Find cheap flights from Caribbean to Portland from $97
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 12/11. 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.
Round-trip
1 adult
Economy
Sat 10/28
Sat 11/4
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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
8.1
JetBlueOverall score based on 19485 reviews
79entertainment
83boarding
86crew
82comfort
78food
82overall
Airline reviews
Cons: "Leaving on time. Delayed more than an hour. No explanation given."
Cons: "Leaving on time. Delayed more than an hour. No explanation given."
Cons: "Flights delayed!!! 4 hrs!! Rude help ! Delayed getting on cuz of no wheelchair had to wait additional 10 just for a wheel chair !! Then attendant set off door alarm!! So now had to wait for police to turn off alarm!!! By this time enough!!!!!!!! Worst ever and I’m traveling with three young child."
Pros: "The captain was excellent and he greeted everybody and he's a great pilot."
Pros: "The schedule of a late-night"
Cons: "No chargers, terrible seats and tony screens (mine didn’t work.) Somwone needs to service this route better"
Pros: "A quite enjoyable experience."
Cons: "There was a fascist on the flight, which was uncomfortable."
Pros: "Got randomly given a seat with extra leg room. First time on jetblue but the setup was nice!"
Pros: "The times of the flights, the cost, the legroom"
Cons: "The seat was narrow and somehow uncomfortable, perhaps too hard."
Pros: "The crew is always accommodating and friendly. They ground crew works very hard to make the flight attendants job a little easier."
Pros: "I got more room than most, sitting in the front row."
Cons: "Skipped for drink service. My eyes were closed, I wasn't sleeping, but by the time I was aware of the steward, he was gone down the aisle and serving the people behind me. Also, even though I am disabled, the steward did not help me to put my bag up in the overhead compartment, even though he insisted, the very moment I sat down that my bag needed to be placed up top. No visible plugs for headsets, or USB to charge phones. This plane looks older than I am and I'm 47 years old!"
Pros: "I've been flying budget airlines for so long that I was almost shocked to fly an airline that actually cares about its passengers! I kid you not, when they offered coffee to all passengers, I was so sure they would charge us I turned it down. Then, I noticed no one else was paying for it. The next time free snacks and drinks came around, I made sure to grab some! I also appreciated the few extra inches of leg room in every row. Being 6'3", not many planes are designed with your comfort in mind. I fit fairly comfortably in a non-emergency row seat. Last time I flew to Baltimore for work, I had a terrible experience with a different airline. It was $200 less expensive than most airlines, but I ended up paying more in baggage fees and seats. It was only a 1 hour flight and My boss said, "Cheap things usually cost you more, in money, time, and emotion" and nothing has been truer. I always assumed that flights were always unpleasant experiences. Now, I know better."
Cons: "The seats, while having more than average leg room, still weren't very comfortable. Not that I'm expecting a luxury experience while flying economy, but I felt as though the headrest was farther back than average. I can usually fall asleep on a plane and wake up without neck pain, but I really struggled to even figure out a relaxing position this time around. I also did not know that JetBlue did not serve meals on cross-country flights. Or, on any flights for that matter. Had I known, I probably would've picked up a breakfast sandwich before boarding."
Cons: "There was a family with kids climbing all over the Sears. Would have been nice if the crew reigned then in a bit."
Pros: "The two people who were in charge of boarding the plane were especially nice, efficient, and accommodating. I really really liked them."
Cons: "The flight was too warm."
Cons: "Food was terrible. Paid for first class, expected something better than coach. Our food choice was a ham sandwich, there were better choices but the crew took them for themselves so nothing left for the 1st class passengers. Similar situation on our eastbound flight the week earlier. I doubt if Delta knows or cares that this occurs. After paying more than twice the coach fare, we expect something better than a ham sandwich on a coast to coast flight."
Pros: "New long haul service is a real improvement in quality"
Pros: "The crew on both legs of our trip were nice and accommodating."
Pros: "The delta crew both ways between Portland and London was excellent! They saw to our every need and were smiling every air mile of the way. Plane"
Cons: "Need to have food choices available for those with allergies. Almost everything had gluten and soy in it and I am very allergic to those. I had to give away all snacks and most of my food. Even in comfort+ class the seats are tiny with little legroom. Also, please clean the bathroom every few hours"
Pros: "The crew was very friendly. Boarding was quick."
Cons: "Seat size in Comfort+ was still cramped. The person sitting next to me(in the middle was a fairly large (height not weight) and his arms and shoulders were pretty much flowing into my seat( I sat by the window). Leg room of course was fine. Very cold draft coming from the airplane(window?)"
