Find cheap flights from Massachusetts to the Cayman Islands

Find cheap flights from Massachusetts to the Cayman Islands

Search hundreds of travel sites at once for deals on flights to the Cayman Islands

Round-trip
Economy
Boston (BOS)
Cayman Islands
Fri 6/18
Fri 6/25
Any month
Compare vs. KAYAK |
There are travel restrictions to Cayman Islands. Learn more
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Good to know

Low season

SeptemberBest time to beat the crowds with an average 3% drop in price.

High season

DecemberMost popular time to fly with an average 8% increase in price.

Average price round-trip

$596(avg. price over the last 2 weeks)

Good deal round-trip

$171or less

Good deal one-way

$71or less

FAQs for booking flights from Massachusetts to the Cayman Islands

How does KAYAK find such low prices on flights from Massachusetts to the Cayman Islands?

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What is the Hacker Fare option on flights from Massachusetts to the Cayman Islands?

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Top 3 airlines serving from Massachusetts to the Cayman Islands

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,576 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "It was a little bumpy. Probably nothing to be done about that."

Pros: "MINT CLASS is amazing"

Pros: "I love JetBlue! Roomy, well-appointed, great amenities and clean."

Pros: "only complaint is WiFi doesn't work"

Pros: "Fast, clean and good"

Cons: "We waited in the runway for 2 hours after landing. Not the airlines fault however completely unacceptable."

Pros: "Everything"
Cons: "Nothing"

Cons: "Information on delays, accurate information on where our bags were, offer to help short missed connections"

Pros: "Love the little sleeping packet they provide you with earplugs and eyemask."
Cons: "No complaints here!"

Cons: "Hour-long maintenance delay. Rule 1, run on schedule."

Cons: "They need to solve problems better so people do not have to wait 3hour layover for there fight"

Pros: "Form Boston to Pittsburgh, aircraft cabinet was very cold. Every other things were very good"

Cons: "Not boarding us 30 minutes late then keeping us at the gate for another 30 minutes after landing"

Cons: "JetBlue is amazing and my favorite airlines for domestic travel."

Cons: "Aircraft felt and sounded old. Lots of extra cracks and rattles while taxiing."

Cons: "It was way too hot in the plane."

Pros: "Nice planes, better treatment than other airlines."
Cons: "Fly at Mach 2!"

Cons: "My daughters video screen didn’t work."

Pros: "Competent staff"
Cons: "Rude TSA employee"

Pros: "Movie selection"

Pros: "Ease of boarding, rest comfort"

Cons: "It took over 2.5 hours to decide to switch airplanes"

Cons: "The little child next to me keep kicking my legs"

Pros: "Great end to end domestic product."
Cons: "Nothing"

Pros: "Plane and staff were fine"
Cons: "Why couldn’t they get another plane. I missed an important meeting because we were 3hours late"

Cons: "Seat"

Pros: "I like everything"
Cons: "I can't complain"

Pros: "Hassle free"

Cons: "I was not emailed or texted a copy of my boarding pass. I did receive for trip from detroit to Boston but not the return trip."

Pros: "Non chaotic boarding, efforts by gate agents to gate check carryon bags to ensure there would be enough space for those bags."

Cons: "No working internet or video"

Pros: "everything was easy and smooth."

Cons: "connection in jfk was much too tight"

Cons: "Limited movie options."

Pros: "Efficiency"

Cons: "Everything and everyone"

Pros: "The dunkin donuts coffee in a nice touch"

Pros: "Free beer!"
Cons: "Nothing, it was excellent!"

Pros: "Being on time is the most important thing for me! Thank you for landing earlier."

Cons: "Most TVs in the seatbacks were glitching and had picture issues."

Pros: "Got in early!"

Pros: "Ability to change reservation so easily"
Cons: "That I made reservation for wrong time!"

Cons: "No AC and seat 11A didn't recline"

Pros: "Nothing"

Pros: "price"

Cons: "Tsa precheck line was long and then the"

Pros: "On time all aro"
Cons: "N/A"

Pros: "Nothing."
Cons: "That it was cancelled."

Pros: "Good but could improve on food. We need more food, beside that I am satisfied"
Cons: "Service in general, nice plane it's new and large seating spaces"

Cons: "None"

Pros: "Everything! the best part was that the they kept the middle seat empty!"
Cons: "nothing"

Cons: "For some reason, we were asked several times for Passports. This didn’t make any sense since we are US citizens with drivers license. They even had TSA talk to us. This has to be fixed. Otherwise, Delta experience was great."

Cons: "Nothing, really. Airlines unfortunately can’t make people patient or polite, & I can’t afford a private jet, so I’ll have to settle for an eye roll or twelve."

