$193 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 9/5. 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.
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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$384
Scarborough
Scarborough2 stops$1,076
Port of Spain
Port of Spain1 stop$384
Scarborough
Scarborough2 stops$1,076

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

Fri, Sep 5 - Fri, Sep 12
Air Canada Logo
6:00 am - 1:20 amBOS-POS
19h 20m1 stop
Air Canada Logo
2:25 am - 10:39 pmPOS-BOS
20h 14m1 stop
$384Air Canada
Find Deal
Fri, Sep 5 - Fri, Sep 12
Air Canada Logo
6:00 am - 1:20 amBOS-POS
19h 20m2 stops
Air Canada Logo
2:25 am - 5:55 pmPOS-BOS
15h 30m2 stops
$401Air Canada
Find Deal
Fri, Sep 5 - Fri, Sep 12
Air Canada Logo
6:00 am - 1:20 amBOS-POS
19h 20m1 stop
Air Canada Logo
2:25 am - 5:55 pmPOS-BOS
15h 30m2 stops
$408Air Canada
Find Deal
Wed, Oct 15 - Mon, Oct 27
Copa Airlines Logo
8:41 am - 1:46 amBOS-POS
17h 05m1 stop
Copa Airlines Logo
3:51 am - 2:13 pmPOS-BOS
10h 22m1 stop
$462Copa Airlines
Find Deal
Tue, Sep 16 - Mon, Sep 22
Copa Airlines Logo
3:49 pm - 1:46 amBOS-POS
9h 57m1 stop
Copa Airlines Logo
3:51 am - 7:22 pmPOS-BOS
15h 31m1 stop
$482Copa Airlines
Find Deal
Sun, Oct 5 - Sat, Oct 25
JetBlue Logo
8:35 pm - 2:34 pmBOS-POS
17h 59m1 stop
JetBlue Logo
3:45 pm - 7:41 amPOS-BOS
15h 56m1 stop
$487JetBlue
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Thu, Sep 11 - Tue, Sep 23
JetBlue Logo
5:23 am - 2:34 pmBOS-POS
9h 11m1 stop
JetBlue Logo
3:59 pm - 12:14 amPOS-BOS
8h 15m1 stop
$488JetBlue
Find Deal
Wed, Oct 1 - Tue, Oct 7
United Airlines Logo
10:00 am - 11:23 pmBOS-POS
13h 23m1 stop
United Airlines Logo
12:30 am - 4:22 pmPOS-BOS
15h 52m2 stops
$513United Airlines
Find Deal
Sun, Oct 5 - Sat, Oct 25
American Airlines Logo
5:47 am - 2:16 pmBOS-POS
8h 29m1 stop
American Airlines Logo
7:00 am - 12:34 amPOS-BOS
17h 34m1 stop
$525American Airlines
Find Deal
Sun, Oct 5 - Sat, Oct 25
American Airlines Logo
5:47 am - 2:16 pmBOS-POS
8h 29m1 stop
American Airlines Logo
7:00 am - 11:34 pmPOS-BOS
16h 34m2 stops
$529American Airlines
Find Deal
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 September, when tickets cost $498 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $907 and $807 respectively.

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

The average price of all round-trip flights from Boston to Trinidad and Tobago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Boston to Trinidad and Tobago, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Trinidad and Tobago, Thursday is the cheapest day to fly and Monday is the most expensive.

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 2 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$193
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 24% 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.

  • What is the cheapest time of day to fly to Trinidad and Tobago?

    The cheapest time of day to fly to Trinidad and Tobago is generally in the morning, when round-trip flights cost $615 on average. Morning departures are around 2% cheaper than evening flights, on average. The most expensive time of day to fly to Trinidad and Tobago is generally at night, which is peak travel time and where the average cost of a ticket is $663.

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.
7.5
Copa AirlinesOverall score based on 1510 reviews
7.4Comfort
6.8Food
8.1Crew
6.8Entertainment
7.8Boarding
Airline reviews

Great experience with a crew always thinking in the passenger

10.0 ExcellentJuan Carlos, Jul 2025PTY - IAD
Read more Copa Airlines reviews

Great experience with a crew always thinking in the passenger

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

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

Did upgrade, travel in business it was great (more room I could sleep)

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

Seats not reclining, no vegetarian food option, no snacks. 7.5 hr flight should have been more comfortable. Luggage limits are unusually small. Will never fly Copa again and will tell friends and family to avoid this airline.

We had a five hour layover in the way home from Colombia. I read the "bout your flight" email carefully before we checked bags. We had to go through security right at the gate. Almost lost our ground coffee because that airport only allows 16 ounce of coffee and we had 18. I've been to 48 countries and never heard of a coffee restriction. I can't follow a rule I don't know about. I requested they bring our coffee to our checked luggage. Instead tey gate checked our bag for free. Back to planning transfers in Dallas I guess

It was ok. However, the food was quite poor since I don't eat pasta.

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

It is clear that someone knew, and competent, is in charge of food at United Airlines at least for the international flights. I was flying in coach, but the choices of the dinner were excellent. Tasty, and appropriate size. I had the beef, which was a little bit like a shepherds pie, and it was good. Nothing comparable has been served on a United flight in years. It will not be confused with three star food, but it is very good for airline food. Even better was the breakfast choice between a cinnamon roll and a breakfast sandwich. I chose the breakfast sandwich which was absolutely delicious and which I would happily order again at my local Starbucks or Panera. It is clear that someone knew indifferent is in charge of the food and it’s about time.

The flight was comfortable with the exit row and great service

Had to cancel first flight because Airporter Bus took over 3 hrs to get to airport which resulted in an extra $378 dollar fare . Is there anyway I can be reimbursed for initial fare since it was not my fault? Sent from my iPhone EJ Ledet

Plane was crowded and even when we hit altitude, the plane was hot, not enough air flow.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

The pilots were late and it made us 1 hour late. The meat was tough and bok choy was also tough.

Flight was delayed 3 hours. No food and drink vouchers was provided. They offered a mini pretzel bag and water .

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

Delayed flight that lead to a missed connection and a 5-hour trip became a 12-hour flight 🙄

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Pretty good. The food was just mediocre, the boarding and crew were good.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

Sat on the ground in Cincinnati for 50 minutes before deplaning

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

flight was delayed for hours with no explanation. The plane was a very old aircraft.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

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