am - 10:50 amBOS-GCM
4h 28mnonstop
JetBlue Logo
12:54 pm - 5:05 pmGCM-BOS
4h 11mnonstop
$315JetBlue
Find Deal
Sat, Nov 1 - Sat, Nov 8
Delta Logo
5:40 am - 12:35 pmBOS-GCM
6h 55m1 stop
Delta Logo
1:50 pm - 1:22 amGCM-BOS
11h 32m1 stop
$323Delta
Find Deal
Sun, Nov 9 - Tue, Nov 18
JetBlue Logo
6:00 am - 2:55 pmBDL-GCM
8h 55m1 stop
JetBlue Logo
3:55 pm - 11:59 pmGCM-BDL
8h 04m1 stop
$328JetBlue
Find Deal
Thu, Dec 4 - Tue, Dec 9
American Airlines Logo
5:30 am - 11:10 amBOS-GCM
6h 40m1 stop
American Airlines Logo
8:25 am - 4:12 pmGCM-BOS
6h 47m1 stop
$330American Airlines
Find Deal
Tue, Oct 21 - Sat, Oct 25
American Airlines Logo
6:45 am - 3:00 pmBOS-GCM
8h 15m1 stop
American Airlines Logo
9:00 am - 12:51 amGCM-BOS
15h 51m1 stop
$331American Airlines
Find Deal
Sat, Nov 8 - Tue, Nov 11
Multiple Airlines Logo
7:55 pm - 12:25 pmBOS-GCM
16h 30m1 stop
Multiple Airlines Logo
11:55 am - 12:40 amGCM-BOS
12h 45m1 stop
$361Multiple Airlines
Find Deal
Thu, Nov 27 - Thu, Dec 4
Delta Logo
6:03 am - 11:35 amALB-GCM
6h 32m1 stop
Delta Logo
1:05 pm - 11:57 pmGCM-ALB
9h 52m1 stop
$446Delta
Find Deal
Sun, Oct 26 - Thu, Oct 30

United Airlines flights from Massachusetts to Grand Cayman

Our best United Airlines deals on Massachusetts to Grand Cayman flight tickets
United Airlines
Nov 29
BOS6:00 amBoston Logan Intl
7h 15m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Dec 9
GCM5:45 pmGeorge Town Owen Roberts Intl
18h 36m
1 stop
BOS12:21 pmBoston Logan Intl
$270
Find similar
United Airlines
Nov 29
BOS6:00 amBoston Logan Intl
7h 15m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Dec 6
GCM5:30 pmGeorge Town Owen Roberts Intl
17h 19m
2 stops
BOS10:49 amBoston Logan Intl
$274
Find similar
United Airlines
Nov 8
BOS7:00 amBoston Logan Intl
9h 20m
1 stop
GCM4:20 pmGeorge Town Owen Roberts Intl
Nov 15
GCM2:25 pmGeorge Town Owen Roberts Intl
8h 23m
1 stop
BOS10:48 pmBoston Logan Intl
$294
Find similar

JetBlue flights from Massachusetts to Grand Cayman

Our best JetBlue deals on Massachusetts to Grand Cayman flight tickets
JetBlue
Nov 1
BOS7:22 amBoston Logan Intl
4h 28m
GCM10:50 amGeorge Town Owen Roberts Intl
Nov 8
GCM12:54 pmGeorge Town Owen Roberts Intl
4h 11m
BOS5:05 pmBoston Logan Intl
$315
Find similar
JetBlue
Dec 4
BDL6:00 amHartford Bradley Intl
8h 55m
1 stop
GCM2:55 pmGeorge Town Owen Roberts Intl
Dec 9
GCM3:55 pmGeorge Town Owen Roberts Intl
8h 04m
1 stop
BDL11:59 pmHartford Bradley Intl
$328
Find similar
JetBlue
Nov 29
BOS8:19 amBoston Logan Intl
4h 28m
GCM12:47 pmGeorge Town Owen Roberts Intl
Dec 6
GCM3:55 pmGeorge Town Owen Roberts Intl
7h 16m
1 stop
BOS11:11 pmBoston Logan Intl
$349
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Grand Cayman 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 September 19, 2025.
Use the filters below to find and compare flights from Massachusetts to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/29

