$104 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 11/16. 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 Town2 stops$313
Cayman Brac
Cayman Brac2 stops$764
George Town
George Town2 stops$313
Cayman Brac
Cayman Brac2 stops$764

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

Fri, Jul 3 - Sat, Jul 11
United Airlines Logo
8:15 pm - 3:10 pm
BOS
-
GCM
19h 55m
2 stops
United Airlines Logo
1:50 pm - 11:21 pm
GCM
-
BOS
8h 31m
1 stop
$313United Airlines
Sat, Jun 6 - Wed, Jun 10
Delta Logo
5:35 am - 11:54 am
BOS
-
GCM
7h 19m
1 stop
Delta Logo
12:59 pm - 1:31 am
GCM
-
BOS
11h 32m
1 stop
$317Delta
Sat, Nov 7 - Wed, Nov 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
$318United Airlines
Tue, Jun 2 - Fri, Jun 5
Delta Logo
5:35 am - 11:54 am
BOS
-
GCM
7h 19m
1 stop
Delta Logo
1:19 pm - 1:28 am
GCM
-
BOS
11h 09m
1 stop
$321Delta
Sat, Jun 6 - Tue, Jun 9
United Airlines Logo
5:47 am - 12:30 pm
BOS
-
GCM
7h 43m
1 stop
United Airlines Logo
1:35 pm - 8:17 am
GCM
-
BOS
17h 42m
2 stops
$322United Airlines
Tue, Aug 25 - Tue, Sep 1
Delta Logo
5:30 am - 11:39 am
BOS
-
GCM
7h 09m
1 stop
Delta Logo
12:56 pm - 1:06 am
GCM
-
BOS
11h 10m
1 stop
$335Delta
Wed, Jun 3 - Tue, Jun 9
Delta Logo
5:35 am - 11:54 am
BOS
-
GCM
7h 19m
1 stop
Delta Logo
12:59 pm - 11:14 pm
GCM
-
BOS
9h 15m
1 stop
$339Delta
Sat, Nov 7 - Sat, Nov 21
United Airlines Logo
9:50 am - 4:35 pm
BOS
-
GCM
6h 45m
1 stop
United Airlines Logo
2:50 pm - 1:02 am
GCM
-
BOS
10h 12m
1 stop
$348United Airlines
Sat, Nov 7 - Sat, Nov 21
United Airlines Logo
9:50 am - 4:35 pm
BOS
-
GCM
6h 45m
1 stop
United Airlines Logo
5:30 pm - 10:39 am
GCM
-
BOS
17h 09m
2 stops
$353United Airlines
Fri, Jun 5 - Sat, Jun 13
Air Canada Logo
6:55 pm - 10:00 am
BOS
-
GCM
16h 05m
1 stop
Air Canada Logo
10:55 am - 9:27 pm
GCM
-
BOS
9h 32m
2 stops
$357Air Canada
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 7 days was to George Town, at $478 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 7 days was $478.

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 $526 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 $526.

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 $460 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 $72 (return) on average. On the other hand, the most expensive months are October and September, when the average cost of round-trip tickets is $329 and $297 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$104
Best time to beat the crowds with an average 11% 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.

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 8437 reviews
8.5Crew
7.2Food
7.8Comfort
7.8Entertainment
8.1Boarding
Airline reviews

Planes were clean, no water or snacks on either flight.

6.0 GoodAnonymous, May 2026
ECP - ATL
Read more Delta reviews

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Lost of requested seat assignments. Lost my husband's meal choice

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

This flight is a quick way to get to Chicago, but a bit expensive.

Very comfortable seating and the Flight staff were very attentive. The premium economy section that I was seated in was very clean, updated, and well appointed. I would highly recommend flying United Airlines as this experience was better than the Japan Airlines business class that I flew several months ago.

Our flight was canceled same day and we were never informed. Had to pay more and worse seating on another airline.

Not very happy because of the long delaying which causes our luggages were not on the connection flight and nearly missed our connection flight.

JetBlue was good. Kayak offered us a deal if we bundled the rental car. This was a complete scam. Kayak said the total was $222... but when we went to pick up the car the agent at Rent a wreck said that we had to pay "fees and taxes" for a grand total of $750. I would recommend not using kayak or rent a wreck. They are both complicit in this scam. JetBlue worked out well.

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

Cancelled flight. Still waiting to get home for grand daughter’s graduation .

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

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

Information on your arrival and departure airports