
Cheap Flights from Boston to Caribbean
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Boston to Caribbean Plane Tickets
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KAYAK's insights & trends for Boston to Caribbean flights
Get data-powered insights and trends into flights from Boston to Caribbean to help you find the cheapest flights, the best time to fly and much more.
What is the cheapest Boston to Caribbean flight route?
The cheapest ticket to Caribbean from Boston found in the last 5 days was to Santo Domingo, at $243 round-trip. The most popular route is from Boston (BOS) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $268.
What is the cheapest time of day to fly to Caribbean?
The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $352 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $412.
Can I save money by flying with a layover from Boston to Caribbean?
No, with an average price for the route of $704, prices are generally cheapest when you fly direct.
What is the cheapest month to fly from Boston to Caribbean?
The cheapest month for flights from Boston to Caribbean is March, when tickets cost $431 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $612 and $552 respectively.
What’s the cheapest day of the week to fly from Boston to Caribbean?
When flying from Boston to Caribbean, you should consider leaving on a Sunday and avoid Fridays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Wednesdays and the most expensive ones on Sundays.
How far in advance should I book a flight from Boston to Caribbean?
To get a below average price on the flight from Boston to Caribbean, you should book around 3 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.
Which airlines fly non-stop between Boston and Caribbean?
There are 7 airlines that fly nonstop from Boston to Caribbean. They are: American Airlines, Frontier, JetBlue, Delta, Hahn Air, Arajet and WorldTicket. The cheapest price of all airlines flying this route was found with Frontier at $89 for a round-trip flight to San Juan Luis Munoz Marin Intl Airport (SJU). On average, Frontier offers the best prices for nonstop flights between Boston and Caribbean.
Which airlines fly most frequently between Boston and Caribbean?
Boston and Caribbean are connected by different airlines. The airlines that fly that route the most regularly are JetBlue (52 flights per week), TAP AIR PORTUGAL (14 flights per week), and Qatar Airways (10 flights per week).
How long does a flight from Boston to Caribbean take?
The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Boston are to Nassau, which takes 3h 33m, Santiago de los Caballeros, which takes 3h 50m, and Santo Domingo, which takes 4h 02m.
Which cabin class options are there for flights between Boston and Caribbean?
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
What’s the earliest departure time from Boston to Caribbean?
The earliest flight from Boston to Caribbean departs at 5:32 am, landing in San Juan at 10:32 am.
What’s the latest departure time from Boston to Caribbean?
If you prefer to fly at night, the latest flight from Boston to Caribbean jets off at 8:16 pm and lands in San Juan at 1:21 am.
Good to know
Low season | September |
|---|---|
High season | December |
Cheapest flight | $85 |
FAQs - booking Caribbean flights
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Reviews of the top 5 airlines serving from Boston to Caribbean
The flight was delayed to board, then delay in landing and extremely bumpy landing.
The flight was delayed to board, then delay in landing and extremely bumpy landing.
Could have been on time and not missed my connection
Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?
Terrible - the flight was delayed taking off after boarding. Then the flight circled lga before landing. Significant delay
The flight was delayed at the very last minute and no information, both of my round trip flights were delayed at least the BNA to Boston was informed earlier but the return one was horrible
Delayed, then set on termac before taking off for 45 minutes. After landing had to sit on termac for another 30-40 minutes. Total disaster of a flight
Stewardess was not accommodating when I requested a second drink.
Although I know the Airlines cannot control the situation when there’s a ground stoppage, it would’ve been nicer if we would have had more up-to-date information clarity around the delays. Additionally, I think the delays also took a toll on the Cabin crew, particularly the lead flight attendant in first class. She was not very friendly when we boarded the plane for many of the passengers. Number one she refused to hang a garment bag in the front closet for a first class passenger, she was unwilling to dispose of an empty bottle in the trash as I was boarding (despite drinking a bottle of water herself and needing to disregard), and she was very combative with a passenger, who needed to access something from his bag that was Gate checked. Frankly, it was really unfortunate as I’ve never seen a flight attendant behave that way directly to the passengers, particularly when none of us had done anything wrong.
Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!
Very good seat and service. No complaints about the food. Take off delayed due to airport traffic
Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.
Great, except the canon was so cold. Even the flight attendants put jackets on
The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying
The pre-order only approach for fresh food is really challenging
Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.
I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.
Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.
It was Swiss. Our kosher meals were literally frozen solid and therefore inedible, and the crew didnt care.
Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.
The flight was delayed, they didn’t even have water for the toilets or for drinks
There is a considerable amount of people that use the wheel chair pre boarding along of large groups of family / friends. This is not right should be limited only to the person in need and the airline assistant. Some of these people use overhead bins that do not belong to them. The aircraft had a non functional wifi . The service was bad.
Overall, it was a fantastic experience had no movies up charge for everything haven’t flown in many many years. Crew is fantastic. Flight was good overall great experience.
My sons tv wasn’t working and they didn’t give him a kids meal I have to request it prior and no one told me!!! Then the 2nd flight they split us up. My two year old can’t sit alone on the plane hello?????
Thought the economy premium experience would match that of the Amsterdam to Boston flight. Aircraft was older: chair didn’t lean back. I had to buy a blanket, which on the flight over was complimentary. Flight crew seemed disinterested all around.
Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!
The series of delays were very unfortunately - first the captain timed out, then the new captain didn't show up when we were told he would, then the first officer timed out. Those delays were compounded by after boarding, weather came in - obviously that's out of JB's control but it was frustrating after all of the other delays that seemed avoidable.
3 hours late JetBlue flight made me miss my connecting flight to Nairobi Kenya, they did not even offer me hotel accommodation, I paid out of my pocket, they did not know where my luggage was, let say my experience with JetBlue was nightmare.
Crew at first tried to SELL snack boxes (for an hour-long flight?!?), and it was the only leg of four on which I was charged for a hard seltzer. 😕 Spent extra to select seats in Row 8 for quicker disembarking only to be seated in Row 25. Someone owes me $38 for that!
It was my worse flying experience. It was my first time and last time flying with Jet Blue.
Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.
Boston sucks. Everything after 4p is delayed. AA switched planes on us so we ended up being 1.5 hours late (plus the delay at Logan). Not sure why the airline says it is on time until 1 h before the flight and then it becomes a rolling delay when they knew the incoming flight was arriving after our scheduled departure time. The crew was great as were the gate agent and ground crew. Just operations that sucked.
Flight was 2 hr late but at least I was upgraded to first class
I've flown American several times this summer and I have yet to get a flight that leaves on time. However, a delay is better than a cancel. So far I have had four canceled flights and two delayed flights
The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off
They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.
Horrific. We were delayed due a flight attendant stuck in traffic en route to the airport. Over 100 people were then stuck in Charolette. Then I ran to make my layover only to find that my connection didn’t have a plane anymore. Waited 2.5 hours without any updates. On the flight we had to beg for even a pretzel option.
Because I bought my ticket from Underpricer, I could not check in online. I could only check in at the airport and that was deeply frustrating because I had to arrive very early. The flight also departed 45 min late and passengers were given no explanations about why we were delayed. I was worried I would miss my connecting flight. Once on board, however, the flight was fine.
Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.
The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.
Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.
Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.
Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.
Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.
Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.
Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.
Horrible service. No communication from the crew as to why a 6 hour delay then cancellation
We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line
The food for sale on board has opportunity for improvement.
The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.
My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this