Find cheap flights from Caribbean to Portland

Find cheap flights from Caribbean to Portland

Round-trip
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Washington (WAS)
Portland
Tue 3/2
Tue 3/9
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Good to know

Low season

June Best time to beat the crowds with an average 6% drop in price.

High season

July Most popular time to fly with an average 1% increase in price.

Average price round-trip

$455 (avg. price over the last 2 weeks)

Good deal round-trip

$159 or less

Good deal one-way

$202 or less

FAQs for booking flights from Caribbean to Portland

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Top 4 airlines serving Caribbean to Portland

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,035 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Comfortable seats Friendly staff Soft landing"

Pros: "The aircraft was extremely clean. Crews were helpful and patient with passengers as they boarded and asked questions."

Cons: "Not a thing!"

Pros: "Cabin crew was great. Was told they don’t feel they can do a good job of serving 48 passengers in Premium Select with 2 crew."
Cons: "Image recognition step slowed boarding down a lot. Food and amenities on Delta Premium Select seem to be getting worse"

Pros: "Great flight attendants and service. Plenty of entertainment selection to make the long flight enjoyable. The boarding was chaotic because of the airport facility."
Cons: "The airport is too small for loading a full international flight."

Pros: "Fast service and precise timing"

Pros: "Great comfortable seats"
Cons: "Crowds in airport"

Pros: "Comfort is excellent"
Cons: "When traveling with the pet, personally always travel to Puerto Rico, we take our cat, I would like Delta to have the option of making the reservation online until paying for it, although you should always call to confirm, that would be super excellent."

Pros: "Clean plane. On time"

Cons: "They have to improve the boarding process a bit."

Pros: "Smooth ride"
Cons: "Seating"

Pros: "Flights were both timely"
Cons: "WiFi on flight from Atl to Tallahassee wasn’t working at first"

Pros: "Amazing service from crew"

Pros: "The entertainment"
Cons: "Space between"

Pros: "I missed my flight and you guys helped me catch the next one :D I was able to still make it yo my final destination within the same day"

Pros: "On flight entertainment was very good. Flight was smooth and ran ahead of schedule."
Cons: "They were out of vegetarian meal options. Really poor for a six hour flight. Also, the family behind us was atrocious, but that’s not Delta’s fault."

Cons: "Was refused to use the 1st clas restrooms but 10 minutes layer the flight attendant allowed an older gentleman and a lady to use them. I was in 10A with my service dog"

Cons: "Bigger personal space"

Cons: "Plane was way too hot and stuffy, wasn't until about 20 min into flight before started to cool down."

Cons: "No room to move very cramped"

Pros: "Excelent flight excelent service.."
Cons: "The entrance in the gate to the plane always disorganized"

Pros: "My flight from STX was delayed some 30 minutes. That made a dent in the 57 minutes I had to catch my Delta flight. Naturally we landed at gate A2 and Delta was boarding at Terminal 2 gate B9. Me with my knee replacement can’t run and my wheelchair was not in sight. Thank goodness I had a carryon with wheels. I was out of breath when I got to Delta and the last passengers were boarding. I started panicking and interrupted the ground steward who asked me to wait with a smile. I waited . So when I told them I was standby they waved me on after showing my passport. I couldn’t find my boarding pass. I was pleasantly surprised to get a seat in first class. I was so thankful. My first time. Good things come to those who wait! Thank you Delta."

Cons: "Entertainment system wasn’t working"

Pros: "Flight was on time and arrived a little early."
Cons: "I was seated next to a very large man (6’5” he said) and had no room in my seat. Thankfully the seats in front of us were empty and the flight attendant moved him."

Cons: "Ran out of snacks by the time they got to my row"

Pros: "I like the fact that entertainment and technology is always good."
Cons: "Boarding is always a horrible experience. I never know what zone is boarding. Your agents at the gates are overwhelmed with so many things."

Pros: "Service was great, crew was responsive, snacks were good per usual."
Cons: "The AC was blasting at an all time high, felt frozen to my seat, even asked for a blanket but “ they didn’t have any more “, had to tuck in my arms into my layered shirt. this was a morning flight and no breakfast was served ... they didn’t even have food available for purchase."

