Find cheap flights from Massachusetts to Caribbean

Find cheap flights from Massachusetts to Caribbean

Round-trip
Economy
Boston (BOS)
Caribbean
Fri 3/5
Fri 3/12
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Caribbean

Good to know

Low season

AugustBest time to beat the crowds with an average 5% drop in price.

High season

DecemberMost popular time to fly with an average 13% increase in price.

Average price round-trip

$390(avg. price over the last 2 weeks)

Good deal round-trip

$129or less

Good deal one-way

$74or less

FAQs for booking flights from Massachusetts to Caribbean

Which airlines have a flexible cancellation policy for flights from Massachusetts to Caribbean due to COVID-19?

Which airlines apply social distancing measures on flights from Massachusetts to Caribbean due to COVID-19?

How does KAYAK find such low prices on flights from Massachusetts to Caribbean?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Caribbean?

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

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Massachusetts to Caribbean?

Top 4 airlines serving from Massachusetts to Caribbean

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,046 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

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."

Pros: "Don’t go overboard"
Cons: "Cleaner"

Pros: "Good"
Cons: "Good for now"

Cons: "Top carrier"

Pros: "Well organized and easy to check in."
Cons: "No"

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: "Was boarded promptly"

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: "Better allergy aware food."

Cons: "Wonderful"

Pros: "I love ice cream and chocolate"
Cons: "Healthy vegetarian meal choice"

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: "Good service this morning"
Cons: "All good"

Pros: "We left early"

Pros: "Arrived ahead of time"

Cons: "We left 30 minutes late due to congestion and I missed a layover. Otherwise it was a great experience"

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

Pros: "The cheese bites were amazing!"

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!"

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

Pros: "A3A"
Cons: "Ĺ"

Cons: "insufficient overhead luggage space"

Pros: "Food was plenty."
Cons: "Long security lines at Logan. No free WiFi"

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

Pros: "Comfort Plus allowed us to board early, useful USB ports."

Pros: "Service vey Good. Nice choices. Comfort seating very nice"
Cons: "WiFi awful. Useless."

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: "on time, good food, good films enough space to sleep in economy."
Cons: "the stewardess only went up one side of the plane offering eye shades and when i asked for one she seemed really miffed."

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: "Whole thing was easy, plane was nicely updated on the interior"

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

Pros: "I like Delta. They are organized and professional. They treat traveler with dignity."

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: "Everything else"

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

Cons: "Jet airways sucks"

Pros: "red"
Cons: "red"

Pros: "Everything operated according to schedule."

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

Pros: "Lack of elbow room, even in aisle seats."

Pros: "My legs were sandwiched behind the seat in front of me. I hate that kind of seat spacing."

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

Pros: "Customer Service was acceptable."
Cons: "Flights were cancelled and bags were lost!"

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

Cons: "The chairs"

Pros: "Uneventful"
Cons: "Diet Gingerale please"

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

Cons: "Overall good business class trip."

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: "The gate attendant was very hard to understand and so I couldn’t hear what she was saying."

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

Pros: "Boarded in Boston and pulled away from the gate. An engine starter was bad so had to tow back to gate. After time to figure out the issue we were deplaned and began rebooking process. Not satisfied"
Cons: "See above"

Pros: "Ease of boarding with the group numbers"

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

Cons: "Too cold"

Cons: "Too many delays as usual"

Cons: "Our luggage was ruined and our stuff inside in bubble wrap was smashed to bits!"

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

Pros: "We had to wait in the airplane upon arrival in La Guardia NY because wheelchair was not ready."

Cons: "Seat space very narrow and uncomfortable seats"

Pros: "Uneventful and on time"

Pros: "Everything great. Rate food and entertainment moderate because there was no dinner, which we did not require, and we went to sleep so didn't pay attention to entertainment."

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."

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

Pros: "Nada"
Cons: "Overbooked Long lines Lost bag for my son Rude agents Absude EU 33 charge to book a seat. Bad website. Not a decent customer service. End this airline"

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

Cons: "Seats are uncomfortable and inadequate for a comfortable ride."

Cons: "No wifi or any video"

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

Cons: "We didn't have hot beverage service due to turbslsnce and the attendant never came back to offer my 84 year old mother another choice"

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"

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: "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."

Cons: "Being stuck in a high dollar city for an additional night when i should have made it to the lower intermediary city and flown standby the next day."

