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Flight Deals
Cheap Flights from Portland to Caribbean
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Portland to Caribbean Plane Tickets
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Caribbean 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 Portland to Caribbean
Mon, Jan 11 - Thu, Jan 14
6:00 am - 3:15 pmPWM Portland-NAS Nassau Intl
9h 15m1 stop New York LaGuardia
4:25 pm - 11:06 pmNAS Nassau Intl-PWM Portland
6h 41m1 stop New York LaGuardia
$328Delta
Tue, Jan 19 - Fri, Jan 22
6:00 am - 3:15 pmPWM Portland-NAS Nassau Intl
9h 15m1 stop New York LaGuardia
1:20 pm - 11:49 pmNAS Nassau Intl-PWM Portland
10h 29m1 stop New York John F Kennedy Intl
$328Delta
Thu, Dec 3 - Thu, Dec 10
7:00 am - 1:48 pmPWM Portland-NAS Nassau Intl
6h 48m1 stop Newark
12:55 pm - 9:12 pmNAS Nassau Intl-PWM Portland
8h 17m1 stop Newark
$337United Airlines
Sat, Jan 30 - Sat, Feb 6
10:52 am - 11:59 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
12h 07m1 stop Philadelphia
8:15 am - 9:43 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
14h 28m2 stops Philadelphia Washington, D.C. Reagan-National
$356American Airlines
Sat, Jan 30 - Sat, Feb 6
10:52 am - 9:30 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
9h 38m2 stops Philadelphia Miami
8:15 am - 9:43 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
14h 28m2 stops Philadelphia Washington, D.C. Reagan-National
$356American Airlines
Sat, Feb 6 - Sat, Feb 13
3:14 pm - 12:36 amPWM Portland-SJU San Juan Luis Munoz Marin Intl
8h 22m1 stop Newark
8:05 am - 2:41 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
7h 36m1 stop Washington, D.C. Dulles Intl
$356United Airlines
Wed, Feb 3 - Sat, Feb 13
12:50 pm - 12:40 amPWM Portland-SJU San Juan Luis Munoz Marin Intl
10h 50m2 stops Baltimore/Washington Orlando
5:40 am - 3:30 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
10h 50m1 stop Orlando
$356Southwest
Wed, Feb 3 - Sat, Feb 13
12:50 pm - 11:05 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
9h 15m1 stop Baltimore/Washington
5:40 am - 3:30 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
10h 50m1 stop Orlando
$356Southwest
Sat, Dec 5 - Sat, Dec 12
7:12 pm - 10:23 amPWM Portland-SJU San Juan Luis Munoz Marin Intl
14h 11m1 stop Tampa
3:27 pm - 4:55 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
50h 28m2 stops Hartford Bradley Intl Charleston
$358Multiple Airlines
Sat, Oct 31 - Tue, Nov 3
9:48 am - 1:50 amPWM Portland-SJU San Juan Luis Munoz Marin Intl
16h 02m1 stop Orlando
3:55 am - 4:24 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
13h 29m2 stops Orlando Raleigh-Durham
$373Multiple Airlines
Recent one-way flight deals from Portland to Caribbean
Sun, Nov 15
6:47 pm - 1:45 pmPWM Portland-AUA Oranjestad Reina Beatrix
17h 58m1 stop Philadelphia
$145American Airlines
Sun, Nov 15
6:47 pm - 3:10 pmPWM Portland-AUA Oranjestad Reina Beatrix
19h 23m2 stops Philadelphia Miami
$151American Airlines
Wed, Dec 30
7:44 pm - 11:49 amPWM Portland-NAS Nassau Intl
16h 05m1 stop Newark
$162United Airlines
Mon, Dec 7
6:00 am - 4:57 pmPWM Portland-MBJ Montego Bay Sangster Intl
10h 57m1 stop Atlanta Hartsfield-Jackson
$167Delta
Fri, Feb 19
4:48 pm - 6:15 amPWM Portland-SJU San Juan Luis Munoz Marin Intl
12h 27m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$178United Airlines
Mon, Nov 2
6:01 am - 4:27 pmPWM Portland-MBJ Montego Bay Sangster Intl
10h 26m1 stop Atlanta Hartsfield-Jackson
$198Delta
Tue, Dec 1
5:15 am - 2:45 pmPWM Portland-MBJ Montego Bay Sangster Intl
9h 30m2 stops Baltimore/Washington Orlando
$208Southwest
Sat, Oct 31
5:09 pm - 3:29 pmPWM Portland-MBJ Montego Bay Sangster Intl
