Find flights
Deals
When to book
FAQs & Tips
Airlines

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
Wed 6/12
Wed 6/19

Search hundreds of travel sites at once for deals on flights to Caribbean

In the last 7 days travelers have searched 41,771,603 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Best Caribbean Flight Deals

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

Punta Cana
Punta Cana2 stops$393
Montego Bay
Montego Bay1 stop$343
Santo Domingo
Santo Domingo1 stop$219
Oranjestad
Oranjestad1 stop$291
Nassau
Nassau1 stop$342
Kingston
Kingston1 stop$335
Simpson Bay
Simpson Bay1 stop$225
Providenciales
Providenciales1 stop$370
Port of Spain
Port of Spain1 stop$445
Bridgetown
Bridgetown1 stop$235
George Town
George Town2 stops$333
Aguadilla
Aguadilla1 stop$285
Castries
Castries3 stops$1,302
Willemstad
Willemstad1 stop$432
St. John's
St. John's1 stop$432

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 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 8% 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 10736 reviews
8.6Crew
8.0Entertainment
8.2Boarding
7.4Food
7.9Comfort
Airline reviews

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

2.0 MediocreDevan, May 2024AUS - BOS
Read more about Delta reviews

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The plane was FREEZING SEATS UNCOMFORTABLE Otherwise smooth Thank you

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

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.

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.

Not a fan of the diagonal partially enclosed business class seats or how they have to be converted to beds manually by crew. I prefer more isolation and user control for switching to lie flat.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

We ended up with seats in the very back. So they did not recline. Have no idea why, we reserved and checked in very early. The isles were very narrow and the seats had very little leg room. But they did give us water, and a snack.

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

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.

Liked - nothing. Disliked - delayed 35+ min sitting on the plane. Caused me to miss my connection in Charlotte. American Airlines is the worst US Air Carrier company with atrocious customer service.

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

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.

They stuck us with multiple extra fees. I will never fly spirit again

Arrived 3 hours early and never made it past baggage drop

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

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.

Book cheap flights from Boston to Caribbean

Recent round-trip flight deals

5/29Wed
1 stop
11h 18mBOS-SJU
6/2Sun
nonstop
4h 21mSJU-BOS
$114
6/4Tue
nonstopFrontier
4h 12mBOS-SJU
6/11Tue
nonstopFrontier
4h 08mSJU-BOS
$115
6/2Sun
nonstopSpirit Airlines
4h 06mBOS-SJU
6/6Thu
nonstopSpirit Airlines
4h 14mSJU-BOS
$119
6/3Mon
nonstopSpirit Airlines
4h 06mBOS-SJU
6/8Sat
nonstopSpirit Airlines
4h 14mSJU-BOS
$120
6/13Thu
nonstopJetBlue
4h 05mBOS-SJU
6/24Mon
nonstopJetBlue
4h 00mSJU-BOS
$213
6/14Fri
nonstopJetBlue
4h 05mBOS-SJU
6/20Thu
nonstopJetBlue
4h 05mSJU-BOS
$248
6/1Sat
1 stopAmerican Airlines
14h 57mBOS-MBJ
6/7Fri
1 stopAmerican Airlines
8h 56mMBJ-BOS
$364
5/26Sun
2 stopsAmerican Airlines
18h 14mBOS-STI
5/29Wed
2 stopsAmerican Airlines
10h 37mSTI-BOS
$367
8/31Sat
1 stopDelta
9h 03mBOS-PLS
9/3Tue
1 stopDelta
11h 14mPLS-BOS
$370
9/27Fri
1 stopDelta
17h 09mBOS-PLS
9/30Mon
1 stopDelta
19h 35mPLS-BOS
$375

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/9Sun
nonstopFrontier
4h 00mBOS-SJU
$69
6/20Thu
nonstopFrontier
4h 00mBOS-SJU
$75
6/12Wed
nonstopSpirit Airlines
4h 14mBOS-SJU
$76
6/3Mon
1 stopSpirit Airlines
12h 29mBOS-SJU
$79
5/21Tue
1 stopJetBlue
8h 06mBOS-NAS
$117
6/14Fri
nonstopJetBlue
4h 05mBOS-SJU
$142
7/9Tue
1 stopAmerican Airlines
9h 56mBOS-MBJ
$153
7/23Tue
1 stopAmerican Airlines
7h 56mBOS-PLS
$153
6/6Thu
1 stopDelta
17h 00mBOS-PLS
$154
5/22Wed
1 stopDelta
9h 15mBOS-PUJ
$231

Search by stops

Search by airline

Search by price

Last minute flights from Boston to Caribbean

Last minute flight, train and bus deals

5/18Sat
nonstopSpirit Airlines
4h 06mBOS-SJU
5/22Wed
nonstopSpirit Airlines
4h 24mSJU-BOS
$174
5/18Sat
multi-stop
9h 47mBOS-SJU
5/22Wed
nonstop
4h 24mSJU-BOS
$180
5/16Thu
multi-stopAmerican Airlines
13h 27mBOS-SJU
5/20Mon
multi-stopAmerican Airlines
8h 15mSJU-BOS
$351
5/14Tue
multi-stopAmerican Airlines
7h 15mBOS-SJU
5/14Tue
multi-stopAmerican Airlines
7h 06mSJU-BOS
$363
5/17Fri
nonstopJetBlue
3h 59mBOS-SJU
5/19Sun
multi-stopJetBlue
10h 10mSJU-BOS
$386
5/18Sat
multi-stopDelta
11h 25mBOS-SDQ
5/25Sat
multi-stopDelta
8h 47mSDQ-BOS
$390
5/15Wed
multi-stopJetBlue
8h 43mBOS-STI
5/21Tue
nonstopJetBlue
4h 05mSTI-BOS
$416
5/14Tue
multi-stopUnited Airlines
8h 41mBOS-SJU
5/17Fri
multi-stopUnited Airlines
7h 35mSJU-BOS
$425
5/18Sat
multi-stopUnited Airlines
19h 54mBOS-MBJ
5/25Sat
multi-stopUnited Airlines
16h 52mMBJ-BOS
$448
5/14Tue
multi-stopDelta
11h 26mBOS-STI
5/16Thu
multi-stopDelta
16h 41mSTI-BOS
$485

Search by stops

Search by airline

Search by price

Boston - Caribbean Flights