$151 Find Cheap Flights from Boston to Trinidad and Tobago

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 Trinidad and Tobago departing on 7/13. 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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Cheap Flights from Boston to Trinidad and Tobago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Port of Spain
Port of Spain1 stop$356
Scarborough
Scarborough2 stops$1,222
Port of Spain
Port of Spain1 stop$356
Scarborough
Scarborough2 stops$1,222

Book Cheap Boston to Trinidad and Tobago Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Trinidad and Tobago 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 Boston to Trinidad and Tobago

Thu, Jul 2 - Mon, Jul 6
United Airlines Logo
10:58 am - 12:50 am
BOS
-
POS
13h 52m
1 stop
United Airlines Logo
12:30 am - 12:28 pm
POS
-
BOS
11h 58m
1 stop
$356United Airlines
Fri, Oct 16 - Wed, Oct 21
American Airlines Logo
7:21 pm - 2:00 pm
BOS
-
POS
18h 39m
2 stops
American Airlines Logo
3:45 pm - 12:17 pm
POS
-
BOS
20h 32m
2 stops
$360American Airlines
Thu, Jul 2 - Mon, Jul 6
United Airlines Logo
10:58 am - 12:50 am
BOS
-
POS
13h 52m
1 stop
United Airlines Logo
2:00 am - 1:16 pm
POS
-
BOS
11h 16m
1 stop
$368United Airlines
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
3:21 pm - 2:14 pm
BOS
-
POS
22h 53m
1 stop
American Airlines Logo
7:00 am - 10:50 pm
POS
-
BOS
15h 50m
2 stops
$369American Airlines
Fri, Aug 21 - Mon, Aug 24
United Airlines Logo
7:25 am - 11:23 pm
BOS
-
POS
15h 58m
1 stop
United Airlines Logo
2:00 am - 11:17 am
POS
-
BOS
9h 17m
1 stop
$371United Airlines
Tue, Sep 1 - Tue, Sep 8
United Airlines Logo
11:00 am - 12:50 am
BOS
-
POS
13h 50m
1 stop
United Airlines Logo
12:30 am - 2:22 pm
POS
-
BOS
13h 52m
2 stops
$375United Airlines
Tue, Jul 7 - Thu, Jul 16
United Airlines Logo
8:00 am - 12:50 am
BOS
-
POS
16h 50m
1 stop
United Airlines Logo
2:00 am - 11:16 am
POS
-
BOS
9h 16m
1 stop
$376United Airlines
Tue, Oct 13 - Mon, Oct 19
Copa Airlines Logo
8:47 am - 1:47 am
BOS
-
POS
17h 00m
1 stop
Copa Airlines Logo
3:50 am - 2:39 pm
POS
-
BOS
10h 49m
1 stop
$386Copa Airlines
Fri, Aug 21 - Mon, Aug 24
United Airlines Logo
9:33 am - 11:23 pm
BOS
-
POS
13h 50m
2 stops
United Airlines Logo
2:00 am - 11:17 am
POS
-
BOS
9h 17m
1 stop
$390United Airlines
Wed, Jul 1 - Mon, Jul 6
American Airlines Logo
5:01 am - 11:00 pm
BOS
-
POS
17h 59m
1 stop
American Airlines Logo
3:18 pm - 10:16 am
POS
-
BOS
18h 58m
1 stop
$393American Airlines
Booking Insights

KAYAK's insights & trends for Boston to Trinidad and Tobago flights

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

What is the cheapest month to fly from Boston to Trinidad and Tobago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Trinidad and Tobago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Trinidad and Tobago is July, when tickets cost $47 (return) on average. On the other hand, the most expensive months are November and May, when the average cost of round-trip tickets is $477 and $354 respectively.

How far in advance should I book a flight from Boston to Trinidad and Tobago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Trinidad and Tobago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Trinidad and Tobago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$151
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Boston to Port of Spain

FAQs - booking Trinidad and Tobago flights

  • How can I make my trip from Boston to Trinidad and Tobago more sustainable?

    The airline on which you choose to fly considerably impacts the sustainability of your travels. For example, Air Canada is a pioneer of e-freight, an industry-wide initiative in which the many departments of air travel, including carriers, ground handlers, shippers, and others, replace paper documents with electronic messages. Once fully adopted, e-freight can save an estimated 7800 tons of paper document waste yearly.

  • Where will I have a layover when I fly between Boston and Trinidad and Tobago?

    Flights to Trinidad’s Piarco International Airport typically have layovers at Miami International Airport (MIA) or John F. Kennedy International Airport (JFK), hubs for international travel. Flights might also layover at Charlotte Douglas International Airport (CLT), American Airlines’ second-largest hub. Flights to Tobago’s ANR Robinson International Airport (TAB) typically stop at Toronto Pearson International Airport (YYZ) and Piarco International Airport.

  • What do I need to enter Trinidad and Tobago from the U.S.?

    Travelers entering Trinidad and Tobago should bring their valid U.S. passport, which does not expire during their stay and is good for six months beyond their departure date. Travelers only need a visa to visit Trinidad and Tobago if they plan to stay beyond 90 days.

  • How many carry-on bags can I take when flying from Boston to Trinidad and Tobago?

    Many airlines, including American Airlines, JetBlue, United, Air Canada, British Airways, and Caribbean Airlines, allow passengers to bring one carry-on bag and one personal item within their introductory economy class. However, check your flight’s allowance, as classes can have subtle differentiations, and carry-on allowance may vary by aircraft and route.

  • How does KAYAK find such low prices on flights from Boston to Trinidad and Tobago?