23h 20m3 stops Raleigh-Durham Orlando Atlanta Hartsfield-Jackson
$237Multiple Airlines
Mon, Apr 19
1:05 pm - 10:10 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
9h 05m2 stops Baltimore/Washington Tampa
$259Southwest
Fri, Feb 19
5:00 pm - 12:37 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
18h 37m3 stops Charleston Tampa Fort Lauderdale
$307Multiple Airlines
Recent last minute flight deals from Portland to Caribbean
Thu, Oct 22 - Mon, Oct 26
6:01 am - 4:49 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
12:50 pm - 11:35 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
10h 45m1 stop Atlanta Hartsfield-Jackson
$538Delta
Tue, Oct 27 - Thu, Oct 29
6:30 am - 3:55 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
9h 25m1 stop New York John F Kennedy Intl
3:20 pm - 11:43 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
8h 23m1 stop New York John F Kennedy Intl
$584JetBlue
Thu, Oct 22 - Mon, Oct 26
6:01 am - 1:49 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
7h 48m1 stop Atlanta Hartsfield-Jackson
1:15 pm - 12:10 amSJU San Juan Luis Munoz Marin Intl-PWM Portland
10h 55m1 stop New York John F Kennedy Intl
$584Delta
Tue, Oct 27 - Wed, Oct 28
8:32 am - 11:36 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
15h 04m2 stops Chicago O'Hare Intl Newark
1:05 am - 9:00 amSJU San Juan Luis Munoz Marin Intl-PWM Portland
7h 55m1 stop Newark
$592United Airlines
Tue, Oct 27 - Wed, Oct 28
5:50 am - 1:40 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
7h 50m1 stop Newark
1:05 am - 2:16 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
13h 11m2 stops Newark Chicago O'Hare Intl
$592United Airlines
Thu, Oct 22 - Mon, Oct 26
5:30 am - 3:38 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
10h 08m2 stops Philadelphia Miami
12:21 pm - 11:28 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
11h 07m2 stops Miami Philadelphia
$640American Airlines
Thu, Oct 22 - Mon, Oct 26
7:00 am - 10:02 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl
15h 02m2 stops Philadelphia Miami
7:30 am - 6:56 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland
11h 26m1 stop Philadelphia
$640American Airlines
Thu, Oct 22 - Thu, Oct 29
6:01 am - 1:40 pmPWM Portland-SXM Simpson Bay Princess Juliana
7h 39m1 stop Atlanta Hartsfield-Jackson
3:05 pm - 1:12 pmSXM Simpson Bay Princess Juliana-PWM Portland
22h 07m2 stops Atlanta Hartsfield-Jackson New York LaGuardia
$725Delta
Thu, Oct 22 - Thu, Oct 29
6:00 am - 1:25 pmPWM Portland-SXM Simpson Bay Princess Juliana
7h 25m1 stop New York John F Kennedy Intl
2:50 pm - 11:43 pmSXM Simpson Bay Princess Juliana-PWM Portland
8h 53m1 stop New York John F Kennedy Intl
$982JetBlue
Thu, Oct 22 - Thu, Oct 29
6:00 am - 1:25 pmPWM Portland-SXM Simpson Bay Princess Juliana
7h 25m1 stop New York John F Kennedy Intl
2:50 pm - 11:43 pmSXM Simpson Bay Princess Juliana-PWM Portland
8h 53m1 stop New York John F Kennedy Intl
$985JetBlue
Booking Insights
KAYAK's insights & trends for Portland to Caribbean flights
Get data-powered insights and trends into flights from Portland to Caribbean to help you find the cheapest flights, the best time to fly and much more.
Prices
Airlines
More
What is the cheapest month to fly from Portland to Caribbean?
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Portland to Caribbean is January, when tickets cost $410 (return) on average. On the other hand, the most expensive months are April and July, when the average cost of round-trip tickets is $725 and $696 respectively.
How far in advance should I book a flight from Portland to Caribbean?
To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Portland to Caribbean, you should book around 2 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.