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Tue 12/9

5:45 pm-12:21 pm

1 stop18h 36m

$270

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/29

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 12/6

5:30 pm-10:49 am

2 stops17h 19m

$274

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/8

7:00 am-4:20 pm

1 stop9h 20m

George Town Owen Roberts Intl

Sat 11/15

2:25 pm-10:48 pm

1 stop8h 23m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/1

7:22 am-10:50 am

Nonstop4h 28m

George Town Owen Roberts Intl

Sat 11/8

12:54 pm-5:05 pm

Nonstop4h 11m

$315

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 11/9

5:40 am-12:35 pm

1 stop6h 55m

George Town Owen Roberts Intl

Tue 11/18

1:50 pm-1:22 am

1 stop11h 32m

$323

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Thu 12/4

6:00 am-2:55 pm

1 stop8h 55m

George Town Owen Roberts Intl

Tue 12/9

3:55 pm-11:59 pm

1 stop8h 04m

$328

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 10/21

5:30 am-11:10 am

1 stop6h 40m

George Town Owen Roberts Intl

Sat 10/25

8:25 am-4:12 pm

1 stop6h 47m

$330

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/8

6:45 am-3:00 pm

1 stop8h 15m

George Town Owen Roberts Intl

Tue 11/11

9:00 am-12:51 am

1 stop15h 51m

$331

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 11/27

7:55 pm-12:25 pm

1 stop16h 30m

George Town Owen Roberts Intl

Thu 12/4

11:55 am-12:40 am

1 stop12h 45m

$361

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sun 10/26

6:03 am-11:35 am

1 stop6h 32m

George Town Owen Roberts Intl

Thu 10/30

1:05 pm-11:57 pm

1 stop9h 52m

$446

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 Grand Cayman from

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

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 Grand Cayman?

The cheapest month to fly to Grand Cayman from Massachusetts is in January. Flight prices, which tend to average around $376, are often lower during this time because this is during the off-season. If you don’t want to visit Grand Cayman in January, then you should wait until March to fly from Massachusetts, when ticket prices are also cheap, with an average price of $399.

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

The cheapest day to depart from Massachusetts to Grand Cayman is on a Thursday when prices can be found for as low as $317. On the other hand, Saturday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $538.

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

Our most recent data shows that the best time of day to fly to Grand Cayman is in the afternoon. Flights from Massachusetts to Grand Cayman during this time can be as low as $305. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $452 on average. Flights to Grand Cayman 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 Grand Cayman flight route?

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

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

You are more likely to see cheaper flights to Grand Cayman from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Grand Cayman for around $499 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Grand Cayman from Massachusetts for as low as $351 on momondo.

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

There is only 1 cabin class available to choose from on Massachusetts to Grand Cayman 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 Grand Cayman flights?

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

Cheap Massachusetts to Grand Cayman flight deals and tips

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

Fastest flight time

4h 22m

Direct flights

Sun

Airports in Grand Cayman

1 airport
The fastest flight from Massachusetts to Grand Cayman takes 4h 22m
Direct flights go from Massachusetts to Grand Cayman on Sunday. There are no airlines offering direct flights.
There is 1 airport near Grand Cayman: George Town Owen Roberts Intl (GCM)
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  • When did momondo last update prices for flights from Massachusetts to Grand Cayman?

    Prices for flights from Massachusetts to Grand Cayman refresh daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Grand Cayman.

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

    The necessary travel and health documents for your Grand Cayman trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Massachusetts to Grand Cayman

Compare and see reviews for airlines that fly from Massachusetts to Grand Cayman with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $214Free CancellationRating
7.9
7,964 reviews
Search Delta flights
JetBluePriceFrom $257Free CancellationRating
7.2
2,911 reviews
Search JetBlue flights
United AirlinesPriceFrom $270Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $314Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Air CanadaPriceFrom $457Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
SouthwestPriceFrom $469Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Why use momondo?

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

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 Grand Cayman from Massachusetts.

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

Yes. All flights to Grand Cayman from Massachusetts on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

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 Grand Cayman.

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

If you are simply researching potential flights to Grand Cayman, momondo offers a useful price alert feature which will track prices for flights to Grand Cayman from Massachusetts and alert you when they change.

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