$161 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 2/18. 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
$359
Southwest
Fri 3/20Mon 3/23
SJU - PWM • 1 stop
Cheapest one-way
$161
Typical prices: $211-$218
United Airlines
Wed 2/18
SJU - PWM • 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

Fri, Mar 20 - Mon, Mar 23
Southwest Logo
5:00 am - 2:15 pm
SJU
-
PWM
9h 15m
1 stop
Southwest Logo
2:50 pm - 12:25 am
PWM
-
SJU
9h 35m
1 stop
$359Southwest
Fri, May 8 - Mon, May 11
American Airlines Logo
6:00 am - 11:22 pm
SJU
-
PWM
17h 22m
1 stop
American Airlines Logo
10:43 am - 10:05 pm
PWM
-
SJU
11h 22m
1 stop
$376American Airlines
Fri, Mar 20 - Mon, Mar 23
Southwest Logo
5:30 am - 4:45 pm
SJU
-
PWM
11h 15m
2 stops
Southwest Logo
12:35 pm - 11:35 pm
PWM
-
SJU
11h 00m
2 stops
$434Southwest
Fri, May 8 - Mon, May 11
United Airlines Logo
1:25 pm - 11:59 pm
SJU
-
PWM
10h 34m
2 stops
United Airlines Logo
3:15 pm - 11:50 pm
PWM
-
SJU
8h 35m
1 stop
$498United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
2:45 pm - 11:30 pm
SJU
-
PWM
9h 45m
1 stop
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$549United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
5:50 pm - 2:31 pm
SJU
-
PWM
21h 41m
1 stop
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$550United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
2:45 pm - 2:31 pm
SJU
-
PWM
24h 46m
2 stops
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$560United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
2:45 pm - 11:30 pm
SJU
-
PWM
9h 45m
1 stop
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$569United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
4:52 pm - 1:56 pm
SJU
-
PWM
22h 04m
2 stops
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$605United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
4:52 pm - 2:31 pm
SJU
-
PWM
22h 39m
2 stops
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$625United Airlines
Useful Info

Good to know

Cheapest flight$161
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 8039 reviews
8.1Boarding
7.8Entertainment
7.2Food
7.9Comfort
8.5Crew
Airline reviews

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

8.0 ExcellentG, Jan 2026
FLL - ATL
Read more Delta reviews

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

Both flights delayed. 2nd flight over 3 hours late mechanical issues

l really enjoy very much the flight was very pleasant

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

Flight was delayed 45 minutes because originating flight was coming from Newark. No complimentary snacks were offered on this 5+ hour flight. No screens for the flight, but movies offered if you had already downloaded the United app (which I hadn't on my ipad). No USB ports, only a flimsy plug-in port near the bottom of the seat that was hard to see and kept coming unplugged.

It was good but only meal served is very less. Meantime good to add rice and chicken in one of meal

Teeny tiny bathrooms, crew was not realistic about when we'd arrive.

Check-in, boarding and the flight from Phoenix to Houston was quick and easy. The flight from Houston to Shreveport was delayed 5 hours. It was frustrating but I think United handled it the best they could.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Little warm on the plane and delayed for an hour

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Bags took over and hour to come out. Delays due to wind caused rebooking.

Services, food products, and crew friendliness on American Airlines international flights is mediocre compared to Emirates, Qatar, and Singapore Airways. American does not do much to differentiate its product on international routes. Its menu options are similar on international flights. American Airlines flight attendants do not call elite frequent travelers by their names; American Airlines flight attendants do not seem to be motivated to go above and beyond in the service they provide. American Airlines personnel do not seem to take pride in their work.

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Lower WiFi prices; allow us to see our flight on a map; more variety of drink choices.

I was originally scheduled on AA 1763. When I landed in Miami, I went to the counter for flight AA 2115 to try to move my flight to this one. I was in a first class seat on AA 1763. While they moved to me this flight, I was told that there were no other 1st class seats available and they assigned me into coach. However, when I was getting off the plane I noticed that one of the pilots who was also in line to go jump seat - somehow miraculously got a 1st class seat on this flight. It is actually infuriating that I had a paid 1st class seat yet somehow they would move an AA employee ahead of that. At a bare minimum, they should have compensated me for the fare difference and I really think paying customers should ALWAYs get the premiere seats.

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

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