Cons: "N!A"

Pros: "Overall experience was awesome. Always love to fly delta. Nice spacious and clean aircraft. Enjoyed the entertainment system."

Pros: "Nothing"
Cons: "Flight delay 5+ hours poor Service"

Cons: "The bulkhead sears had no electrical outlet"

Pros: "The flight is short"
Cons: "Delayed from 930pm to 6am. Didn't tell us till almost midnight. Because of scheduling issues not weather or anything. The check in people had no idea what I was talking about when I tried to check in for my 6am rescheduled flight."

Cons: "Cancel my flight at 7:50 am to 1:50pm"

Cons: "All was well"

Pros: "Everything. I really loved that I could track where my checked luggage was, so when I arrived to my final destination I knew my bag was going to be there. The individual TV for my seat, so I could watch what I wanted. Having an USB port to charge my devices."
Cons: "Liked everything."

Pros: "No hubo retraso y salió todo el vuelo a tiempo. El personal fue atento."
Cons: "El espacio entre asientos es mínimo y es súper incómodo. La experiencia fue de incomodidad."

Pros: "In flight entertainment interface and options were great!"
Cons: "Very uncomfortable!! Spent the entire flight with my knees pressed against the seat pocket. One flight attendant was somewhat rude and unpleasant."

Cons: "I don't know why delta's service has deteriorated so much in the last few years. Last two times that I flew the service and attitude at the gate has been horrible. Seat assignment has become a dread. Upgrade options are over priced. I guess I will be looking for a new airline."

Pros: "Everything"

Cons: "Headphones suck"

Pros: "Flight attendants were competent."
Cons: "Air conditioning was extremely noisy."

Pros: "Excellent flight. Nice new aircraft."

Pros: "The plane was surprisingly comfortable. The seats had USB ports. The touch screens were clear and responsive. Most importantly, the service of the flight attendants was excellent. I was quite happy."

Pros: "Smooth boarding, no delays, quiet easy flight, arrived on time and quick deplaning."

Pros: "Just absolutely uneventful and quick."
Cons: "TSA"

Cons: "Just the nature of regional jet travel. Cramped, noisy. No problems, but harder to accept at the end of a 17 hour travel day."

Pros: "The onboard entertainment system was awesome.seats were comfortable."
Cons: "Flight was a bit bumpy."

Pros: "The gate agent was very helpful."
Cons: "The seat was very tight because the person who was next to me leaked over the arm rest into my space. I had a window seat. Also I had a torn ACL and requested a seat with more leg room and it was not assugned."

Pros: "Got my first class seat, smooth ride, early arrival"

Pros: "Everything was great. But the American Airlines can improve on not letting non-first class passengers use the restroom up front."
Cons: "The food! Bring back real food please"

Cons: "Free WiFi"

Cons: "Free WiFi"

Pros: "Fast transportation"
Cons: "It could be better if the pandemic was over, I think everything could be better."

Pros: "Everything was clean and new feeling"
Cons: "Food on offer was uninspiring."

Cons: "Personal monitors. Free food."

Cons: "Normal los azafato tienen que estar más pendiente ala tripulación que anda con nenes chiquitos los papas se se duermen y los salvajitos se creen que están en un campamento de verano.y quieren romper el avión más pendiente a eso"

Pros: "Super comfortable"
Cons: "Excellent"

Pros: "It left on time and arrived on time"
Cons: "Service, comfort and food as I would rate these below 0 if there was that option."

Pros: "Yes"

Pros: "Desde PR comenzó todo mal por supuesto desperfecto y los de servicio al cliente su solución fue que no podía hacer nada, cuando llegara a Miami resolviera lo de mi próximo vuelo. Fue un pésimo servicio"
Cons: "Pudo haber sido resolver para no perder la conexión a mi destino final."

Cons: "It was OK, no big issues or concerns."

Pros: "Old aircraft. Ucomfortable seat."
Cons: "uncomfortable seat"

Pros: "Communication"

Pros: "New onboard entertainment"

Cons: "My screen was not responsive most of the time"

Cons: "All the different prices for seats. I think it is a stupid system. Miss the good old days of air travel."