Pros: "On time"

Pros: "The boarding was stress free."
Cons: "Comfort."

Pros: "Price. Crew was very polite."
Cons: "Late departing due to fueling"

Pros: "The service was POOR! This was my firsts time booking through this Airline and NO ONE told me about checking in 2 hrs early according to the phone phone rep or 45 minutes early according to the RUDE rep in the airport either way I arrived at the airport an hour before my flight and couldn’t board!"
Cons: "Frontier could take some time to better inform their first time customers of airport arrival times. I lost my seat AND was forced to book ANOTHER flight for 231.00 because Frontier didn’t think of their customer FIRST! Not to mention that was the ONLY flight leaving Boston until Wednesday"

Pros: "Friendly crew"

Pros: "The anouncements in Islip explaining the boarding process and warning people about bringing carry ons that they did not pay for were clear, loud and understandable. Crew was great."
Cons: "the seats hurt my butt, not sure if I could do a longer flight on this plane"

Pros: "For the price it's a good option. Just be aware of uncomfortable seats and cramped conditions ahead of a long flight."

Pros: "Plane late to pick up/board and had no gate to inboard when we arrived."

Cons: "Poor customer service"

Pros: "I usually don’t mind Frontier for short flights. And I say short because most of the seats don’t recline and it’s uncomfortable. For the most part, my flights leave and land on time without hassle. However, today the attendants at the flight desk were rushing passengers onto the plane saying “if we get everyone onto the plane we can leave early!” Of course this sounds appealing to anyone with a child and work at 6am the next day. After being rushed onto the plane, we took off MAYBE 10 minutes early. While In flight, the pilot got on the speaker and assured us a gate was open for our arrival. All of this just so we could land in Denver and sit on the plane waiting for a gate to open for 20 minutes. A little food for thought- no one would ever prefer to sit on a damn plane instead of in the airport. What was the point of all this rushing just to sit and wait? Ridiculous. Now instead of being on time, we’re actually late. What a joke."
Cons: "Read above"

Pros: "Nothing positive to say about this whole experience."
Cons: "1. I do not like the surprise fees for bags or in order to pick your seat. 2. Flight was delayed out of Indy. 3. Sat on the runway for 40 minutes once we arrived in Orlando."

Pros: "Not much"
Cons: "Same as previous flight"

Pros: "I thought the crew was very nice, seats were comfortable although many may not agree. There is more legroom since the chairs are thinner and lighter."
Cons: "Didn't realize there was a carry-on fee which is my own fault but will cost you minimum of 70 round trip. It is hard Tom figure it out in their site however. For that cost they should at least have wifi on the plane which they do not."

Pros: "On the flight was OK. The flight crew was kind and friendly despite everyone being a little annoyed at the boarding process. Gotta say though I feel a little nickel and dimed on Frontier as you actually have to pay $3 for a can of coke that costs 25 cents. It doesn't take much to offer a beverage service other than water to make the flight a bit more enjoyable, but getting charged for everything makes things more stressful than needed."
Cons: "I got to the gate 5 minutes before boarding and there was no one there. I walked around for a bit came back and asked some flight attendants working the flight what time they were actually going to board and they couldn't be bothered to help telling me to check my ticket and that is when the flight will board (the time on the ticket was already 10 minutes ago)! After an hour went by and a very large crowd formed at the gate and absolutely NO update or any communication as to when boarding would be they finally started boarding. Very disorganized boarding process. Just wish someone would have provided an update or something, so I could have gotten something to eat instead of hanging around the gate for an hour."

Pros: "I suffered from a backache the entire flight due to the seats, despite 4tylenol"
Cons: "The seats."

Pros: "I arrived at my destinations safe on both occasions."
Cons: "The seats are hard as granite rocks, no leg room at all & they don't recline back at all, oh except if you want to pay for an emergency exit where you have to sign your life away to have a better seat. No complimentary beverages besides tap water. It's like we're doing your Airlines a favor by flying with you. I would never board an aircraft with the name Frontier on it again. Plus you charge a ridiculous rate for a checked bag. Never again & I bet you can guess what I will tell everyone I come across."

Cons: "They kept pitching their credit card. They charge extra for every little thing (carry ons, drinks), why would I want their card?"

Pros: "The crew was nice."
Cons: "The airline charges for carry-on bag!"

Cons: "They charge you for EVERYTHING, don't fly frontier!!"