Pros: "How does one describe spending 10+ hours in a metal tube approximately 18 feet wide at 30,000 feet with 300 of your closest friends breathing the same air while having the seat in front of you pushed back so you cannot adequately see the passenger monitor because it's too close to focus on as your knees are under your chin? Flying in "steerage" is not comfortable as humans get larger and airplane seats get squeezed smaller. Please unsqueeze! Cabin crew members were excellent. Other than that, Europe was great!"
Cons: "See other side."
Pros: "On the fight back I had enough space; good service; fine food. Great trip. On the way to Amsterdam, I sat next to a very overweight woman and her body hung over my seat. I couldn't move around enough and I ended up with a trigger point problem which immobilized me for 3 days and kept me from sleeping at night. It was very disappointing, since this was a family visit trip."
Cons: "See above!"
Pros: "Free wine and spirits and food really not too bad in economy Very large movie and tv show library - something for everyone Friendly cabin crew"
Cons: "Overhead bins a bit small on this older 767-300"
Heathrow is a nightmare in general (crowded, etc). BA was great - having to take a bus between the gate and the plane is a bummer.
American Airlines customer service was extremely poor. They canceled our flights multiple times. Then put us on standby trying to get on flights instead of booking us on a confirmed flight to get us home. So flight after flight we kept our hopes up just to be disappointed and stuck from a connecting flight. We had never been to Dallas so we were sleeping on the floor at the airport waiting to get home.
Pros: "Crew was friendly and nice"
Cons: "Absolutely no covid regulations in place, completely packed flight, boarding was horrendous everyone going in at once"
Pros: "Crew was good"
Cons: "Seating sucked, did I say sucked. Greed never give the customers that pay your bills better comfort and leg room. Greed greed greed. Scumbags"
Cons: "The head phone jacks were loose so watching a movie was extremely difficult. The aisle is so small you can’t even walk down it without bumping people who are seated. It seemed like none of the crew wanted to be there."
Cons: "The flight attendants were friendly, watched a movie, thanks for the ear buds to listen to the movie. There was a lot of turbulence but I feel our pilot managed it very well bringing us in safely and smoothly as possible. I can't think of anything that could have been improved on."
Pros: "On time, crew was nice."
Cons: "Seats are too tight. Board from the outsides in, not front to back. Windows seats in the back go first (after first class, ADA, etc), and fill the cheap seats back to front. As it is, literally everyone with an aisle seat ends up on first and overheads fill before people have a chance to know, requiring a lot of against-the-flow foot traffic and delays pushing away from gate."
Pros: "Good crew"
Cons: "The boarding process was terrible. The boarding time changed every 5 minutes"
Pros: "None"
Cons: "I had very bad emotions sickness from London to Dallas TX. After I got on the plane I asked one crew member if I have any chance to switch the seat to sit by the bathroom because I am very sick, but seems no one cares. They said there is nothing they can do and tell me to get back to my seat. The whole fight I was sick. It was a horrible no crews member were asked me how I felt. No crews member checked me if I were ok. I had fever and so sick. There were late. I never have any bad fight like this forever."
Pros: "Good service in-flight. Pretty comfortable seats and decent in-flight food/beverage options."
Cons: "Crew was slamming overhead compartments before take-off and would ignore questions from passengers. Late take-off, very late gate change and late arrival. No help from crew on the plan to get bags taken care of so boarding took forever."
Pros: "Customer service at the Denver made my scheduled 18 hr itinerary from STL to PDX via Denver a mere 7 hour one. That saved me so much money in dining out and hotel rooms that I can’t thank them enough."
Cons: "The food choices weren’t great on the Denver to PDX flight but that’s usually how it is."
Pros: "Seats comfortable. Cabin and bathrooms really clean. Crew friendly and efficient."
Cons: "Pockets on back of seat need to be bigger/deeper."
Cons: "Getting to San Francisco flight was canceled, make a line for 3.30 hours to let us know what they were going to do with us, they give the place to go at 3 a.m with not directions were to take a bus , later someone come and told us the bus stop running at that time and I have to go upstairs to take a taxi, I was alone and not use to be alone at that time never in my live I had to pretend I was afraid. Of course the hotel only take you until 12pm so I spend so many hours in the airport waiting for re ticketing they told us to be at 6pm we wait and I got my ticket leaving at 9.45pm but the crew come one hour and half late. From Panama to Lima flight was late . I had a conference very important to be Saturday morning, I lost my investment and relationships with the company I was going to start a business there excuse was they couldn’t relay on my punctuality, honestly. I got there more than a day and half LATE. If you ask me how was my trip I will tell you horrible and I can’t recommend anybody, this company doesn’t have any personality at all"
Cons: "The gate changed, the United App did not update and we did not look at the flight status board upon arrival as we were relying on the United App. Ran all the way to the 'old' gate (90) only to realize b/c we heard something over the loudspeaker about a flight to Portland at Gate 60 (we had just landed from IAD right near that gate). Looked at the board and realized the gate had changed, had to run all the way back to the other gate and it wasn't boarding yet. When I mentioned all this to the gate agent, she told me i should have checked the board & refreshed my app...i refreshed my App 6 times and it still didn't update - i'm not an idiot but she made me feel like one. She had no sympathy and was not nice or helpful. When we got on the flight, realized it was empty and we were sitting WAY in the back when there were plenty of open seats, so we moved up thank God!"