    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 Trinidad and Tobago.

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

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

    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 Trinidad and Tobago 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 Trinidad and Tobago?

    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 Trinidad and Tobago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Trinidad and Tobago

  • Travelers who plan to visit the south Caribbean twin island nation of Trinidad and Tobago can find plenty of flights with competitive rates when they depart from Boston Logan International Airport (BOS). Boston Logan International Airport offers service to destinations worldwide and is a Cape Air and Delta hub. This airport is also an operating base for JetBlue.
  • Trinidad, the largest of the two islands, offers sports, festivals, nightlife, museums, and an urban Caribbean feel in its modern capital, Port-of-Spain. Piarco International Airport (POS) serves Trinidad, and passengers can find flights on American Airlines, JetBlue, United Airlines, Air Canada, Caribbean Airlines, and British Airways. Flights between Boston and Trinidad will have at least one layover.
  • Tobago is known for ecotourism, and the smaller islands have a rainforest that has been protected since 1776. Tobago is served by ANR Robinson International Airport (TAB), and Air Canada and Caribbean Airlines offer service between Boston and Tobago. Flights between Boston and Tobago typically have 2 stops.
  • Many travelers enjoy taking advantage of airport lounges before departing on a long flight. Boston Logan International Airport offers several airline lounges, including American Airlines Admirals Club, United Club, and Delta Sky Club.
  • Travelers who want the quickest flight times should plan to fly to Piarco International Airport in Trinidad, which offers the shortest flight durations from Boston. Flights from Boston to Piarco International Airport average around 9-11 hours, while accessing Tobago directly takes about 19 hours.

Reviews of the top 5 airlines serving from Boston to Trinidad and Tobago

 
Need help choosing which airline to fly with from Boston to Trinidad and Tobago? 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.
7.6
Copa AirlinesOverall score based on 1569 reviews
6.9Food
8.1Crew
6.8Entertainment
7.4Comfort
7.8Boarding
Airline reviews

They didn’t have any headphones for the entertainment screen and their USB port didn’t accommodate a USB-C for more modern phones. The food was just ok. The staff was friendly but the seats were very uncomfortable for a full flight.

6.0 GoodAnonymous, May 2026
SCL - PTY
Read more Copa Airlines reviews

They didn’t have any headphones for the entertainment screen and their USB port didn’t accommodate a USB-C for more modern phones. The food was just ok. The staff was friendly but the seats were very uncomfortable for a full flight.

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Boarding was confusing from staff telling going to preboard and than to group 1 Airplane was not cooling at the beginning

Flight got delayed; had to go through security three times.

Copa staff at PTY and one particular crew member were unhelpful & rude.

Horrible. No TV or any type of entertainment on board. Passwnger listening to/watching stuff on their own phone with no headphones making it noise and uncomfortable for everyone else, little/tiny food portions, old seats, useless wifi (cant access anything). Horrible exlerience especially it was a lomg distance flight with kids.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

Some of the Air hostesses are not that friendly. Need improvement

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

The entertainment they offer could use some games, and maybe they could add some cookies to the snack menu. And the automated messages are a bit repetitive. But it was comfortable temperature wise and the seats were comfortable. The crew is very polite and helpful

The entertainment is a bit limited, it would be better if they added some games to play besides the movies and tv shows. But the seats are comfortable and the crew is polite

This planes staff was top tier. Everything went great and had a great flight home.

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.

This was an overnight flight, and in the morning they did know coffee service. How you can throw passengers in a San Francisco airport at 5:40 a.m. in the morning and not giving them Coffee is a crime.

I was promised by United Airline (operated by ANA) that I will be seated together with my kids as I am the only adult flying with two minors. We did not get seats together in our 11 hours flight from LA to Tokyo. When asked at the gate, ANA representative said United Airline should have informed them that there is a parent flying with two minors. He said they can’t do anything in the system as the flight is full. He ask me to ask passengers next to me and the kids if they are willing to change seats. This is ridiculous! However, I went in the flight and asked other passages but no one willing to change seats. 11 hours and we were seating separately. I was very disappointed with this. It made things super inconvenient for me.

Our flight was delayed several Times due to mechanical issues. Although I understand this may happen at times, it was very inconvenient and we had to book a hotel for an overnight stay. We were traveling with my 3-yo grandson and waiting at the airport from noon until 6:30pm with no reassurance that our next rescheduled flight would depart, we had to decide what’s best for him. A day later, I found out that I may be able to demand compensation if my flight is delayed more than 4 hours. I will hav to read the fine print next time.

Flight cancelled instead of leaving Friday am now, maybe, leaving Sunday

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

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.

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

1didnt have wheel chair I ordered wheel chair in my ticket flight

Flight was overbooked and seats assigned to multiple passengers. Delay 1 hour to sort out.

Good but I don’t received my bags yet is been 5days still no update

It was pretty straight forward, no glitches or hidden costs

It was a short flight so, everything went smoothly and we got to where we needed to be safely.

Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight

No TV on the flight. The charging outlet was not working. No food, even a sandwich. The served orange was poor quality.

Selected seats 5 months prior to date. Had email confirmation and seats were not honoured. Family did not sit together

Loved and was pleasantly surprised by the food!! Request Lufthansa to help transiting passengers at Munich (confusion whether to go thru passport control or not).

The flight was comfortable and the staff were helpful and friendly. However, we did not know we were flying PAL until we arrived in Canada, so it was a bit disconcerting. In addition, which port we were leaving from was confusing.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

Everything you need to know for your flight from Boston to Trinidad and Tobago

Information on your arrival and departure airports