Pros: "MCO airport is nice"
Cons: "The mix of LAX and frontier is enough to drive you mad. Delays with the airline and, no joke, 70 mins latter still waiting for the baggage carousel to even to on...."

Cons: "Delays for hours (5) and missed connections. On top of that, they couldn't get me to me San Diego destination. The best they could do was L.A....three hours away ! The offered no voucher and I would have to pay for my own hotel for the extra night stuck in Denver."

Pros: "The staff was friendly."
Cons: "Ticket prices marked down to charge for bags, drinks/snacks, seats, and comfort. It may seem more affordable but after fees, you are paying basically the same for a less comfortable, more dangerous/horrifying, delayed flight."

Pros: "Efficient and on time. Great price!!!"
Cons: "App did not work for checking in on return flight. Friendly customer service but needs a bit more training."

Pros: "Nice to be on a brand new Airbus."

Pros: "Nothing"
Cons: "I was so appauled at the lack of customer service that Frontier Airlines lacks. I did not even take my flight with Frontier due to hidden fees, $99 change fees, carry on bag fees etc...I just called Southwest and they gave me a new ticket the night before my flight for LESS than what my fees would have been with Frontier. I also got 2 free bags and could bring a carry on. Not to mention they actually serve drinks on their flight. I was so disappointed with EVERYTHING about your airline company. The worst part is....a supervisor from Frontier said they would call me back in an hour (I wanted to discuss with my husband if it was even worth it to pay the fees or not) and he didn't even do it! It shows how much you guys don't care about your customers or business. As soon and I noticed he wouldn't call I just called Southwest and explained my situation and I was off the phone in less than 10 minutes with a new ticket and FREE BAGS!! I will NEVER fly Frontier ever again."

Pros: "The flight was early"
Cons: "I was charged baggage"

Pros: "I've learned to pack whatever I need into a backpack that's within their personal item limits. This makes traveling on cheap flights easy."

Pros: "Clean airplane. Crew was nice."
Cons: "Cheap seats. Noisy. It rattles and shook worried me."

Pros: "They miss my bag in Denver"

Pros: "Nothing"
Cons: "Sat all the way in the back against the bathrooms, AGAIN. They wouldn't let me switch to seats that were clearly wide open because of "weight distribution." This company is a bunch of clowns."

Cons: "No complimentary snack or drink (provided by basically every other airline). Also, no free carry on (also provided by basically every other airline)."

Pros: "Took off on time reached before schedule, price was unbelievable ,very comfortable all great."

Cons: "Gate changes and delays with excuses like waiting on paperwork to be approved. Really? Didn't you know we were taking off soon?"

Pros: "Non"
Cons: "Boarding process- need better communication Don't have hidden fees such as carry on bag and for seats Have planes that have seats the can move back and bigger tables"

Cons: "Delayed"

Pros: "After reading some reviews I was nervous about flying frontier but everything was perfect!"

Pros: "Absolutely nothing."
Cons: "Uncomfortable seats, no entertainment, and the airline prompts us to tip? The seats don't even recline & most snacks were unavailable. Never Frontier again!"

Pros: "Attention of the fly attender was very good"
Cons: "My fly was delayed for almost 6 hrs in I don't recive any information about that no email no txt message"

Cons: "Delayed two hours. Seats very uncomfortable"

Cons: "Yet another delay in leaving (unrelated to weather from what we could determine)... Arrived in San Francisco at roughly midnight instead of 9 pm."

Cons: "I arrived at airport about 11:30 am which is two and half hours earlier than departure time (2:00 pm) but boarding service started from about 12:30. And I got very upset when front desk lady told me that she will charge $45 for my carry-on baggage but charge $ 40 when I check in my baggage. So I checked in my baggage for $ 40 instead of carry my baggage. I do not understand why carry it cost more than check in."

Pros: "The color of their uniforms were very nice and professional. The animal themed planes were fun as well!"
Cons: "Poor customer service. We got to the airport 3 hours ahead of time and it took well over an hour for them to check in baggage (keep in mind we checked in our bags online and there were only 8 people in front of us) we made it to our gate 30min ahead of time. It was terrible. Tried to be kind to the staff but they were not having it. Very inconsiderate of others and doing their job in a timely fashion. They also lost my luggage. Since the airline is so cheep they don't keep staff on hand to handle issues after the flight lands. No desk to report to, no phone number to call; as if you never even flown with them. It was very alarming as I had important clothing for an interview, medicine, and other personal items that would not easily be replaced. Never flying frontier again."

