$74 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 1/16. 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 Town1 stop$252
Cayman Brac
Cayman Brac2 stops$695
George Town
George Town1 stop$252
Cayman Brac
Cayman Brac2 stops$695

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

Mon, Dec 15 - Sun, Dec 21
Delta Logo
5:40 am - 12:35 pmBOS-GCM
6h 55m1 stop
Delta Logo
1:52 pm - 9:08 pmGCM-BOS
7h 16m1 stop
$252Delta
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Thu, Jan 15 - Fri, Jan 23
Delta Logo
5:00 pm - 2:40 pmBOS-GCM
21h 40m2 stops
Delta Logo
3:55 pm - 3:57 pmGCM-BOS
24h 02m2 stops
$257Delta
Find Deal
Thu, Jan 29 - Sun, Feb 1
Spirit Airlines Logo
5:28 am - 1:53 pmBOS-GCM
8h 25m1 stop
Spirit Airlines Logo
2:49 pm - 11:57 pmGCM-BOS
9h 08m1 stop
$265Spirit Airlines
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Sat, Jan 31 - Sat, Feb 7
United Airlines Logo
7:22 pm - 1:15 pmBOS-GCM
17h 53m2 stops
United Airlines Logo
2:25 pm - 9:57 pmGCM-BOS
7h 32m1 stop
$270United Airlines
Find Deal
Sat, Feb 7 - Thu, Feb 12
American Airlines Logo
6:23 pm - 11:26 amBOS-GCM
17h 03m1 stop
American Airlines Logo
12:54 pm - 9:49 pmGCM-BOS
8h 55m1 stop
$274American Airlines
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Thu, Mar 5 - Mon, Mar 9
United Airlines Logo
7:15 am - 4:30 pmBOS-GCM
9h 15m1 stop
United Airlines Logo
4:45 pm - 10:50 amGCM-BOS
17h 05m2 stops
$275United Airlines
Find Deal
Tue, Jan 20 - Sun, Jan 25
United Airlines Logo
6:00 am - 1:15 pmBOS-GCM
7h 15m1 stop
United Airlines Logo
2:50 pm - 10:52 amGCM-BOS
20h 02m1 stop
$277United Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
American Airlines Logo
7:27 pm - 12:24 pmBOS-GCM
16h 57m2 stops
American Airlines Logo
1:25 pm - 11:44 pmGCM-BOS
10h 19m2 stops
$279American Airlines
Find Deal
Mon, Apr 13 - Fri, Apr 17
Multiple Airlines Logo
6:45 pm - 3:25 pmBOS-CYB
21h 40m2 stops
Multiple Airlines Logo
8:30 am - 10:38 pmCYB-BOS
13h 08m2 stops
$695Multiple Airlines
Find Deal
Sat, Apr 11 - Sat, Apr 18
Multiple Airlines Logo
4:35 pm - 3:25 pmBOS-CYB
23h 50m2 stops
Multiple Airlines Logo
6:20 pm - 10:38 pmCYB-BOS
27h 18m2 stops
$815Multiple Airlines
Find Deal
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 $315 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 $315.

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 $503 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 $630 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 Wednesday, 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 2 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$74
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 20% 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 evening, when round-trip flights cost $305 on average. Morning departures are around 59% more expensive than evening flights, 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 $484.

Reviews of the top 5 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.
8.0
SouthwestOverall score based on 4244 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Even though we were delayed, we were able to make our connection

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

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

Information on your arrival and departure airports