Pros: "Í like al the fligth ."

Pros: "The un seat entertainment"

Pros: "Spacious aircraft for a relatively short flight. I usually take a smaller aircraft that requires us to check our luggage. I'm reconsidering where I will have layovers now."
Cons: "Nothing"

Pros: "Arrived 30 minutes early"
Cons: "We had to wait 40 minutes in the runway before parking at the gate."

Pros: "That I arrived at my destination"
Cons: "Everything"

Pros: "Boarding was quick."
Cons: "1. No individual monitors. The pull down shared monitors are antiquated and not the standard now. 2. Would not fly AA from SJU again because of this. Unless I preloaded my iPad with movies."

Cons: "The flight attendant was arrogant. This is her job... just for $$$"

Pros: "comfortable"

Pros: "On time departure"
Cons: "Please use the A330 for the return trip..."

Pros: "Quick boarding and on time departure"

Cons: "I traveled with this carry on for numerous flights and for the last three legs of this trip w/of having to check it. For some reason they made me check it. because I had to spend time at the baggage claim carousels I almost missed the last train of the night back home. Fortunately all is fine, but it caused unnecessary stress."

Pros: "AA is excellent."

Pros: "Everithing is excelent."

Pros: "Is AA ever slightly embarrassed by the fact that their planes look like they're from the 80?"
Cons: "Shared TV?!!"

Pros: "That it went smooth and had room on the flight. Crew was good."
Cons: "Need more than just pretzels on the plane to give out"

Pros: "Flights were on time. Airport was clean."

Pros: "I had a great experience overall. I don't give 5 stars because there is always room for improvement no matter how good your service is."
Cons: "Size of the snacks"

Pros: "Todo muy bueno"

Pros: "More confortable seats."

Cons: "20 min delay at Dallas International"

Pros: "It was great."
Cons: "Everything was good."

Cons: "My stroller was taken right before boarding (as expected), when it was returned after the flight it was broken. We were delayed when leaving PR, after a slow boarding process. Then delayed once more when arriving."

Pros: "The flight to Miami was changed to Chicago but it was still comfortable. The seats were nice and having overhead tv was still nice."

Cons: "Cancelled flight, not notified in timely manner. Delayed Five hours due to be placed on connecting flights instead of a direct flight which is what I paid for."

Pros: "Todo estubo muy bien"

Pros: "Easy booking, Great prices"

Cons: "Arrived to the airport as suggested based on my departure time; only to find out that my flight was going to be delayed. Delays happen, i understand; however this delay impacted me catching my next connecting flight. There were no attendant at the designated gates to help me in Puerto Rico and calling directly was a nightmare. Never made it to Miami or to lax. Instead I was put on an even longer flight, San Juan to Philadelphia."

Pros: "Nothing"

Cons: "Flight delayed about two hours"

Pros: "My experience with American Airlines was horrible I was on flight 1357 and me and my husband started boarding the plane my husband stopped so put the bag in his seat the flight attendant Sonya #695655 taliago Portuguese was very nasty rude and disrespectful and came off very racist she told my husband to sit down and move out the house as he was placed in his bag on top of his seat then when my husband told her he was placing his bag up over the seats she asked to see his pass his boarding pass then he told her he just wanted to put his bag up over the other seat because there was no more bathroom over his seat she argue with my husband after my husband left the situation alone she then comes in with another flight attendant who was more Ruder than her it was a 20-minute delay with the both of them yelling at us and threatening to kick us off the plane then didn't offer us any drinks or snacks she kept giving my huaband nasty looks the whole 4hours she was very racist and I would never take American Airlines again experience was horrible"
Cons: "This is my first time flying American Airlines and my last time I'm a human being I am African American and Puerto Rican and just because of the color of my skin I was going to get put off the plane bad experience"

Pros: "The videos"
Cons: "Seats are small"

Cons: "Flite was late."

Pros: "I like just about everything, and the updates were great"

Pros: "The service of the air hostess."
Cons: "Definitely more space is better."

