$168 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 4/16. 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

to., apr. 30 - to., mai 7
United Airlines Logo
2:40 pm - 10:59 pm
MBJ
-
PDX
10h 19m
1 stop
United Airlines Logo
7:05 pm - 12:50 pm
PDX
-
MBJ
39h 45m
2 stops
$353United Airlines
to., apr. 30 - to., mai 7
United Airlines Logo
2:40 pm - 10:38 pm
MBJ
-
PDX
33h 58m
2 stops
United Airlines Logo
5:30 am - 1:30 pm
PDX
-
MBJ
30h 00m
3 stops
$389United Airlines
ti., apr. 21 - lø., apr. 25
American Airlines Logo
11:43 am - 10:56 pm
SJU
-
PDX
14h 13m
2 stops
American Airlines Logo
6:00 am - 11:02 pm
PDX
-
SJU
14h 02m
1 stop
$456American Airlines
fr., aug. 14 - to., aug. 20
Southwest Logo
5:30 am - 3:00 pm
SJU
-
PDX
12h 30m
1 stop
Southwest Logo
10:45 pm - 2:30 pm
PDX
-
SJU
12h 45m
1 stop
$468Southwest
ti., mai 19 - to., mai 28
American Airlines Logo
1:15 pm - 10:47 pm
MBJ
-
PDX
11h 32m
1 stop
American Airlines Logo
9:47 pm - 11:19 am
PDX
-
MBJ
11h 32m
1 stop
$470American Airlines
ti., mai 19 - to., mai 28
American Airlines Logo
4:37 pm - 12:58 pm
MBJ
-
PDX
22h 21m
2 stops
American Airlines Logo
9:47 pm - 11:19 am
PDX
-
MBJ
11h 32m
1 stop
$475American Airlines
ma., mai 11 - lø., mai 16
Multiple Airlines Logo
6:41 pm - 1:02 pm
SJU
-
PDX
45h 21m
3 stops
Multiple Airlines Logo
7:45 am - 2:08 am
PDX
-
SJU
15h 23m
2 stops
$497Multiple Airlines
ti., apr. 14 - ti., apr. 21
Multiple Airlines Logo
3:35 pm - 8:35 pm
SDQ
-
PDX
32h 00m
1 stop
Multiple Airlines Logo
12:07 pm - 5:29 am
PDX
-
SDQ
14h 22m
2 stops
$590Multiple Airlines
fr., apr. 24 - lø., mai 2
Delta Logo
6:05 am - 10:42 pm
SDQ
-
PDX
19h 37m
2 stops
Delta Logo
5:45 pm - 12:31 pm
PDX
-
SDQ
15h 46m
2 stops
$600Delta
fr., apr. 24 - sø., mai 3
Delta Logo
6:05 am - 10:16 pm
SDQ
-
PDX
19h 11m
1 stop
Delta Logo
7:00 am - 12:17 am
PDX
-
SDQ
14h 17m
1 stop
$623Delta
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$168
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 6% lower on average.
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 8286 reviews
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

No pilots so we were two hours late taking off and then no gate agents when we arrived in Salt Lake.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Terrible experience! delay 2 time and say i dont have ticket

Both my flight where delayed Had 25min to make it to my transfer flight

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

Everything was on time and service on the flight was great!

The boarding in Buenos Aires (at the on ramp) was not great. They had to check every carry on. Not a United problem but was a Buenos Aires problem.

Staff and aircraft were good. However, weather in Houston lee to a ground stop. We were looking at circling behind three other planes until the stop was lifted. Pilot said we didn’t have enough fuel for that. So we flew on to New Orleans as the closest port with immigration and customs staff. Landed there and sat in the plane for two hours plus while staff was sorted. Turned away by ICE. Waited for pilots to be switched out, but after they were approved by ICE. Then had to wait to get a runway because so many planes were ahead of us. Finally took off and flew back to Houston. We all missed our connecting flights because it took too long. Hotel voucher from United was only a link to booking site. Total BS. Finally got a flight out the next day after a night without sleep because all the Houston hotels were booked by rodeo and spring break crowds.

We changed our flight because of weather. Unfortunately we were on hold for over an hour, but since we were 5 people who all booked individually, we felt more comfortable doing it with an agent. It all worked out in the end.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Movie selections were very limited. Meals were not f So good.

Older airplane with worn out seats. No entertainment system at all. Connecting to Wi-Fi was problematic and hit and miss.

AA is flying sub par aging 787's to Tokyo. I fly other 787's long haul and these are at the bottom. Seats don't work well, tray tables don't work well and were dirty. The flight was great, the plane was not.

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