$161 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 11/26. 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

Sun, Oct 18 - Sat, Oct 24
United Airlines Logo
1:00 am - 9:08 am
SJU
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PWM
8h 08m
1 stop
United Airlines Logo
7:58 am - 11:50 pm
PWM
-
SJU
15h 52m
2 stops
$218United Airlines
Fri, Aug 21 - Sat, Aug 29
Delta Logo
5:50 pm - 12:59 am
SJU
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PWM
7h 09m
1 stop
Delta Logo
6:05 am - 4:38 pm
PWM
-
SJU
10h 33m
1 stop
$276Delta
Sun, Oct 18 - Sat, Oct 24
United Airlines Logo
1:00 am - 10:02 am
SJU
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PWM
9h 02m
2 stops
United Airlines Logo
6:00 am - 8:38 pm
PWM
-
SJU
14h 38m
2 stops
$294United Airlines
Mon, Sep 14 - Wed, Sep 16
United Airlines Logo
1:00 am - 9:08 am
SJU
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PWM
8h 08m
1 stop
United Airlines Logo
6:06 am - 1:53 pm
PWM
-
SJU
7h 47m
1 stop
$318United Airlines
Fri, Aug 21 - Sat, Aug 29
Delta Logo
5:50 pm - 12:59 am
SJU
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PWM
7h 09m
1 stop
Delta Logo
6:05 am - 4:38 pm
PWM
-
SJU
10h 33m
1 stop
$322Delta
Fri, Aug 21 - Sat, Aug 29
American Airlines Logo
7:30 am - 10:00 pm
SJU
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PWM
14h 30m
1 stop
American Airlines Logo
6:02 am - 4:57 pm
PWM
-
SJU
10h 55m
2 stops
$347American Airlines
Mon, Sep 14 - Wed, Sep 16
United Airlines Logo
1:00 am - 10:04 am
SJU
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PWM
9h 04m
2 stops
United Airlines Logo
6:06 am - 8:38 pm
PWM
-
SJU
14h 32m
2 stops
$358United Airlines
Fri, Aug 21 - Sat, Aug 29
American Airlines Logo
7:30 am - 10:00 pm
SJU
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PWM
14h 30m
1 stop
American Airlines Logo
5:30 am - 2:51 pm
PWM
-
SJU
9h 21m
2 stops
$370American Airlines
Thu, Sep 24 - Sun, Sep 27
JetBlue Logo
9:30 am - 11:52 pm
SJU
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PWM
14h 22m
2 stops
JetBlue Logo
6:00 am - 1:34 pm
PWM
-
SJU
7h 34m
1 stop
$375JetBlue
Fri, Oct 16 - Sun, Oct 18
United Airlines Logo
4:55 pm - 11:59 pm
SJU
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PWM
7h 04m
1 stop
United Airlines Logo
6:00 am - 1:45 pm
PWM
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SJU
7h 45m
1 stop
$404United Airlines
Useful Info

Good to know

Cheapest flight$161
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 11768 reviews
7.2Comfort
7.9Crew
7.5Boarding
6.8Entertainment
6.4Food
Airline reviews

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

2.0 MediocreKrishna, Jun 2026
MHT - ORD
Read more American Airlines reviews

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

My flight was delayed twice. The first time because of “plane maintenance” and the second because the previous flight who supposedly “arrived early” took an obnoxiously long time to get off the plane. Total delay was over an hour for no reason. Not to mention your airline repeatedly changed our gate from one end of the terminal to the other. Not very happy about this experience. My previous flights with American haven’t had this many issues.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

Very efficient boarding and quick flight. Attendants don’t come by often so would often have a lot of trash at seat.

We’ve had a year of delays with American, and this one was another flight to add to that list. It just reduced our vacation by a day! So frustrating. In-flight entertainment (TVs) weren’t working, There was no drinks service due to delivery issues.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

2 hours delay on my flight causing me to miss my connecting flight. Cause was for maintenance. I understand maintenance is important but maintenance should be done before boarding people!

Better perks for corporate employees whom travel often and spend a lot of money with the airlines. Snacks were terrible chips crackers are ideas. Flight and crew were great comfort was fine entertainment not so great so so called status members means nothing

90 min delay for a food cart that needed to be fixed.

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