$223 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 5/14. 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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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

Sat, May 30 - Sat, Jun 6
United Airlines Logo
4:33 pm - 7:18 pm
MBJ
-
PDX
28h 45m
1 stop
United Airlines Logo
11:59 pm - 3:26 pm
PDX
-
MBJ
13h 27m
1 stop
$353United Airlines
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
6:30 am - 4:35 pm
SJU
-
PDX
13h 05m
2 stops
Southwest Logo
6:05 am - 10:15 pm
PDX
-
SJU
13h 10m
2 stops
$466Southwest
Thu, May 7 - Tue, May 12
Delta Logo
6:15 am - 6:06 pm
SJU
-
PDX
14h 51m
2 stops
Delta Logo
7:00 am - 11:35 pm
PDX
-
SJU
13h 35m
1 stop
$496Delta
Thu, May 14 - Fri, Jun 12
Delta Logo
2:35 pm - 10:02 pm
SJU
-
PDX
10h 27m
1 stop
Delta Logo
12:31 am - 3:11 pm
PDX
-
SJU
11h 40m
1 stop
$513Delta
Thu, May 28 - Thu, Jun 4
American Airlines Logo
12:31 pm - 11:59 pm
MBJ
-
PDX
13h 28m
1 stop
American Airlines Logo
11:43 pm - 4:17 pm
PDX
-
MBJ
14h 34m
1 stop
$528American Airlines
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
6:00 am - 5:21 pm
SJU
-
PDX
14h 21m
2 stops
American Airlines Logo
10:59 pm - 2:51 pm
PDX
-
SJU
12h 52m
1 stop
$530American Airlines
Fri, May 22 - Mon, Jun 1
Multiple Airlines Logo
3:35 pm - 8:50 pm
PUJ
-
PDX
32h 15m
1 stop
Multiple Airlines Logo
5:00 am - 10:35 am
PDX
-
PUJ
26h 35m
2 stops
$626Multiple Airlines
Fri, May 22 - Thu, May 28
Multiple Airlines Logo
3:35 pm - 8:50 pm
PUJ
-
PDX
32h 15m
1 stop
Multiple Airlines Logo
5:00 am - 1:30 pm
PDX
-
PUJ
29h 30m
2 stops
$676Multiple Airlines
Thu, May 28 - Thu, Jun 4
Air Canada Logo
12:30 pm - 9:30 am
MBJ
-
PDX
23h 00m
3 stops
Air Canada Logo
7:45 pm - 11:20 am
PDX
-
MBJ
13h 35m
2 stops
$1,007Air Canada
Thu, May 28 - Thu, Jun 4
Air Canada Logo
12:30 pm - 9:30 am
MBJ
-
PDX
23h 00m
3 stops
Air Canada Logo
3:30 pm - 11:20 am
PDX
-
MBJ
17h 50m
3 stops
$1,239Air Canada
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$223
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Montego Bay 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 8409 reviews
8.5Crew
7.2Food
7.9Comfort
8.1Boarding
7.8Entertainment
Airline reviews

The tray table was broken and the food was terrible.

4.0 OkayJeremy, Apr 2026
BNA - BOS
Read more Delta reviews

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Lounges are packed and very poor, food is really bad, for business class in an airline is well below expectations

The international / itallian speakers did not seem as friendly and professional as the others. Drink selections were denied ( a beer) until questioned about lack of ANY beer on the plane and then four options were given.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Packed in plane small uncomfortable seats elbow to elbow nobody wants to be in that situation for the money they paid

It was a more comfortable seat don't get stuck in middle, makes for uncomfortable situation

Business class would have been better , poor quality blanket , services

First time flying with UA and it was a great experience. Thank you

Overall flight was ok. Flight attendant was receptive to assisting passengers with tight connections.

Checking in united could not figure out my star alliance gold. Baggage did not get marked priority and didn't receive boarding passes. When got to SFO lounge personal fixed everything Immediately

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

American Airlines is a miserable experience. It is predictably miserable, in the sense that every time I fly American, I brace myself for the certainty that it will be unpleasant and uncomfortable. But it is unpredictable in the sense that I never know if the flight will be on time or delayed nine hours (both happened to me this week). I never know if I will be able to sit in the seat that I selected when I purchased the ticket or if I will be told by Customer Service (!!!) that I must relocate from first class to a seat in the back of the aircraft with no explanation (both happened to me this week). Will the food be frozen and half defrosted, or scalding hot? Will the drinks be warm? Will the flight attendants be surly and mean? Will the toilets be cramped and foul? Will the seats be narrow and uncomfortable? Will there be a real electric outlet at the seat, or just an unreliable USB-2 port? Will there be enough seats in the boarding lounge or just a few? Will the boarding process be smooth and efficient, or will the gate agents mess it up and delay it needlessly for 30 or 40 minutes? Will the catering and cleaning crew be prompt or will they take an extra 30 minutes? Will the brakes on the aircraft work properly, or will the pilot delay takeoff for four hours while the ground crew attends to what can only be described as routine maintenance that should have been done the night before? I've eexperienced every one of these unpleasant things this year, 2026. The only thing I can reliably count on is that American will find a new way to make the experience of flying as miserable as they possibly can.

Flight was fine, but not having WiFi was a major negative

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

Wifi was spotty. Tray table was very dirty when I sat down.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

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