Good to know
Low season | September |
|---|---|
High season | April |
Cheapest flight | $145 |
FAQs - booking Caribbean flights
Reviews of the top 5 airlines serving from Portland to Caribbean
7.9
SouthwestOverall score based on 4208 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.4Entertainment
7.0Food
Airline reviews
It was great and arrived home a little sooner than expected which is nice.
10.0 ExcellentJennifer, Oct 2026
It was great and arrived home a little sooner than expected which is nice.
I fly out every other weekend and this is the 4th time my flight has been delayed at Southwest. I will be flying out twice a month on average for the next 6-7 months. If this is your average ‘on time’ I’ll probably be flying another airline.
WiFi was inoperable - second in four recent Southwest flights where that was true. I need WiFi for work and if Southwest cannot provide, I’ll stop using it
It’s too cold like fridge and they don’t offer a blanket with expensive price
Boarding now takes twice as long since going with assigned seats.
Smooth flights, connection, and friendly crew in the air and at the gate.
Flight was delayed again. I fly out every other weekend and lately the flight is delayed 3 out of five times 🤷🏻♀️
A List preferred boarding was nice Asked for a mask and cheerfully received Denver bag check-in is tricky. Not near other checking desk. Have to navigate to east security and up to level six for bag checkin. TSA busy and 20 minutes process thru pre lines Denver train to gates quick but one more thing to plan time for and long concourse walk to gate
Not exactly Southwest’s problem, but the new Burbank airport is not great. No restaurants open and tons of work still to be completed. Can’t believe they opened the airport in that condition.
Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.
attendents were rude and the boarding was disjointed and poor
Delta keep on impressing me. Right now Delta airline is the best of them all
Very good- all went as planned. Flight was on time. Seating was a little sub , as always. Snacks and entertainment were basic. We arrived on time- no problems.
Everything was great, from the flight and crew to the seating and snacks.
Rude staff from baggage check to gate crew. Poor instructions. Inconsistent application of baggage rules.
There was an incredibly surly flight attendant that ruined the experience
Good but since we got in early we had to wait on runway for our gate. That was kind of a bummer but we still got in earlier than planned For entertainment I was watching a movie and getting close to the end of it with 15 min left but it kept jumping automatically to the next movie before finishing.
Delta seems to be getting worse. They are trying to take any comfort away from poorer people to make more money selling it to the rich. I paid for delta comfort and on my flight from Rome to jfk I had a tv that would go on and off automatically and literally no electrical outlets or usbs worked which was advertised in the price of the fare. The infotainment system wasn’t fully working. Luckily the movies worked and the plane was needing a lot of repairs. The jfk to Tampa flight they stuck me next to this really larger guy who was half in my seat and they should have made other accommodations for him because now you’re interfering with the fare class I paid for and act like I shouldn’t care because I didn’t pay for first class. I couldn’t even pull out my tray table because of this guy. The safety video tv screen you couldn’t even see it. It made me a little scared to fly delta anymore, because if these planes are this much in need of servicing, I have to wonder if the plane is going to make it to the destination.
Delayed departure, 30min. but arrived nearly on time. Crew was reassuring.
Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED
Short. Nice quick flight, appreciated after Munich to DC leg.
Flight was so congested it was disgusting. Hals of the hostesses clearly seemed to be racist. no sanitation maintained in the restrooms.
United, from whom we bought this code-shared flight, mid-flight canceled our tickets for the rest of our itinerary, without explanation. After long delay they tried to re-issue the tickets, but Air Canada could not find the re-issue. It finally resolved after escalation to several layers of supervisors.
Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!
The WiFi went out an hour before the flight was due to land so I did not get my money's worth.
I have been flying united for a long time but now I’m done
It's not United, but TSA security at Terminal A in Newark is a disaster and seriously makes me consider switching to flying out of JFK. The touchless TSA pre-check had a line of over 50 people and the bag screening was so slow that it limited the flow of people through the facial recognition process. It is the only airport that I frequent that has this issue and makes me reconsider whether I should fly out of Newark given the wasted time and frustration it causes. As I said, it is not a United issue but will impact United if people choose to stop utilizing Newark airport because of the poor experience.
Both my flight where delayed Had 25min to make it to my transfer flight
I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.
They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.
