BOS - POS

$236 Find Cheap Flights from Boston to Port of Spain

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

KAYAK searches hundreds of travel sites at once for deals on flights to Port of Spain

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Port of Spain, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Port of Spain, as well as popular online travel agencies
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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

Mon, Sep 15 - Sun, Sep 21
Air Canada Logo
10:20 am - 1:20 amBOS-POS
15h 00m2 stops
Air Canada Logo
2:25 am - 6:10 pmPOS-BOS
15h 45m1 stop
$437Air Canada
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Mon, Sep 8 - Tue, Sep 23
American Airlines Logo
5:47 am - 2:16 pmBOS-POS
8h 29m1 stop
American Airlines Logo
3:25 pm - 12:59 amPOS-BOS
9h 34m1 stop
$444American Airlines
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Sun, Sep 14 - Mon, Sep 22
Air Canada Logo
4:45 pm - 1:20 amBOS-POS
8h 35m1 stop
Air Canada Logo
2:25 am - 3:59 pmPOS-BOS
13h 34m1 stop
$447Air Canada
Find Deal
Mon, Sep 8 - Tue, Sep 23
American Airlines Logo
5:47 am - 2:16 pmBOS-POS
8h 29m1 stop
American Airlines Logo
3:25 pm - 1:12 pmPOS-BOS
21h 47m2 stops
$449American Airlines
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Thu, Oct 23 - Wed, Oct 29
United Airlines Logo
10:00 am - 11:23 pmBOS-POS
13h 23m1 stop
United Airlines Logo
12:30 am - 5:43 pmPOS-BOS
17h 13m1 stop
$463United Airlines
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Thu, Oct 23 - Wed, Oct 29
United Airlines Logo
8:00 am - 11:23 pmBOS-POS
15h 23m2 stops
United Airlines Logo
12:30 am - 3:17 pmPOS-BOS
14h 47m2 stops
$466United Airlines
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Sun, Sep 14 - Sat, Sep 20
 Logo
2:18 pm - 4:15 amBOS-POS
13h 57m1 stop
 Logo
9:10 am - 1:23 pmPOS-BOS
28h 13m1 stop
Mon, Sep 15 - Mon, Sep 22
 Logo
6:10 am - 8:00 pmBOS-POS
13h 50m1 stop
 Logo
10:10 am - 11:55 pmPOS-BOS
13h 45m1 stop
Tue, Sep 16 - Tue, Sep 23
JetBlue Logo
7:08 am - 2:34 pmBOS-POS
7h 26m1 stop
JetBlue Logo
3:59 pm - 12:14 amPOS-BOS
8h 15m1 stop
$524JetBlue
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Sat, Sep 13 - Sat, Sep 20
JetBlue Logo
5:23 am - 2:38 pmBOS-POS
9h 15m1 stop
JetBlue Logo
4:45 pm - 7:58 amPOS-BOS
15h 13m1 stop
$543JetBlue
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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.

What’s the cheapest day of the week to fly from Boston to Port of Spain?

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

If your flying dates are flexible, you should consider flying to Port of Spain on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Boston to Port of Spain. For your return ticket, we recommend flying on a Thursday and avoiding Mondays for the best deals.

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 $474 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $907 and $839 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 2 weeks before departure, which saves you about 28% 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$236
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 30% 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 3 days, the lowest price for a flight from Boston to Port of Spain was $236 for a one-way ticket and $437 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?

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

  • What is the most popular layover when flying to Port of Spain from Boston?

    Miami is the most popular layover city among KAYAK users traveling from Boston to Port of Spain.

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

    The two airlines most popular with KAYAK users for flights from Boston to Port of Spain are United Airlines and American Airlines. With an average price for the route of $649 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $622 and an overall rating of 7.2.

  • 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.
7.5
Copa AirlinesOverall score based on 1493 reviews
8.1Crew
7.8Boarding
6.8Entertainment
7.4Comfort
6.8Food
Airline reviews

horrible service, food was an embarrassment, no charging for cellphones, stay away

2.0 MediocreAnonymous, Jul 2025PTY - IAD
Read more Copa Airlines reviews

horrible service, food was an embarrassment, no charging for cellphones, stay away

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

The flighr attandants were very rude they ignored me didnt offer me anything to drink throughoit the 4 hour flight i feel i was targeted and ignored because i was a darkskin latino man.

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.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

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

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

The best airline I have ever travel , really good customer service, attention and service !!

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

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

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The plane was broken so we had to change planes.

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

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

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