$116 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 5/12. 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 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

lun, mag 4 - mer, mag 6
United Airlines Logo
1:00 am - 10:18 am
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PWM
9h 18m
2 stops
United Airlines Logo
3:39 pm - 11:50 pm
PWM
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SJU
8h 11m
1 stop
$460United Airlines
lun, mag 4 - mer, mag 6
United Airlines Logo
1:00 am - 8:49 am
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PWM
7h 49m
1 stop
United Airlines Logo
3:39 pm - 11:50 pm
PWM
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SJU
8h 11m
1 stop
$467United Airlines
ven, giu 12 - lun, giu 29
Southwest Logo
5:15 pm - 12:05 am
SJU
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PWM
6h 50m
1 stop
Southwest Logo
5:20 pm - 12:15 am
PWM
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SJU
6h 55m
1 stop
$496Southwest
lun, mag 4 - mer, mag 6
United Airlines Logo
1:00 am - 10:18 am
SJU
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PWM
9h 18m
2 stops
United Airlines Logo
6:00 am - 8:34 pm
PWM
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SJU
14h 34m
2 stops
$512United Airlines
mer, apr 8 - gio, apr 9
Southwest Logo
5:05 am - 3:20 pm
SJU
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PWM
10h 15m
1 stop
Southwest Logo
4:50 pm - 11:40 pm
PWM
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SJU
6h 50m
1 stop
$522Southwest
mar, mag 5 - mer, mag 6
United Airlines Logo
4:55 pm - 11:59 pm
SJU
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PWM
7h 04m
1 stop
United Airlines Logo
5:30 am - 12:34 pm
PWM
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SJU
7h 04m
1 stop
$532United Airlines
ven, apr 3 - gio, apr 9
Southwest Logo
5:30 am - 4:45 pm
SJU
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PWM
11h 15m
2 stops
Southwest Logo
4:50 pm - 11:40 pm
PWM
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SJU
6h 50m
1 stop
$579Southwest
ven, giu 12 - lun, giu 29
Southwest Logo
1:15 pm - 12:05 am
SJU
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PWM
10h 50m
2 stops
Southwest Logo
3:10 pm - 12:05 am
PWM
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SJU
8h 55m
2 stops
$590Southwest
ven, apr 3 - gio, apr 9
Southwest Logo
5:30 am - 4:45 pm
SJU
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PWM
11h 15m
2 stops
Southwest Logo
2:50 pm - 11:55 pm
PWM
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SJU
9h 05m
2 stops
$647Southwest
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Good to know

Cheapest flight$116
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 airline 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.
7.1
American AirlinesOverall score based on 11468 reviews
7.9Crew
6.4Food
7.5Boarding
6.9Entertainment
7.2Comfort
Airline reviews

We changed our flight because of weather. Unfortunately we were on hold for over an hour, but since we were 5 people who all booked individually, we felt more comfortable doing it with an agent. It all worked out in the end.

10.0 ExcellentShelley, Mar 2026
CUN - PHL
Read more American Airlines reviews

We changed our flight because of weather. Unfortunately we were on hold for over an hour, but since we were 5 people who all booked individually, we felt more comfortable doing it with an agent. It all worked out in the end.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Movie selections were very limited. Meals were not f So good.

Older airplane with worn out seats. No entertainment system at all. Connecting to Wi-Fi was problematic and hit and miss.

AA is flying sub par aging 787's to Tokyo. I fly other 787's long haul and these are at the bottom. Seats don't work well, tray tables don't work well and were dirty. The flight was great, the plane was not.

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