$160 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 5/13. 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.
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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.

Recent round-trip flight deals from Caribbean to Portland

KAYAK's recommended round-trip deals from the most popular airlines that fly from Caribbean to Portland.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
1:33 am - 4:45 pmSJU-PDX
42h 12m2 stops
 Logo
4:35 pm - 11:31 amPDX-SJU
39h 56m3 stops
Wed, May 21 - Mon, May 26
Spirit Airlines Logo
1:33 am - 4:45 pmSJU-PDX
42h 12m2 stops
Spirit Airlines Logo
1:37 pm - 12:44 pmPDX-SJU
20h 07m2 stops
$369Spirit Airlines
Find Deal
Wed, May 21 - Mon, May 26
Delta Logo
1:12 pm - 11:15 pmSJU-PDX
13h 03m1 stop
Delta Logo
7:14 am - 11:42 pmPDX-SJU
13h 28m1 stop
$379Delta
Find Deal
Wed, May 28 - Sun, Jun 1
Delta Logo
2:15 pm - 11:48 pmSJU-PDX
12h 33m2 stops
Delta Logo
5:45 pm - 1:10 pmPDX-SJU
16h 25m2 stops
$416Delta
Find Deal
Sat, Sep 20 - Fri, Oct 3
American Airlines Logo
6:10 am - 11:07 pmSJU-PDX
19h 57m1 stop
American Airlines Logo
9:38 pm - 8:33 pmPDX-SJU
19h 55m1 stop
$451American Airlines
Find Deal
Thu, May 22 - Fri, May 30
American Airlines Logo
1:30 pm - 11:59 pmSJU-PDX
13h 29m2 stops
American Airlines Logo
10:24 pm - 12:39 pmPDX-SJU
11h 15m1 stop
$462American Airlines
Find Deal
Wed, May 21 - Fri, May 30
United Airlines Logo
1:05 am - 6:31 pmSJU-PDX
20h 26m3 stops
United Airlines Logo
6:27 pm - 12:00 pmPDX-SJU
14h 33m2 stops
$469United Airlines
Find Deal
Fri, Sep 19 - Fri, Oct 3
JetBlue Logo
12:55 pm - 10:15 pmSJU-PDX
12h 20m1 stop
JetBlue Logo
11:35 pm - 3:49 pmPDX-SJU
13h 14m1 stop
$474JetBlue
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Tue, Jun 17 - Tue, Jun 24
United Airlines Logo
1:05 am - 3:25 pmSJU-PDX
17h 20m2 stops
United Airlines Logo
3:44 pm - 12:00 pmPDX-SJU
17h 16m2 stops
$506United Airlines
Find Deal
Thu, Sep 4 - Fri, Sep 12
JetBlue Logo
12:35 pm - 10:10 pmSJU-PDX
12h 35m1 stop
JetBlue Logo
11:35 pm - 4:40 pmPDX-SJU
14h 05m1 stop
$561JetBlue
Find Deal
Thu, Jul 17 - Mon, Jul 21
Useful Info

Good to know

Low seasonMarch
High seasonJuly
Cheapest flight$160
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 17% 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.

Top 5 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 4293 reviews
8.2Boarding
8.6Crew
8.0Comfort
7.6Entertainment
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

I needed to make changes to my flights. When I called customer service, they assisted me with care professionalism.

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

A bit rush for transit. Food and entertainment are not available

So far so good but food and entertainment are not available for this flight

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

The gate and ground staff were excellent, friendly, went out of their way to acknowledge my Mosaic status. The plane was an older Airbus, so the seats were a little worn. The in flight attendant was not very nice, and seemed to be annoyed to be at work or be on this flight. Flight was fast and we landed early and pilots kept us informed.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

The inflight system with their wifi is a hot mess and doesn't work. Separately they do, but when you try to do theoretically simple things like pair a device for control it all falls apart

It was too hot in the cabin. The AC did not help.

The regular feedback of any changes to our flights. The Jetblue staff were very helpful. Our flights were great. Lots of leg room!

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

Pitch was very small. Knees were on the seat back in front of me.

Paid $35 and not able to access the internet at all.

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Flight was delayed bc of mechanical issue. New plane had different configuration so some seats had to be switched. They called all passengers who needed new boarding cards. They did not call us so we thought our seats were the same and fine. When we boarded they informed us our receipts had changed and we are now all sitting separate and in the back row. Both my daughters had meltdowns and started to cry and once we got on the flight, we figured out how we could sit closer to each other, but this was very upsetting.

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