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Cheap flights from Boston to the Cayman Islands from $94

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 9/12. 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 Boston to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 am - 11:30 am
BOS
-
GCM
6h 30m
1 stop
American Airlines Logo
5:12 pm - 12:59 am
GCM
-
BOS
6h 47m
1 stop
$286American Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
5:00 am - 10:55 am
BOS
-
GCM
6h 55m
1 stop
American Airlines Logo
5:12 pm - 12:59 am
GCM
-
BOS
6h 47m
1 stop
$293American Airlines
Sat, May 30 - Thu, Jun 4
American Airlines Logo
7:00 am - 4:11 pm
BOS
-
GCM
10h 11m
2 stops
American Airlines Logo
2:17 pm - 12:40 am
GCM
-
BOS
9h 23m
1 stop
$298American Airlines
Tue, May 26 - Sat, May 30
American Airlines Logo
6:00 am - 4:11 pm
BOS
-
GCM
11h 11m
1 stop
American Airlines Logo
11:55 am - 10:06 am
GCM
-
BOS
21h 11m
1 stop
$302American Airlines
Mon, Jun 1 - Sat, Jun 13
American Airlines Logo
6:00 am - 4:11 pm
BOS
-
GCM
11h 11m
1 stop
American Airlines Logo
12:31 pm - 12:15 am
GCM
-
BOS
10h 44m
2 stops
$303American Airlines
Wed, May 27 - Sat, May 30
American Airlines Logo
6:53 pm - 11:31 am
BOS
-
GCM
17h 38m
1 stop
American Airlines Logo
2:10 pm - 10:02 am
GCM
-
BOS
18h 52m
1 stop
$309American Airlines
Fri, May 8 - Mon, May 11
American Airlines Logo
6:53 pm - 3:03 pm
BOS
-
GCM
21h 10m
1 stop
American Airlines Logo
12:35 pm - 12:25 am
GCM
-
BOS
10h 50m
2 stops
$312American Airlines
Fri, May 8 - Wed, May 13
United Airlines Logo
5:45 am - 3:10 pm
BOS
-
GCM
10h 25m
1 stop
United Airlines Logo
4:15 pm - 10:20 am
GCM
-
BOS
17h 05m
1 stop
$328United Airlines
Sat, May 16 - Sat, May 23
United Airlines Logo
5:45 am - 3:10 pm
BOS
-
GCM
10h 25m
1 stop
United Airlines Logo
4:15 pm - 11:16 am
GCM
-
BOS
18h 01m
2 stops
$333United Airlines
Sat, May 16 - Sat, May 23
Multiple Airlines Logo
10:50 am - 8:05 am
BOS
-
CYB
46h 15m
2 stops
Multiple Airlines Logo
6:15 pm - 10:38 pm
CYB
-
BOS
27h 23m
2 stops
$744Multiple Airlines
Sun, Jul 26 - Fri, Jul 31

American Airlines flights from Boston to Cayman Islands

Our best American Airlines deals on Boston to Cayman Islands flight tickets
American Airlines
Jun 2
BOS6:00 amBoston Logan Intl
6h 30m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
Jun 9
GCM5:12 pmGeorge Town Owen Roberts Intl
6h 47m
1 stop
BOS12:59 amBoston Logan Intl
$286
American Airlines
May 30
BOS5:00 amBoston Logan Intl
6h 55m
1 stop
GCM10:55 amGeorge Town Owen Roberts Intl
Jun 4
GCM5:12 pmGeorge Town Owen Roberts Intl
6h 47m
1 stop
BOS12:59 amBoston Logan Intl
$293
American Airlines
May 26
BOS7:00 amBoston Logan Intl
10h 11m
2 stops
GCM4:11 pmGeorge Town Owen Roberts Intl
May 30
GCM2:17 pmGeorge Town Owen Roberts Intl
9h 23m
1 stop
BOS12:40 amBoston Logan Intl
$298

United Airlines flights from Boston to Cayman Islands

Our best United Airlines deals on Boston to Cayman Islands flight tickets
United Airlines
Apr 27
BOS6:00 amBoston Logan Intl
7h 45m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
May 4
GCM1:35 pmGeorge Town Owen Roberts Intl
20h 26m
2 stops
BOS11:01 amBoston Logan Intl
$321
United Airlines
Apr 27
BOS6:00 amBoston Logan Intl
7h 45m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
May 4
GCM1:35 pmGeorge Town Owen Roberts Intl
21h 41m
1 stop
BOS12:16 pmBoston Logan Intl
$324
United Airlines
Apr 26
BOS6:00 amBoston Logan Intl
7h 45m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Apr 29
GCM1:50 pmGeorge Town Owen Roberts Intl
18h 35m
1 stop
BOS9:25 amBoston Logan Intl
$325

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 April 21, 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
Quickest round-trip

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 6/2

6:00 am-11:30 am

1 stop6h 30m

George Town Owen Roberts Intl

Tue 6/9

5:12 pm-12:59 am

1 stop6h 47m

$286

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 5/30

5:00 am-10:55 am

1 stop6h 55m

George Town Owen Roberts Intl

Thu 6/4

5:12 pm-12:59 am

1 stop6h 47m

$293

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 5/26

7:00 am-4:11 pm

2 stops10h 11m

George Town Owen Roberts Intl

Sat 5/30

2:17 pm-12:40 am

1 stop9h 23m

$298

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 6/1

6:00 am-4:11 pm

1 stop11h 11m

George Town Owen Roberts Intl

Sat 6/13

11:55 am-10:06 am

1 stop21h 11m

$302

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 5/27

6:00 am-4:11 pm

1 stop11h 11m

George Town Owen Roberts Intl

Sat 5/30

12:31 pm-12:15 am

2 stops10h 44m

$303

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 5/8

6:53 pm-11:31 am

1 stop17h 38m

George Town Owen Roberts Intl

Mon 5/11

2:10 pm-10:02 am

1 stop18h 52m

$309

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 5/8

6:53 pm-3:03 pm

1 stop21h 10m

George Town Owen Roberts Intl

Wed 5/13

12:35 pm-12:25 am

2 stops10h 50m

$312

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 5/16

5:45 am-3:10 pm

1 stop10h 25m

George Town Owen Roberts Intl

Sat 5/23

4:15 pm-10:20 am

1 stop17h 05m

$328

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 5/16

5:45 am-3:10 pm

1 stop10h 25m

George Town Owen Roberts Intl

Sat 5/23

4:15 pm-11:16 am

2 stops18h 01m

$333

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Sun 7/26

10:50 am-8:05 am

2 stops46h 15m

Cayman Brac Gerrard-Smith

Fri 7/31

6:15 pm-10:38 pm

2 stops27h 23m

$744

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 $436.

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 to 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 $506 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 $413 on momondo.

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

There is only 1 cabin class available to choose from on Boston Logan Intl 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?

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

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 20m

Direct flights

None
The fastest flight from Boston to Cayman Islands takes 4h 20m
There are no direct flights from Boston to Cayman Islands. There are no popular flight routes from Boston to Cayman Islands.
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
8,434 reviews
Search Delta flights
United AirlinesPriceFrom $193Free CancellationRating
7.4
9,613 reviews
Search United Airlines flights
JetBluePriceFrom $315Free CancellationRating
7.2
2,948 reviews
Search JetBlue flights
American AirlinesPriceFrom $338Free CancellationRating
7.1
11,644 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.

An easier way to manage your Cayman Islands trip

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Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom $252
Flights to Cayman Bracfrom $340
Flights to Little Caymanfrom $380