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$249 Find cheap flights from Caribbean Islands to Portland, Maine

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Portland departing on 6/9. 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
0 bags
Mon 7/1
Mon 7/8

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Good to know

Low season

March

High season

April

Cheapest flight

$249
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from San Juan to Portland

FAQs for booking flights from Caribbean Islands to Portland

  • How does KAYAK find such low prices on flights from Caribbean Islands to Portland?

    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 Caribbean Islands to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Caribbean Islands 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 Caribbean Islands to Portland?

    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 Portland with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Portland?

    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 Portland from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Caribbean Islands to Portland?

Find which airlines fly direct from Caribbean Islands to Portland, which days they fly and book direct flights.

Nonstop departures

Caribbean Islands to Portland

Monday

Aeromexico, Air Canada, Air France, +25 more

Aeromexico, Air Canada, +26 more

Tuesday

Aeromexico, Air Canada, Air France, +24 more

Aeromexico, Air Canada, +25 more

Wednesday

Aeromexico, Air Canada, Air France, +24 more

Aeromexico, Air Canada, +25 more

Thursday

Aeromexico, Air Canada, Air France, +25 more

Aeromexico, Air Canada, +26 more

Friday

Aeromexico, Air Canada, Air France, +24 more

Aeromexico, Air Canada, +25 more

Saturday

Aeromexico, Air Canada, Air France, +24 more

Aeromexico, Air Canada, +25 more

Sunday

Aeromexico, Air Canada, Air France, +25 more

Aeromexico, Air Canada, +26 more

See more direct flights

Nonstop returns

Portland to Caribbean Islands

Monday

Aeromexico, Air Canada, Air France, +25 more

Aeromexico, Air Canada, +26 more

Tuesday

Aeromexico, Air Canada, Air France, +24 more

Aeromexico, Air Canada, +25 more

Wednesday

Aeromexico, Air Canada, Air France, +24 more

Aeromexico, Air Canada, +25 more

Thursday

Aeromexico, Air Canada, Air France, +25 more

Aeromexico, Air Canada, +26 more

Friday

Aeromexico, Air Canada, Air France, +24 more

Aeromexico, Air Canada, +25 more

Saturday

Aeromexico, Air Canada, Air France, +24 more

Aeromexico, Air Canada, +25 more

Sunday

Aeromexico, Air Canada, Air France, +25 more

Aeromexico, Air Canada, +26 more

See more direct flights
See more direct flights

Top airlines flying from Caribbean Islands to Portland

 
Need help choosing which airline to fly with from Caribbean Islands to Portland? 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
JetBlueOverall score based on 4351 reviews
7.5Entertainment
7.1Food
7.8Comfort
8.3Crew
7.8Boarding
Airline reviews

Overall fine but both ways for this trip was delayed.

6.0 GoodJackie, May 2024BOS - SYR
Read more about JetBlue reviews

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Nothing, terrible travel experience due to weather and maintenance delays and was left stranded in Austin.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

28 hour delay at Fort Worth/Dallas airport, part due to weather which was unavoidable, but various other reasons - no pilot, no fa, mechanical problem, plane too small, too big, crew out of flying time, seat configuration problems.... endless and hourly updates with a different excuse. Finally told us about 3.00 am, that the flight was delayed to hours later.

Experience was bad. 3.5 hour delay for a 2.5 hour trip. There was no r Transparency about the reason for the delay and it was done 30 mins at a time.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

Flight was 1/2 hour delayed leaving Phoenix. Otherwise it was an average flight. Flight crew on this trip was very nice.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

Book cheap flights from Caribbean Islands to Portland

Recent round-trip flight deals

7/4Thu
1 stopJetBlue
7h 40mSJU-PWM
7/8Mon
1 stopJetBlue
6h 48mPWM-SJU
$342
7/4Thu
2 stops
24h 51mSJU-PWM
7/8Mon
1 stop
13h 20mPWM-SJU
$398
7/4Thu
2 stops
24h 51mSJU-PWM
7/8Mon
2 stops
23h 36mPWM-SJU
$402
7/4Thu
3 stops
26h 11mSJU-PWM
7/8Mon
2 stops
23h 36mPWM-SJU
$432
7/4Thu
3 stops
26h 11mSJU-PWM
7/8Mon
3 stops
28h 56mPWM-SJU
$473
7/1Mon
1 stopJetBlue
6h 29mSJU-PWM
7/20Sat
1 stopJetBlue
6h 48mPWM-SJU
$540
6/12Wed
1 stopAmerican Airlines
6h 39mSJU-PWM
6/12Wed
1 stopAmerican Airlines
7h 07mPWM-SJU
$570
7/1Mon
1 stopAmerican Airlines
16h 39mSJU-PWM
7/20Sat
2 stopsAmerican Airlines
10h 44mPWM-SJU
$574
7/3Wed
2 stopsUnited Airlines
22h 48mSJU-PWM
7/8Mon
1 stopUnited Airlines
8h 37mPWM-SJU
$771
6/11Tue
1 stopUnited Airlines
7h 19mSJU-PWM
6/12Wed
1 stopUnited Airlines
8h 07mPWM-SJU
$824

Search by stops

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Recent one-way flight deals

6/9Sun
1 stopAmerican Airlines
9h 33mSJU-PWM
$249
7/11Thu
2 stops
31h 13mSJU-PWM
$255
7/12Fri
1 stopJetBlue
7h 49mSJU-PWM
$258
7/12Fri
2 stops
21h 50mSJU-PWM
$280
6/9Sun
2 stopsAmerican Airlines
23h 57mSJU-PWM
$293
7/11Thu
3 stops
33h 30mSJU-PWM
$298
6/8Sat
1 stopUnited Airlines
7h 19mSJU-PWM
$302
6/8Sat
2 stops
32h 34mSJU-PWM
$319
6/9Sun
3 stops
35h 33mSJU-PWM
$334
7/11Thu
1 stopUnited Airlines
8h 55mSJU-PWM
$534

Search by stops

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Last minute flights from Caribbean Islands to Portland

Last minute flight, train and bus deals

6/6Thu
multi-stopJetBlue
9h 55mSJU-PWM
6/10Mon
multi-stopJetBlue
9h 35mPWM-SJU
$644
6/6Thu
multi-stop
31h 54mSJU-PWM
6/10Mon
multi-stop
23h 36mPWM-SJU
$660
6/6Thu
multi-stop
31h 54mSJU-PWM
6/10Mon
multi-stop
29h 16mPWM-SJU
$693
6/6Thu
multi-stop
31h 54mSJU-PWM
6/10Mon
multi-stop
14h 55mPWM-SJU
$706
6/6Thu
multi-stopUnited Airlines
13h 16mSJU-PWM
6/10Mon
multi-stopUnited Airlines
6h 59mPWM-SJU
$824

Search by stops

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Flights to Portland

Destination:

Portland (PWM)United States

Return flight deals:

Portland - Caribbean Islands

Cabin classes:

$506
$315
$251
$38