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Find cheap flights from Boston to Caribbean from $69

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 6/9. 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 6/8
Sat 6/15

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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 Cana3 stops$394
Montego Bay
Montego Bay1 stop$277
Santo Domingo
Santo Domingo1 stop$213
Oranjestad
Oranjestad1 stop$359
Nassau
Nassau1 stop$342
Kingston
Kingston2 stops$457
Simpson Bay
Simpson Bay2 stops$256
Providenciales
Providenciales1 stop$357
Port of Spain
Port of Spain2 stops$434
Bridgetown
Bridgetownnonstop$408
George Town
George Town1 stop$333
Aguadilla
Aguadilla1 stop$285
Castries
Castries3 stops$1,150
Willemstad
Willemstad1 stop$432
St. John's
St. John's1 stop$435

Good to know

Low season

September

High season

February

Cheapest flight

$69
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 3% 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 4% 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 10778 reviews
8.6Crew
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

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!

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.

I’ve had a couple flights this week on United that were delayed by an hour or more

Flight was delayed 2.5 hours - a big deal on an overnight when you plan to sleep.

I feel like they have upgraded the app since I last flew United and I found it to be super helpful. I had stopped flying United unless absolutely necessary and my experience on this trip indicates they have been working hard to improve their services.

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. Very comfortable business seats with nice bedding. Good food. We were delayed to let late passengers on the flight, but otherwise great experience.

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Horrible - they lied to me about baggage & boarding, even though I specifically spoke to their agents the day before my flight about my issue. When I showed up they did not let me board and stranded me at my airport until I bought a new flight with money I did not have to spend.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

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

Book cheap flights from Boston to Caribbean

Recent round-trip flight deals

6/4Tue
nonstopFrontier
4h 12mBOS-SJU
6/9Sun
nonstopFrontier
4h 08mSJU-BOS
$113
6/11Tue
nonstop
4h 00mBOS-SJU
6/15Sat
nonstop
4h 14mSJU-BOS
$115
6/12Wed
nonstopSpirit Airlines
4h 14mBOS-SJU
6/19Wed
nonstopSpirit Airlines
4h 14mSJU-BOS
$119
5/30Thu
nonstopSpirit Airlines
4h 06mBOS-SJU
6/6Thu
nonstopSpirit Airlines
4h 14mSJU-BOS
$120
6/12Wed
nonstopJetBlue
4h 01mBOS-SJU
6/16Sun
nonstopJetBlue
4h 00mSJU-BOS
$213
6/14Fri
nonstopJetBlue
4h 05mBOS-SJU
7/4Thu
nonstopJetBlue
4h 10mSJU-BOS
$248
5/26Sun
2 stopsAmerican Airlines
8h 10mBOS-STI
5/29Wed
2 stopsAmerican Airlines
10h 37mSTI-BOS
$347
5/28Tue
2 stopsAmerican Airlines
10h 40mBOS-STI
5/30Thu
1 stopAmerican Airlines
10h 58mSTI-BOS
$348
5/21Tue
1 stopDelta
6h 03mBOS-STT
5/25Sat
1 stopDelta
7h 46mSTT-BOS
$348
5/20Mon
1 stopDelta
16h 49mBOS-STI
6/18Tue
1 stopDelta
13h 53mSTI-BOS
$355

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Recent one-way flight deals

6/9Sun
nonstopFrontier
4h 00mBOS-SJU
$69
6/9Sun
nonstopFrontier
4h 00mBOS-SJU
$72
6/12Wed
1 stopSpirit Airlines
13h 15mBOS-SJU
$74
5/31Fri
nonstopSpirit Airlines
4h 06mBOS-SJU
$76
5/31Fri
1 stopAmerican Airlines
13h 27mBOS-SJU
$115
6/8Sat
1 stopJetBlue
7h 34mBOS-NAS
$117
5/14Tue
1 stopAmerican Airlines
8h 55mBOS-PLS
$136
6/14Fri
nonstopJetBlue
4h 05mBOS-SJU
$142
5/17Fri
1 stopDelta
28h 04mBOS-PLS
$149
5/16Thu
1 stopDelta
28h 05mBOS-PLS
$172

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Last minute flights from Boston to Caribbean

Last minute flight, train and bus deals

5/14Tue
nonstopSpirit Airlines
4h 06mBOS-SJU
6/4Tue
nonstopSpirit Airlines
4h 24mSJU-BOS
$174
5/12Sun
nonstopSpirit Airlines
4h 06mBOS-SJU
6/1Sat
nonstopSpirit Airlines
4h 24mSJU-BOS
$194
5/11Sat
multi-stopAmerican Airlines
9h 35mBOS-SJU
6/1Sat
multi-stopAmerican Airlines
5h 50mSJU-BOS
$302
5/13Mon
nonstopJetBlue
3h 59mBOS-SJU
5/17Fri
nonstopJetBlue
4h 17mSJU-BOS
$323
5/13Mon
nonstopJetBlue
3h 59mBOS-SJU
5/19Sun
nonstopJetBlue
4h 17mSJU-BOS
$333
5/14Tue
multi-stopDelta
9h 26mBOS-STI
5/16Thu
multi-stopDelta
12h 46mSTI-BOS
$345
5/11Sat
multi-stopAmerican Airlines
9h 35mBOS-SJU
5/17Fri
multi-stopAmerican Airlines
8h 15mSJU-BOS
$352
5/11Sat
multi-stopUnited Airlines
8h 12mBOS-STI
5/15Wed
multi-stopUnited Airlines
8h 37mSTI-BOS
$374
5/11Sat
multi-stopUnited Airlines
17h 46mBOS-STI
5/15Wed
multi-stopUnited Airlines
8h 37mSTI-BOS
$379
5/14Tue
multi-stopDelta
6h 02mBOS-STI
5/16Thu
multi-stopDelta
12h 46mSTI-BOS
$435

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Boston - Caribbean Flights