Pros: "Everything"
Cons: "Nothing"

Cons: "No mechanical failures or delays would be nice"

Cons: "The inoperative TV screens should be repaired."

Pros: "this is the airline"

Cons: "Plane was late taking off. Crew did not provide water when requested. They were busy with beverages that they could sell at a cost."

Cons: "Wonderful"

Pros: "The only thing I liked about the experience and flight was the Delta Sky Club"
Cons: "Everything"

Pros: "Seat was comfortable and I got extra Biscoff Cookies"
Cons: "Great trip"

Pros: "Great food and service in first class"
Cons: "Water waiting on table on arrival"

Pros: "Seating was fine"
Cons: "Did not have a wheelchair waiting for my wife when we arrived in LAX"

Pros: "room and services"
Cons: "can't think of anything"

Cons: "Even the baggage was quick (highly unusual for Columbus, Ohio)! Everything went smoothly."

Cons: "Delays due to Democrats not making deal"

Pros: "Smooth flight."
Cons: "Tight seat. Small space."

Pros: "We left early"

Pros: "Arrived ahead of time"

Cons: "My sit changed last minute, noisy babies"

Pros: "Great service"
Cons: "Look, if your kid is so young that he can’t get in a plane without screaming for four hours, you shouldn’t bring him on a plane and subject 200 people to that. It’s rude and selfish."

Cons: "My luggage is lost."

Cons: "I understand Mother Nature causes issues tkayakhat no one can control but when I'm receiving updates from the 3rd party travel app that isn't the airline before receiving any information directly from the airline via the gate agent or Deltas travel app and the gate agent not being able to verify the 3rd party travel app something is wrong."

Cons: "After we boarded and were already sitting in our sits the stewardess came and removed our bags from the overhead compartment for another person with a larger bag! We ended up storing our bags under the sits in-front. The way it was done it was rude and with no consideration for our comfort."

Cons: "Delays, delays, delays... first class ticket from BOS to MSP got me a 6 hour delay and a middle seat in econ main cabin at the back of the plane. Delta you suck!"

Cons: "Tray table was broken, I was downgraded from Comfort plus to main cabin after a plane swap with no mention by anyone and no compensation. Flight was delayed 45 minutes because a flight attendant was running late and then to top it off, at the end of. The flight the attendants blocked anyone fromaim cabin from leaving until all of first class had departed, even when no one was coming they still Blocked it off. This is a practice I have never seen on delta and haven't seen in aviation in almost 20 years in the US"

Pros: "Easy and quick"
Cons: "No complaints"

Pros: "Plane was on time."
Cons: "My seat assignment was in the last row of the plan when the plane was not full"

Pros: "A3A"
Cons: "Ĺ"

Pros: "We were in the plane for 3 hours before we could depart. No one offered us a drink or snack."

Cons: "The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings."

Pros: "The selection of movies to watch was very good."
Cons: "No snacks passed out"

Pros: "The staff. They were very helpful and polite!"
Cons: "We didn’t leave on time"

Pros: "i liked the aircraft and the fact that you could watch movies on your phone!"
Cons: "you couldn't hear the staff when they started boarding the plane"

Pros: "Quick flight"
Cons: "Paid $30 for wifi and it never worked. Would like a refund"

Pros: "The staff are wonderful and helpful. Best wishes to Delta. Please keep the great employees."

Pros: "the service in general very nice"

Cons: "Delay in leaving from the airport there were issues with Web checkin Crew wasnt able to give me my boarding pass for the connecting flight and kept saying going to the other counter"

Cons: "Much older plane. Not as comfortable as some other planes I've been on."

Pros: "Nice people. Very helpful."
Cons: "LOST MY BAG IN BOSTON BEFORE EVEN TAKING OFF!!!! Did not make it, and then won't deliver it when it makes it to Kathmandu! This is most distressing."

Pros: "Everything else"

Pros: "I was thankful for the early boarding with a lap infant and was very pleased with the options for entertainment on the TV monitor."
Cons: "The main issue I had was that we sat in row 34 and the noise from the engines often made it difficult to hear announcements, even with headphones in. Look into possibly zoning the audio and turning it up a click or two for rows behind the engines."

Cons: "My wife was told she could not board our flight from Boston to Paris because her passport was expired, even though it was not expired. We were told that in Europe passports cannot expire within 3 months of your departure. However, Delta never let us know about this rule until we literally were boarding the plane. How they could not make us aware of this until we were boarding the airplane is unbelievable and unacceptable. This has ruined our vacation which has been in planning for the last six months."

