$103 Find Cheap Flights from Boston to Caribbean Islands - Compare and Save

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Cheap Flights from Boston to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$375
Santo Domingo
Santo Domingononstop$324
Montego Bay
Montego Bay1 stop$438
Oranjestad
Oranjestad2 stops$383
Nassau
Nassau1 stop$342
Kingston
Kingston1 stop$477
Simpson Bay
Simpson Bay1 stop$305
Providenciales
Providenciales1 stop$359
Port of Spain
Port of Spain1 stop$405
Bridgetown
Bridgetown1 stop$364
George Town
George Town1 stop$325
Willemstad
Willemstad2 stops$310
Castries
Castries2 stops$727
Aguadilla
Aguadilla1 stop$282
St. John's
St. John's1 stop$442
Puerto Plata
Puerto Plata1 stop$437
Punta Cana
Punta Cana1 stop$375
Santo Domingo
Santo Domingononstop$324
Montego Bay
Montego Bay1 stop$438
Oranjestad
Oranjestad2 stops$383
Nassau
Nassau1 stop$342
Kingston
Kingston1 stop$477
Simpson Bay
Simpson Bay1 stop$305
Providenciales
Providenciales1 stop$359
Port of Spain
Port of Spain1 stop$405
Bridgetown
Bridgetown1 stop$364
George Town
George Town1 stop$325
Willemstad
Willemstad2 stops$310
Castries
Castries2 stops$727
Aguadilla
Aguadilla1 stop$282
St. John's
St. John's1 stop$442
Puerto Plata
Puerto Plata1 stop$437
Booking Insights

KAYAK's insights & trends for Boston to Caribbean Islands flights

Get data-powered insights and trends into flights from Boston to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Boston to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Boston found in the last 5 days was to San Juan, at $258 round-trip. The most popular route is from Boston (BOS) to Oranjestad (AUA), and the cheapest round-trip airline ticket found on this route in the last 5 days was $278.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $346 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $406.

Can I save money by flying with a layover from Boston to Caribbean Islands?

No, with an average price for the route of $562, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Boston to Caribbean Islands?

The cheapest month for flights from Boston to Caribbean Islands is May, when tickets cost $471 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $677 and $584 respectively.

What’s the cheapest day of the week to fly from Boston to Caribbean Islands?

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Boston to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Boston to Caribbean Islands?

To get a below average price on the flight from Boston to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low season

September

Cheapest flight

$103
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Boston to Simpson Bay

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to Caribbean Islands 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 Islands?

    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 from Boston to Caribbean Islands with an airline and back with another airline.

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

    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 from Boston to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Boston to Caribbean Islands

 
Need help choosing which airline to fly with from Boston to Caribbean Islands? 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.
7.8
DeltaOverall score based on 8564 reviews
7.8Entertainment
8.5Crew
7.8Comfort
8.1Boarding
7.2Food
Airline reviews

Could have been on time and not missed my connection

6.0 GoodAnonymous, Sep 2026
Read more Delta reviews

Could have been on time and not missed my connection

Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?

Terrible - the flight was delayed taking off after boarding. Then the flight circled lga before landing. Significant delay

The flight was delayed at the very last minute and no information, both of my round trip flights were delayed at least the BNA to Boston was informed earlier but the return one was horrible

Delayed, then set on termac before taking off for 45 minutes. After landing had to sit on termac for another 30-40 minutes. Total disaster of a flight

Stewardess was not accommodating when I requested a second drink.

Although I know the Airlines cannot control the situation when there’s a ground stoppage, it would’ve been nicer if we would have had more up-to-date information clarity around the delays. Additionally, I think the delays also took a toll on the Cabin crew, particularly the lead flight attendant in first class. She was not very friendly when we boarded the plane for many of the passengers. Number one she refused to hang a garment bag in the front closet for a first class passenger, she was unwilling to dispose of an empty bottle in the trash as I was boarding (despite drinking a bottle of water herself and needing to disregard), and she was very combative with a passenger, who needed to access something from his bag that was Gate checked. Frankly, it was really unfortunate as I’ve never seen a flight attendant behave that way directly to the passengers, particularly when none of us had done anything wrong.

Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!

Very good seat and service. No complaints about the food. Take off delayed due to airport traffic

It is usually very pleasant. Good service for the price, international flights are even better

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

Great, except the canon was so cold. Even the flight attendants put jackets on

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

The pre-order only approach for fresh food is really challenging

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

It was Swiss. Our kosher meals were literally frozen solid and therefore inedible, and the crew didnt care.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

I've flown American several times this summer and I have yet to get a flight that leaves on time. However, a delay is better than a cancel. So far I have had four canceled flights and two delayed flights

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

Horrific. We were delayed due a flight attendant stuck in traffic en route to the airport. Over 100 people were then stuck in Charolette. Then I ran to make my layover only to find that my connection didn’t have a plane anymore. Waited 2.5 hours without any updates. On the flight we had to beg for even a pretzel option.

Because I bought my ticket from Underpricer, I could not check in online. I could only check in at the airport and that was deeply frustrating because I had to arrive very early. The flight also departed 45 min late and passengers were given no explanations about why we were delayed. I was worried I would miss my connecting flight. Once on board, however, the flight was fine.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!

The series of delays were very unfortunately - first the captain timed out, then the new captain didn't show up when we were told he would, then the first officer timed out. Those delays were compounded by after boarding, weather came in - obviously that's out of JB's control but it was frustrating after all of the other delays that seemed avoidable.

3 hours late JetBlue flight made me miss my connecting flight to Nairobi Kenya, they did not even offer me hotel accommodation, I paid out of my pocket, they did not know where my luggage was, let say my experience with JetBlue was nightmare.

Crew at first tried to SELL snack boxes (for an hour-long flight?!?), and it was the only leg of four on which I was charged for a hard seltzer. 😕 Spent extra to select seats in Row 8 for quicker disembarking only to be seated in Row 25. Someone owes me $38 for that!

It was my worse flying experience. It was my first time and last time flying with Jet Blue.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental