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Cheap flights from Boston to the Cayman Islands from $108

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to the Cayman Islands departing on 7/28. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Boston to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
6:43 pm - 12:30 pm
BOS
-
GCM
18h 47m
2 stops
United Airlines Logo
1:50 pm - 1:14 am
GCM
-
BOS
10h 24m
1 stop
$331United Airlines
Fri, Jul 3 - Sat, Jul 11
United Airlines Logo
6:00 am - 4:35 pm
BOS
-
GCM
10h 35m
2 stops
United Airlines Logo
5:45 pm - 10:53 am
GCM
-
BOS
17h 08m
2 stops
$336United Airlines
Sat, Nov 14 - Tue, Nov 17
Delta Logo
5:45 am - 11:40 am
BOS
-
GCM
6h 55m
1 stop
Delta Logo
12:55 pm - 1:17 am
GCM
-
BOS
11h 22m
1 stop
$344Delta
Fri, Sep 11 - Mon, Sep 14
United Airlines Logo
6:00 am - 1:15 pm
BOS
-
GCM
7h 15m
1 stop
United Airlines Logo
5:45 pm - 12:35 pm
GCM
-
BOS
18h 50m
1 stop
$350United Airlines
Sat, Nov 14 - Tue, Nov 17
United Airlines Logo
8:31 pm - 3:30 pm
BOS
-
GCM
19h 59m
2 stops
United Airlines Logo
4:45 pm - 9:24 am
GCM
-
BOS
15h 39m
2 stops
$355United Airlines
Sat, Oct 24 - Wed, Oct 28
Air Canada Logo
3:35 pm - 11:25 am
BOS
-
GCM
44h 50m
2 stops
Air Canada Logo
12:25 pm - 9:55 am
GCM
-
BOS
20h 30m
1 stop
$364Air Canada
Tue, Sep 1 - Mon, Sep 7
Air Canada Logo
6:50 pm - 11:25 am
BOS
-
GCM
41h 35m
2 stops
Air Canada Logo
12:25 pm - 6:07 pm
GCM
-
BOS
28h 42m
2 stops
$368Air Canada
Tue, Sep 1 - Mon, Sep 7
Air Canada Logo
6:55 pm - 11:30 am
BOS
-
GCM
17h 35m
1 stop
Air Canada Logo
12:25 pm - 4:10 pm
GCM
-
BOS
26h 45m
1 stop
$377Air Canada
Fri, Sep 11 - Mon, Sep 14
Multiple Airlines Logo
6:55 pm - 8:05 am
BOS
-
CYB
38h 10m
2 stops
Multiple Airlines Logo
6:20 pm - 4:10 pm
CYB
-
BOS
44h 50m
2 stops
$747Multiple Airlines
Wed, Sep 30 - Wed, Oct 7
Multiple Airlines Logo
7:15 pm - 3:25 pm
BOS
-
CYB
21h 10m
2 stops
Multiple Airlines Logo
3:55 pm - 4:08 pm
CYB
-
BOS
47h 13m
2 stops
$868Multiple Airlines
Fri, Jun 19 - Sun, Jun 21

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Air Canada flights from Boston to Cayman Islands

Our best Air Canada deals on Boston to Cayman Islands flight tickets
Air Canada
Sep 1
BOS3:35 pmBoston Logan Intl
44h 50m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
Sep 7
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 30m
1 stop
BOS9:55 amBoston Logan Intl
$364
Air Canada
Sep 1
BOS6:50 pmBoston Logan Intl
41h 35m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
Sep 7
GCM12:25 pmGeorge Town Owen Roberts Intl
28h 42m
2 stops
BOS6:07 pmBoston Logan Intl
$368
Air Canada
Sep 11
BOS6:55 pmBoston Logan Intl
17h 35m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
Sep 14
GCM12:25 pmGeorge Town Owen Roberts Intl
26h 45m
1 stop
BOS4:10 pmBoston Logan Intl
$377

United Airlines flights from Boston to Cayman Islands

Our best United Airlines deals on Boston to Cayman Islands flight tickets
United Airlines
Jul 3
BOS6:43 pmBoston Logan Intl
18h 47m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Jul 11
GCM1:50 pmGeorge Town Owen Roberts Intl
10h 24m
1 stop
BOS1:14 amBoston Logan Intl
$331
United Airlines
Nov 14
BOS6:00 amBoston Logan Intl
10h 35m
2 stops
GCM4:35 pmGeorge Town Owen Roberts Intl
Nov 17
GCM5:45 pmGeorge Town Owen Roberts Intl
17h 08m
2 stops
BOS10:53 amBoston Logan Intl
$336
United Airlines
Nov 14
BOS6:00 amBoston Logan Intl
7h 15m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Nov 17
GCM5:45 pmGeorge Town Owen Roberts Intl
18h 50m
1 stop
BOS12:35 pmBoston Logan Intl
$350

momondo Fare Finder

 
Customize your flight search to find flights from Boston 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 June 8, 2026.
Use the filters below to find and compare flights from Boston to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 7/3