Pros: "Nice big plane, good movies, good overhead storage"
Cons: "Better food"

Cons: "Gate changes 6 different time Delays a lot Bad airline horror not recommended"

Pros: "Efficient"
Cons: "Free wifi"

Cons: "Cabin felt quite warm"

Pros: "One attendant did it all. And very well. Impressive."
Cons: "More snack options."

Cons: "Long delay."

Cons: "It took a very long time and multiple stops to get to my destination which should not have taken so long. Also it was extremely expensive for such a difficult itenerary to go from SJU to PVD."

Pros: "The respect for the time and the organization to boarding"
Cons: "My baggage did not arrive to my destination"

Pros: "United flew from Puerto Rico to Newark - did not attempt to schedule through airports affected by the hurricane in the southern US"
Cons: "United flights out of San Juan were expensive for those of us who were stuck by hurricane Irma and delayed. I paid almost double what my original carrier charged, but at least we got out 4 days earlier. I see that the carriers have dropped/frozen rates for customers stranded by hurricane Maria, but United was listed at least $100-$200 per ticket above other carriers"

Pros: "The airplane was nice, has power outlet, entretainment, and comfort."

Pros: "A list we were given a nother. Day to travel"

Pros: "Nothing whatsoever"
Cons: "The personnel was very rude. They charged me for my Service Dog which is illegal. Personnel yelled at me for having my service dog with me in the seat. They changed our seats, even though we picked them when buying them for a reason and my boyfriend and I ended up sitting in different lanes. Horrible experience. Landing and take off of the plane felt horrible. They double charged for one service dog. Even though I provided the Dr's note and her service dog tag."

Pros: "Nothing"
Cons: "That I had to pay for baggage separate from tickets purchased"

Cons: "Horible!!! Tanto tiempo viajando por United Airlines y nunca me habían cancelado el vuelo una hora antes como me sucedió el dia de hoy."

Cons: "2 hours delay"

Pros: "The atención!! Was really good"

Pros: "Comfort and food"
Cons: "wasn't comfortable and didn't have USB to charge"

Pros: "Not really impressed"

Pros: "Late"
Cons: "To late"

Pros: "Nothing it was late as hell"
Cons: "Nothin"

Pros: "Speed when they change us from gate"

Pros: "Nothing"
Cons: "Everything"

Pros: "Great experience"

Pros: "It was quick to checkin but considering we were one of the few flights it should have been that way."
Cons: "No snacks were given to my kids cuz they were sleeping, the plane was freezing took a lil while until someone finally listened to the complaints and turned the heat up. No one was able to give us direction at San Juan airport all information desk were closed. It was a very stressful frustrating time at the airport. We were flying with 2 young kids at 2am and there was no body there to help, anyone we asked question we were given the wrong info not pleased one bit."

Pros: "Good service. Good communication from the pilot."
Cons: "Uncomfortable seats. Should be widerr."

Cons: "Excelent service from kayak and the airline"

Pros: "Early arrival"

Pros: "Excelente"

Cons: "The gate agent for United at Newark was very rude and dismissive. Would not answer any of my questions or anyone who attempted after me. His attitude was very poor and seemed to not care about his job. Plane was late arriving in Portland Maine."

Pros: "On time...."
Cons: "Bigger plane than usual.."

Pros: "Nothing even went i got thete 55 minute early they didn't allow me to board the plaine i wad sent to anothrr airline and i. Still stuck in north carolina to 10:00 pm went i could been in my bed by now no more united for me."

Pros: "Overall, it was easy going"
Cons: "They didn't even provide nuts!! No snacks at all after the long trip."

Pros: "Everything went smoothly"
Cons: "Crampy seats"

Pros: "Everything"

Cons: "I was upgraded to first class. This was the first time this has happened to me, and I was excited. I had a great experience there and am grateful for it! The trip was quick, with low turbulence and no air pockets. I felt good. Thanks."

Pros: "Smooth ride"
Cons: "No drinks or snacks Well think it was only water or orange juice available"

Pros: "Everything"
Cons: "I have no complaints so far"

Cons: "Having to pay for food and WiFi access."

Cons: "That you have to pay for a movie and snacks."

Pros: "Staff was friendly and professional."
Cons: "N/A"

Cons: "The space between the seats, so small. Every time someone next to you needs to get out you have to get up too. So annoying. And the restrooms were not clean."

