$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 3/8. 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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Flight Deals

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, Apr 11 - Sat, Apr 18
United Airlines Logo
6:00 am - 12:35 pm
BOS
-
GCM
7h 35m
1 stop
United Airlines Logo
4:10 pm - 10:15 am
GCM
-
BOS
17h 05m
2 stops
$348United Airlines
Mon, Jun 1 - Thu, Jun 11
Air Canada Logo
5:10 am - 11:30 am
BOS
-
GCM
7h 20m
1 stop
Air Canada Logo
12:25 pm - 9:45 am
GCM
-
BOS
20h 20m
2 stops
$349Air Canada
Mon, Apr 20 - Tue, Apr 28
Delta Logo
8:45 pm - 12:00 pm
BOS
-
GCM
16h 15m
1 stop
Delta Logo
1:25 pm - 11:58 pm
GCM
-
BOS
9h 33m
1 stop
$351Delta
Mon, Mar 2 - Thu, Mar 5
United Airlines Logo
7:19 pm - 1:15 pm
BOS
-
GCM
17h 56m
2 stops
United Airlines Logo
5:45 pm - 10:49 am
GCM
-
BOS
17h 04m
2 stops
$352United Airlines
Sun, Mar 1 - Thu, Mar 5
United Airlines Logo
6:00 am - 1:45 pm
BOS
-
GCM
7h 45m
1 stop
United Airlines Logo
5:45 pm - 12:49 pm
GCM
-
BOS
19h 04m
2 stops
$353United Airlines
Mon, Jun 1 - Sat, Jun 13
Air Canada Logo
5:10 am - 11:30 am
BOS
-
GCM
7h 20m
1 stop
Air Canada Logo
12:25 pm - 9:54 am
GCM
-
BOS
20h 29m
1 stop
$355Air Canada
Fri, Apr 24 - Fri, May 1
United Airlines Logo
6:00 am - 12:45 pm
BOS
-
GCM
7h 45m
1 stop
United Airlines Logo
1:35 pm - 11:01 am
GCM
-
BOS
20h 26m
2 stops
$356United Airlines
Mon, Jun 1 - Sat, Jun 13
Air Canada Logo
5:10 am - 11:30 am
BOS
-
GCM
7h 20m
1 stop
Air Canada Logo
12:25 pm - 9:45 am
GCM
-
BOS
20h 20m
2 stops
$359Air Canada
Tue, Apr 28 - Sat, May 2
United Airlines Logo
6:00 am - 11:45 am
BOS
-
GCM
6h 45m
1 stop
United Airlines Logo
1:45 pm - 12:59 am
GCM
-
BOS
10h 14m
1 stop
$360United Airlines
Thu, Mar 12 - Wed, Mar 18
United Airlines Logo
6:00 am - 12:45 pm
BOS
-
GCM
7h 45m
1 stop
United Airlines Logo
1:25 pm - 9:41 pm
GCM
-
BOS
7h 16m
1 stop
$361United 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 $281 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 $281.

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 $394 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $656 and $606 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$104
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 19% 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 $511 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 $511.

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 8208 reviews
7.9Comfort
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
Airline reviews

First flight out and was 85 minutes delayed. Notification came out way too late

4.0 OkayJason, Feb 2026
SEA - SLC
Read more Delta reviews

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

As great a red-eye flight as red-eye flights can be.

Once boarding started it was pretty quick. Food was inedible; cold and salty..

Entertainment kept turning itself off. Gave up on watching a movie.

Both the WIFI and entertainment did not work for 2.5h

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

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

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

No Snacks or Entertainment. The flight was short, snacks should still be given.

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

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.

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

Information on your arrival and departure airports