BOS - POS

$165 Find Cheap Flights from Boston to Port of Spain - Compare and Save

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 Port of Spain departing on 8/19. 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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Everything you should know

Cheapest round-trip
$376
Typical prices: $556-$665
Air Canada
Tue 8/18Mon 8/24
BOS - POS • 1 stop
Cheapest one-way
$165
Typical prices: $277-$364
Air Canada
Wed 8/19
BOS - POS • 1 stop
Top airlines
Cheapest • from $376 (round-trip)
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Boston and Port of Spain. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $500 (round-trip)
Shortest trip • 8h 34m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 27% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Port of Spain!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Boston to Port of Spain (BOS-POS)

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

Tue, Aug 18 - Mon, Aug 24
Air Canada Logo
7:25 pm - 12:15 am
BOS
-
POS
28h 50m
1 stop
Air Canada Logo
1:25 am - 4:03 pm
POS
-
BOS
14h 38m
1 stop
$376Air Canada
Sun, Aug 23 - Wed, Aug 26
Air Canada Logo
6:00 am - 12:15 am
BOS
-
POS
18h 15m
1 stop
Air Canada Logo
1:25 am - 4:03 pm
POS
-
BOS
14h 38m
1 stop
$376Air Canada
Tue, Oct 27 - Tue, Nov 3
Copa Airlines Logo
8:47 am - 1:54 am
BOS
-
POS
17h 07m
1 stop
Copa Airlines Logo
3:40 am - 10:01 pm
POS
-
BOS
19h 21m
1 stop
$392Copa Airlines
Wed, Oct 28 - Tue, Nov 3
Copa Airlines Logo
3:55 pm - 1:54 am
BOS
-
POS
9h 59m
1 stop
Copa Airlines Logo
3:40 am - 1:27 pm
POS
-
BOS
10h 47m
1 stop
$392Copa Airlines
Wed, Aug 19 - Sun, Aug 23
JetBlue Logo
8:41 am - 6:35 pm
BOS
-
POS
9h 54m
1 stop
JetBlue Logo
3:17 pm - 11:59 pm
POS
-
BOS
8h 42m
1 stop
$463JetBlue
Tue, Aug 18 - Fri, Aug 21
JetBlue Logo
7:12 am - 6:35 pm
BOS
-
POS
11h 23m
1 stop
JetBlue Logo
3:14 pm - 11:59 pm
POS
-
BOS
8h 45m
1 stop
$463JetBlue
Thu, Oct 1 - Tue, Oct 6
American Airlines Logo
5:00 am - 2:06 pm
BOS
-
POS
9h 06m
1 stop
American Airlines Logo
3:07 pm - 10:17 am
POS
-
BOS
19h 10m
1 stop
$466American Airlines
Sun, Aug 23 - Wed, Aug 26
United Airlines Logo
9:26 am - 12:50 am
BOS
-
POS
15h 24m
1 stop
United Airlines Logo
2:00 am - 11:17 am
POS
-
BOS
9h 17m
1 stop
$466United Airlines
Wed, Aug 19 - Sat, Aug 22
United Airlines Logo
9:25 am - 11:23 pm
BOS
-
POS
13h 58m
2 stops
United Airlines Logo
2:00 am - 11:17 am
POS
-
BOS
9h 17m
1 stop
$466United Airlines
Thu, Oct 1 - Tue, Oct 6
American Airlines Logo
5:00 am - 2:06 pm
BOS
-
POS
9h 06m
1 stop
American Airlines Logo
3:07 pm - 8:40 am
POS
-
BOS
17h 33m
2 stops
$470American Airlines
Booking Insights

KAYAK's insights & trends for Boston to Port of Spain flights

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

How much is a round-trip flight from Boston to Port of Spain?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Boston to Port of Spain departing in August.

Flight prices are below average for this route right now.

Flights to Port of Spain from Boston usually cost between $556 and $665 in August.
The lowest price found in the past 5 days was $376 on Air Canada (Aug 18-Aug 24).

What is the cheapest month to fly from Boston to Port of Spain?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Port of Spain, 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 Port of Spain is September, where tickets cost $391 (return) on average. On the other hand, the most expensive months are July and February, where the average cost of round-trip tickets is $633 and $625 respectively.

How far in advance should I book a flight from Boston to Port of Spain?

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 Port of Spain, 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 Port of Spain, 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 season

November

Cheapest flight

$165
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Boston to Port of Spain

When to book flights from Boston to Port of Spain

Are your dates flexible? Find out the best times to travel from Boston to Port of Spain based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Boston to Port of Spain

  • What is the cheapest flight from Boston to Port of Spain?

    In the last 5 days, the lowest price for a flight from Boston to Port of Spain was $165 for a one-way ticket and $376 for a round-trip.

  • Do I need a passport to fly between Boston and Port of Spain?

    Yes, you’ll need a passport to travel to Port of Spain from Boston.

  • Which aircraft models fly most regularly from Boston to Port of Spain?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Boston to Port of Spain?

    oneworld, and Star Alliance are the airline alliances operating flights between Boston and Port of Spain, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Boston to Port of Spain, Copa Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Boston to Port of Spain are Copa Airlines and United Airlines. With an average price for the route of $420 and an overall rating of 7.6, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $556 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Boston to Port of Spain?

    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 Port of Spain.

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

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

    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 Port of Spain with an airline and back to Boston with another airline. Booking your flights between Boston and POS can sometimes prove cheaper using this method.

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

    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 Port of Spain from Boston 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 Boston to Port of Spain

 
See real verified KAYAK customer reviews for airlines flying from Boston to Port of Spain. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Port of Spain? 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 1558 reviews
7.4Comfort
7.8Boarding
8.1Crew
6.8Entertainment
6.9Food
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.

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

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.

Poor and identical to the first two legs, except for the crew who were patient, professional and of pleasant and jovial disposition!

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.

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.

The seat could not recline. This was not indicated as such when I paid for the seat. So itvwad not the most comfortable ride. At boarding, the staff could have more pleasant even though it may be an intense time.

WiFi was not working from pos to Mia…. As well as they rushed us to the gate as if the flight was already here and leaving shortly when the plane never even arrived and took off until the scheduled time so then why rush us to the gate and have us thinking we will miss our flight.

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."

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

We were several hours delayed due to confusion during boarding. Evidently the crew could not match the manifest with the boarded customers. After significant time trying to find individuals on board, a crew member walked through the entire plane re-scanning each of our boarding passes. Then we had to wait for a new slot to depart, and when we landed, our gate was not ready. It was a complete goat rodeo from start to finish.

Horrible. Flight was cancelled, jet blue app not working to rebook, no phone number available to call Jet Blue, 400 ish people in line for the help desk, stuck in Boston for 2 more days had to book new flight with a different airline and still not sure if I will be able to get any refund.

Flight was delayed many times. The crew was friendly but you eleven had to buy headphones to access the movies in the plane. $8 is not a lot for one person but it is when you travel with all your family.

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!

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

Everything you need to know for your flight from Boston to Port of Spain

Information on your arrival and departure airports