$97 Find Cheap Flights from Caribbean to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Boston departing on 5/23. 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
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Caribbean to Boston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Boston

Thu, Apr 9 - Mon, Apr 13
Multiple Airlines Logo
6:00 am - 10:16 am
SJU
-
BOS
4h 16mnonstop
Multiple Airlines Logo
3:23 pm - 7:19 pm
BOS
-
SJU
3h 56mnonstop
$147Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
Multiple Airlines Logo
6:00 am - 10:16 am
SJU
-
BOS
4h 16mnonstop
Multiple Airlines Logo
3:23 pm - 7:19 pm
BOS
-
SJU
3h 56mnonstop
$150Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
Spirit Airlines Logo
10:00 am - 2:18 pm
SJU
-
BOS
4h 18mnonstop
Spirit Airlines Logo
6:01 am - 11:58 pm
BOS
-
SJU
17h 57m
1 stop
$151Spirit Airlines
Fri, Apr 10 - Sat, Apr 11
Spirit Airlines Logo
10:00 am - 2:18 pm
SJU
-
BOS
4h 18mnonstop
Spirit Airlines Logo
3:23 pm - 7:19 pm
BOS
-
SJU
3h 56mnonstop
$164Spirit Airlines
Thu, Apr 16 - Wed, Apr 22
JetBlue Logo
11:39 am - 2:59 pm
NAS
-
BOS
3h 20mnonstop
JetBlue Logo
2:00 pm - 5:25 pm
BOS
-
NAS
3h 25mnonstop
$319JetBlue
Thu, Apr 16 - Thu, Apr 23
JetBlue Logo
3:23 pm - 6:47 pm
NAS
-
BOS
3h 24mnonstop
JetBlue Logo
2:00 pm - 5:25 pm
BOS
-
NAS
3h 25mnonstop
$344JetBlue
Tue, May 5 - Tue, May 12
Delta Logo
8:59 pm - 11:15 am
STI
-
BOS
14h 16m
1 stop
Delta Logo
9:05 am - 7:28 pm
BOS
-
STI
10h 23m
1 stop
$347Delta
Tue, May 12 - Tue, Jun 2
American Airlines Logo
1:32 pm - 10:02 am
STI
-
BOS
20h 30m
1 stop
American Airlines Logo
6:00 am - 12:21 pm
BOS
-
STI
6h 21m
1 stop
$350American Airlines
Fri, May 1 - Tue, May 12
American Airlines Logo
1:32 pm - 10:01 am
STI
-
BOS
20h 29m
2 stops
American Airlines Logo
5:40 pm - 12:23 pm
BOS
-
STI
18h 43m
2 stops
$353American Airlines
Wed, Apr 29 - Sat, May 9
Delta Logo
4:00 pm - 7:25 am
NAS
-
BOS
15h 25m
1 stop
Delta Logo
9:30 am - 12:52 pm
BOS
-
NAS
3h 22mnonstop
$357Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$97
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from San Juan Airport to Boston

Flights from Caribbean to Boston: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Caribbean to Boston 
JasmaryFlew with Spirit Airlines
SJU
-
BOS
Feb 2026
I would advice passengers to bring their own snack as most items are out of stock
slovely08Flew with JetBlue
AUA
-
BOS
Dec 2024
Be prepared for long security times, you have to clear customs in Aruba, and there can be a substantial line if you get there at the wrong time. They tell you to be there 3 hours early for a reason.

FAQs for booking flights from Caribbean to Boston

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

    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 Caribbean to Boston.

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

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

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

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

    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 Boston from Caribbean 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 Caribbean to Boston

 
Need help choosing which airline to fly with from Caribbean to Boston? 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.
7.9
DeltaOverall score based on 8358 reviews
7.9Comfort
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
Airline reviews

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

10.0 ExcellentCharlean, Mar 2026
LAS - ATL
Read more Delta reviews

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Wonderful crew, great movie selection and good food. I prefer Airbus to Boeing, much more comfortable

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

I lost my plane and spend 5 hours at the airport arriving at Buffalo at 1 am taxis are very expensive at that time.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

For the price point it was very good. Definitely leave on the earlier flights as it can become terribly crowded later in the day

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Delayed our flight to accommodate another flight but didn’t make the decision to do so until we were supposed to board despite having all the same information hours prior. Arrived so delayed that we didn’t get a gate and had to deplane on the tarmac and get bussed to terminal in the rain after 1am. Arrived to the terminal and due to construction could not get a ride share - had to either take the air train to Howard beach or stand in line with 200 other people waiting for a taxi.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Well, its a hit or miss when boarding most of the time your employees just let everyone enter immediately In one bum rush. Then out of know where tell the passengers only let A can enter then b then c etc. So make a decision and stick to it. Do it by alphabet and have famn strick compliance. Let the public know. That makes easier on passengers.

Arrived as recommended at 8:15 a.m. for an 1115 flight, that kept getting delayed delayed and delayed and then finally canceled. Instructed for the split flight to go to Fort Lauderdale, and then find our way from there back to New York. I don't think I will ever trust flying with JetBlue again. This was my second horrific experience and I am really angry.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

Delays with no explanation. It could have been handled better.

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.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

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

We had to take a bus to the plane with a old woman and carry on bags, and at landing at the airport we have to wait one hour seating on the plane waiting for a gate. We came back from Australia Bussines class Quantas 16 hours traveling, then wait in Dallas 7 hours for connection...honestly waiting 1 hour more at the plane was the worst part.

Flight delayed twice (not Spirit fault) No food served* No entertainment * *in response to my choices in the rating. None was provided so couldn’t rate properly

Delayed over two hours. Only knew about a 30 minute delay in advance

Poor service but I guess that’s what you get for picking cheap flight. Overacted with all extra up-charge fees, so annoying.

They canceled both the flight to Myrtle beach and the return flight. They are an awful airline and they ruined my trip. I will never book with Spirit again.

The flight was a big joke very uncomfortable I had a horrible experience and I will never fly with them again everything about the flight was bogus and I’m not happy with it at all this experience makes me not want to fly ever again

Pricing, boarding time communication, over priced baggage and overall service is lacking, seating unconfortable

Flight attendant was all so sweet and pilot got us to our destination safely and on time

we boarded the plane and then sat for OVER AN HOUR on it, first waiting for fuel and then the crew timed out. the flight kept getting delayed longer and longer, a 9:30pm flight is still on the ground at 1:15am.

The airplane rattled near the left wing as if several screws were loose. Then after we landed in Fort Lauderdale, we had to sit and wait on the runway for quite some time. It was very scary and TOTALLY unacceptable!

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