Find cheap flights from Boston to the Cayman Islands

Find cheap flights from Boston 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
Mon 7/26
Mon 8/2
Any month
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Good to know

Low season

AugustBest time to beat the crowds with an average 4% drop in price.

High season

DecemberMost popular time to fly with an average 7% increase in price.

Average price round-trip

$746(avg. price over the last 2 weeks)

Good deal round-trip

$361or less

Good deal one-way

$179or less

Top tips for finding cheap flights to the Cayman Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to the Cayman Islands is March.

FAQs - booking Cayman Islands flights

How long is the flight to the Cayman Islands from Boston?

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Can I fly to Cayman Islands? Are there any travel restrictions when entering Cayman Islands?

Can I fly to Cayman Islands without having to quarantine on arrival?

Do I need to take a coronavirus (Covid-19) test before flying to Cayman Islands?

What other coronavirus (Covid-19) restrictions are there in Cayman Islands?

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

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Top 5 airlines serving Boston Logan Intl to Cayman Islands

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,638 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: "I love JetBlue! Roomy, well-appointed, great amenities and clean."

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

Pros: "Fast, clean and good"

Pros: "Everything"
Cons: "Nothing"

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

Cons: "Fuel and Gas Smell in the airplane, not sure is it leaking somewhere when it departs."

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: "Super cold"

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

Pros: "great!"
Cons: "great!"

Cons: "Just flying with no 3h delays."

Cons: "Better notification about delays"

Pros: "Nothing really that wows me ."
Cons: "Would have been better if it was on time. Delays are expected though being on the air a lot of times."

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

Cons: "Free water at least"

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"

Cons: "2 hr delay. Poor ventilation"

Pros: "Everything except checked bag wait in sd"
Cons: "Bags took too long"

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."

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"

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: "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: "The crew was so lovely and accommodating, flight was smooth, and I was impressed with the meal service. I travel a lot and this was one of my best experiences. I will definitely favor Delta in the future."

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: "Lisa @ the Boston Delta check-in counter is AMAZING! She's super helpful and essentially saved our vacation! Her coworkers say she's the best and I couldn't agree more! Delta is very lucky to have someone like Lisa on their team!"
Cons: "Nothing to complain about! If I really head to be picky maybe the in-flight meals were smaller than I expected. But again, nothing that bothered me"

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

Pros: "We left early"

Pros: "Arrived ahead of time"

Pros: "wonderfu crew... very helpul`"
Cons: ".."

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: "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: "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: "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: "Movies"
Cons: "Not supplying headphones Crew not to helpful, one unpolite Refreshments ridiculous"

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: "arrived early"

Pros: "Impressed with food and crew!!"

Pros: "Problems started at check in and it went downhill from there"
Cons: "Customer service mostly"

Pros: "Crew were wonderful."
Cons: "It would be good if ba could stop losing my luggage."

Pros: "Wonderful crew!"
Cons: "It is impossible to get comfortable in those seats."

Pros: "Clean"
Cons: "3+ hours late"

Pros: "BA lounge at Boston Airport"
Cons: "Departure delayed more than 2 hours"

Pros: "I’m always impressed with the friendly and caring nature of the British Airlines staff. They always go the extra mile (or km) to make sure that you’re happy."
Cons: "The food, but who flys for the meal"

Cons: "Too many delays"

Pros: "Ease of boarding"

Pros: "New bedding is comfortable!"
Cons: "1. No toiletries were available for business class even on this flight. 2. There was no food choice especially if you prefer vegetarian. 3. Even if One presses a button to request for some water, no one comes to the seat; this habit of BA continues for the good part of the last decade. Reminded me why I stopped flying BA! 4. No wifi even in Business class! Someone in senior management of BA needs to fly SQ, Cathay, Qatar, Emirates and learn what can be improved. Most of these airlines have better service in economy than business on BA!"

Pros: "Nothing"
Cons: "Incredibly poor customer service and their policy's are full of sneaky loop holes. Will NEVER fly with them again."

Pros: "Clean plane and excellent flight overall. The food was very good and the cabin crew were very nice."

Pros: "Wonderful service ....i like everything"
Cons: "Everything was okay"

Pros: "Flight left on time, plane was clean, entertainment options were good and flight attendants were cordial."
Cons: "Food was marginal- avoid the chicken curry."

Pros: "Crew was great, food was excellent."

Pros: "6 hours, no audio port to listen to movies or music or news, poor food “Mechanical” steward service"

Pros: "Checking in efficient, lounge comfortable"
Cons: "Average service. Crew not very interested."

Pros: "The flight attendants were very friendly and helpful - much better than my experiences recently on SwissAir and TAP. That made the difference between an acceptable flight experience and a good one. Food and entertainment options were fine - nothing to write home about."
Cons: "My food tray was broken - okay to eat on but hopefully fixed soon."