Cons: "1. The flights within the US and Canada was delayed. 2. The United Airline staff in San Francisco told me to pick up my luggage when I get to Seattle despite of the fact that my final destination was Vancouver. I questioned the staff about this ata this seemed odd, but he insisted that I pick up my luggage in Seattle. Upon arrival to Seattle I went to the baggage claim area to find out that my luggage was already put through to the connecting airline to Vancouver. This resulted in me having to go through a long line of passengers to do all of the security checks again to enter the international airport gates. This almost resulted in me missing my connecting flight to Vancouver. The only saving grace was that the flight was delayed by another hour. 3. Changes made on my connecting flights were only given to me during my check in at Auckland. My previous booking was Auckland -San Francisco - Portland - Vancouver. The boarding pass I was given in Auckland omitted Portland and was changed to Seattle. I was never informed about this by United Airlines. 4. United Airlines website NOT allowing me to log in using my e-mail."
Pros: "Nothing."
Cons: "We had to fly from Chicago to Atlanta then watch to delta just to get to Portland. Unbelievable."
Pros: "Nothing"
Cons: "Never got to do this flight because of the previous flight which is reviewed below: My seat was broken and wouldn't stay in upright position. This really pissed off the passenger behind me. Crew kept telling me to put my seat upright, I kept having to tell them the seat was broken. Old airplane with no in-seat entertainment. they advertise on the seat that you can watch all their entertainment content for free, but then you have to pay for wifi to watch so it's not free then, is it? Every movie or show requires "additional software" so you have to purchase internet to do the download. This is an 11 hour flight, I would have appreciated being able to watch a movie or something without forking out $30. Flight was delayed, so we were low on time to make our connection. I asked a flight attendant twice if we could get help deplaning early or at least get moved up some rows since we were in the very back of a 747 (there were plenty of vacant seats). They said no, and told us that customs would only take a minute and that the other united flight knew we'd be coming and would wait. I don't usually fly united; other airlines typically will actively take steps to help (like moving connecting passengers to the front shortly before landing) if they are the cause of the delay. Customs had only one agent working and we were pretty much last in line so that process took over an hour. Just moving us 10 rows forward before landing would have made all the difference because our connecting flight closed its doors and taxied for takeoff less than 5 minutes before we arrived. They had some united employees guiding and directing a couple of passengers that were going to be late for a connection to LAX, but no help for those of us connecting to portland. Customer service didn't even offer a verbal apology. Last time I flew with united, I also had a terrible experience for different reasons. I did not intend to fly united for this flight, but I purchased tickets through and for Lufthansa, and this flight was regrettably operated by united. Another thing I don't like - the food was horrendous. It was a breakfast sandwich that was advertised as "hot and fresh" on the packaging but was served straight from the refrigerator. I was in the middle seats with one person to my left and two people to my right. Everyone took only one bite and threw away the rest. Just don't bother serving the food if it's going to be that bad, it's very wasteful. I always appreciate a hot towelette after a long overnight flight. United offered no such thing which was a first for me. Regarding boarding: they called us all up to line up in boarding groups and then we had to stand in line for 65 minutes. I have a bad back and had to sit on the carpet to avoid being last in line and not having space for my carry on bag. Would have been nicer if they would have just let us sit in the chairs at the gate in comfort until they were ready to board."
Pros: "The older planes of United Airlines could use some remodeling. The entertainment system with controls in the middle of the arm rest where the elbow rests is such a bad idea, didn't even bother with this crappy unintuitive system. It was annoying and flashy with bright advertisements or something popping up on a night time flight just sooooooo annoying, turning it off was not intuitive and had to ask the flight attendants how to turn it off during their very busy work of handing out packages with five miniature pretzels and drinks to the passengers, was happy to get a whole cab of juice to myself though."
Pros: "The crew was courteous, the pilot was the best one out of the 4 flights I had taken that weekend."
