$129 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 3/7. 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
$386
Typical prices: $492-$590
Southwest
Tue 4/28Tue 5/5
SJU - PDX • 2 stops
Cheapest one-way
$129
Typical prices: $233-$323
Frontier
Sat 3/7
SJU - PDX • 2 stops
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Flight Deals
Useful Info
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

Tue, Apr 28 - Tue, May 5
Southwest Logo
11:25 am - 11:10 pm
SJU
-
PDX
14h 45m
2 stops
Southwest Logo
5:40 am - 9:05 pm
PDX
-
SJU
12h 25m
2 stops
$386Southwest
Fri, Apr 3 - Mon, Apr 6
American Airlines Logo
6:00 am - 12:22 am
SJU
-
PDX
21h 22m
1 stop
American Airlines Logo
11:30 pm - 2:20 pm
PDX
-
SJU
11h 50m
1 stop
$440American Airlines
Thu, Apr 30 - Tue, May 5
American Airlines Logo
1:31 pm - 11:57 pm
SJU
-
PDX
13h 26m
2 stops
American Airlines Logo
11:40 pm - 2:52 pm
PDX
-
SJU
12h 12m
2 stops
$450American Airlines
Sun, May 10 - Sat, May 16
American Airlines Logo
5:45 am - 11:53 pm
SJU
-
PDX
21h 08m
1 stop
American Airlines Logo
11:40 pm - 11:02 pm
PDX
-
SJU
20h 22m
1 stop
$461American Airlines
Thu, Mar 5 - Tue, Mar 17
United Airlines Logo
8:05 am - 7:14 pm
SJU
-
PDX
15h 09m
2 stops
United Airlines Logo
11:10 pm - 12:17 pm
PDX
-
SJU
10h 07m
1 stop
$466United Airlines
Wed, Mar 18 - Wed, Mar 25
Multiple Airlines Logo
10:19 am - 11:44 pm
SDQ
-
PDX
16h 25m
2 stops
Multiple Airlines Logo
9:30 pm - 2:40 am
PDX
-
SDQ
26h 10m
1 stop
$518Multiple Airlines
Fri, Apr 24 - Sun, May 3
United Airlines Logo
1:10 pm - 9:48 am
SDQ
-
PDX
23h 38m
2 stops
United Airlines Logo
10:16 pm - 11:55 am
PDX
-
SDQ
10h 39m
1 stop
$520United Airlines
Wed, Mar 18 - Wed, Mar 25
Multiple Airlines Logo
10:19 am - 8:35 pm
SDQ
-
PDX
13h 16m
1 stop
Multiple Airlines Logo
9:30 pm - 2:40 am
PDX
-
SDQ
26h 10m
1 stop
$524Multiple Airlines
Fri, Apr 24 - Sun, May 3
Delta Logo
6:05 am - 10:16 pm
SDQ
-
PDX
19h 11m
1 stop
Delta Logo
6:05 pm - 12:31 pm
PDX
-
SDQ
15h 26m
2 stops
$529Delta
Wed, Jun 17 - Wed, Jun 24
Delta Logo
8:50 pm - 11:43 am
STI
-
PDX
17h 53m
1 stop
Delta Logo
10:05 pm - 7:25 pm
PDX
-
STI
18h 20m
1 stop
$708Delta
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$129
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 3% increase in price.
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 4 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.
8.0
SouthwestOverall score based on 4283 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

8.0 ExcellentChad, Feb 2026
BNA - PHX
Read more Southwest reviews

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

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

Smooth boarding, pleasant and professional lady checking us in. Crew service was excellent, again pleasant, but professional. Nice touch-down on landing! Thank you Delta. 💗

Originally, I was booked in economy. I paid several hundred additional dollars to upgrade to first class. Then I paid several more hundred dollars to change my flight to a slightly earlier flight. I asked if the changed flight would also seat me in first class, and I was told that it would. When I boarded the plane, however, I was seated in economy. So, I paid $500-600 more than I paid for my original ticket for an upgrade and a changed flight - received the changed flight (which was nice), but did not receive the upgrade. So, I was not completely satisfied.

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.

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.

Flight was on time and the meal and service were good.

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