Cons: "4-hour delay, switched to other flight. Luckily I wasn't in too much of a rush."

Pros: "Great crew"
Cons: "Old entertainment system"

Pros: "Airline accommodated the delay with free room and meal voucher."
Cons: "Flight was delayed 24 hours. Text message was sent on route that the flight was on time. Mechanical problems."

Pros: "the meal, the aircraft, the friendliness of the flight crew, the on time departure and arrival."

Pros: "Food, seats pretty good , movies offered some good choices much better than US carriers"
Cons: "Heathrow airport at 4:30 AM not fun at all"

Pros: "Ticket price"
Cons: "It's third time British airways lost our baggage. Come on BA, you can do better than this!"

Pros: "Everything"

Pros: "The food on the flight was good and the wheelchair assistance was good too."

Cons: "Seat was very uncomfortable and food was not good! Staff was so so!"

Cons: "Had a horrible time reserving a seat ( willing to pay) because the confirmation number changed and I was not informed. Took several calls to BA, a trip to the airport and an act of god to finally mange it. Was very stressful."

Pros: "The crew was very nice, and I enjoyed the complimentary glass of wine with the meal!"
Cons: "The entertainment was kind of blah and the food was horrible."

Cons: "Only had 1 breakfast on the flight and nothing else."

Cons: "Headphone jack was broken and due to an issue at baggage check in Boston I stood in line of less than 30 people for 2 hours and almost missed my flight."

Pros: "I always try to fly British Airways whenever possible."

Pros: "They got me on a direct flight to Madrid on Iberia. That worked out though I had to leave 2 hours earlier. Good service."

Pros: "Great Service"
Cons: "Check in"

Cons: "Overall was excellent"

Cons: "Nothing"

Cons: "Cabin crew seemed uninterested in passengers. Hot food was honestly disgusting and there were no snacks other than a sugary chocolate bar"

Pros: "Very much enjoyed the pleasant flight attendants. And we enjoyed the complimentary cocktails"
Cons: "The curry chicken was horrible, sorry."

Cons: "Flight attended was unfrontly.. bad food..."

Pros: "crew was very welcoming which made our journey very comfortable"

Pros: "Everything! Best airline ever."

Pros: "The entertainment controls give many options which is nice to help pass the time."
Cons: "The attendants were not as helpful as I thought they should have been and actually were a bit unpleasant."

Pros: "Food ok"
Cons: "Couldn't get seat to go flat. Not the only seat with this problem. Seat too narrow in business. No place to put stuff conveniently. Kind of miserable on this A780. Or whatever the big plane is called."

Pros: "Entertainment, timely boarding"
Cons: "Delayed landing, one or the attendants was very rude"

Cons: "Lost luggage"

Pros: "On time."
Cons: "Economy seat space is inappropriate for any paying customer."

Pros: "Live counters for dinner Boarding directly from lounge"

Pros: "Good entertainment options, crew was nice, ride was smooth."
Cons: "I had a very tight layover and it took forever to get off of the plane, I nearly missed my next flight - it would be nice if short layover passengers got de-boarding priority."

Pros: "The flight got us there safely."
Cons: "The security area was crowded and loud with a man shouting instructions you could barely hear. No one was helpful. No one was there to answer questions. An extremely unpleasant experience."

Pros: "Ear phones for those of us who did not bring any. Having a meal and drink available and at no extra cost."
Cons: "Not knowing if I could get an extra drink after the food was served, would have been helpful. Snacks of chips, pretzels would be tasty. Offering more water or a larger container offered would help. Explaining how u have to get to the next terminal would help. Having to go to many shuttles is confusing."

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

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

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

Cons: "The chairs"

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

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."

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

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

Cons: "4 hour mechanical delay and shitty communication"

Pros: "Quick boarding"
Cons: "Very cold."

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"

Pros: "On time, kept informed."

Pros: "Everything."
Cons: "None."

Cons: "Terrible turbulence"

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."

Cons: "The captain informed us AFTER take off that we could not wash our hands, take care when flushing, etc. Was this this hygienic? See"

Cons: "Coach seating is too tight"

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

Pros: "strategic boarding to avoid standing in the cold"
Cons: "WASNT ENOUGH ROOM FOR CARRY ONS"

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"

Pros: "On time"
Cons: "Terrible entertainment. A 1980s common screen. Horrible movies nobody wanted to watch and no choice was available given the common screen,"

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: "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: "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."

