$138 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 2/27. 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
$236
American Airlines
Thu 2/5Sun 2/8
SJU - PWM • 2 stops
Cheapest one-way
$138
Typical prices: $211-$218
Delta
Fri 2/27
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

Thu, Feb 5 - Sun, Feb 8
American Airlines Logo
2:28 pm - 11:43 pm
SJU
-
PWM
10h 15m2 stops
American Airlines Logo
6:00 am - 11:56 pm
PWM
-
SJU
16h 56m1 stop
$236American Airlines
Thu, Apr 23 - Sun, Apr 26
JetBlue Logo
3:00 pm - 10:59 pm
SJU
-
PWM
7h 59m1 stop
JetBlue Logo
7:00 am - 1:29 pm
PWM
-
SJU
6h 29m1 stop
$244JetBlue
Fri, May 1 - Sat, May 16
Delta Logo
5:45 pm - 12:46 am
SJU
-
PWM
7h 01m1 stop
Delta Logo
6:30 am - 4:23 pm
PWM
-
SJU
9h 53m1 stop
$275Delta
Thu, Jan 22 - Thu, Jan 29
American Airlines Logo
1:58 pm - 11:43 pm
SJU
-
PWM
10h 45m2 stops
American Airlines Logo
5:20 am - 8:50 pm
PWM
-
SJU
14h 30m2 stops
$309American Airlines
Fri, May 1 - Sat, May 16
American Airlines Logo
11:59 pm - 11:34 am
SJU
-
PWM
11h 35m2 stops
American Airlines Logo
1:15 pm - 12:10 am
PWM
-
SJU
10h 55m1 stop
$376American Airlines
Thu, Jan 8 - Sun, Jan 18
American Airlines Logo
6:00 am - 4:37 pm
SJU
-
PWM
11h 37m2 stops
American Airlines Logo
6:00 am - 11:56 pm
PWM
-
SJU
16h 56m1 stop
$401American Airlines
Thu, Jan 8 - Sun, Jan 18
Delta Logo
6:05 pm - 12:20 am
SJU
-
PWM
7h 15m1 stop
Delta Logo
5:30 am - 2:31 pm
PWM
-
SJU
8h 01m1 stop
$410Delta
Thu, Feb 12 - Sun, Feb 15
American Airlines Logo
2:30 pm - 11:50 pm
SJU
-
PWM
10h 20m2 stops
American Airlines Logo
10:53 am - 11:40 pm
PWM
-
SJU
11h 47m2 stops
$442American Airlines
Thu, Jan 8 - Sun, Jan 18
American Airlines Logo
6:07 am - 3:31 pm
SJU
-
PWM
10h 24m1 stop
American Airlines Logo
6:00 am - 6:22 pm
PWM
-
SJU
11h 22m2 stops
$446American Airlines
Wed, Jan 7 - Sun, Jan 18
United Airlines Logo
2:05 am - 2:39 pm
SJU
-
PWM
13h 34m2 stops
United Airlines Logo
3:42 pm - 6:11 am
PWM
-
SJU
13h 29m2 stops
$453United Airlines
Useful Info

Good to know

Cheapest flight$138
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 8017 reviews
8.5Crew
8.1Boarding
7.2Food
7.9Comfort
7.9Entertainment
Airline reviews

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

8.0 ExcellentBrian, Dec 2025
DTW - TPA
Read more Delta reviews

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

I went to washroom twice and once there was no toilet seat cover and the other no toilet paper at all. I don't think it was ever replenished or checked before we boarded as it was very early on in the flight.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

Flight was delayed. De-icing took a while. When we landed had to wait for another plane to vacate our gate. Just an overall bad experience.

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

I boarded flight UA#1318 at Sacramento International Airport going back to Houston TX. The flight was scheduled at 5:10am. I was able to check in virtually using the United Airlines app. When I entered the airport, there was no one outside assisting with checked bags as it was for Delta Airlines. Immediately upon entering, there was a LONG, EXTREMELY LONG line to the kiosks to get boarding passes. I stand in line to get boarding passes then had to move to ANOTHER EXTREMELY LONG line to get my bags checked in. While standing in this line, we noticed an agent taking customers to 3 at a time to her station to check their bags in. Lucky for me, she called me back, checked my bags for me and I was on my way. I then encountered another long line at the TSA check and to avoid I ending up having to sign up for CLEAR to bypass it. So glad, I did.,...Both of my flights were great with no issues, butthe check in progress at Bush Airport was so much smoother. Check-in at SMF airport needs to be anaylzed and corrected. Do better United, I know you can....thanks

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

Pushed back only to get deplaned due to a tire damaged by ground crew. They did at least go pretty fast. The bathrooms should be banned under the Geneva convention. No room to even sit straight on the toilet. The under-seat entertainment units block what little leg room there is.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

It was good, although we could not get our preferred seats, we did enjoy the whole experience from Costa Rica. I still don't understand why our luggage is not the first to come out at the band.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

everything was pretty good. Houston airport is awful. Unnecessarily inefficient; people working there are rude. Badly run

Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

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