$116 Find Cheap Flights from Caribbean to Portland

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 3/28. 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
$295
American Airlines
Wed 2/18Sat 2/21
SJU - PWM • 2 stops
Cheapest one-way
$116
Typical prices: $303-$527
JetBlue
Sat 3/28
SJU - PWM • 1 stop
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Flight Deals

Cheap Flights from Caribbean to Portland

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

Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
5:47 pm - 10:27 amSJU-PWM
17h 40m2 stops
American Airlines Logo
7:00 am - 4:19 pmPWM-SJU
8h 19m1 stop
$295American Airlines
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Fri, Jan 30 - Thu, Feb 5
American Airlines Logo
2:28 pm - 10:54 pmSJU-PWM
9h 26m1 stop
American Airlines Logo
6:00 am - 11:56 pmPWM-SJU
16h 56m1 stop
$298American Airlines
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Fri, Dec 12 - Mon, Dec 15
Delta Logo
6:35 pm - 11:59 pmSJU-PWM
6h 24m1 stop
Delta Logo
2:34 pm - 11:59 pmPWM-SJU
8h 25m1 stop
$341Delta
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Sat, Dec 6 - Mon, Dec 8
Delta Logo
7:19 am - 1:54 pmSJU-PWM
7h 35m1 stop
Delta Logo
2:34 pm - 11:59 pmPWM-SJU
8h 25m1 stop
$344Delta
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Thu, Jan 29 - Thu, Feb 5
United Airlines Logo
2:05 am - 9:01 amSJU-PWM
7h 56m1 stop
United Airlines Logo
6:00 am - 9:00 pmPWM-SJU
14h 00m2 stops
$356United Airlines
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Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
12:49 pm - 11:37 pmSJU-PWM
11h 48m2 stops
American Airlines Logo
5:17 pm - 10:09 amPWM-SJU
15h 52m2 stops
$361American Airlines
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Thu, Jan 29 - Thu, Feb 5
United Airlines Logo
2:05 am - 9:01 amSJU-PWM
7h 56m1 stop
United Airlines Logo
3:12 pm - 12:36 amPWM-SJU
8h 24m1 stop
$365United Airlines
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Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
2:36 pm - 11:37 pmSJU-PWM
10h 01m2 stops
American Airlines Logo
5:34 am - 10:09 pmPWM-SJU
15h 35m2 stops
$378American Airlines
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Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
5:47 pm - 10:27 amSJU-PWM
17h 40m2 stops
American Airlines Logo
5:35 am - 9:26 pmPWM-SJU
14h 51m2 stops
$382American Airlines
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Thu, Jan 29 - Thu, Feb 5
United Airlines Logo
2:05 am - 2:39 pmSJU-PWM
13h 34m2 stops
United Airlines Logo
6:00 am - 9:00 pmPWM-SJU
14h 00m2 stops
$388United Airlines
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Good to know

Cheapest flight$116
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.

Reviews of the 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.
7.9
DeltaOverall score based on 8003 reviews
8.1Boarding
7.3Food
7.9Entertainment
8.5Crew
7.9Comfort
Airline reviews

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

8.0 ExcellentAnonymous, Nov 2025SFO - MSP
Read more Delta reviews

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

the over had ligth did not work'd for the all way

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

United has come a long way, it’s been a fantastic experience traveling with them.

Even though we were delayed, we were able to make our connection

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

Great crew, excellent landing, good food. Over all great experience. Thank you!

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

flight was good until we arrived at cmh ten minutes early but then sat on tarmac for twenty minutes because a plane was at our gate, so we had to wait despite the pilot tellling us that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

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