$144 Find Cheap Flights from Portland to Caribbean - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Caribbean departing on 10/17. 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.
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Cheap Flights from Portland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$381
Santo Domingo
Santo Domingo1 stop$534
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$439
Nassau
Nassau1 stop$380
Kingston
Kingston1 stop$486
Simpson Bay
Simpson Bay2 stops$380
Providenciales
Providenciales1 stop$423
George Town
George Town2 stops$362
Puerto Plata
Puerto Plata1 stop$688
Punta Cana
Punta Cana2 stops$381
Santo Domingo
Santo Domingo1 stop$534
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$439
Nassau
Nassau1 stop$380
Kingston
Kingston1 stop$486
Simpson Bay
Simpson Bay2 stops$380
Providenciales
Providenciales1 stop$423
George Town
George Town2 stops$362
Puerto Plata
Puerto Plata1 stop$688

Book 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

Thu, Oct 29 - Mon, Nov 2
American Airlines Logo
4:40 pm - 12:58 pm
PWM
-
STT
20h 18m
2 stops
American Airlines Logo
3:15 pm - 10:37 am
STT
-
PWM
20h 22m
2 stops
$280American Airlines
Wed, Oct 28 - Sun, Nov 1
American Airlines Logo
4:54 pm - 12:58 pm
PWM
-
STT
20h 04m
2 stops
American Airlines Logo
4:53 pm - 10:37 am
STT
-
PWM
18h 44m
2 stops
$285American Airlines
Sat, Sep 19 - Sat, Sep 26
Delta Logo
6:00 am - 4:49 pm
PWM
-
SJU
10h 49m
1 stop
Delta Logo
1:16 pm - 11:56 pm
SJU
-
PWM
10h 40m
1 stop
$342Delta
Mon, Nov 30 - Fri, Dec 4
Delta Logo
6:00 am - 2:15 pm
PWM
-
MBJ
8h 15m
1 stop
Delta Logo
2:20 pm - 10:23 pm
MBJ
-
PWM
8h 03m
1 stop
$352Delta
Sun, Nov 1 - Fri, Nov 6
Southwest Logo
5:20 am - 5:00 pm
PWM
-
SJU
10h 40m
2 stops
Southwest Logo
5:35 am - 4:30 pm
SJU
-
PWM
11h 55m
2 stops
$353Southwest
Mon, Aug 24 - Fri, Aug 28
United Airlines Logo
6:03 am - 2:44 pm
PWM
-
SJU
8h 41m
1 stop
United Airlines Logo
4:55 pm - 11:59 pm
SJU
-
PWM
7h 04m
1 stop
$360United Airlines
Sat, Nov 7 - Sat, Nov 14
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
United Airlines Logo
8:05 am - 2:33 pm
SJU
-
PWM
7h 28m
1 stop
$361United Airlines
Tue, Oct 20 - Mon, Oct 26
Southwest Logo
11:35 am - 9:50 pm
PWM
-
SJU
10h 15m
2 stops
Southwest Logo
6:30 am - 4:55 pm
SJU
-
PWM
10h 25m
2 stops
$384Southwest
Wed, Sep 16 - Wed, Sep 23
JetBlue Logo
6:00 am - 4:51 pm
PWM
-
SJU
10h 51m
2 stops
JetBlue Logo
9:30 am - 11:52 pm
SJU
-
PWM
14h 22m
2 stops
$387JetBlue
Mon, Sep 21 - Mon, Oct 19
JetBlue Logo
6:00 am - 4:51 pm
PWM
-
SJU
10h 51m
2 stops
JetBlue Logo
1:00 pm - 11:52 pm
SJU
-
PWM
10h 52m
1 stop
$394JetBlue
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.

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 $468 (return) on average. On the other hand, the most expensive months are July and April, when the average cost of round-trip tickets is $696 and $688 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

September

Cheapest flight

$144
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Portland to Saint Thomas Island

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Portland to Caribbean?

    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 Portland to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to 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 Portland to Caribbean?

    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 from Portland to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Caribbean?

    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 from Portland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Portland to Caribbean

 
Need help choosing which airline to fly with from Portland to Caribbean? 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 4234 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

10.0 ExcellentTamara, Jul 2026
MCO - DEN
Read more Southwest reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

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.

My flight was canceled, and instead of rebooking me on a non-stop first-class flight for the same day, which I originally had, Delta rebooked me on a one-stop flight for the following day. When I checked the Delta app, I noticed that there were available flights for both the same day and the next day. I believe this indicates poor management on their part.

The Columbus-based WestJet crews that cover Delta commuter flights between LGA and CMH are excellent - this team included. Our flight today landed 40 minutes early, which is unheard of when flying out of LaGuardia. I've flown with the same crew in more challenging conditions, and they always rise to the occasion with helpful communication to the passengers so that we may manage expectations.

Easy on easy off and the staff onboard were wonderful. Left on time, arrived a bit early.

Weather in Atlanta necessitated an hour's hold on the tarmac before we could leave Detroit. The plane was packed, and I expected some surliness. But no! The crew was fantastic (jovial even!), responsive to people's needs, and kept us informed. Consequently, the passengers took the delay in stride, and what could have been an ugly situation turned out to be no more than a minor inconvenience. The crew were the stars here.

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

My flight was delayed and I got back around 3.5 hours later than expected. I had to get a new connecting flight

Seat was too small for someone as tall as I am. I was behind an exit row making my leg room even less. There flights were delayed by multiple hours. Some weather related and others staff related. The plane was hot. Horrible experience.

The Atlanta airport had thunderstorms, which caused our flight to be delayed by multiple hours. Once we were able to board.the gate agent was rude and was trying to rush us onto the plane because the team in the plane was about to run out of hours once we were all aboard the plane they ran into an issue where the catering truck was filling up the back of the plane and they left and had to come back because they didn’t fill it up all the way, causing even more of a delay. My seat was very tight. I didn’t have a lot of legroom overall this was a miserable experience.

Flight delayed due to ground hold. Republic airways did a great job.

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Our flight gor canceled and there was no one to help us but told us to scan the qr code and fill the forms on-line. Very poor service especially we are tourists traveling to Washington DC for the 1st time.

1. Everything was satisfactory concerning the flight. 2. Can't think of what could be better right now.

Onboard staff was courteous, helpful, responsive and friendly. The boarding process was disorganized, poorly communicated, and disheveled. Gate agents were yelling instead of using the PA system, didn’t communicate the timing delay of our flight, and created an atmosphere of chaos rather than order and communication. As far as I know, there was no reason for their. I would hate to see how it operated under extreme conditions. I’ve never seen United Airlines operations in such a state.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

Unbelievably smooth boarding at IAH and the flight attendants were top notch.

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’ve been on 8 flights with American Airlines in the last 2 months and 4 have been delayed.

The flight was ok, i understand Houston-Dallas is a short distance. The plane is really small: no TV, no snacks, but other than that, all was good. We had a bid delay but luckily it did not affect my connection

Horrific. We were delayed due a flight attendant stuck in traffic en route to the airport. Over 100 people were then stuck in Charolette. Then I ran to make my layover only to find that my connection didn’t have a plane anymore. Waited 2.5 hours without any updates. On the flight we had to beg for even a pretzel option.

Uncomfortable seats, spotty WiFi, only Biscoff for snack (no one likes those).

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

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.

I just for my TSA. So security line is short and upgraded to one group up. I do think the ground crew should learn new way of boarding - the passengers sitting in higher number seat should board first to prevent traffic jam.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

It was a smooth flight and the pilot was very pleasant

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports