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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 5 days
Sort by: Cheapest
Port of Spain
8h 32m2 stops
from $444per person
Scarborough
22h 50m6 stops
from $1,089per person
Booking Insights

Price, demand and travel trends for Boston to Trinidad and Tobago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Boston to Trinidad and Tobago right now?

The cheapest fares from Boston to Trinidad and Tobago on KAYAK in the last week were to Port of Spain Piarco Intl (POS) from $444 round-trip, and to Scarborough ANR Robinson Intl (TAB) from $1,089 round-trip.

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

March is the cheapest time of year to fly, with average fares of $453. Prices are highest in February, when average flight costs increase to around $768.

When is the best time to book flights from Boston to Trinidad and Tobago?

Book your flights 4 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 25% compared to booking last-minute (within 2 weeks of departure).

Which airport in Trinidad and Tobago is the cheapest to fly to from Boston?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into Trinidad and Tobago are:

• Port of Spain Piarco Intl (POS) from $586
• Scarborough ANR Robinson Intl (TAB) from $1,178

What’s the cheapest day to fly from Boston to Trinidad and Tobago?

Monday tends to be the cheapest day to fly from Boston to Trinidad and Tobago, while Sunday is the most expensive. Fares run about 24% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Boston to Trinidad and Tobago?

Data from the past 12 months shows it's cheapest to fly to Trinidad and Tobago during the afternoon with average prices of $528. The evening is the most expensive time to fly, with average prices of $614.

Key details for Boston to Trinidad and Tobago flights

Low season

October

Cheapest flight

$221
One-way flight from Boston to Port of Spain

Your Boston to Trinidad and Tobago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Boston to Trinidad and Tobago?

    Yes. Fares from Boston to Trinidad and Tobago are low right now. As a rule of thumb, a round-trip under $452 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Boston to Trinidad and Tobago?

    Over the past 12 months, round-trip fares from Boston to Trinidad and Tobago have ranged from $452 to $761.

  • What are the main airports serving Trinidad and Tobago?

    Flights to Trinidad and Tobago use two main airports, Port of Spain Piarco Intl (POS) and Scarborough ANR Robinson Intl (TAB).

  • What airlines fly nonstop from Boston to Trinidad and Tobago?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Boston to Trinidad and Tobago. One-stop options include:

    • American Airlines
    • JetBlue
    • United Airlines

  • Which cabin classes are available on flights from Boston to Trinidad and Tobago?

    On flights from Boston to Trinidad and Tobago you can book Economy Class or First Class.

  • 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.

Your guide to booking Boston to Trinidad and Tobago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 4 weeks before your trip. KAYAK data shows fares in this window are around 25% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for March when flights are typically cheapest and avoid February when prices are at their highest.
  • Flying on Monday is usually the cheapest. Flights on Sunday cost about 24% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Port of Spain Piarco Intl (POS) is the cheapest airport to fly into from Boston. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Port of Spain, which is the most popular destination in Trinidad and Tobago. From there, it's easy to continue on to other popular destinations such as Crown Point, Scarborough and Piarco.
  • 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 1546 reviews
6.9Entertainment
7.8Boarding
7.4Comfort
6.9Food
8.1Crew
Airline reviews

It is not a good experience with Copa Airlines: flight delay, luggage delay, etc.

6.0 GoodAnonymous, Aug 2026
Read more Copa Airlines reviews

It is not a good experience with Copa Airlines: flight delay, luggage delay, etc.

We where skipped for this flight will not head to Panama until tonight..

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

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

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

Very happy with my flight. I would definitely recommend it.

the planes are not modern there are no phone chargers

As usual, the flight with normal legroom was not very comfortable, but the second flight was much better because we had paid for extra legroom. It was very nice to check our bags without an extra fee.

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

Liked they had tv screens on plane but no service for drinks and a snack when other airlines do

The plane was very cramped and no room to move. Other passengers brought suitcases that didn't fit in the overhead bins. This made boarding and departing extremely slow.

I bought a ticket from Kayak. When I got to the airport, the was no ticket. I had to pay 5X to get to my destination. No response received from Kayak. I will NEVER use them again.

everything was fine. but paying for 1 piece of check-in luggage and denying passengers to board with carry-on luggage which by air line's standards does not fit is not acceptable. when one travels for a longer time one needs to have some essentials

Pearson Airport could not properly handle all the passengers who they needed to process in order to properly get them on board. As a result, I missed the departure of my flight from Toronto. The only saving grace is that Air Canada found a flight that only delayed me by one hour. However, this was no thanks to Pearson Airport!

I had a good experience. I liked being informed about the status of my luggage

The staff could have been friendlier. And Having the flight on time would have been much more convenient.

Old, noisy plane, bad coffee, delayed. Flight attendant was very nice.

We boarded 1.5 hours late. Long wait for the bags when we got to Mexico City. Long wait to get on plane with people mover truck. Friendly staff. They answered all questions as best the could. Such a long, long walk from the plane to customs. Thank you, Michael A. Burris Cambridge, Massachusetts USA

I was forced to check my carry-on bag, which I don't appreciate.

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

My overall experience with JetBlue was pretty poor and disappointing. We originally booked a DIRECT flight home from Boston on 9/28 at 8:00pm even though it cost more than the non direct flights. With no reason other than "unforeseen circumstances", our flight home Monday was cancelled and we were rebooked on a 7:00am flight on 9/29 with a layover in JFK. We were traveling with sick kids coming home from a funeral of a loved one and needed to be at work on Tuesday so paying extra for a flight home Monday was something we had to do. The original direct flights were considerably more expensive than the non direct flights- so I don't understand how Jetblue did absolutely NOTHING to compensate or right their mistake. We will not be booking with them in the future because they are not reliable and they showed no remorse nor did they make any attempt to make things right. The least they could have done was credit the difference in cost of flight because I know our original flights cost more than the one we were rebooked on. Once again- we will not be flying with them in the future and will advise family and friends to be aware of the risk you run when giving them your business. Do better.

Terrible. We originally booked a direct flight from BOS to MCO on 9/28 at 8:00pm and it was cancelled due to unforeseen circumstances and the flight we were rebooked on was on 9/29 at 7:00am with a layover in JFK. We were traveling with sick kids so leaving at such an early hour was absolutely miserable, and on top of that we all missed work which we couldn’t afford. On top of that- we paid a fortune for our flights to be direct without a layover and the flights with layovers were cheaper so at the very minimum we should have been refunded the difference. With absolutely no explanation or sympathy from JetBlue- we will avoid using them in the future due to the fact they aren’t reliable nor do they correct their mistakes.

Experience with JetBlue was poor. We were originally suppose to fly home on a direct flight on Monday the 28th at 8:00pm and we it was canceled due to “unforeseen circumstances” and we were rebooked on a 7am flight on Tuesday the 29th with a layover in JFK. Traveling with sick kids and waking up at an ungodly hour was miserable, and not only that it caused all of us to miss work. We intentionally flew our Monday on a direct flight and the direct flight was far more than the non direct flights on any given day. There was no compensation provided let alone a reasonable explanation. When you are charging people those type of prices for domestic same coast flights- you should be at least refunding the cost difference of the flights if you are rebooking them on a cheaper flight. I will never fly JetBlue again because they are unreliable and don’t correct their mistakes.

Wasn’t very happy with our flight home due to the fact it was cancelled with absolutely no reason. It was a direct flight at 8:00pm on Monday and they rebooked us for a 7am flight on Tuesday with a layover. Traveling with sick kids, getting up that early was miserable and on top of that we all missed a day of work that we couldn’t afford to with absolutely no apology or compensation from JetBlue. The original cost of the flights were astronomical because we flew out on Monday over Tuesday and also we paid extra for the direct flight then we would have for the flight with a layover. Super disappointed Jetblue truly could have cared less. Will avoid them in the future due to the fact they aren’t reliable nor compassionate for the inconvenience these changes cost their clients.

No WiFi, no power to charge phone, confusing boarding, delays

There is a considerable amount of people that use the wheel chair pre boarding along of large groups of family / friends. This is not right should be limited only to the person in need and the airline assistant. Some of these people use overhead bins that do not belong to them. The aircraft had a non functional wifi . The service was bad.

Overall, it was a fantastic experience had no movies up charge for everything haven’t flown in many many years. Crew is fantastic. Flight was good overall great experience.

My sons tv wasn’t working and they didn’t give him a kids meal I have to request it prior and no one told me!!! Then the 2nd flight they split us up. My two year old can’t sit alone on the plane hello?????

Thought the economy premium experience would match that of the Amsterdam to Boston flight. Aircraft was older: chair didn’t lean back. I had to buy a blanket, which on the flight over was complimentary. Flight crew seemed disinterested all around.

Boston sucks. Everything after 4p is delayed. AA switched planes on us so we ended up being 1.5 hours late (plus the delay at Logan). Not sure why the airline says it is on time until 1 h before the flight and then it becomes a rolling delay when they knew the incoming flight was arriving after our scheduled departure time. The crew was great as were the gate agent and ground crew. Just operations that sucked.

Flight was 2 hr late but at least I was upgraded to first class

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.

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