Cons: "Food could have been provided"

Cons: "I didn’t expect to pay to $30 for a carry on luggage"

Cons: "Reliability"

Pros: "i was able to change my seat away from a breastfeeding mom and 2 screaming children"
Cons: "i paid 21.00 for internet which sucked.,buffeted the whole time..couldn’t watch netflix..will be petitioning to get my money back!.."

Pros: "Honestly, don’t care for this airline. There’s always some hiccups with boarding, ride staff, mediocre cabin, etc."
Cons: "Why do they always want to check bags that are your everyday carryon items (large purse, medium backpac, etc.), but allow people to carryon their larger carry on suitcases filling up the overhead bins. Those are the people they should be making check their “carry-one.” And then be rude about it on top of that."

Pros: "Loved the direct Tv"
Cons: "Turbulence"

Cons: "Really expensive internet"

Pros: "Great. they upgraded us to First since my husband was silver premier"

Pros: "it was very punctual and easy to get around."

Cons: "The food selection. For someone like me who cannot eat cheese. there was absolutely no choice. Everything on the menu had cheese."

Cons: "Long delay."

Pros: "New remodeled gate waiting areas plane"
Cons: "Plane is too old"

Cons: "Multiple delays"

Cons: "It was quite late"

Cons: "The food was terrible."

Pros: "awesome, caring staff"

Cons: "Only sent a code for bad wifi on one of two trips. I wish united airlines would step up their game. At least I didn't get dragged off."

Cons: "United sucks soooooo bad"

Pros: "Competent, organized, pleasant and efficient staff, on time"

Pros: "Everything !"

Pros: "Nothing at all"
Cons: "The flights were late and annoying"

Pros: "Took off late but landed on time"
Cons: "Packed in like sardines. Hot on board."

Cons: "Everything"

Pros: "Efficient"
Cons: "Bumpy ride"

Cons: "The plane delay wasn't explained"

Pros: "Very polite clean nice great experience"

Pros: "Service"

Pros: "Nothing"
Cons: "Everything"

Pros: "delayed"

Pros: "Everything"
Cons: "NA"

Cons: "I wished there was a snack."

Pros: "Everything except the wifi not working"
Cons: "The wifi not working"

Cons: "Were held up by TSA in San Francisco because we were not given receipt for our dog who traveled with us. (We had a 2 hour layover in SF and took dog outside the security area for relief). Then the ticket counter in SF was understaffed and it took a long time to get the receipt printed (Once at the counter the agent was very helpful, efficient and quick). Should have a pet area inside the security of airports, like Palm Springs does."

Cons: "They mis-tagged my bag and still haven't found it and have not been helpful or informative when I call to check the status"

Pros: "It was a comfy plane ride."
Cons: "I liked everything."

Cons: "Unreliable wifi."

Pros: "Getting off the plane"
Cons: "Bathrooms weren't working, huge lines in aisle, lackluster service. Overhead bins were full by Group 3. late takeoff."

Cons: "I like everything from this."

Pros: "Did get last seat in business class!"
Cons: "The seat assigned online not valid because of change of equipment. Did result in upgrade to business. Very happy outcome."

Cons: "Seat/space"

Pros: "Curbside checkin and luggage check"
Cons: "Nothing"

Pros: "Attendants were friendly and helpful."
Cons: "One of the attendants was pushy and rude."

Pros: "Broading was seamless"

Pros: "Very satisfied."

Pros: "The flights were delayed nd alot of terbulance"

Pros: "My dinner was delicious"

Cons: "Two time delayed"

Pros: "went smoothly"
Cons: "lack of free peanuts"

Pros: "Horrible airline"
Cons: "Uncomfortable, hidden fees"

Pros: "Easy boarding process"
Cons: "Not enough legroom"

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Boston to the Cayman Islands

Airlines flying from Boston 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 Boston to the Cayman Islands

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Book cheap flights from Boston to Cayman Islands

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American Airlines
8h 06m
BOS - GCM
11/6
Sat
1 stop
United Airlines
5h 55m
BOS - GCM
12/27
Mon
2 stops
United Airlines
20h 05m
BOS - GCM
12/16
Thu
2 stops
United Airlines
10h 10m
BOS - GCM
12/27
Mon
1 stop
United Airlines
20h 30m
BOS - GCM
12/26
Sun
2 stops
American Airlines
8h 12m
BOS - GCM
11/6
Sat
3 stops
Multiple Airlines
44h 28m
BOS - GCM
12/26
Sun
1 stop
Multiple Airlines
24h 54m
BOS - GCM
1/15
Sat
3 stops
British Airways
22h 55m
BOS - GCM
12/16
Thu
3 stops
Multiple Airlines
31h 10m
BOS - GCM
12/15
Wed
3 stops
American Airlines
29h 24m
BOS - GCM
12/26
Sun
3 stops
British Airways
22h 55m
BOS - GCM
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