Pros: "Friendly staff, great drink selection, and comfortable seats"
Cons: "Could not find pricing for movie selection without first swiping my card"

Cons: "The seats didn't bend back to be comfortable. Only 1 inch!!! The back was restless"

Cons: "Deverted to Newark to get to portland"

Cons: "Checked luggage took close to 45 mins to arrive"

Pros: "Great service. ...communicate with customers about changes at all times."

Pros: "The service for wheel chair people was excellent"

Pros: "Row A"
Cons: "My checked bag was left in Chicago. Major inconvenience"

Pros: "The crew was great. Nice and very polite and was a very nice landing."
Cons: "Delats delays and more delays, also I'm a 6'5 guy who needs his space, very little leg room."

Pros: "Crew was amazing!"
Cons: "Social Distancing"

Pros: "Nothing. Not clean at all."
Cons: "Clean the plane. Space people out. Passengers were bunched together while other spaces were wide open. Not cool"

Pros: "Ok."
Cons: "Nothinh"

Pros: "Yes"
Cons: "No"

Pros: "nothing, I was trying and calling Fortine Airlines to change the flight because the situation of coronavirus and I didn't get answer ...Calling more that 500 times ... This is a scam"
Cons: "nothing, I was trying and calling Fortine Airlines to change the flight because the situation of coronavirus and I didn't get answer ...Calling more that 500 times ... This is a scam"

Pros: "Crew was friendly and amazing"
Cons: "Seats recline. At least free water/coffee for refreshment."

Cons: "Los precios son muy populares por lo que la incomodidad de los asientos se te olvida. En general todo es bueno. Aparentaba estar limpio y el servicio fue excelente."

Pros: "Nothing, 2 hrs delay waiting for a crew member and plane was ~25% full, no snacks or beverages"

Pros: "The softest landing on our whole trip!"

Pros: "Maria at the San Juan counter was very nice and helpful. I recently widowed and was very nervous about flying with Frontier. She put me at ease."
Cons: "I have nothing to add here"

Pros: "Seats are not that small . It’s comfortable"

Pros: "Nothing"
Cons: "Everything"

Pros: "Crew it was really nice"

Pros: "Good"

Pros: "2 hours waiting in the airport inside the plane"
Cons: "Notify what happen..."

Cons: "Some free snack and soda or water"

Pros: "Yea"

Cons: "Seats didn’t recline, it was a bumpy ride nothing was free! That’s what we (didn’t) pay for!"

Cons: "No dieron gratis nada de café ni agua .y las azafatas estaban burlándose de los pasajeros es una falta de respeto"

Cons: "Tickets were purchased together but yet one ticket was zone 1 and the other two were zone 3"

Pros: "The crew was polite and knowledgeable"
Cons: "The seats were very uncomfortable overnight flight could not sleep"

Cons: "Free food and baggage"

Cons: "The flight came in early which was great, but it Took 2 hours to get our luggage. Apparently there were not enough Frontier personnel."

Pros: "Crew was fine, there need to be a great improvement on the seats"
Cons: "Seats"

Cons: "Make seats recline"

Cons: "No TV no music not entertaining"

Pros: "I live in Orlando. I made a mistake. The travel was supoused to be from Orlando to San Juan ."

Cons: "I believe the pilot flew to high. Me and my friends ears popped severely and caused pain."

Pros: "Price, on time and cleaness."
Cons: "No entertainment (magazines, movie, tv) and seats a little uncomfortable."

Pros: "Quick and easy"
Cons: "I’m a small person.... and i barely had room sitting inside the aircraft"

Pros: "On time flight. Friendly crew."
Cons: "No free beverages, very cramped seating."

Pros: "non-stop, pilot made up time of initial delay due to medical, price"

Pros: "Nothing"
Cons: "That they charged me $65 for a carry on bag ..the person told me an amount went to the machine get a card get charged $5 extra for the card go to the counter they tell me a diffrent amount have to get a diffrent card more money..i made a facebook post to never fly with this company ever again"

Pros: "Efficient, cost effective."
Cons: "Chairs don't recline, food for "purchase" only."