Pros: "Crew was friendly."
Cons: "No free sodas nor peanuts."

Pros: "The cabin was clean, and the staff was friendly."
Cons: "I was disappointed in the surprise costs of luggage. I packed everything in a carryon so that I wouldn't have to pay for a check bag, but turns out a carry on costs $40 at check in. I understand it was a cheap flight, but I may have made a different decision if I knew there was an extra hidden cost of $80 round trip. On other notes, on the first flight of my two, the plane was swerving back and forth on takeoff and landing. The weather was fine, and I've flown plenty enough to know this wasn't normal. My second flight was fine. It was on the same plane, but the crew changed, so I guess it was pilot causing it to be this way? The seats were uncomfortable in coach for long periods of time compared to other airlines, and did not recline."

Pros: "The cheap airfare that's it!"
Cons: "Baggage is to pricey and the seats are very uncomfortable and you can't even get any peanuts!"

Pros: "safely arriving at my destination."
Cons: "this takes no fails to a new level. a tray table the size of my hand, seat backs do not recline, no music or option for any entertainment, paying to not sit in a middle seat."

Cons: "Bags were crushed, things broken inside, they charge you for everything. Machines were down last flight."

Cons: "The ticket was a little cheap but it's a trick! They charge you for whatever they can find that any other airline would give you for free. They charge you for a carry-on bag and if you don't register it when you get your boarding pass you have to pay extra. The poor girl in front of me in line had to pay $60 to get her carry-on onto the plane. Even checked bags cost more than any other airline. Instead of complimentary drinks and snacks Frontier Airlines charges for theirs. Altogether it turns out to be more expensive for an unpleasant experience worsened by cramped spaces, dogged by anal, demanding, and unrelenting crew, and speckled throughout by expensive and surprising fines. I will not fly with frontier again."

Pros: "Not much"
Cons: "Plane was 1.5 hours late. Seats are terrible. Charge for everything."

Pros: "Nothing at all"
Cons: "The customer service and the constant delays"

Pros: "Crew was great, the flight was cheap, everything went off without a hitch"
Cons: "You get what you pay for sadly. Carry on is limited to what you can fit under the seat in front of you, for my two day trip my back pack worked perfectly. anything else was an extra charge. I realize this is how they make the flights cheaper so don't take this as a terrible thing, just wish I could have taken more with me. Pro tip: add your luggage online when you book the flight or even when you check in, it's a lot cheaper"

Cons: "1 hour delay with minimal explanation, no water for hand washing in bathrooms, tea and coffee not available, not standard weight requirements for checked luggage. These are all significant inconveniences."

Cons: "This was my first time that I choose this Airline and also the last time too. This Airline didn’t care the customer. Never has a solution and also never depart on time. They charge the passenger for everything. Nothing is free. My humble opinion is don’t fly with them. I flew with them this time because I found a cheap ticket but at the final I paid more. The prices are very attractive but isn’t true. For me was a headache."

Pros: "Good service"
Cons: "Everything was good."

Cons: "Delayed both ways"

Pros: "No frills or personality"

Pros: "Great ticket price. I don't mind packing light to save money."

Cons: "No wifi"

Cons: "They charged me three times"

Cons: "Fight was delayed"

Pros: "Price"
Cons: "Can't think of anything"

Pros: "The story I came away with."
Cons: "The speed at which the 22 year old girl sitting between the eye-drop salesmen fled the plane when we landed. Atlantic City is a funny destination."

Cons: "The 'low' fare is a fraud, you can't actually get a seat at that price. I checked there was one row, adjacent to the toilets at the back of the plane, and it was booked. Rather, you're going to pay $40-100 RT to actually sit down on the plane. And $50 for a carry-on bag?? Seriously??? I won't fly with them anymore."

Pros: "Quick boarding."
Cons: "It was hot. I had to pay way too much for a carry-on"

Cons: "Delayed.... Delayed... Delayed"

Pros: "Nothing"
Cons: "Everything"

Cons: "the damn fees. you need to make them clear when tickets are purchased."

Cons: "Long lines, delays and unhappy employees"

Pros: "Nothing"
Cons: "It got canceled on my way to the airport"

Pros: "The temperature was decent, relatively clean seat area, no terrible smells."
Cons: "The 9 emails updates about the delays, fluctuating both ways so as to not allow the passengers to know when exactly to get to the airport."