Cons: "Missed our connection. Spent the night in Minneapolis. Luckily we had no urgent reason to get home to."

Cons: "Jet airways sucks"

Pros: "Free first checked bag, comfy seats"
Cons: "Would have liked more movie selection"

Pros: "red"
Cons: "red"

Pros: "Delta service and conford are great."
Cons: "Pay for wifi"

Pros: "Flight on time"
Cons: "Unfriendly sataff. Not informed that we have to me know in with a difrnt confirmation number related to the operating Claire. I had to spent one hour to fit this information to be able to check in.? It was an international flight but it was treated like a domestic flight. We were not even offered the curtesy snake for a domestic flight by unfriendly stewards apparently unhappyted with her job. Apparanty all American carrier staffs has no respect for customers. It is not only s united problem. Curtesy and respects goes both ways. They need to be retrained in public relation."

Pros: "Crew members were okay"
Cons: "Wifi could be better"

Pros: "Fast boarding"
Cons: "WiFi didn’t work"

Pros: "Easy no hassle check in and board."
Cons: "Absolutely nothing. Thank you!"

Pros: "It was on time,!!!"

Cons: "Baggage claim number was wrong. They almost took my bag away"

Cons: "The chairs"

Pros: "It was fast"
Cons: "They could have offered headphones, the charging outlet didn’t work"

Pros: "Nothing"
Cons: "I am quite sure there was a booking error and no one was willing to make any accommodation. Should have been charlotte to boston. I ate the cost. Tried to reschedule with cheapo air and voila wrong again. That cost me another $50.00"

Pros: "Drink service- Dr Pepper. Clean bathroom."
Cons: "The seat was very hard but I was sitting in economy."

Pros: "Everything."
Cons: "Nothing"

Pros: "Everything"
Cons: "No idea. I thought everything was good."

Cons: "PHX airport baggage claim was a mess. I had to wait 40 min to pick up the luggages."

Cons: "We were told to board quickly so we could leave on time, boarded and sat for more than a half hour. The landing at Monterey was dreadful, hit hard first touchdown and then two more bounces."

Pros: "Coffee"
Cons: "Only snacks available at 5am"

Pros: "Very comfortable, fast, nice staff"
Cons: "They didn’t offer a snack!"

Pros: "Flight crew were very apologetic"
Cons: "Missed connecting flight from Miami. Only one flight per day. Had to take a flight to an alternative location, drive for an hour down the coast and take a ferry to my final destination."

Pros: "Ease of boarding with the group numbers"

Pros: "Best landing I’ve experienced recently!"

Cons: "Too cold"

Cons: "Too many delays as usual"

Pros: "Generally clean plane with good entertainment system and technology overall. Diabetic meal much better than in the past."
Cons: "Didn't announce meal choices at the start so flight attendant had to repeat herself every. Single. Row. They forgot my diabetic meal on the last part them forgot to include cutlery and it took a long time to sort out but they were otherwise lovely."

Pros: "Nice flight, great leg room, staff was friendly and flight was on time."

Pros: "The plane is updated and very comfortable."
Cons: "The change in policy of the 1 bag under seat, caught me by surprise."

Pros: "Friendly attendants, plenty of coffee. Great service."

Pros: "Due to a strong tailwind we arrived 45 minutes ahead of schedule. Great service with attentive attendants. However the plane was older than me, no real entertainment system or outlets to plug in smart devices."
Cons: "Plane needs to be retired or retrofitted to accommodate smart device charging."

Cons: "Boarding chaos at Miami airport."

Pros: "Uneventful and on time"

Cons: "None"

Pros: "Good meals"
Cons: "Not much legroom. Good movie shown but would have like personal options like other airlines."

Pros: "Was on time"

Cons: "Lots of time changes. 1 piece of luggage sent wrong destination."

Cons: "Delayed 3 hrs and then sat on runway upon arrival at ohare. I was forced to check my rollerboard even though I've fit it perfectly in the overhead compartment just yesterday on my previous flight (also American airline)."

Cons: "Paid for extra legroom, got a seat that didn't recline :("

Cons: "No wifi or any video"

Pros: "smooth disembarking"
Cons: "30 mins delay"

Pros: "Got in an hour early. Booya."

Pros: "Everything went fine and was uneventful. For me, an uneventful travel day is a good travel day!"

Cons: "I dislike how early the entertainment system shuts off"

Pros: "Fabulous crew and service, absolutely fantastic."
Cons: "Having to get off!"

Pros: "The plane was new and beautiful"
Cons: "The attendants at the gate we're completely unhelpful. We had booked our tickets separately and we're attempting to get a seat together it took a very long time for the person to say no to us but he said he was helping us and then did that reprinting the same seats we had. He just didn't seem to care at all about anything that was going around."

