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$119 Find cheap flights from Caribbean 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 5/18. 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
Thu 6/6
Thu 6/13

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Good to know

Low season

March

High season

April

Cheapest flight

$119
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 to Portland

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Caribbean 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 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 with another airline.

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

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

Nonstop departures

Caribbean 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

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 3 airlines serving from Caribbean to Portland

 
Need help choosing which airline to fly with from Caribbean 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.
8.0
DeltaOverall score based on 10810 reviews
8.6Crew
7.9Comfort
8.0Entertainment
7.4Food
8.2Boarding
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

It was okay, no wifi or entertainment real disappointment. Staff onboard not very friendly.

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

It started with multiple delays, cancellations, re booking, 5 hour lay over and finally on a plane from Chicago to Pittsburgh. Gates, times, etc were changed multiply times. Once on the plane, staff was fine, but built in tv did not work and could not even turn it off. Light at eye level the entire trip, so sleeping was near impossible. No snacks or drinks given.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

Only water and pretzels served on six hour flight. Did not see crew rest of flight. No video screens and so no wired audio. Poor sound on plan so did not understand anything said by crew. This is a safety issue. Electrical socket did not retain charging block so could not charge phone. No video screen so could not watch movies. Phone is not a substitute.

It was fine. Flight was on time and arrived at destination with 15 min to spare.

My bag was lost with my medicine and I am very inconvenienced. I don’t know what happened, however I want you to do a better job on getting people’s bag back

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The food that was offered based on class level of your ticket was absolutely ridiculous and disgusting. They didn't even hot tea to serve, the food was horrible. On our departure flight I was seated in premium plus economy and considering the cost of the flight the food was literally some of the worst I've ever eaten. On the return flight I sat in economy with extra leg room and was given a thin little throw "blanket" and a flimsy little pillow. The air condition was on artic and the seating arrangement wasn't really worth the money. The seat didn't recline good enough and the foot rest was laughable. Total waste.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Horrible - they lied to me about baggage & boarding, even though I specifically spoke to their agents the day before my flight about my issue. When I showed up they did not let me board and stranded me at my airport until I bought a new flight with money I did not have to spend.

All four American Airlines flights I took in last seven days were delayed. Caused me loads of problems, missed meetings, loss of time and money.

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

They ocer booked the connecting flight. My bags took a long time to come out, nevertheless I got to the gate in time to board, but they have given my seat to another passenger. They were aware I was connecting from another flight that was a little late, but they did not care. The customer representatives were rude. A horrible experience.

Book cheap flights from Caribbean to Portland

Recent round-trip flight deals

9/24Tue
1 stopJetBlue
6h 15mSJU-PWM
9/25Wed
1 stopJetBlue
7h 20mPWM-SJU
$302
9/24Tue
2 stopsAmerican Airlines
17h 05mSJU-PWM
9/25Wed
2 stopsAmerican Airlines
21h 14mPWM-SJU
$321
9/24Tue
1 stopAmerican Airlines
8h 48mSJU-PWM
9/25Wed
2 stopsAmerican Airlines
21h 14mPWM-SJU
$380
5/30Thu
2 stops
13h 58mSJU-PWM
6/3Mon
3 stops
33h 11mPWM-SJU
$461
5/30Thu
2 stops
13h 58mSJU-PWM
6/3Mon
2 stops
31h 10mPWM-SJU
$463
5/30Thu
1 stopJetBlue
9h 55mSJU-PWM
6/3Mon
1 stopJetBlue
6h 37mPWM-SJU
$491
9/23Mon
1 stopUnited Airlines
6h 50mSJU-PWM
9/25Wed
1 stopUnited Airlines
8h 02mPWM-SJU
$508
9/23Mon
1 stopUnited Airlines
6h 50mSJU-PWM
9/25Wed
2 stopsUnited Airlines
32h 15mPWM-SJU
$515
5/30Thu
1 stopUnited Airlines
7h 19mSJU-PWM
6/2Sun
1 stopUnited Airlines
15h 54mPWM-SJU
$533
5/30Thu
2 stops
13h 58mSJU-PWM
6/2Sun
2 stops
22h 23mPWM-SJU
$539

Search by stops

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Recent one-way flight deals

5/18Sat
1 stopFrontier
28h 02mSJU-PWM
$119
5/28Tue
2 stopsAmerican Airlines
29h 11mSJU-PWM
$167
5/27Mon
1 stopFrontier
13h 00mSJU-PWM
$237
5/17Fri
1 stopFrontier
29h 54mSJU-PWM
$249
5/26Sun
1 stopFrontier
29h 34mSJU-PWM
$287
5/28Tue
1 stopUnited Airlines
7h 03mSJU-PWM
$302
5/27Mon
1 stopJetBlue
9h 55mSJU-PWM
$333
5/26Sun
2 stops
13h 58mSJU-PWM
$385
5/18Sat
2 stopsAmerican Airlines
28h 46mSJU-PWM
$401
5/27Mon
2 stopsUnited Airlines
22h 53mSJU-PWM
$505

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Last minute flights from Caribbean to Portland

Last minute flight, train and bus deals

5/9Thu
multi-stopAmerican Airlines
17h 52mSJU-PWM
5/12Sun
multi-stopAmerican Airlines
9h 20mPWM-SJU
$601
5/8Wed
multi-stopJetBlue
9h 50mSJU-PWM
5/12Sun
multi-stopJetBlue
6h 51mPWM-SJU
$717
5/9Thu
multi-stopAmerican Airlines
21h 16mSJU-PWM
5/12Sun
multi-stopAmerican Airlines
11h 05mPWM-SJU
$741
5/8Wed
multi-stopUnited Airlines
13h 46mSJU-PWM
5/12Sun
multi-stopUnited Airlines
14h 06mPWM-SJU
$844

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Flights to Portland

Destination:

Portland (PWM)United States

Return flight deals:

Portland - Caribbean

Cabin classes: