$151 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 8/9. 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

Tue, Sep 15 - Sat, Sep 19
Delta Logo
7:00 am - 1:54 pm
SJU
-
PWM
6h 54m
1 stop
Delta Logo
2:35 pm - 11:44 pm
PWM
-
SJU
9h 09m
1 stop
$302Delta
Fri, Oct 23 - Sun, Oct 25
American Airlines Logo
8:35 am - 8:14 pm
SJU
-
PWM
11h 39m
2 stops
American Airlines Logo
8:01 am - 12:05 am
PWM
-
SJU
16h 04m
1 stop
$342American Airlines
Thu, Aug 6 - Thu, Aug 13
Delta Logo
5:50 pm - 12:59 am
SJU
-
PWM
7h 09m
1 stop
Delta Logo
6:00 am - 4:33 pm
PWM
-
SJU
10h 33m
1 stop
$379Delta
Sun, Oct 25 - Wed, Oct 28
United Airlines Logo
1:05 am - 8:19 am
SJU
-
PWM
7h 14m
1 stop
United Airlines Logo
6:00 am - 1:40 pm
PWM
-
SJU
7h 40m
1 stop
$388United Airlines
Sun, Oct 25 - Wed, Oct 28
United Airlines Logo
1:05 am - 8:19 am
SJU
-
PWM
7h 14m
1 stop
United Airlines Logo
9:10 am - 9:22 pm
PWM
-
SJU
12h 12m
2 stops
$392United Airlines
Sun, Oct 25 - Wed, Oct 28
United Airlines Logo
1:05 am - 8:19 am
SJU
-
PWM
7h 14m
1 stop
United Airlines Logo
6:00 am - 1:40 pm
PWM
-
SJU
7h 40m
1 stop
$398United Airlines
Sun, Oct 25 - Wed, Oct 28
United Airlines Logo
1:05 am - 8:19 am
SJU
-
PWM
7h 14m
1 stop
United Airlines Logo
9:10 am - 9:22 pm
PWM
-
SJU
12h 12m
2 stops
$402United Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
10:33 am - 8:10 pm
SJU
-
PWM
9h 37m
2 stops
American Airlines Logo
6:00 am - 6:24 pm
PWM
-
SJU
12h 24m
2 stops
$417American Airlines
Thu, Aug 6 - Thu, Aug 13
Multiple Airlines Logo
9:24 am - 9:12 am
SJU
-
PWM
23h 48m
1 stop
Multiple Airlines Logo
7:00 am - 4:05 pm
PWM
-
SJU
33h 05m
2 stops
$441Multiple Airlines
Tue, Sep 15 - Sat, Sep 19
United Airlines Logo
4:55 pm - 11:59 pm
SJU
-
PWM
7h 04m
1 stop
United Airlines Logo
6:00 am - 8:38 pm
PWM
-
SJU
14h 38m
2 stops
$445United Airlines
Useful Info

Good to know

Cheapest flight$151
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 11665 reviews
6.9Entertainment
7.5Boarding
6.4Food
7.2Comfort
7.9Crew
Airline reviews

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

6.0 GoodAnonymous, May 2026
DTW - DFW
Read more American Airlines reviews

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

The small flights with Valet Luggage has a poor service

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

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)