Cons: "There was a delay that was not announced at the gate"

Pros: "More comfortable than I expected"
Cons: "Fees are too complicated"

Cons: "supposed to leave at 9 p.m. didn't leave until 12:30 a.m.. Had to find another way to get back to Balto. No reimbursement at all."

Cons: "Everything was fine. A little slow at checkin but all was pretty good"

Pros: "Nothing."
Cons: "Everything!"

Pros: "Nothing"
Cons: "Upcharges make you as expensive as other airlines but service is terrible so not worth it"

Pros: "Yes very much"

Pros: "Worst thing ever."

Pros: "Piloting of plane on take off and landing was smooth."
Cons: "Nickel & dimed start to finish. Well, lots more than nickels and dimes. Charges left and right for things that shouldn't be charged. Hated it. Won't take Spirit again."

Cons: "They charge way too much for bags, carry on or checked!"

Pros: "Nothing"
Cons: "Everything. Delay. Expensive luggage."

Pros: "Me trataron bien"
Cons: "Que me cobraron la maleta deben de mejorar eso"

Cons: "cancelled after 4 gate changes and beginning boarding. no rebooking."

Pros: "Only the price"
Cons: "Charge for bags ...gate change ..tight seating don't recline."

Pros: "i was assigned randomly the unassigned seat 1a, first class despite only purchasing economy. lucky me!"

Cons: "Crazy loud unruly passengers chaotic cabin and constant jostling from the aisle"

Pros: "Nothing, nothing at all"
Cons: "Everything from the size of"

Pros: "Nothing"
Cons: "Outragious charges for carry-on and checked luggage. Misleading information regarding seat pitch on website. Charged for extra legroom. Didn't get extra legroom. Refusal to refund charge for extra legroom."

Cons: "Hour long delay"

Pros: "Nothing"
Cons: "Everything, everything is about money and nothing is about the customer"

Cons: "I will not use them again as they charged me an extra $100 for 2 bags. With American they would have been free.............who ever heard of charging for in the cab bags!"

Pros: "Nothing I will not recommend spriit to any friends of colleagues"
Cons: "Service was terrible. The cabin had no amenities. The tray table was so small I couldn't even open my laptop and there was no wifi to get work done anyway. Terrible for a business traveler."

Pros: "Nothing"
Cons: "Everything"

Cons: "Staff are the rudest most unhelpful people imaginable"

Cons: "Ya que no hay mas que tu asiento, que este limpio. Fue decepcionante al meter la mano en el compartimento del frente del asiento estuviera lleno de basura al igaul que sucio. El abordaje en Orlando fue rudo ya que el personal transmitía su descontento."

Cons: "See above."

Pros: "If you just need to get from here to there, you can't beat it!"
Cons: "Everything costs extra"

Cons: "late"

Pros: "Boarding process was speedy"
Cons: "Expensive baggage prices, also having to pay to choose a seat"

Pros: "good. functional. cheap."

Pros: "nothing"
Cons: "Spirit airlines is the worst ever"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Massachusetts to Caribbean

Airlines flying from Massachusetts to Caribbean 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 Caribbean

Mandatory masks

Masks required on board, masks provided on flights from Massachusetts to Caribbean

