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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 9/11. 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
Sat 7/6
Sat 7/13

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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$223
Montego Bay
Montego Bay1 stop$285
Santo Domingo
Santo Domingo1 stop$229
Oranjestad
Oranjestadnonstop$411
Nassau
Nassau1 stop$323
Kingston
Kingston2 stops$393
Simpson Bay
Simpson Bay1 stop$243
Providenciales
Providenciales1 stop$332
Port of Spain
Port of Spain1 stop$445
Bridgetown
Bridgetown1 stop$252
George Town
George Town2 stops$343
Aguadilla
Aguadilla1 stop$248
Willemstad
Willemstad1 stop$428
Castries
Castries3 stops$1,674
St. John's
St. John's1 stop$435

Good to know

Low season

September

High season

February

Cheapest flight

$48
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 4% 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 2% cheaper 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 10368 reviews
8.0Entertainment
7.4Food
7.9Comfort
8.2Boarding
8.6Crew
Airline reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Overall fine but both ways for this trip was delayed.

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.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

Everything was pretty good except for food. They need to improve on it compared to other airlines.

Flight was delayed due to the late arrival of the catering truck, which is quite unacceptable. There was a beverage service, but no pretzel, or cookie, or nuts were served in coach.

Not worth the premium paid for the first class ticket

Not worth the price of premium class ticket paid, felt more like steerage.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

I flew Delta last week and United Airlines is a poor substitute mechanical problems with the plane and shitty food among other things made my travel experience what’s become to be expected from United no way is it ever worth the money they make us pay

I had a great flight. Everything went smoothly and the flight arrived early.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Terrible. I didn’t fly and I had an important meeting the next day.

Missed this flight due to the first AA flight delay

Equipment swap led to 2+ hour delay on international flight. And to top it off, boarding took forever.

Wretched scheduling - they got themselves into a critical crew situation and didn’t try to address it until 15 minutes before they had to cancel my flight

They cancelled two flight and got us onto another airline, which was also delayed.

Nothing, terrible travel experience due to weather and maintenance delays and was left stranded in Austin.

Missed connection from Philadelphia to London because flight from DC was seriously delayed. Was re-routed the next day (had to pay for hotel) to Zurich and was given a main cabin middle seat while I had paid for premium. Great job AA!!!

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

28 hour delay at Fort Worth/Dallas airport, part due to weather which was unavoidable, but various other reasons - no pilot, no fa, mechanical problem, plane too small, too big, crew out of flying time, seat configuration problems.... endless and hourly updates with a different excuse. Finally told us about 3.00 am, that the flight was delayed to hours later.

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

Book cheap flights from Boston to Caribbean

Recent round-trip flight deals

8/13Tue
nonstopFrontier
4h 05mBOS-SJU
8/22Thu
nonstopFrontier
4h 08mSJU-BOS
$113
8/13Tue
nonstop
4h 05mBOS-SJU
8/21Wed
nonstop
4h 19mSJU-BOS
$115
7/10Wed
nonstopSpirit Airlines
4h 14mBOS-SJU
7/17Wed
nonstopSpirit Airlines
4h 14mSJU-BOS
$117
7/10Wed
nonstopSpirit Airlines
4h 14mBOS-SJU
7/17Wed
nonstopSpirit Airlines
4h 14mSJU-BOS
$120
7/5Fri
nonstopJetBlue
4h 05mBOS-SJU
7/25Thu
nonstopJetBlue
4h 04mSJU-BOS
$213
7/3Wed
nonstopJetBlue
4h 05mBOS-SJU
7/9Tue
nonstopJetBlue
4h 00mSJU-BOS
$223
8/5Mon
2 stopsAmerican Airlines
16h 32mBOS-STT
8/14Wed
2 stopsAmerican Airlines
14h 56mSTT-BOS
$330
9/7Sat
1 stopDelta
6h 17mBOS-PLS
9/14Sat
1 stopDelta
10h 59mPLS-BOS
$332
9/7Sat
2 stopsAmerican Airlines
17h 05mBOS-PLS
9/14Sat
2 stopsAmerican Airlines
16h 24mPLS-BOS
$337
9/4Wed
1 stopDelta
7h 47mBOS-PLS
12/15Sun
1 stopDelta
11h 14mPLS-BOS
$351

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Recent one-way flight deals

9/11Wed
1 stopSpirit Airlines
10h 29mBOS-SJU
$48
8/13Tue
nonstopFrontier
4h 05mBOS-SJU
$55
6/28Fri
nonstopJetBlue
4h 05mBOS-SJU
$112
6/18Tue
1 stopJetBlue
6h 20mBOS-NAS
$117
7/20Sat
1 stopAmerican Airlines
17h 05mBOS-STT
$163
7/4Thu
2 stopsAmerican Airlines
10h 22mBOS-STT
$164
9/7Sat
1 stopUnited Airlines
7h 56mBOS-STI
$165
9/7Sat
2 stopsUnited Airlines
15h 36mBOS-STI
$171
8/16Fri
1 stopDelta
7h 26mBOS-MBJ
$174
8/3Sat
1 stopDelta
7h 03mBOS-STT
$193

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Last minute flights from Boston to Caribbean

Last minute flight, train and bus deals

6/11Tue
nonstop
4h 00mBOS-SJU
6/18Tue
nonstop
4h 14mSJU-BOS
$141
6/11Tue
nonstopFrontier
4h 00mBOS-SJU
6/25Tue
nonstopFrontier
4h 08mSJU-BOS
$159
6/11Tue
nonstopSpirit Airlines
4h 14mBOS-SJU
6/18Tue
nonstopSpirit Airlines
4h 14mSJU-BOS
$174
6/8Sat
multi-stopSpirit Airlines
11h 09mBOS-SJU
6/23Sun
nonstopSpirit Airlines
4h 14mSJU-BOS
$177
6/8Sat
nonstopJetBlue
3h 51mBOS-SJU
6/10Mon
nonstopJetBlue
4h 08mSJU-BOS
$363
6/8Sat
multi-stopAmerican Airlines
11h 08mBOS-STT
6/12Wed
multi-stopAmerican Airlines
9h 17mSTT-BOS
$374
6/8Sat
multi-stopDelta
16h 16mBOS-MBJ
6/12Wed
multi-stopDelta
17h 12mMBJ-BOS
$374
6/10Mon
nonstopJetBlue
3h 57mBOS-SDQ
6/15Sat
multi-stopJetBlue
7h 48mSDQ-BOS
$387
6/8Sat
multi-stopAmerican Airlines
11h 08mBOS-STT
6/11Tue
multi-stopAmerican Airlines
9h 06mSTT-BOS
$390
6/8Sat
multi-stopDelta
16h 16mBOS-MBJ
6/15Sat
multi-stopDelta
17h 12mMBJ-BOS
$394

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Boston - Caribbean Flights