6:43 pm-12:30 pm

2 stops18h 47m

George Town Owen Roberts Intl

Sat 7/11

1:50 pm-1:14 am

1 stop10h 24m

$331

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/14

6:00 am-4:35 pm

2 stops10h 35m

George Town Owen Roberts Intl

Tue 11/17

5:45 pm-10:53 am

2 stops17h 08m

$336
Quickest round-trip

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 9/11

5:45 am-11:40 am

1 stop6h 55m

George Town Owen Roberts Intl

Mon 9/14

12:55 pm-1:17 am

1 stop11h 22m

$344

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/14

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Tue 11/17

5:45 pm-12:35 pm

1 stop18h 50m

$350

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 10/24

8:31 pm-3:30 pm

2 stops19h 59m

George Town Owen Roberts Intl

Wed 10/28

4:45 pm-9:24 am

2 stops15h 39m

$355

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 9/1

3:35 pm-11:25 am

2 stops44h 50m

George Town Owen Roberts Intl

Mon 9/7

12:25 pm-9:55 am

1 stop20h 30m

$364

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 9/1

6:50 pm-11:25 am

2 stops41h 35m

George Town Owen Roberts Intl

Mon 9/7

12:25 pm-6:07 pm

2 stops28h 42m

$368

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 9/11

6:55 pm-11:30 am

1 stop17h 35m

George Town Owen Roberts Intl

Mon 9/14

12:25 pm-4:10 pm

1 stop26h 45m

$377

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Wed 9/30

6:55 pm-8:05 am

2 stops38h 10m

Cayman Brac Gerrard-Smith

Wed 10/7

6:20 pm-4:10 pm

2 stops44h 50m

$747

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Fri 6/19

7:15 pm-3:25 pm

2 stops21h 10m

Cayman Brac Gerrard-Smith

Sun 6/21

3:55 pm-4:08 pm

2 stops47h 13m

$868

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 Boston 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 $145.

What is the cheapest Boston Logan Intl to Cayman Islands flight route?

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

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

You are more likely to see cheaper flights to Cayman Islands from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $501 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cayman Islands from Boston for as low as $422 on momondo.

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

There is only 1 cabin class available to choose from on Boston 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 Boston to Cayman Islands flights?

You could potentially save up to 3% on your flight if you consider stops on a Boston to Cayman Islands flight.

Cheap Boston to Cayman Islands flight deals and tips

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

Fastest flight time

4h 28m

Direct flights

Sun

Airports in Cayman Islands

6 airports
The fastest flight from Boston to Cayman Islands takes 4h 28m
Direct flights go from Boston to Cayman Islands on Sunday. There are no airlines offering direct flights.
There are 6 airports in Cayman Islands. From Boston there are direct flights to George Town Owen Roberts Intl (GCM).
Search flight deals

Frequently asked questions about flying from Boston to the Cayman Islands

  • When did momondo last update prices for flights from Boston Logan Intl Airport to Cayman Islands?

    Prices for flights from Boston Logan Intl Airport to Cayman Islands are refreshed on a daily basis.

  • How many operators does momondo search for flights from Boston Logan Intl Airport to Cayman Islands?

  • How old do you have to be to fly from Boston Logan Intl Airport 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 Boston Logan Intl Airport to Cayman Islands.

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

    The travel and health documents you'll need for your trip to Cayman Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cayman Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Boston to Cayman Islands

Compare and see reviews for airlines that fly from Boston to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $72Free CancellationRating
7.9
8,395 reviews
Search Delta flights
United AirlinesPriceFrom $193Free CancellationRating
7.4
9,785 reviews
Search United Airlines flights
JetBluePriceFrom $315Free CancellationRating
7.1
2,978 reviews
Search JetBlue flights
American AirlinesPriceFrom $332Free CancellationRating
7.1
11,642 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Boston 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 Boston.

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

Flights from Boston to Cayman Islands with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Cayman Islands from Boston.

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

Yes momondo offers price alerts on flights to Cayman Islands from Boston. 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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