$121 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 5/9. 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
1 adult, Economy, 0 bags

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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

Sat, Aug 1 - Thu, Aug 13
American Airlines Logo
6:00 am - 9:44 pm
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15h 44m
1 stop
American Airlines Logo
8:01 am - 10:56 pm
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14h 55m
2 stops
$324American Airlines
Fri, May 22 - Mon, May 25
Southwest Logo
4:25 pm - 11:25 pm
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7h 00m
1 stop
Southwest Logo
5:30 am - 2:55 pm
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SJU
9h 25m
2 stops
$385Southwest
Thu, May 21 - Mon, May 25
Southwest Logo
5:35 am - 12:10 pm
SJU
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6h 35m
1 stop
Southwest Logo
5:30 am - 2:55 pm
PWM
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SJU
9h 25m
2 stops
$387Southwest
Fri, May 22 - Mon, May 25
Southwest Logo
4:25 pm - 11:25 pm
SJU
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PWM
7h 00m
1 stop
Southwest Logo
5:30 am - 12:10 pm
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SJU
6h 40m
1 stop
$394Southwest
Tue, Aug 4 - Wed, Aug 12
American Airlines Logo
7:20 am - 10:40 pm
SJU
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15h 20m
1 stop
American Airlines Logo
8:01 am - 11:41 pm
PWM
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SJU
15h 40m
1 stop
$396American Airlines
Fri, May 22 - Mon, May 25
Southwest Logo
2:00 pm - 11:25 pm
SJU
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PWM
9h 25m
2 stops
Southwest Logo
5:30 am - 2:55 pm
PWM
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SJU
9h 25m
2 stops
$406Southwest
Tue, Aug 4 - Wed, Aug 12
United Airlines Logo
1:00 am - 9:11 am
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8h 11m
1 stop
United Airlines Logo
5:15 am - 12:54 pm
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SJU
7h 39m
1 stop
$407United Airlines
Thu, Jun 25 - Mon, Jun 29
Southwest Logo
5:15 pm - 12:05 am
SJU
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PWM
6h 50m
1 stop
Southwest Logo
5:35 am - 12:25 pm
PWM
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SJU
6h 50m
1 stop
$412Southwest
Tue, Aug 4 - Wed, Aug 12
United Airlines Logo
7:40 am - 11:51 pm
SJU
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PWM
16h 11m
2 stops
United Airlines Logo
5:15 am - 12:54 pm
PWM
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SJU
7h 39m
1 stop
$431United Airlines
Thu, May 21 - Mon, May 25
Southwest Logo
5:05 am - 2:10 pm
SJU
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PWM
9h 05m
2 stops
Southwest Logo
5:30 am - 2:55 pm
PWM
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SJU
9h 25m
2 stops
$438Southwest
Useful Info

Good to know

Cheapest flight$121
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 airline flying 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.
7.1
American AirlinesOverall score based on 11375 reviews
7.5Boarding
6.4Food
7.2Comfort
8.0Crew
6.9Entertainment
Airline reviews

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

4.0 OkayMitchell, Mar 2026
PHL - CMH
Read more American Airlines reviews

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

The flight attendants as well as the gate agent were out to lunch. Nothing extraordinary about their service. American just keeps getting worse every year.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

It was good experience this time. The flight was on time.

I very rarely fly American and my experience today reenforces that is the correct decision. While the staff were all very courteous, our flight was first thing in the morning so there was no reason to be delayed, yet appropriate maintenance checks weren’t completed prior to our flight so we were delayed multiple times. Not a great showing, American Airlines.

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