Cons: "We used to get more for our money. 20 minutes isn't enough time to use the restroom and find and eat food after hauling from one terminal to another on the light rail. Then we are given a mystery snack mix and a drink, I remember we used to get meal service for flights that long. Boarding was very confusing for people in groups 3, 4, & 5 as we were all grouped in one line. Group 3 was called and 4 & 5 tried to board. A simple PA saying that group 3 should be in line first would help the confusion. The lady performing the boarding call was rude. Saying "I don't care I will just take thier bags and check them, they don't have a choice". That's a great way to start an argument. Then the seat pitch is awful, I'm not the only person flying that is over 6ft tall. My knees were directly impacting the meal tray arms of the seat in front of me the entire flight. Shorter flights weren't bad, but sitting on the ramp waiting for takeoff for at least 30 minutes plus the flight time was pretty painful."
Pros: "We didn't die in a fiery explosion. The flight attendants were nice too"
Cons: "I know that I was in economy, but JEEZ! Everything was super cramped. I don't take up much room, but you couldn't do anything. I had a larger dude partway into my seat, my seat barely leaned back (and would slowly creep it's way to upright anyway), and of course I had no leg room at all, not that I was expecting that. Also, a six hour flight with just a snack offered is pretty absurd. I know cutting corners saves money, but I'm still paying money and it would be nice to have a slightly more pleasant experience. This was easily one of my worst flight experiences"
Pros: "They were timely."
Cons: "I don’t think I showed good judgement using this airline. The “low fares” are a gimmick because the price is comparable to a normal airline once all the add ins are taken into account. I think charging for a carry on ridiculous. The cabin wasn’t clean. A brown fluid dropped from the in cabin baggage compartment on my clothes during the flight. Never again."
Cons: "Flight was delayed staff seemed stressed and too familiar with unsatisfied customers"
Cons: "The attendant at the gate was rude and trying to rush us through . Did not want to wait for me to get my boarding passes on the phone. She was agitated by the time it took to unlock my phone and get them shown."
Cons: "I don’t think I will fly with them again. They charge for everything. Not cool. They charged for my carry on which is completely ridiculous. I’m regretting my decision to buy a ticket from them big time."
Pros: "My refund"
Cons: "The lack of customer care at the airport counter and on the phone until a Supervisor was finally connected. I appreciate Jam, for all her help and she apologized for the staff! Thank you"
Pros: "Everyone was nice."
Cons: "No free water...now that's cheap. $40 of the savings on the flight eaten by the baggage fee was expected, but a 40 lb. limit on said bag was a bummer."
Cons: "I do not like how they just roughly tossed your suitcase and belongings around things are very breakable that are in luggage and I was surprised that they were unable to put a tag on my suitcase that said I had fragile items in it I personally seen how they take the luggage and just throw it onto the luggage belt most of the time it's thrown and Landing upside down instead of right side up the way it is so roughly tossed around things can end up being broken"
Pros: "Boarding was efficient, planes were on time, crew was nice."
Cons: "When we arrived at our destination we sat on the runway for nearly an hour before we could deplane, we were given an estimated wait time of 20-25min. This airline will also nickel and dime you for everything. Charged $40+ for carry on luggage or checked baggage and more if you dont add the luggage when you check in online, which makes the low fare completely irrelevant. Didn't even have free water on the plane, had to buy a $3 bottle. They also charge you $10 if you don't print your own boarding pass and $8 to pick your seat. Won't fly with them again."
Pros: "The crew was great even though the airline was having problems."
Cons: "The terminal was DISGUSTING. Food wrappers everywhere. The air condition was not working. The flight was delayed twice."
Pros: "It was the same as the first leg of my flight. Not good"
Cons: "The same as the first flight. I will not fly Spirit Airlines ever again."
Book cheap flights from Caribbean to Portland
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10h 15mSJU-PDX
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16h 45mPDX-MBJ
$399
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10/2Mon
multi-stopSpirit Airlines
37h 23mSJU-PDX
10/11Wed
multi-stopSpirit Airlines
35h 44mPDX-SJU
$421
10/3Tue
multi-stopSpirit Airlines
33h 12mSJU-PDX
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multi-stopSpirit Airlines
35h 44mPDX-SJU
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multi-stopFrontier
15h 03mPDX-SDQ
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48h 15mSDQ-PDX
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35h 33mPDX-SDQ
$529
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multi-stopDelta
10h 40mSJU-PDX
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11h 36mPDX-SJU
$600
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$609
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$629
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multi-stopDelta
10h 40mSJU-PDX
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multi-stopDelta
11h 36mPDX-SJU
$645
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multi-stopJetBlue
14h 07mSDQ-PDX
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multi-stopJetBlue
10h 30mPDX-SDQ
$767
9/29Fri
multi-stopJetBlue
14h 07mSDQ-PDX
10/17Tue
multi-stopJetBlue
10h 30mPDX-SDQ
$835