$119 Find Cheap Flights from Boston to the Cayman Islands - Compare and Save

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 8/10. 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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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$334
Cayman Brac
Cayman Brac2 stops$839
George Town
George Town1 stop$334
Cayman Brac
Cayman Brac2 stops$839

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, Aug 6 - Thu, Aug 13
Delta Logo
8:45 pm - 11:39 am
BOS
-
GCM
15h 54m
1 stop
Delta Logo
1:04 pm - 10:25 pm
GCM
-
BOS
8h 21m
1 stop
$334Delta
Sat, Aug 29 - Sat, Sep 5
Delta Logo
5:30 am - 11:39 am
BOS
-
GCM
7h 09m
1 stop
Delta Logo
1:04 pm - 12:38 am
GCM
-
BOS
10h 34m
1 stop
$343Delta
Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
6:00 am - 1:35 pm
BOS
-
GCM
8h 35m
1 stop
United Airlines Logo
1:35 pm - 11:38 pm
GCM
-
BOS
9h 03m
1 stop
$347United Airlines
Sat, Nov 7 - Wed, Nov 11
United Airlines Logo
6:00 am - 4:20 pm
BOS
-
GCM
10h 20m
2 stops
United Airlines Logo
5:45 pm - 10:23 am
GCM
-
BOS
16h 38m
2 stops
$348United Airlines
Sun, Nov 1 - Sat, Nov 7
United Airlines Logo
5:45 am - 4:30 pm
BOS
-
GCM
10h 45m
2 stops
United Airlines Logo
5:30 pm - 9:25 am
GCM
-
BOS
15h 55m
2 stops
$352United Airlines
Mon, Jan 4 - Tue, Jan 12
United Airlines Logo
7:14 am - 4:00 pm
BOS
-
GCM
8h 46m
1 stop
United Airlines Logo
2:25 pm - 10:53 am
GCM
-
BOS
20h 28m
2 stops
$356United Airlines
Thu, Sep 24 - Sun, Sep 27
United Airlines Logo
8:31 pm - 12:25 pm
BOS
-
GCM
40h 54m
2 stops
United Airlines Logo
1:35 pm - 11:39 pm
GCM
-
BOS
9h 04m
1 stop
$357United Airlines
Thu, Oct 1 - Sun, Oct 4
United Airlines Logo
8:31 pm - 12:25 pm
BOS
-
GCM
40h 54m
2 stops
United Airlines Logo
1:35 pm - 11:39 pm
GCM
-
BOS
9h 04m
1 stop
$362United Airlines
Mon, Nov 2 - Mon, Nov 9
United Airlines Logo
7:25 am - 4:30 pm
BOS
-
GCM
9h 05m
1 stop
United Airlines Logo
5:45 pm - 12:05 pm
GCM
-
BOS
18h 20m
1 stop
$373United Airlines
Wed, Sep 2 - Sun, Sep 6
Multiple Airlines Logo
10:50 am - 3:25 pm
BOS
-
CYB
29h 35m
2 stops
Multiple Airlines Logo
6:20 pm - 4:05 pm
CYB
-
BOS
44h 45m
2 stops
$839Multiple 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 5 days was to George Town, at $3,536 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 5 days was $3,536.

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 $530 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 $530.

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.

No, with an average price for the route of $503, prices are generally cheapest when you fly direct.

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 $72 (return) on average. On the other hand, the most expensive months are October and July, when the average cost of round-trip tickets is $329 and $324 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 1 week before departure.

Good to know

Low seasonSeptember
Cheapest flight$119
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 14% 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.
7.8
DeltaOverall score based on 8459 reviews
8.5Crew
7.2Food
8.1Boarding
7.8Entertainment
7.8Comfort
Airline reviews

Flight attendant was very poor in taking care or showing attention. I slept up front for a few and missed the snacks. She saw me many times, went by me many times and never once asked if I needed anything. The whole 2 hours flight. And this is to a Diamond member in first.

2.0 MediocreKrishan, Jul 2026
BOS - CMH
Read more Delta reviews

Flight attendant was very poor in taking care or showing attention. I slept up front for a few and missed the snacks. She saw me many times, went by me many times and never once asked if I needed anything. The whole 2 hours flight. And this is to a Diamond member in first.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

The flight was smooth, the crew was great but the plane was quite old

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

It was Swiss. Our kosher meals were literally frozen solid and therefore inedible, and the crew didnt care.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

It’s always a great time flying with united airlines.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

Because I bought my ticket from Underpricer, I could not check in online. I could only check in at the airport and that was deeply frustrating because I had to arrive very early. The flight also departed 45 min late and passengers were given no explanations about why we were delayed. I was worried I would miss my connecting flight. Once on board, however, the flight was fine.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

Great experience. Good dinner and service. FA's were very nice and attentive.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

We were several hours delayed due to confusion during boarding. Evidently the crew could not match the manifest with the boarded customers. After significant time trying to find individuals on board, a crew member walked through the entire plane re-scanning each of our boarding passes. Then we had to wait for a new slot to depart, and when we landed, our gate was not ready. It was a complete goat rodeo from start to finish.

Horrible. Flight was cancelled, jet blue app not working to rebook, no phone number available to call Jet Blue, 400 ish people in line for the help desk, stuck in Boston for 2 more days had to book new flight with a different airline and still not sure if I will be able to get any refund.

Flight was delayed many times. The crew was friendly but you eleven had to buy headphones to access the movies in the plane. $8 is not a lot for one person but it is when you travel with all your family.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

Flight left 2 hours late with no explanation as to the delay

I like everything. Blythe at DCA is the absolute best!

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

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

Information on your arrival and departure airports