$162 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 5/2. 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

Thu, May 28 - Fri, May 29
JetBlue Logo
1:45 pm - 10:25 pm
SJU
-
PDX
11h 40m
1 stop
JetBlue Logo
11:40 pm - 4:05 pm
PDX
-
SJU
13h 25m
1 stop
$393JetBlue
Thu, Apr 30 - Tue, May 5
Delta Logo
1:25 pm - 10:16 pm
SJU
-
PDX
11h 51m
1 stop
Delta Logo
7:00 am - 11:59 pm
PDX
-
SJU
13h 59m
1 stop
$450Delta
Sat, Apr 4 - Fri, Apr 10
American Airlines Logo
10:07 am - 12:22 am
MBJ
-
PDX
16h 15m
1 stop
American Airlines Logo
12:59 am - 1:10 pm
PDX
-
MBJ
10h 11m
1 stop
$454American Airlines
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
10:07 am - 12:22 am
MBJ
-
PDX
16h 15m
1 stop
American Airlines Logo
11:47 pm - 3:37 pm
PDX
-
MBJ
13h 50m
2 stops
$459American Airlines
Tue, Apr 21 - Sat, Apr 25
Delta Logo
12:55 pm - 10:02 pm
SJU
-
PDX
12h 07m
1 stop
Delta Logo
6:28 am - 11:12 pm
PDX
-
SJU
13h 44m
1 stop
$470Delta
Thu, May 28 - Fri, May 29
Southwest Logo
2:00 pm - 12:10 am
SJU
-
PDX
13h 10m
2 stops
Southwest Logo
3:00 pm - 8:55 am
PDX
-
SJU
14h 55m
2 stops
$491Southwest
Mon, May 11 - Fri, May 15
Southwest Logo
6:50 am - 8:10 pm
SJU
-
PDX
16h 20m
2 stops
Southwest Logo
3:00 pm - 8:55 am
PDX
-
SJU
14h 55m
2 stops
$505Southwest
Fri, Apr 24 - Sun, May 3
United Airlines Logo
1:10 pm - 9:59 pm
SDQ
-
PDX
11h 49m
1 stop
United Airlines Logo
10:15 pm - 2:10 pm
PDX
-
SDQ
12h 55m
1 stop
$548United Airlines
Fri, Apr 24 - Sun, May 3
United Airlines Logo
1:10 pm - 11:44 am
SDQ
-
PDX
25h 34m
3 stops
United Airlines Logo
10:55 pm - 2:10 pm
PDX
-
SDQ
12h 15m
2 stops
$576United Airlines
Wed, Apr 29 - Sun, May 3
Air Canada Logo
1:55 pm - 9:10 am
KIN
-
PDX
21h 15m
2 stops
Air Canada Logo
3:25 pm - 1:55 pm
PDX
-
KIN
20h 30m
2 stops
$602Air Canada
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$162
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 4% 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.

Reviews of the top 4 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 4295 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Great plane, great attendants,great flight crew,on time. Wonderful flight home..

10.0 ExcellentAnonymous, Feb 2026
CUN - STL
Read more Southwest reviews

Great plane, great attendants,great flight crew,on time. Wonderful flight home..

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

This is my worse experience with Delta. My colleagues and I were traveling to ICT for work. Usually we connect in Dallas, but this year we decided to book with Delta and connect in Atlanta. We were excited to fly with Delta because we hear great things and Delta is one of my top choices when choosing an airline for travel. On the connecting flights to and from Wichita/Atlanta - it felt hot and uncomfortable on the plane. The plane to ICT was smaller and older and did not have any wi-fi or entertainment. The most terrible experience was at boarding in Atlanta both times traveling to Wichita and then back to Tampa. First on our flight from ATL to ICT - the attendant scanning our boarding pass made us go back to the line when we went up to scan our passes to wait. After a few minutes, she allowed us to come back up to scan but then she asked what boarding zone we were. We told her zone 5, and since we were standing on the wrong side of the small rope partition, she made us go back to stand on the right side. There was another gentleman that came up to board and scan his pass, and she mentioned he was also on the wrong side but she let him go through. Our group had to walk back and forth for no reason, causing an unnecessary delay to board the plane. We have never experienced anything like this, especially when the boarding area was completely empty and everyone already boarded since boarding was earlier than the original boarding time. On our flight from ATL to TPA, the attendants scanning our boarding passes had us scan our passes twice, not explaining to us what was going on. They automatically started tagging our carry on bags and did not explain to us or tell us what was going on and why this was happening. Obviously we knew our bags were being forced to check in but with no reason. There was no announcement or mention and I have never had anyone force me to check in my bag before boarding the plane. We assumed the overhead bins were full but when we boarded the plane, there was a lot of empty bins and a lot of spaces to put our bags. We all were disappointed and frustrated with Delta and will be hesitant to fly Delta again or anytime soon.

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

The landing was the worst I’ve experienced with a flight.

Overall we had a good experience during our flight from San Francisco to Houston.

Airport terminal was outdated, flight was on a small jet with no wifi

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Nothing also dont give to people that disgusting blanket and pilow.

it was a very short flight so my expectations were low.

Good until I was put on air canada flight Houston Vancouver not even one cookie

So bad, flight was been cancelled due to aircraft problem, so ended up buying anothet ticket.

As great a red-eye flight as red-eye flights can be.

Good flight. However, when booked flight with United, assumed the layover included by United in San Francisco of 1 hr and 40 minutes was sufficient . Not so and would recommend at least 2 hours or more. Needed to go through US immigration (very long lineups), then pick up bags, take all the way to another terminal, running because we did not have sufficient time. We made the flight because they held the door for us but luggage didn’t follow.

Very old flight - time to retire it for newer airplanes

Waiting for gate in RDU for more than 20mins is crazy.

Flight was on time and there was an empty seat next to me. That makes for a good flight!

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

I like that the flight attendant was very attentive and helpful. The meal menu could have more of an variety of food choices.

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

No Snacks or Entertainment. The flight was short, snacks should still be given.

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

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