$143 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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Everything you should know

Cheapest round-trip
$389
JetBlue
Fri 6/5Sun 6/7
SJU - PWM • 1 stop
Cheapest one-way
$143
Typical prices: $208-$543
Delta
Fri 4/17
SJU - PWM • 1 stop
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Flight Deals
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Flight Deals

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

Fri, Jun 5 - Sun, Jun 7
JetBlue Logo
6:00 am - 1:23 pm
SJU
-
PWM
7h 23m
1 stop
JetBlue Logo
6:00 am - 12:49 pm
PWM
-
SJU
6h 49m
1 stop
$389JetBlue
Fri, Jun 5 - Sun, Jun 7
Southwest Logo
1:15 pm - 12:05 am
SJU
-
PWM
10h 50m
2 stops
Southwest Logo
5:30 am - 12:25 pm
PWM
-
SJU
6h 55m
1 stop
$416Southwest
Fri, Jun 5 - Sun, Jun 7
Southwest Logo
1:15 pm - 12:05 am
SJU
-
PWM
10h 50m
2 stops
Southwest Logo
5:30 am - 4:25 pm
PWM
-
SJU
10h 55m
2 stops
$435Southwest
Fri, Jun 12 - Sun, Jun 14
United Airlines Logo
4:55 pm - 11:50 pm
SJU
-
PWM
6h 55m
1 stop
United Airlines Logo
5:20 am - 8:34 pm
PWM
-
SJU
15h 14m
2 stops
$507United Airlines
Thu, Mar 5 - Tue, Mar 10
United Airlines Logo
2:05 am - 10:49 am
SJU
-
PWM
9h 44m
1 stop
United Airlines Logo
3:44 pm - 11:36 pm
PWM
-
SJU
7h 52m
1 stop
$514United Airlines
Thu, Jun 11 - Sun, Jun 14
American Airlines Logo
12:40 am - 4:46 pm
SJU
-
PWM
16h 06m
1 stop
American Airlines Logo
5:36 pm - 4:35 am
PWM
-
SJU
10h 59m
1 stop
$534American Airlines
Thu, Mar 5 - Tue, Mar 10
United Airlines Logo
2:05 am - 3:14 pm
SJU
-
PWM
14h 09m
2 stops
United Airlines Logo
3:44 pm - 11:36 pm
PWM
-
SJU
7h 52m
1 stop
$567United Airlines
Fri, Jul 10 - Sun, Jul 12
American Airlines Logo
10:23 am - 11:45 pm
SJU
-
PWM
13h 22m
2 stops
American Airlines Logo
5:36 pm - 4:32 am
PWM
-
SJU
10h 56m
1 stop
$582American Airlines
Fri, Jul 10 - Sun, Jul 12
American Airlines Logo
10:23 am - 11:45 pm
SJU
-
PWM
13h 22m
2 stops
American Airlines Logo
7:23 am - 12:17 am
PWM
-
SJU
16h 54m
1 stop
$590American Airlines
Fri, Jun 12 - Sun, Jun 14
United Airlines Logo
4:55 pm - 11:50 pm
SJU
-
PWM
6h 55m
1 stop
United Airlines Logo
5:20 am - 8:34 pm
PWM
-
SJU
15h 14m
3 stops
$633United Airlines
Useful Info

Good to know

Cheapest flight$143
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 3 airlines serving 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.
7.9
DeltaOverall score based on 8193 reviews
7.9Comfort
7.2Food
8.5Crew
8.1Boarding
7.8Entertainment
Airline reviews

This was my first time flying Delta ever and I had a great experience!

10.0 ExcellentAnna, Feb 2026
TPA - DTW
Read more Delta reviews

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The gate agent was most helpful in getting me on to fly standby. I greatly appreciate it.

bulkhead seat had very little legroom - even in bsiness class.

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

This is the first time I've been disappointed with Delta. I was called by Delta to see if I would volunteer to change flights since my original flight home was overbooked. I accepted. The modified booking only provided me a 35 minute layover - when you subtract the fact that boarding closes for a flight 15 minutes early, that gave me 20 minutes to run for one end of the airport to the other. I barely made it. On the 2.5 hour flight to Tampa, the crew repeatedly let us know over the intercom that they cannot serve drinks or snacks due to safety/turbulence. I would have accepted this reason if they did not CONTINUALLY SERVE DRINKS AND COOKED FOOD to First class. If safety is the excuse then the entire plane should be strapped in for safety. On top of this the air conditioning vents were not working correctly and the plane was uncomfortably warm. I love Delta and am a loyal Delta traveler, and I have never had an experience like this. I don't know if there's a disconnect between availability among third-party sites like KAYAK and the airlines or what, but when overbooking causes issues like this for travelers it should be reviewed and changes to the booking process should be made. I blame BOTH KAYAK and Delta for this terrible experience.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

Both of my flights arrived early and check in process was smooth

Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Much better than Spirit. I was please by the easy fast check in and boarding

Crew was great. 2 1/2 hour delay was due to staff needing "rest" was avoidable and self inflicted as United not willing to hire enough crew to keep flight on time.. Ridiculous. The crew and the passengers both suffered due to this.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Waited for oxygen tanks for 30 minutes after boarding was complete.

The seats are too uncomfortable for anyone over 5ft 8in. I'm 5'10" with a back and hip issue and I was in pai for the full duration of the flight.

The gates should be ready when we land. Waiting on the runway for a hour is ridiculous.

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

One day, I do so hope for a gluten free snack! Seems like with the rest of the world FINALLY figuring out what gluten free is, American Airlines would too. Fingers crossed!!

The flight was significantly delayed for 6.5 hours because of snow. There was no communication once the plane returned to the gate regarding when the flight would resume. Other flights were departing while our flight was being unloaded for reasons unknown. Our flight also seemed out of the queue regarding further deicing, refueling, and waiting to Taxi to the runway.

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