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Find cheap flights from Boston to Caribbean from $53

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 7/21. 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
Thu 7/11
Thu 7/18

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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$225
Montego Bay
Montego Bay1 stop$299
Santo Domingo
Santo Domingo1 stop$238
Oranjestad
Oranjestad1 stop$277
Nassau
Nassau1 stop$323
Kingston
Kingston1 stop$353
Simpson Bay
Simpson Bay2 stops$283
Providenciales
Providenciales1 stop$322
Port of Spain
Port of Spain2 stops$459
Bridgetown
Bridgetownnonstop$408
George Town
George Town2 stops$327
Aguadilla
Aguadilla1 stop$302
Willemstad
Willemstad1 stop$383
Castries
Castries3 stops$1,017
St. John's
St. John's1 stop$435

Good to know

Low season

September

High season

February

Cheapest flight

$53
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 6% 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 10277 reviews
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
8.6Crew
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

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.

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.

The entertainment wasn’t playing in the app or online.

Lady was a bit rude during boarding and I was being nice to her.

Why does it have to be painful to fly long distances?

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Original plane sidelined. Had to wait an hour for replacement.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

Horrible, the flights kept delaying, so it is obvious that we won't be able to make it to the next connection. No easier/real agent on site to help you figure this out. UA agent on other counters refuse to assist you and direct us to use the QR code/call customer service. So inefficient and poor. While technology seems convenient, but it's not the best interest/experience for customers need help while there is active issue need assistance.

Food is very bad and entertint not too many options ... flight attendet service is not good

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.

Paid for premium economy had no tv the whole time the crew tried to reset/reboot but would not work they said they would put a trouble ticket in for it. We had 3 seats my tv was the only one that didn't work. They cancelled our flight re worked us on another that left us at airport over night on the floor I have a ten year old and a 78 diabetic mother which also had shingles and suffers from nerve pain in legs and back. Requested wheelchair service at all airports after the re route NO wheelchair service was there to help. WORST experience we have ever had. Went to American airlines assistance it was closed. I AM FURIOUS!!! I expect some sort of compensation from this traumatic experience and no need for flying points we don't plan on using American airlines again!!!!

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Information when booking said the flight would be with American Airlines but the flight was actualy with British Airways. Check in from Orlando was nice and quick. I agreed to put my cabin case in the checked luggage as it was a full flight. Case came back damaged (unable to put the handle down) so will have to dispose of it. Seats were quite cramped with very little leg room, even for economy. This was the experience of both the outgoing and return flight. Cabin crew were ok and flight time was punctual.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

The flight was delayed several times without explanation. The seats were terribly uncomfortable and wifi isn’t included. All these make for a less than ideal flight.

The flights was delayed by hours and it was the firmest landing I have experienced in my life. My back is still sore.

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.

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

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

Book cheap flights from Boston to Caribbean

Recent round-trip flight deals

8/13Tue
nonstopFrontier
4h 05mBOS-SJU
8/22Thu
nonstopFrontier
4h 08mSJU-BOS
$80
8/13Tue
nonstopFrontier
4h 05mBOS-SJU
8/22Thu
nonstopFrontier
4h 08mSJU-BOS
$81
9/10Tue
1 stopSpirit Airlines
14h 27mBOS-SJU
9/10Tue
1 stopSpirit Airlines
13h 42mSJU-BOS
$96
7/8Mon
nonstopSpirit Airlines
4h 14mBOS-SJU
7/12Fri
nonstopSpirit Airlines
4h 14mSJU-BOS
$108
9/2Mon
nonstopJetBlue
4h 02mBOS-SJU
9/6Fri
1 stopJetBlue
7h 14mSJU-BOS
$247
7/10Wed
nonstopJetBlue
4h 06mBOS-SJU
7/15Mon
nonstopJetBlue
4h 04mSJU-BOS
$258
8/6Tue
1 stopAmerican Airlines
17h 40mBOS-STT
8/14Wed
2 stopsAmerican Airlines
14h 56mSTT-BOS
$330
9/7Sat
1 stopDelta
6h 17mBOS-PLS
9/14Sat
1 stopDelta
9h 35mPLS-BOS
$332
9/7Sat
1 stopAmerican Airlines
7h 58mBOS-PLS
9/14Sat
2 stopsAmerican Airlines
16h 24mPLS-BOS
$337
7/1Mon
1 stopDelta
11h 17mBOS-NAS
7/3Wed
1 stopDelta
12h 53mNAS-BOS
$343

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Recent one-way flight deals

7/21Sun
nonstopSpirit Airlines
4h 14mBOS-SJU
$53
7/21Sun
1 stopFrontier
28h 57mBOS-SXM
$54
8/24Sat
nonstopJetBlue
4h 05mBOS-SJU
$112
7/7Sun
nonstopJetBlue
3h 25mBOS-NAS
$114
8/13Tue
2 stopsAmerican Airlines
7h 25mBOS-NAS
$118
11/9Sat
1 stopDelta
6h 07mBOS-NAS
$138
8/5Mon
2 stopsAmerican Airlines
18h 30mBOS-NAS
$153
10/9Wed
2 stopsUnited Airlines
9h 27mBOS-STI
$165
9/7Sat
2 stopsUnited Airlines
19h 46mBOS-STI
$171
11/10Sun
1 stopDelta
16h 59mBOS-STI
$192

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Last minute flights from Boston to Caribbean

Last minute flight, train and bus deals

6/16Sun
multi-stopSpirit Airlines
10h 18mBOS-SJU
6/20Thu
nonstopSpirit Airlines
4h 14mSJU-BOS
$180
6/16Sun
multi-stop
10h 18mBOS-SJU
6/20Thu
nonstop
4h 08mSJU-BOS
$181
6/14Fri
multi-stopAmerican Airlines
15h 20mBOS-SJU
6/18Tue
multi-stopAmerican Airlines
15h 43mSJU-BOS
$352
6/14Fri
nonstopJetBlue
4h 05mBOS-SJU
6/14Fri
nonstopJetBlue
4h 00mSJU-BOS
$357
6/14Fri
multi-stopAmerican Airlines
16h 20mBOS-SJU
6/16Sun
multi-stopAmerican Airlines
10h 24mSJU-BOS
$369
6/12Wed
nonstopJetBlue
3h 54mBOS-STT
6/26Wed
multi-stopJetBlue
5h 53mSTT-BOS
$374
6/12Wed
multi-stopDelta
6h 15mBOS-STT
6/25Tue
multi-stopDelta
11h 57mSTT-BOS
$433
6/15Sat
multi-stopDelta
10h 35mBOS-STT
6/21Fri
multi-stopDelta
12h 06mSTT-BOS
$467
6/16Sun
multi-stopUnited Airlines
7h 02mBOS-STT
6/19Wed
multi-stopUnited Airlines
10h 39mSTT-BOS
$503
6/16Sun
multi-stopUnited Airlines
8h 50mBOS-AUA
6/24Mon
multi-stopUnited Airlines
7h 57mAUA-BOS
$586

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Boston - Caribbean Flights