Social distancing seating

Middle seats unavailable to book on flights from Massachusetts to Caribbean

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Massachusetts to Caribbean

Book cheap flights from Massachusetts to Caribbean

Recent round-trip flight deals

4/25
Sun
1 stop
Spirit Airlines
6h 57m
BOS - SJU
4/30
Fri
1 stop
Spirit Airlines
13h 38m
SJU - BOS
4/25
Sun
1 stop
Spirit Airlines
14h 00m
BOS - SJU
4/30
Fri
1 stop
Spirit Airlines
13h 38m
SJU - BOS
4/23
Fri
1 stop
Spirit Airlines
14h 00m
BOS - SJU
4/28
Wed
nonstop
Spirit Airlines
4h 35m
SJU - BOS
4/19
Mon
1 stop
Spirit Airlines
6h 57m
BOS - SJU
4/28
Wed
nonstop
Spirit Airlines
4h 35m
SJU - BOS
4/25
Sun
1 stop
Spirit Airlines
6h 57m
BOS - SJU
4/30
Fri
1 stop
Spirit Airlines
13h 38m
SJU - BOS
4/9
Fri
1 stop
Spirit Airlines
15h 52m
BOS - SJU
4/13
Tue
1 stop
Spirit Airlines
17h 10m
SJU - BOS
4/23
Fri
1 stop
Spirit Airlines
14h 00m
BOS - SJU
4/28
Wed
nonstop
Spirit Airlines
4h 35m
SJU - BOS
4/14
Wed
1 stop
Spirit Airlines
8h 28m
BOS - SJU
4/21
Wed
1 stop
Spirit Airlines
13h 38m
SJU - BOS
4/9
Fri
1 stop
Spirit Airlines
15h 52m
BOS - SJU
4/13
Tue
1 stop
Spirit Airlines
17h 10m
SJU - BOS
4/9
Fri
1 stop
Multiple Airlines
8h 37m
BOS - SJU
4/14
Wed
1 stop
Multiple Airlines
11h 26m
SJU - BOS
3/28
Sun
nonstop
Multiple Airlines
4h 13m
BOS - SJU
3/30
Tue
1 stop
Multiple Airlines
30h 54m
SJU - BOS
4/11
Sun
1 stop
Multiple Airlines
15h 31m
BOS - STT
4/16
Fri
1 stop
Multiple Airlines
8h 53m
STT - BOS
4/9
Fri
1 stop
Multiple Airlines
8h 37m
BOS - SJU
4/13
Tue
2 stops
Multiple Airlines
21h 24m
SJU - BOS
4/2
Fri
1 stop
Multiple Airlines
8h 37m
BOS - SJU
4/4
Sun
nonstop
Multiple Airlines
4h 19m
SJU - BOS
3/22
Mon
2 stops
Multiple Airlines
23h 14m
BOS - STT
3/25
Thu
1 stop
Multiple Airlines
17h 36m
STT - BOS
3/14
Sun
1 stop
Frontier
19h 12m
BOS - STT
3/25
Thu
1 stop
Frontier
26h 44m
STT - BOS
4/27
Tue
1 stop
American Airlines
9h 17m
BOS - AUA
5/4
Tue
1 stop
American Airlines
9h 52m
AUA - BOS
3/23
Tue
1 stop
JetBlue
7h 17m
BOS - SXM
3/25
Thu
1 stop
JetBlue
10h 07m
SXM - BOS
4/14
Wed
1 stop
Delta
7h 00m
BOS - SXM
4/19
Mon
1 stop
Delta
8h 41m
SXM - BOS
3/22
Mon
1 stop
United Airlines
20h 35m
BOS - SXM
3/31
Wed
2 stops
United Airlines
21h 41m
SXM - BOS
Show more results

Recent one-way flight deals

4/19
Mon
1 stop
Spirit Airlines
14h 00m
BOS - SJU
4/19
Mon
1 stop
Spirit Airlines
6h 57m
BOS - SJU
4/22
Thu
nonstop
Spirit Airlines
4h 17m
BOS - SJU
3/21
Sun
1 stop
Spirit Airlines
15h 52m
BOS - SJU
3/21
Sun
1 stop
Spirit Airlines
15h 52m
BOS - SJU
4/25
Sun
1 stop
Spirit Airlines
11h 54m
BOS - SJU
3/21
Sun
1 stop
Spirit Airlines
16h 19m
BOS - SJU
3/29
Mon
1 stop
Frontier
9h 29m
BOS - SJU
5/19
Wed
1 stop
Frontier
13h 38m
BOS - SJU
3/16
Tue
1 stop
Multiple Airlines
15h 31m
BOS - STT
3/28
Sun
1 stop
Frontier
15h 28m
BOS - SJU
3/22
Mon
1 stop
Frontier
9h 29m
BOS - SJU
3/24
Wed
1 stop
Frontier
16h 07m
BOS - SJU
3/24
Wed
2 stops
Multiple Airlines
23h 14m
BOS - STT
4/11
Sun
1 stop
Multiple Airlines
15h 31m
BOS - STT
4/23
Fri
2 stops
Multiple Airlines
26h 49m
BOS - STT
3/12
Fri
nonstop
Delta
3h 57m
BOS - STT
3/19
Fri
1 stop
American Airlines
8h 12m
BOS - STT
3/20
Sat
nonstop
JetBlue
3h 23m
BOS - NAS
4/18
Sun
2 stops
United Airlines
23h 24m
BOS - PLS
Show more results
-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First