Cons: "Jetway should not be backed up all the way to the counter. Stop calling so many groups for boarding without knowing that no one is actually getting onboard. Force subsequent groups to step aside until called."

Pros: "Good experience all around."
Cons: "15 minutes late. No big deal though"

Pros: "personal entertainment systems and charging plugs"
Cons: "only pretzels and no headphones offered for the entertainment systems."

Pros: "Not VERY overcrowded"
Cons: "Nothing"

Pros: "Seat were comfortable and I didn't feel claustrophobic."

Pros: "Everything"

Pros: "All good - with every aspect of the trip."

Pros: "On time"

Pros: "Great entertainment system."
Cons: "Over an hour late."

Cons: "Horrible disorganization at boarding. Board from back to front for goodness sake...its common sense."

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Massachusetts to the Cayman Islands

Airlines flying from Massachusetts to the Cayman Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Massachusetts to the Cayman Islands

Mandatory masks

Masks required on board, masks provided on flights from Massachusetts to the Cayman Islands

Social distancing seating

Middle seats unavailable to book on flights from Massachusetts to the Cayman Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Massachusetts to the Cayman Islands

Book cheap flights from Massachusetts to Cayman Islands

Recent round-trip flight deals

11/8
Mon
1 stop
JetBlue
6h 21m
BOS - GCM
11/12
Fri
1 stop
JetBlue
7h 28m
GCM - BOS
10/30
Sat
nonstop
JetBlue
4h 06m
BOS - GCM
11/5
Fri
1 stop
JetBlue
7h 28m
GCM - BOS
10/22
Fri
1 stop
American Airlines
6h 23m
BOS - GCM
10/29
Fri
1 stop
American Airlines
9h 07m
GCM - BOS
10/24
Sun
1 stop
American Airlines
8h 47m
BOS - GCM
10/31
Sun
1 stop
American Airlines
8h 17m
GCM - BOS
9/9
Thu
1 stop
American Airlines
7h 00m
BOS - GCM
9/13
Mon
1 stop
American Airlines
9h 45m
GCM - BOS
10/23
Sat
2 stops
American Airlines
16h 58m
BOS - GCM
10/29
Fri
1 stop
American Airlines
6h 46m
GCM - BOS
9/9
Thu
2 stops
American Airlines
20h 23m
BOS - GCM
9/13
Mon
1 stop
American Airlines
9h 45m
GCM - BOS
10/31
Sun
1 stop
Delta
18h 01m
BOS - GCM
11/7
Sun
1 stop
Delta
7h 18m
GCM - BOS
9/8
Wed
2 stops
American Airlines
19h 30m
BOS - GCM
9/13
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American Airlines
9h 45m
GCM - BOS
10/4
Mon
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American Airlines
7h 00m
BOS - GCM
10/11
Mon
1 stop
American Airlines
17h 49m
GCM - BOS
10/30
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nonstop
JetBlue
4h 06m
BOS - GCM
11/6
Sat
nonstop
JetBlue
4h 01m
GCM - BOS
10/24
Sun
2 stops
Delta
18h 00m
BOS - GCM
10/30
Sat
1 stop
Delta
19h 37m
GCM - BOS
10/24
Sun
2 stops
Delta
18h 00m
BOS - GCM
10/29
Fri
1 stop
Delta
18h 52m
GCM - BOS
12/4
Sat
nonstop
JetBlue
4h 17m
BOS - GCM
12/8
Wed
1 stop
JetBlue
8h 27m
GCM - BOS
7/17
Sat
1 stop
JetBlue
5h 54m
BOS - GCM
7/27
Tue
1 stop
JetBlue
10h 40m
GCM - BOS
10/7
Thu
1 stop
Multiple Airlines
7h 20m
BOS - GCM
10/12
Tue
1 stop
Multiple Airlines
6h 03m
GCM - BOS
10/30
Sat
nonstop
JetBlue
4h 06m
BOS - GCM
11/7
Sun
1 stop
JetBlue
11h 51m
GCM - BOS
10/4
Mon
3 stops
Multiple Airlines
13h 34m
BOS - GCM
10/11
Mon
1 stop
Multiple Airlines
16h 59m
GCM - BOS
10/31
Sun
2 stops
Multiple Airlines
18h 50m
BOS - GCM
11/5
Fri
1 stop
Multiple Airlines
16h 59m
GCM - BOS
10/31
Sun
1 stop
Multiple Airlines
16h 17m
BOS - GCM
11/6
Sat
2 stops
Multiple Airlines
19h 47m
GCM - BOS
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