I am always very pleased with the service u receive from JetBlue employees
Your Jet Blue representative at the check in desk in Boston on Sunday morning, October 13, was unkind and unhelpful. For that reason alone I will avoid JetBlue airlines in the future. No food or beverage on the flight due to turbulence (not your fault). However I paid extra to sit in the upgraded section in the front and did not benefit from most amenities.
we used to fly with a different airline but it shut down. We had to find an alternative airline that we like in order to make domestic trips and this fits the bill. Not only is it a similar price but the customer service and the experience overall is much much better. We will be using JetBlue again.
Uncomfortable seat. No help for my disability. Staff refused to help me put my carry-on in the overhead bin. So I had to check the bag.
Terrible. Quality has gone down significantly. Plane was delayed. No instructions from the staff. Will try to avoid in the future!
The flight left unexpectedly early. Although I checked in at the gate, the crew made no attempt to contact me to inform me that what had been a delayed flight was now departing before the scheduled departure time. No announcement on the PA, no phone call. When I checked back at the gate for the delay status just before the scheduled departure time, I was told the doors were already locked and the flight had left.
Late boarding, had to check the bag even though there was space on the flight and I was I row 7
Our seats were moved for no reason. The plane was old and wifi and tv were slow. The flight was delayed over an hour for a paperwork issue. Only bright spot was the flight attendants good service.
Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.
What's not to like? Value?definitely. Every JetBlue member was extremely friendly on this flight. Very very nice new-ish aircraft,plenty of room. GOOD coffee. Entertainment,I didn't need it,but I think its available. What to do better? Well,there's nothing we can do about the other people, unbelievable how some folks are operating. Just don't allow people to lug all their stuff onto the aircraft. 1 bag. That's it. Be easier for you too. I personally would enjoy more options in schedule. One flight in and out a day is warranted given the local,I understand, but the times are inconvenient. Again, I completely understand why it is that way,It would however be great to have different options.
Flight was delayed a couple of times. Which is annoying, but manageable.
Too little snack and drink for almost 6:00 hr flight. Should have serve some food.
At 5:46 am EST, when I arrived at my departing gate, your gqte agent told me that I could not board the flight because the flight is closed 15 minuets before departure. However, the same gate agent escorted a woman (standing right next to me) at the gate onto the flight which, proves that I could have boarded the flight just like the woman I watched board the flight. The gate agent stated "she was here before you". 1-why was she not already on the flight & 2-how and why was she able to board a "closed" flight that I was not. Additionally, although 6am EST was the time of departure, the plane did not 'pullback' from the gate until 6:15am EST The same gate agent told me that the "boarding closes 15 before departure time" is printed on my boarding pass. This statement is not displayed on my digital boarding pass that I downloaded from AA.com. She also told me that this in stated on AA.com whent I booked my ticket however, since am travelling for work, I booked my flight thru my firm's (Deloitte Consulting) corporate travel app, not AA.com. Marc W Brown
What an amazing plane! We flew a 787 to Miami. Although the Internet was not functioning, it was a wonderful flight.
Although it was a smaller plane, the flight was quick and uneventful.
Both directions of our trip were befuddled by massive delays, one of which led to our connecting flight being grounded mid air due to storms that we’d have missed if we were on time. The other our originating flight was delayed repeatedly until it arrived at our connecting airport later than our final leg was even supposed to have arrived. American cannot seem to manage rebooking s for a family party… both directions we had to come up with a plan to get to Boston stay overnight only one night each direction was covered by the airline -and take a bus to or from our destination. Missed an entire leg of our trip, hotel cancellation fees, expensive stay in Boston and bus ticket expenses are unlikely to be comped and the meal vouchers are worthless.
My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.
The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full
Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.
Seats are so close together. Middle seats should be discounted.
More options for your flight to Caribbean
Complete your trip to Caribbean with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights to Portland
Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Portland
Flights from all regions of Portland to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to popular destinations in Caribbean
Flights to Arubafrom $362
Flights to British Virgin Islandsfrom $946
Flights to Cayman Islandsfrom $462
Flights to Cubafrom $321
Flights to Dominican Republicfrom $447
Flights to Jamaicafrom $409
Flights to Puerto Ricofrom $356
Flights to Saint Luciafrom $1,210
Flights to St. Maartenfrom $498
Flights to The Bahamasfrom $328
Flights to Turks and Caicos Islandsfrom $544
Flights to U.S. Virgin Islandsfrom $360