$141 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 4/17. 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, Apr 18 - Sat, Apr 25
United Airlines Logo
7:20 am - 9:40 pm
SJU
-
PWM
14h 20m
2 stops
United Airlines Logo
3:22 pm - 11:50 pm
PWM
-
SJU
8h 28m
1 stop
$282United Airlines
Sat, Apr 18 - Sat, Apr 25
United Airlines Logo
7:20 am - 9:40 pm
SJU
-
PWM
14h 20m
2 stops
United Airlines Logo
2:12 pm - 11:50 pm
PWM
-
SJU
9h 38m
2 stops
$302United Airlines
Fri, May 1 - Sat, May 9
United Airlines Logo
1:00 am - 2:14 pm
SJU
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PWM
13h 14m
2 stops
United Airlines Logo
3:39 pm - 11:50 pm
PWM
-
SJU
8h 11m
1 stop
$318United Airlines
Fri, Apr 17 - Sat, Apr 25
United Airlines Logo
1:00 am - 8:59 am
SJU
-
PWM
7h 59m
1 stop
United Airlines Logo
3:22 pm - 11:50 pm
PWM
-
SJU
8h 28m
1 stop
$336United Airlines
Fri, Apr 17 - Wed, Apr 22
United Airlines Logo
1:00 am - 3:39 pm
SJU
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PWM
14h 39m
2 stops
United Airlines Logo
6:04 am - 2:44 pm
PWM
-
SJU
8h 40m
1 stop
$340United Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
6:00 am - 11:26 pm
SJU
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PWM
17h 26m
1 stop
American Airlines Logo
11:24 am - 8:51 pm
PWM
-
SJU
9h 27m
2 stops
$342American Airlines
Fri, Apr 17 - Wed, Apr 22
United Airlines Logo
1:00 am - 8:59 am
SJU
-
PWM
7h 59m
1 stop
United Airlines Logo
6:04 am - 2:44 pm
PWM
-
SJU
8h 40m
1 stop
$360United Airlines
Tue, Jun 2 - Sat, Jun 6
JetBlue Logo
3:30 am - 1:35 pm
SJU
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PWM
10h 05m
1 stop
JetBlue Logo
2:37 pm - 10:53 pm
PWM
-
SJU
8h 16m
1 stop
$371JetBlue
Fri, Apr 17 - Wed, Apr 22
United Airlines Logo
1:00 am - 3:39 pm
SJU
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PWM
14h 39m
2 stops
United Airlines Logo
11:09 am - 9:24 pm
PWM
-
SJU
10h 15m
2 stops
$385United Airlines
Mon, Sep 28 - Wed, Sep 30
United Airlines Logo
1:05 am - 9:11 am
SJU
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PWM
8h 06m
1 stop
United Airlines Logo
6:00 am - 8:38 pm
PWM
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SJU
14h 38m
2 stops
$439United Airlines
Useful Info

Good to know

Cheapest flight$141
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 11556 reviews
7.5Boarding
6.4Food
7.9Crew
6.9Entertainment
7.2Comfort
Airline reviews

Seat was VERY uncomfortable. Flight was delayed and then boarded slowly. The crew was super helpful with boarding and supporting maximizing the luggage in the overhead.

4.0 OkayJana, Apr 2026
DFW - EWR
Read more American Airlines reviews

Seat was VERY uncomfortable. Flight was delayed and then boarded slowly. The crew was super helpful with boarding and supporting maximizing the luggage in the overhead.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Early morning flight and no food in First Class except a "salmon" box. No thank you. Was informed before take off by Captain that the plane was not serviced before we boarded in Phoenix. How does that happen? Need more frequent additions/turn over on the Entertainment. Thanks

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Delayed 24 hours. Should have called it much earlier They provided quality accommodations, food vouchers etc. FINALLY The issues started at 8 AM and they cancelled the flight at 11:30 PM, with no plans for a new flight.

Better snacks but flight and crew were amazing on this flight

Traveling to a place near Portland?

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Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland

Portland (PWM)