$83 Find Cheap Flights from Boston to the Cayman Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to the Cayman Islands departing on 4/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Boston to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$315
Cayman Brac
Cayman Brac2 stops$730
George Town
George Town1 stop$315
Cayman Brac
Cayman Brac2 stops$730

Book Cheap Boston to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to the Cayman Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to the Cayman Islands

Sat, May 9 - Sat, May 16
United Airlines Logo
6:00 am - 1:30 pm
BOS
-
GCM
8h 30m
1 stop
United Airlines Logo
4:15 pm - 10:20 am
GCM
-
BOS
17h 05m
2 stops
$315United Airlines
Sat, May 2 - Sat, May 9
United Airlines Logo
9:30 am - 3:10 pm
BOS
-
GCM
6h 40m
1 stop
United Airlines Logo
4:15 pm - 11:59 pm
GCM
-
BOS
6h 44m
1 stop
$318United Airlines
Wed, Apr 15 - Sat, May 2
United Airlines Logo
6:00 am - 11:45 am
BOS
-
GCM
6h 45m
1 stop
United Airlines Logo
4:15 pm - 10:20 am
GCM
-
BOS
17h 05m
2 stops
$322United Airlines
Mon, Jun 1 - Sat, Jun 13
Air Canada Logo
5:10 am - 11:25 am
BOS
-
GCM
7h 15m
1 stop
Air Canada Logo
10:55 am - 9:49 am
GCM
-
BOS
21h 54m
1 stop
$325Air Canada
Mon, Jun 1 - Sat, Jun 13
Air Canada Logo
5:10 am - 11:25 am
BOS
-
GCM
7h 15m
1 stop
Air Canada Logo
10:55 am - 9:45 am
GCM
-
BOS
21h 50m
2 stops
$328Air Canada
Sat, Jun 13 - Sat, Jun 20
Air Canada Logo
6:50 pm - 11:25 am
BOS
-
GCM
41h 35m
2 stops
Air Canada Logo
10:55 am - 10:38 pm
GCM
-
BOS
10h 43m
1 stop
$338Air Canada
Sat, May 9 - Sat, May 16
United Airlines Logo
6:00 am - 12:35 pm
BOS
-
GCM
7h 35m
1 stop
United Airlines Logo
4:15 pm - 10:20 am
GCM
-
BOS
17h 05m
2 stops
$339United Airlines
Sat, Jun 13 - Sat, Jun 20
Air Canada Logo
3:40 pm - 11:25 am
BOS
-
GCM
44h 45m
2 stops
Air Canada Logo
10:55 am - 9:50 am
GCM
-
BOS
21h 55m
2 stops
$341Air Canada
Tue, May 12 - Tue, May 19
United Airlines Logo
7:27 pm - 12:30 pm
BOS
-
GCM
18h 03m
2 stops
United Airlines Logo
1:35 pm - 9:25 am
GCM
-
BOS
18h 50m
2 stops
$342United Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
10:45 am - 3:25 pm
BOS
-
CYB
29h 40m
2 stops
Multiple Airlines Logo
3:40 pm - 7:06 pm
CYB
-
BOS
26h 26m
3 stops
$730Multiple Airlines
Booking Insights

KAYAK's insights & trends for Boston to the Cayman Islands flights

Get data-powered insights and trends into flights from Boston to the Cayman Islands to help you find the cheapest flights, the best time to fly and much more.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Cayman Islands from Boston found in the last 72 hours was to George Town, at $526 round-trip. The most popular route is from Boston (BOS) to George Town (GCM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $526.

What is the cheapest time of day to fly to the Cayman Islands?

The average price for all round-trip flights from Boston to the Cayman Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $537 on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $537.

Can I save money by flying with a layover from Boston to the Cayman Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $489 on average.

What is the cheapest month to fly from Boston to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to the Cayman Islands is January, when tickets cost $388 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $656 and $619 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to the Cayman Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$83
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Boston to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Boston to the Cayman Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to the Cayman Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to the Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to the Cayman Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to the Cayman Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Boston to the Cayman Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to the Cayman Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Boston to the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Boston to the Cayman Islands

 
Need help choosing which airline to fly with from Boston to the Cayman Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8382 reviews
7.2Food
8.5Crew
8.1Boarding
7.8Entertainment
7.9Comfort
Airline reviews

We departed and landed early which was a nice surprise. The boarding process was slow.

10.0 ExcellentBrittany, Apr 2026
DAL - ATL
Read more Delta reviews

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

The wheelchair service is useless. They live you in different spots, not tell you anything just wait. I waited 30 minutes in Frankfurt when decided to walk the 25 minutes distance. In Budapest nobody came.

It was perfect! I've never flown with United before, but I definitely will in the future

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

Fine. The issues I had were associated with luggage being delayed from Turkey to Tanzania

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Human interaction. Thought there would be more service-even a smile would have been nice.

It was canceled at the last minute. While I was literally at the airport. Messed my entire trip up.

Seat was VERY uncomfortable. Flight was delayed and then boarded slowly. The crew was super helpful with boarding and supporting maximizing the luggage in the overhead.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

I cancelled my ticket less than 24 hours deadline but I didn’t get refunded.

Early morning flight and no food in First Class except a "salmon" box. No thank you. Was informed before take off by Captain that the plane was not serviced before we boarded in Phoenix. How does that happen? Need more frequent additions/turn over on the Entertainment. Thanks

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

Everything you need to know for your flight from Boston to the Cayman Islands

Information on your arrival and departure airports