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Find cheap flights from Boston to Caribbean from $48

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Caribbean departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 5/29
Wed 6/5

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$224
Montego Bay
Montego Bay1 stop$244
Santo Domingo
Santo Domingononstop$336
Oranjestad
Oranjestad1 stop$266
Nassau
Nassau1 stop$263
Kingston
Kingston2 stops$392
Simpson Bay
Simpson Bay1 stop$220
Providenciales
Providenciales1 stop$357
Port of Spain
Port of Spain1 stop$464
Bridgetown
Bridgetown1 stop$402
George Town
George Town1 stop$347
Aguadilla
Aguadilla1 stop$236
Castries
Castries2 stops$1,208
Willemstad
Willemstad1 stop$430
St. John's
St. John's1 stop$430

Good to know

Low season

September

High season

April

Cheapest flight

$48
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Boston to San Juan Airport

FAQs - booking Caribbean flights

  • Which destination in the Caribbean is most flown to from Boston?

    Many of the flights from Boston to the Caribbean visit San Juan because the city is close to Boston. This makes it one of the shortest flights from Boston to the Caribbean. When visiting San Juan from Boston, you don’t need a passport as a US citizen, making your travel to the Caribbean city hassle-free. San Juan is also accessible to other Caribbean islands, allowing you to explore the Caribbean easily from the airport.

  • Which airlines with flights from Boston to the Caribbean allow pets in the cabin?

    If you want to take your pet on your flight from Boston to the Caribbean, consider flying Delta Air Lines, which allows small pets up to 20 pounds to travel in the cabin from Boston to the Caribbean. Ensure your pet is in a carrier with dimensions of 18 x 11 x 11 inches.

  • Can a minor fly unaccompanied from Boston to the Caribbean?

    Consider booking Delta, United, and American Airlines, which allow kids between 5 and 14 years to travel alone for an additional fee under the unaccompanied minor service. As the parent or guardian of the child traveling alone, ensure you have the unaccompanied minor form, your identification documents, the contact details of the adult picking up the child at the destination airport, and the child’s birth certificate or passport for proof of age.

  • Does Boston Logan International Airport offer accessibility services?

    If you have special needs, BOS offers airport and wheelchair assistance and has accessible restrooms, parking, and seating to aid passengers with limited mobility. The airport has elevators and escalators for access to terminal levels by passengers with reduced mobility, braille signage for the visually impaired, visual paging, and TTY phones for hard-of-hearing passengers.

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

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

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Caribbean with an airline and back to Boston with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Caribbean from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 16% more expensive than an evening flight, on average*.
  • Flights from Boston to the Caribbean depart from Boston Logan International Airport (BOS), the primary airport serving Boston and surrounding areas. The airport is a hub for Delta Air Lines and is a focus city for JetBlue Airlines. You can connect to several Caribbean destinations from BOS through these airlines, as they offer frequent flights to the Caribbean.
  • Delta Air Lines has a Delta Comfort+ class, which is between Delta's economy class and their first class. Comfort+ offers extra legroom, priority boarding, dedicated overhead bin space, and additional in-flight amenities for a comfortable flight from Boston to the Caribbean.
  • JetBlue offers a generous carry-on baggage allowance with baggage weight up to 22 lb and maximum dimensions of 22 x 14 x 9 inches for economy passengers on flights from Boston to the Caribbean. The airline also allows you to have an extra personal item, such as a laptop bag or purse, with dimensions up to 17 x 13 x 8 inches.
  • If you want to spend less time traveling from Boston to the Caribbean, book a direct flight from Boston to the Caribbean. Many airlines, including Delta, American, JetBlue, and Spirit Airlines, offer direct flights to various Caribbean destinations, including San Juan (SJU), Punta Cana (PUJ), Nassau (NAS), Montego Bay (MBJ), and Aruba (AUA).
  • Most airlines, including JetBlue, Delta, and American Airlines, offering flights from Boston to the Caribbean offer special meals upon request. You can inform the airlines of your dietary needs in advance. The airlines provide vegetarian, vegan, gluten-free, low-sodium, child, and diabetic meals.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Boston to Caribbean

 
Need help choosing which airline to fly with from Boston to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10932 reviews
8.0entertainment
7.4food
8.2boarding
8.6crew
7.9comfort
Airline reviews

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

8.0 ExcellentCynthia, Apr 2024ATL - SJD
Read more about Delta reviews

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

I had back trouble prior to my flight and everyone was great about helping me.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

The boarding and flight were ok, but there were several painful issues. The flight was 3:20 in the air and almost four hours door to door, but they only had snack packs on the plane. They really need to have food on longer flights or make it clear to everyone that they won’t have food. They also advertise free WiFi, but it did not work for 90% of this flight. Again, almost four hours door to door. If I had known I was flying spirit for JetBlue prices then I would have planned differently.

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

I loved the flight and the crew. It was comfortable and smooth.

The crew was openly hostile and condescending to the customers. They spent the majority of that time in the rear talking and seemed really agitated when people asked questions. I heard five different people told that the information they requested was in the handout or safety brief.

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

Crew were fine, drinks and snacks were as well but we were delayed for around 2 hrs which made our entry into Mexico delayed as well with the influx of arrivals at the same time. Sort of wasted our first day of vacation. We left Pittsburgh at 630am and did not arrive in Mexico until late dinner time.

The ride was good but no food ot entertainment hence, it was just over an hour flight.

