$56 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 2/19. 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.
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1 adult, Economy, 0 bags

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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

Thu, Feb 19 - Thu, Feb 26
Spirit Airlines Logo
5:27 am - 1:43 pm
BOS
-
GCM
8h 16m
1 stop
Spirit Airlines Logo
2:49 pm - 11:44 pm
GCM
-
BOS
8h 55m
1 stop
$262Spirit Airlines
Sat, Mar 21 - Sat, Mar 28
Spirit Airlines Logo
5:45 am - 12:20 pm
BOS
-
GCM
7h 35m
1 stop
Spirit Airlines Logo
1:15 pm - 11:59 pm
GCM
-
BOS
9h 44m
1 stop
$277Spirit Airlines
Sat, Mar 21 - Thu, Mar 26
Spirit Airlines Logo
5:45 am - 12:20 pm
BOS
-
GCM
7h 35m
1 stop
Spirit Airlines Logo
1:52 pm - 11:59 pm
GCM
-
BOS
9h 07m
1 stop
$280Spirit Airlines
Sat, Mar 21 - Sat, Mar 28
Spirit Airlines Logo
5:45 am - 12:20 pm
BOS
-
GCM
7h 35m
1 stop
Spirit Airlines Logo
1:15 pm - 11:59 pm
GCM
-
BOS
9h 44m
1 stop
$284Spirit Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
6:00 am - 2:45 pm
BOS
-
GCM
8h 45m
1 stop
American Airlines Logo
2:44 pm - 12:05 am
GCM
-
BOS
8h 21m
1 stop
$285American Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
6:30 am - 2:35 pm
BOS
-
GCM
8h 05m
1 stop
American Airlines Logo
12:05 pm - 10:48 pm
GCM
-
BOS
9h 43m
2 stops
$290American Airlines
Sat, Mar 21 - Wed, Mar 25
American Airlines Logo
5:30 pm - 11:10 am
BOS
-
GCM
18h 40m
1 stop
American Airlines Logo
7:45 am - 12:59 am
GCM
-
BOS
16h 14m
1 stop
$292American Airlines
Sat, Mar 21 - Wed, Mar 25
American Airlines Logo
5:30 pm - 11:10 am
BOS
-
GCM
18h 40m
1 stop
American Airlines Logo
7:45 am - 7:19 pm
GCM
-
BOS
10h 34m
2 stops
$296American Airlines
Thu, Feb 19 - Thu, Mar 5
Spirit Airlines Logo
5:27 am - 1:43 pm
BOS
-
GCM
8h 16m
1 stop
Spirit Airlines Logo
2:49 pm - 11:44 pm
GCM
-
BOS
8h 55m
1 stop
$300Spirit Airlines
Wed, Apr 8 - Thu, Apr 16
Spirit Airlines Logo
5:49 pm - 12:57 pm
BOS
-
GCM
20h 08m
1 stop
Spirit Airlines Logo
1:40 pm - 11:59 pm
GCM
-
BOS
9h 19m
1 stop
$301Spirit 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 $326 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 $326.

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 1 stop layover the cheapest option at $498 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 March, when tickets cost $386 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $649 and $586 respectively.

What’s the cheapest day of the week to fly from Boston to Cayman Islands?

The average price of all round-trip flights from Boston to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Cayman Islands on a Wednesday and more expensive on a Saturday. On your return trip to Boston, you should consider flying back on a Saturday, and avoid Mondays for better deals.

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$56
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 16% 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.

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

    The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $512 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 $512.

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 8172 reviews
7.2Food
8.5Crew
7.9Comfort
7.8Entertainment
8.1Boarding
Airline reviews

The flight was great as well as the airline staff

10.0 ExcellentPatty, Feb 2026
TPA - ATL
Read more Delta reviews

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

Terrible. Our first time back on United for 10 years, the seats in Polaris class are small and uncomfortable. They have squished too many people in to get more $$$. The staff are not friendly and not wanting to accommodate. I asked for two salads rather than a main meal and was advised no we wont do that. Then asked what I would like for breakfast and given something else anyway. I will not be flying United International anytime soon.

Same thing as flight from Pheonix to Newark. Uograded and Promised extra leg room and when I got to the seat it had none.

I upgraded my seat and was promised it would be next to the emergency door for extra leg room and they said it was premium plus but it was at the back of the plane...same thing happened from Newark to Dubai

Everything except the food and entertainment. It was a great experience though

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

The attendant on board was amazing. She should be doing business/first international long haul.

Although our flight was delayed the overall boarding process was very smooth and the crew was accommodating.

This was a horrible experience. I’ve experienced several delays at this point and still not home. I was supposed to be home by 8:30 last night and here I sit at 7 am on a plane STILL unable to go home because of American Airlines.

Lexus in first class was absolutely amazing! Beat flight attendant i’ve ever seen.

Generally good. Flight left on time and the seats are comfortable. Plenty of space in front if you in you choose a comfort plus seat, completely worth spending the extra money given the amount of hours the flight lasts. The food tastes good but I would say it’s a the amount is too little. The crew was friendly and efficient. There was a some turbulence at different points into the flight. American Airlines has good deals to NZ if you book with plenty of time before you plan on going.

the plane was so hot!! the air-conditioning was barely blowing. The flight was delayed, and we had to sit on the hot plane before take off for an extended amount of time, waiting on international passengers. Would not have been so bad if it was not so hot. They said it would get better after take off, but it did not.

They are always late and seats was also not having working charger

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

did not have enough meal for first class passengers so offer us snack

Arrived 40 min early which was great - sat in runway for 35 min so no gain. Then waited for luggage 45 min. They need to staff accordingly knowing its one of the busiest week in Phx

Broke my luggage and I can't get a resolution yet.

My flight got rerouted due to crew rest. I was sent to Dallas customer service was not very polite. Was given a $40 room voucher for Motel 6 and $12 to eat with. It delayed me by a day. Where if I would have just stuck with my original flight Arizona was delayed to Cleveland and I could have made it home. They put me on a 9:00 flight out of Dallas to Cleveland without my knowledge or consent. When originally I was told it would be 8:45 a.m. on February 1st. I told them I could not take the 9:00 flight because I did not have anybody to pick me up from the airport at that time. I'm extremely disappointed in how I was treated. And I will not fly American Airlines again.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

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

Information on your arrival and departure airports