Pros: "i Liked that I was able to fly home"
Cons: "The cost of the flight once you add the cost of carry on or checked bag for that I could’ve flew Delta with snacks"

Pros: "Seats are just not made for trips longer than 2hrs"

Cons: "Flight from sju to mco was delay 3 times. Lost my mco to pvd flight. And then i was send from mco to raleigh and another delay. Then raleigh to pvd with one more delay and loss bags. All frontier gave me was $50voucher when i lost hundreds in hotel and car and taxi and my time. The depart time for the sju flight was 3am i have to be in the airport 2hrs before so this was a allmost 24hrs flight for me because i reach my destination at 4pm. I expect comunication from you."

Pros: "Nothing. The only thing that was good it was that it was a direct flight, however with the delay it make it longer than other flights with stops"
Cons: "Will not use your airline in the future due unreliable flights. Never experienced this with any other airline"

Pros: "The price is good"
Cons: "I don’t like the chairs"

Cons: "I don't like the seats, they have no cushion and they don't recline. Plus the tray table is super small. Also you pay for all drinks. Another thing the pressure is horrible in these planes. It seems they try to cut down on cost so the cabin is not pressurized right to reduced your ears from getting the over pressure from the ascend and descent of the plane."

Pros: "The crew personnel aboard the plane was friendly and the seats confortable."
Cons: "They made me pay $45 for a 16 inches carry on back that I have as my only luggage , because according to the counter employee, my handbag (purse) was too big so it was considered as a second carry on. I requested a waiver, because I’m an Army Veteran, a senior citizen, but it was denied by the counter employee."

Pros: "The atendance and organisation"
Cons: "The seats. They shoul recline and not be steady in one position"

Pros: "Quick Price Nice attendants"
Cons: "Seats don’t lean back. But not bad."

Pros: "I really liked how amazingly friendly all the crew were. They all had a real smile and tried to help every costumer Kindly. Never saw this from ANY airline. They are EXCELLENT!"
Cons: "Many crying babies, most but that's nothing you could do LOL!"

Pros: "Cheap flight"
Cons: "No complimentary snacks at all. I paid $3 for a coke, very little seats with no elbow or leg room nor to lean back. I felt like i was in a can."

Pros: "Fast luggage checking"
Cons: "No cash accepted for overweight baggage"

Pros: "Check in online was easy and gate boarding a breeze, and even got a seat upgrade... THANK YOU!!!"
Cons: "Having to wait to drop off bags in terminal counter rather than curb drop off for those that have the online check in"

Pros: "Best treatment of military personal."
Cons: "Boarding was a bit chaotic."

Pros: "Good price"
Cons: "Worst trip ever"

Pros: "Flight got cancelled at the last minute and they didnt try to communic"
Cons: "Still waiting for my refund"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Caribbean to Portland

Airlines flying from Caribbean to Portland have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Caribbean to Portland

Mandatory masks

Masks required on board, masks provided on flights from Caribbean to Portland

Social distancing seating

Middle seats unavailable to book on flights from Caribbean to Portland

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Caribbean to Portland

Book cheap flights from Caribbean to Portland

Recent round-trip flight deals

3/13
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Frontier
10h 42m
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Recent one-way flight deals

5/3
Mon
2 stops
Frontier
21h 54m
SJU - PWM
3/11
Thu
2 stops
Frontier
12h 23m
SJU - PWM
3/11
Thu
1 stop
Frontier
11h 50m
SJU - PWM
5/2
Sun
2 stops
Frontier
13h 25m
SJU - PWM
3/12
Fri
1 stop
Multiple Airlines
27h 55m
SJU - PWM
5/3
Mon
3 stops
Multiple Airlines
27h 50m
SJU - PWM
3/12
Fri
2 stops
Multiple Airlines
21h 34m
SJU - PWM
5/2
Sun
3 stops
Multiple Airlines
34h 39m
SJU - PWM
3/11
Thu
3 stops
Multiple Airlines
34h 56m
SJU - PWM
6/17
Thu
1 stop
Delta
9h 22m
SJU - PWM
3/12
Fri
3 stops
Multiple Airlines
26h 24m
SJU - PWM
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