$138 Find Cheap Flights from Portland to Caribbean

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 4/29. 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 Portland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$539
Santo Domingo
Santo Domingo1 stop$557
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$613
Nassau
Nassau2 stops$510
Kingston
Kingston2 stops$720
Simpson Bay
Simpson Bay2 stops$627
Providenciales
Providenciales2 stops$551
Bridgetown
Bridgetown2 stops$563
George Town
George Town2 stops$554
Willemstad
Willemstad2 stops$770
St. John's
St. John's2 stops$607
Puerto Plata
Puerto Plata1 stop$598
Aguadilla
Aguadilla1 stop$521
Punta Cana
Punta Cana1 stop$539
Santo Domingo
Santo Domingo1 stop$557
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$613
Nassau
Nassau2 stops$510
Kingston
Kingston2 stops$720
Simpson Bay
Simpson Bay2 stops$627
Providenciales
Providenciales2 stops$551
Bridgetown
Bridgetown2 stops$563
George Town
George Town2 stops$554
Willemstad
Willemstad2 stops$770
St. John's
St. John's2 stops$607
Puerto Plata
Puerto Plata1 stop$598
Aguadilla
Aguadilla1 stop$521

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

Sun, Mar 8 - Wed, Mar 11
American Airlines Logo
11:59 pm - 2:04 pm
PDX
-
MBJ
12h 05m
1 stop
American Airlines Logo
1:27 pm - 11:44 pm
MBJ
-
PDX
12h 17m
1 stop
$352American Airlines
Sat, May 2 - Thu, May 7
American Airlines Logo
11:40 pm - 3:37 pm
PDX
-
MBJ
13h 57m
2 stops
American Airlines Logo
4:37 pm - 11:01 am
MBJ
-
PDX
20h 24m
2 stops
$357American Airlines
Sun, Mar 8 - Wed, Mar 11
United Airlines Logo
11:59 pm - 12:46 pm
PDX
-
MBJ
10h 47m
1 stop
United Airlines Logo
1:48 pm - 10:45 pm
MBJ
-
PDX
10h 57m
1 stop
$362United Airlines
Sun, Mar 8 - Wed, Mar 11
United Airlines Logo
10:54 pm - 1:37 pm
PDX
-
MBJ
12h 43m
1 stop
United Airlines Logo
2:20 pm - 9:54 am
MBJ
-
PDX
21h 34m
2 stops
$367United Airlines
Tue, Apr 7 - Thu, Apr 16
American Airlines Logo
11:23 pm - 1:25 pm
PDX
-
MBJ
12h 02m
1 stop
American Airlines Logo
12:56 pm - 11:53 pm
MBJ
-
PDX
12h 57m
1 stop
$382American Airlines
Mon, Apr 27 - Wed, May 6
Southwest Logo
3:00 pm - 10:35 am
PDX
-
SJU
16h 35m
2 stops
Southwest Logo
11:25 am - 10:00 pm
SJU
-
PDX
13h 35m
2 stops
$386Southwest
Mon, May 4 - Fri, May 8
Southwest Logo
3:00 pm - 10:35 am
PDX
-
SJU
16h 35m
2 stops
Southwest Logo
10:00 am - 10:40 pm
SJU
-
PDX
15h 40m
2 stops
$405Southwest
Mon, May 25 - Thu, May 28
JetBlue Logo
11:40 pm - 11:00 pm
PDX
-
SJU
20h 20m
1 stop
JetBlue Logo
1:45 pm - 10:25 pm
SJU
-
PDX
11h 40m
1 stop
$411JetBlue
Sun, Mar 8 - Wed, Mar 11
Delta Logo
7:43 pm - 11:21 am
PDX
-
MBJ
13h 38m
2 stops
Delta Logo
11:15 am - 10:23 pm
MBJ
-
PDX
13h 08m
2 stops
$427Delta
Tue, Apr 7 - Tue, Apr 21
Delta Logo
12:30 am - 1:27 pm
PDX
-
MBJ
10h 57m
1 stop
Delta Logo
2:10 pm - 10:02 pm
MBJ
-
PDX
9h 52m
1 stop
$442Delta
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 October, when tickets cost $468 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $759 and $683 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 4 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$138
Best time to beat the crowds with an average 22% drop in price.
Flight from Portland to San Juan

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 4289 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

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.

4.0 OkayAnonymous, Feb 2026
BOI - LAS
Read more Southwest reviews

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 attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Once boarding started it was pretty quick. Food was inedible; cold and salty..

Entertainment kept turning itself off. Gave up on watching a movie.

Both the WIFI and entertainment did not work for 2.5h

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

I paid for the seats in row 3 to embark and disembark quicker but the passengers in the 2 rows in front of me take all the overhead bin space so I am forced to put my luggage 5 rows back. I even opened one up right above my seat which had room but as I was going to fit my carry on a flight atendant said it "was reserved", Just giving my money to a regular airline next time.

Terrible Flight was cancelled last minute with no other flights available

I was not informed via text about flight delay and gate change. There should have been a notice by the original gate letting us know that there was a change. A half hour before original flight time we realized there was no one there and were told that the gate was changed so we ran across the airport (I was traveling with my aunt who is in her upper 60s) to try to make the flight and then saw that the flight was actually delayed an hour . If you can do something for us to makeup for this we would appreciate it. Thank you

Terrible. Spirit cancelled the flight with 3 hours notice and were absolutely no help getting another flight. Had to make my own reservation on another airline and arrived in Dallas 12 hours later.

The flight itself was great except for an air traffic controller delay. We left 30 min late but they made up most of the time in flight. The booking was frustrating, as we chose a certain flight and it was changed four times. We got to Orlando several hours later than the original flight we chose.

Crew was very nice. Take off and landing were great. Economy seats are not comfortable. Extra cost for snacks.

Less than acceptable. Family members had flights cancelled with no reason. Multiple hour delay, gate changes, poor communication, less than satisfactory. I will never fly with spirit again, which is a shame because it’s a budget friendly option but quite frankly with all of the hassle and hoops that come with flying spirit. Completely unacceptable.

Everything was terrible. Flight was delayed several hours, crew was abrasive. Stuck on runway for over a hour. There was an argument between passengers that nearly turned into a fight while waiting to exit plane, crew did nothing. Took nearly 3 hours to retrieve luggage at baggage claim. Lost an entire day of vacation. Will never fly spirit again under any circumstance

There absolutely needs to be WiFi on flights. Not sure why this new aircraft did not have the capability, but it made for a very frustrating flight. I honestly would have paid twice as much for another airline to have WiFi as an option, especially as a mom with kids who have disabilities.

More comfortable seats, free snacks and soft drinks, some sort of entertainment or WiFi.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports