$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

Wed, Sep 2 - Sun, Sep 6
Delta Logo
7:00 am - 1:54 pm
SJU
-
PWM
6h 54m
1 stop
Delta Logo
2:35 pm - 11:59 pm
PWM
-
SJU
9h 24m
1 stop
$302Delta
Wed, Sep 2 - Sun, Sep 6
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
$312United Airlines
Wed, Sep 2 - Sun, Sep 6
United Airlines Logo
2:55 pm - 11:59 pm
SJU
-
PWM
9h 04m
2 stops
United Airlines Logo
6:00 am - 8:38 pm
PWM
-
SJU
14h 38m
2 stops
$326United Airlines
Wed, Aug 26 - Mon, Aug 31
American Airlines Logo
10:33 am - 11:51 pm
SJU
-
PWM
13h 18m
2 stops
American Airlines Logo
6:00 am - 2:51 pm
PWM
-
SJU
8h 51m
2 stops
$342American Airlines
Fri, Aug 21 - Sat, Aug 29
Delta Logo
2:59 pm - 11:20 pm
SJU
-
PWM
8h 21m
1 stop
Delta Logo
6:00 am - 4:33 pm
PWM
-
SJU
10h 33m
1 stop
$379Delta
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
10:33 am - 8:17 pm
SJU
-
PWM
9h 44m
2 stops
American Airlines Logo
7:27 am - 12:15 am
PWM
-
SJU
16h 48m
1 stop
$397American Airlines
Fri, Aug 21 - Sat, Aug 29
American Airlines Logo
10:33 am - 8:17 pm
SJU
-
PWM
9h 44m
2 stops
American Airlines Logo
6:00 am - 10:24 pm
PWM
-
SJU
16h 24m
1 stop
$412American Airlines
Fri, Oct 30 - Wed, Nov 4
American Airlines Logo
5:25 am - 7:16 pm
SJU
-
PWM
13h 51m
1 stop
American Airlines Logo
6:00 am - 11:47 pm
PWM
-
SJU
16h 47m
1 stop
$417American Airlines
Fri, Oct 30 - Wed, Nov 4
Southwest Logo
6:00 am - 4:55 pm
SJU
-
PWM
10h 55m
2 stops
Southwest Logo
10:30 am - 10:15 pm
PWM
-
SJU
10h 45m
2 stops
$420Southwest
Fri, Aug 21 - Tue, Aug 25
JetBlue Logo
3:10 pm - 12:14 am
SJU
-
PWM
9h 04m
1 stop
JetBlue Logo
1:17 pm - 7:50 pm
PWM
-
SJU
6h 33m
1 stop
$421JetBlue
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 11641 reviews
6.9Entertainment
7.5Boarding
6.4Food
7.9Crew
7.2Comfort
Airline reviews

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

8.0 ExcellentAnonymous, May 2026
RSW - ORD
Read more American Airlines reviews

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

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

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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)