There was a group of school age passengers that were very loud and unruly with their chaperones were no where to be found.

Boarding was unorganized. They expected passengers to ask people to move their assigned seat they paid for in order to sit together. The seats even in comfort are smaller than other airlines and the flight attendants appeared not to be well prepared

The WiFi didn’t work and the seats are too close together. Very uncomfortable.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

So so. Terrible aircraft choice for that leg of the flight.

Too bad that first class seats do not recline significantly causing discomfort

I think the seats on some of their planes are uncomfortable. You can be ok on a short flight of two hours but no more than that. The delays, and also the refreshments on the plane were not enough.

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Not sure why JAL partnered with American Airlines because their service is no where near similar. Flight attendants were not friendly and didn’t smile. Food was horrible…

this is starting to seem like an american airlines standard. delayed flights and fake apologies… getting tired of it

Terrible boarding , Business class seats are sub standard. As usual crew will miss your food too

Just get Economy Plus for international flights, so worth it the extra room, bigger seats…

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Book cheap flights from Boston to Caribbean

Recent round-trip flight deals

5/31Fri
nonstopSpirit Airlines
4h 06mBOS-SJU
6/5Wed
nonstopSpirit Airlines
4h 14mSJU-BOS
$90
5/31Fri
nonstopSpirit Airlines
4h 06mBOS-SJU
6/5Wed
1 stopSpirit Airlines
9h 40mSJU-BOS
$98
6/2Sun
nonstopJetBlue
3h 59mBOS-SJU
6/25Tue
nonstopJetBlue
4h 00mSJU-BOS
$213
5/21Tue
nonstopJetBlue
3h 59mBOS-SJU
5/23Thu
nonstopJetBlue
4h 17mSJU-BOS
$223
5/10Fri
1 stopDelta
10h 44mBOS-NAS
5/15Wed
1 stopDelta
5h 42mNAS-BOS
$263
5/11Sat
1 stopDelta
6h 19mBOS-NAS
5/14Tue
1 stopDelta
5h 42mNAS-BOS
$293
5/10Fri
1 stopAmerican Airlines
13h 30mBOS-NAS
5/12Sun
1 stopAmerican Airlines
12h 18mNAS-BOS
$318
5/9Thu
2 stopsAmerican Airlines
9h 22mBOS-STI
5/16Thu
2 stopsAmerican Airlines
17h 35mSTI-BOS
$347
5/7Tue
1 stopUnited Airlines
8h 00mBOS-SDQ
5/11Sat
1 stopUnited Airlines
7h 45mSDQ-BOS
$350
5/27Mon
1 stopUnited Airlines
8h 29mBOS-PLS
6/1Sat
1 stopUnited Airlines
7h 54mPLS-BOS
$357

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Recent one-way flight deals

5/14Tue
1 stopSpirit Airlines
13h 01mBOS-SJU
$48
5/12Sun
nonstopSpirit Airlines
4h 06mBOS-SJU
$53
5/14Tue
1 stopAmerican Airlines
14h 55mBOS-NAS
$77
5/15Wed
1 stopDelta
7h 03mBOS-NAS
$78
6/11Tue
nonstopDelta
4h 05mBOS-SJU
$112
5/15Wed
2 stopsAmerican Airlines
11h 45mBOS-NAS
$113
5/28Tue
1 stopJetBlue
8h 06mBOS-NAS
$117
7/12Fri
1 stopJetBlue
11h 14mBOS-NAS
$122
5/8Wed
1 stopUnited Airlines
10h 21mBOS-MBJ
$204
5/9Thu
2 stopsUnited Airlines
13h 38mBOS-SJU
$211

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Last minute flights from Boston to Caribbean

Last minute flight, train and bus deals

5/4Sat
multi-stop
9h 43mBOS-SJU
5/8Wed
nonstop
4h 24mSJU-BOS
$150
5/2Thu
nonstopSpirit Airlines
4h 01mBOS-SJU
5/7Tue
nonstopSpirit Airlines
4h 21mSJU-BOS
$169
5/4Sat
nonstopJetBlue
3h 54mBOS-PLS
5/11Sat
nonstopJetBlue
4h 04mPLS-BOS
$348
5/4Sat
nonstopJetBlue
4h 04mBOS-SDQ
5/15Wed
nonstopJetBlue
4h 05mSDQ-BOS
$351
4/30Tue
multi-stopAmerican Airlines
8h 50mBOS-PLS
5/4Sat
nonstopAmerican Airlines
3h 40mPLS-BOS
$351
5/4Sat
multi-stopAmerican Airlines
9h 30mBOS-SJU
5/8Wed
multi-stopAmerican Airlines
9h 05mSJU-BOS
$351
5/4Sat
multi-stopUnited Airlines
6h 15mBOS-PLS
5/11Sat
multi-stopUnited Airlines
6h 23mPLS-BOS
$357
5/2Thu
multi-stopDelta
11h 40mBOS-STI
5/6Mon
multi-stopDelta
16h 39mSTI-BOS
$376
4/30Tue
nonstopDelta
4h 03mBOS-SJU
5/18Sat
nonstopDelta
4h 20mSJU-BOS
$408
5/4Sat
multi-stopUnited Airlines
12h 28mBOS-SJU
5/6Mon
multi-stopUnited Airlines
9h 21mSJU-BOS
$422

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Boston - Caribbean Flights