$156 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 7/16. 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$366
Scarborough
Scarborough2 stops$777
Port of Spain
Port of Spain1 stop$366
Scarborough
Scarborough2 stops$777

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

Tue, Aug 4 - Tue, Sep 1
United Airlines Logo
9:32 am - 12:50 am
BOS
-
POS
15h 18m
1 stop
United Airlines Logo
2:00 am - 12:47 pm
POS
-
BOS
10h 47m
1 stop
$366United 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 - 12:14 pm
POS
-
BOS
20h 29m
2 stops
$370American Airlines
Sun, Aug 16 - Fri, Aug 21
United Airlines Logo
9:26 am - 12:50 am
BOS
-
POS
15h 24m
1 stop
United Airlines Logo
2:00 am - 12:50 pm
POS
-
BOS
10h 50m
1 stop
$378United Airlines
Thu, Jul 16 - Wed, Jul 22
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
$381United 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, Jul 10 - Thu, Jul 16
United Airlines Logo
5:47 am - 11:23 pm
BOS
-
POS
17h 36m
1 stop
United Airlines Logo
2:00 am - 11:16 am
POS
-
BOS
9h 16m
1 stop
$390United Airlines
Fri, Jul 10 - 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
$393United Airlines
Sun, Aug 16 - Fri, Aug 21
Air Canada Logo
5:45 am - 12:15 am
BOS
-
POS
18h 30m
2 stops
Air Canada Logo
1:25 am - 4:03 pm
POS
-
BOS
14h 38m
1 stop
$400Air Canada
Sun, Aug 16 - Fri, Aug 21
Air Canada Logo
5:45 am - 12:15 am
BOS
-
POS
18h 30m
2 stops
Air Canada Logo
1:25 am - 4:03 pm
POS
-
BOS
14h 38m
1 stop
$401Air Canada
Mon, Aug 10 - Sun, Aug 16
Multiple Airlines Logo
6:00 am - 11:40 am
BOS
-
TAB
29h 40m
2 stops
Multiple Airlines Logo
12:30 am - 9:05 am
TAB
-
BOS
32h 35m
3 stops
$777Multiple 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$156
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 12% 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
7.4Comfort
7.8Boarding
8.1Crew
6.8Entertainment
Airline reviews

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

6.0 GoodOluwaseyi, Feb 2026
PTY - POS
Read more Copa Airlines reviews

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.

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

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.

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.

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

It’s always a great time flying with united airlines.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

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.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

Great experience. Good dinner and service. FA's were very nice and attentive.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

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.

Terrible. Air Canada decided to wait for another flight. Due to the waiting, the weather got worse and connedting flight got cancelled. Air Canada said it was all due to the weather and didn’t pay me for the hotel. Not speaking of 3 hours waiting for my luggage. Never again!

Hard to criticize after the Crowd Strike dilemma. However, when Air Canada says they were "not affected," I expect that is true. My flight delays caused me to miss transportation connections. I understand these things happen, but I don't have to "like it."

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

Flight left 2 hours late with no explanation as to the delay

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

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.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

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

Information on your arrival and departure airports