$188 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 2/15. 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
$225
JetBlue
Thu 4/30Sat 5/9
SJU - PWM • 1 stop
Cheapest one-way
$188
Typical prices: $211-$218
Multiple Airlines
Sun 2/15
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, Apr 30 - Sat, May 9
JetBlue Logo
6:25 am - 1:23 pm
SJU
-
PWM
6h 58m
1 stop
JetBlue Logo
2:18 pm - 12:07 am
PWM
-
SJU
9h 49m
1 stop
$225JetBlue
Thu, Apr 30 - Sat, May 9
Southwest Logo
4:25 pm - 11:25 pm
SJU
-
PWM
7h 00m
1 stop
Southwest Logo
4:35 pm - 11:15 pm
PWM
-
SJU
6h 40m
1 stop
$263Southwest
Thu, Apr 30 - Sat, May 9
Southwest Logo
2:00 pm - 11:25 pm
SJU
-
PWM
9h 25m
2 stops
Southwest Logo
4:35 pm - 11:15 pm
PWM
-
SJU
6h 40m
1 stop
$276Southwest
Fri, May 1 - Sun, May 10
Southwest Logo
2:00 pm - 11:25 pm
SJU
-
PWM
9h 25m
2 stops
Southwest Logo
5:30 pm - 12:05 am
PWM
-
SJU
6h 35m
1 stop
$290Southwest
Wed, Apr 29 - Sat, May 9
United Airlines Logo
1:00 am - 8:49 am
SJU
-
PWM
7h 49m
1 stop
United Airlines Logo
5:30 am - 8:34 pm
PWM
-
SJU
15h 04m
2 stops
$300United Airlines
Thu, Apr 2 - Sun, Apr 5
JetBlue Logo
4:26 pm - 11:56 pm
SJU
-
PWM
7h 30m
1 stop
JetBlue Logo
6:00 am - 2:45 pm
PWM
-
SJU
8h 45m
1 stop
$313JetBlue
Wed, Apr 29 - Fri, May 8
United Airlines Logo
1:00 am - 8:49 am
SJU
-
PWM
7h 49m
1 stop
United Airlines Logo
9:39 am - 8:34 pm
PWM
-
SJU
10h 55m
1 stop
$333United Airlines
Sun, Mar 15 - Wed, Mar 18
Southwest Logo
9:50 pm - 11:55 am
SJU
-
PWM
14h 05m
2 stops
Southwest Logo
4:30 pm - 11:00 pm
PWM
-
SJU
6h 30m
1 stop
$348Southwest
Thu, Apr 30 - Sat, May 9
Southwest Logo
2:00 pm - 11:25 pm
SJU
-
PWM
9h 25m
2 stops
Southwest Logo
5:40 am - 2:50 pm
PWM
-
SJU
9h 10m
2 stops
$365Southwest
Wed, Apr 29 - Sat, May 9
United Airlines Logo
1:00 am - 2:14 pm
SJU
-
PWM
13h 14m
2 stops
United Airlines Logo
9:39 am - 9:24 pm
PWM
-
SJU
11h 45m
2 stops
$368United Airlines
Useful Info

Good to know

Cheapest flight$188
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 8123 reviews
8.1Boarding
8.5Crew
7.8Entertainment
7.9Comfort
7.2Food
Airline reviews

Timing, quality of service, promptness and courtesy of the staff

10.0 ExcellentAjai, Jan 2026
DFW - ATL
Read more Delta reviews

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Very convenient considering that is a non-stop flight, but the Aeromexico still has old model planes, so the entertainment was very poor and the space for carry-on luggage was very limited.

Flight taking off must have been behind, because there was no pre-departure drink for first class like normal. Also, person in front of mine’s seat got stuck in the as far back as it normally goes position for the whole flight even during landing, flight attendant unable to fix it. Gate was not empty when we arrived, but that is MSP’s fault since was overdue for push back, not Delta’s, so had to sit on tarmac for a while and international flight so then still had to go through customs. Flight crew was excellent throughout though!

Flight from MEX to ATL had to divert to Tampa. When we got off the plane, there were non directions on what to do. Nearly 30 minutes just standing around. Finally told to go through security with no boarding passes, and turned away. Then told to to go back. Took forever to leave Tampa for ATL. Missed my connection to Harrisburg.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

This Japanese airline provides great service and very helpful in assisting their passengers.

Good crew. Boarding delays. Almost two hours wait for the bags in DC.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

We were upgraded to Business Class. So comfortable with great service and food options

The flight attendant use 1.5 hours to answer my call. My dirty food tray was unattended.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

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