$108 Find Cheap Flights from Caribbean Islands 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 9/30. 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

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Cheap Flights from Caribbean Islands to Portland

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

Fri, Aug 15 - Tue, Aug 19
American Airlines Logo
7:55 am - 10:59 pmSJU-PWM
15h 04m2 stops
American Airlines Logo
7:09 am - 6:15 pmPWM-SJU
11h 06m2 stops
$431American Airlines
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Tue, Aug 26 - Wed, Sep 3
JetBlue Logo
3:05 am - 1:23 pmSJU-PWM
10h 18m1 stop
JetBlue Logo
2:17 pm - 9:24 pmPWM-SJU
7h 07m1 stop
$455JetBlue
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Thu, Aug 14 - Mon, Aug 18
American Airlines Logo
8:00 am - 10:59 pmSJU-PWM
14h 59m2 stops
American Airlines Logo
6:00 am - 3:00 pmPWM-SJU
9h 00m2 stops
$478American Airlines
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Thu, Aug 14 - Tue, Aug 19
United Airlines Logo
2:05 am - 5:37 pmSJU-PWM
15h 32m2 stops
United Airlines Logo
6:00 am - 1:45 pmPWM-SJU
7h 45m1 stop
$503United Airlines
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Tue, Aug 26 - Wed, Sep 3
United Airlines Logo
1:05 am - 2:26 pmSJU-PWM
13h 21m2 stops
United Airlines Logo
7:30 am - 1:45 pmPWM-SJU
6h 15m1 stop
$669United Airlines
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Thu, Aug 14 - Tue, Aug 19
United Airlines Logo
1:05 am - 9:24 amSJU-PWM
8h 19m1 stop
United Airlines Logo
6:00 am - 1:45 pmPWM-SJU
7h 45m1 stop
$679United Airlines
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Wed, Aug 27 - Wed, Sep 3
United Airlines Logo
1:25 pm - 11:03 pmSJU-PWM
9h 38m1 stop
United Airlines Logo
10:05 am - 11:57 pmPWM-SJU
13h 52m2 stops
$713United Airlines
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Thu, Aug 14 - Tue, Aug 19
United Airlines Logo
2:05 am - 5:37 pmSJU-PWM
15h 32m2 stops
United Airlines Logo
5:02 pm - 3:42 pmPWM-SJU
22h 40m2 stops
$751United Airlines
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Wed, Aug 13 - Mon, Aug 18
United Airlines Logo
1:05 am - 9:24 amSJU-PWM
8h 19m1 stop
United Airlines Logo
4:56 pm - 5:30 amPWM-SJU
12h 34m2 stops
$753United Airlines
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Wed, Aug 13 - Mon, Aug 18
United Airlines Logo
1:05 am - 9:24 amSJU-PWM
8h 19m1 stop
United Airlines Logo
6:01 am - 1:45 pmPWM-SJU
7h 44m1 stop
$770United Airlines
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Good to know

Low seasonFebruary
Cheapest flight$108
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 35% 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.

Reviews of the top 3 airlines serving 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.
8.0
DeltaOverall score based on 7983 reviews
7.3Food
8.5Crew
7.9Entertainment
7.9Comfort
8.2Boarding
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Check in process was terrible. Lady at counter didn’t know what she was doing

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The crew was amazing; Von, Vera and Guadalupe were very friendly and attentive throughout the entire flight. They were friendly and welcoming to everyone. A solid and dedicated team for sure!

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

I found the staff to not be very attentive at all. When paying for Business Class you expect a certain type of service and that was not found. They were almost rude even

Not good , late, and long. We came home so late and spent so much time flying around and taxiing

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.

Had one staff that was not pleasant. Seems they are stressed with too many people to care for.

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

Ok. Get a different kosher caterer. The food was odd.

Food was terrible. Crew was kind but skipped over my row for providing sandwiches and beverages.

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.

Pathetic check in experience once again. Not enough staff scheduled at bag drop or for special assistance at LHR. Really need to rethink the whole self check in procedure. The crew was good. A very decent selection of special meals in this leg as compared to the JFK-LHR leg.

We had to turn around and head back to Manchester. Problem with a plane engine.

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.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

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