$144 Find Cheap Flights from Portland to Caribbean Islands

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 Islands departing on 6/24. 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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KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Caribbean Islands, as well as popular online travel agencies
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Flights Deals

Best Caribbean Islands Flight Deals from Portland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana2 stops$413
Santo Domingo
Santo Domingo2 stops$537
Montego Bay
Montego Bay1 stop$593
Oranjestad
Oranjestad3 stops$569
Nassau
Nassau1 stop$465
Kingston
Kingston2 stops$453
Simpson Bay
Simpson Bay2 stops$416
Providenciales
Providenciales2 stops$612
Bridgetown
Bridgetown2 stops$649
George Town
George Town1 stop$650
Willemstad
Willemstad2 stops$765
St. John's
St. John's1 stop$778
Puerto Plata
Puerto Plata2 stops$549
Aguadilla
Aguadilla2 stops$570
Punta Cana
Punta Cana2 stops$413
Santo Domingo
Santo Domingo2 stops$537
Montego Bay
Montego Bay1 stop$593
Oranjestad
Oranjestad3 stops$569
Nassau
Nassau1 stop$465
Kingston
Kingston2 stops$453
Simpson Bay
Simpson Bay2 stops$416
Providenciales
Providenciales2 stops$612
Bridgetown
Bridgetown2 stops$649
George Town
George Town1 stop$650
Willemstad
Willemstad2 stops$765
St. John's
St. John's1 stop$778
Puerto Plata
Puerto Plata2 stops$549
Aguadilla
Aguadilla2 stops$570

Cheap Flight Deals from Portland to Caribbean Islands (PDX-zzEPX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Caribbean Islands 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.

Recent round-trip flight deals from Portland to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Portland to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
5:40 pm - 9:57 amPDX-STT
13h 17m2 stops
Spirit Airlines Logo
10:52 am - 11:17 amSTT-PDX
27h 25m2 stops
$376Spirit Airlines
Find Deal
Wed, Jun 4 - Wed, Jun 11
Delta Logo
5:40 pm - 12:01 pmPDX-SJU
15h 21m2 stops
Delta Logo
1:12 pm - 11:15 pmSJU-PDX
13h 03m1 stop
$379Delta
Find Deal
Fri, May 30 - Wed, Jun 4
United Airlines Logo
9:54 am - 11:57 pmPDX-SJU
11h 03m1 stop
United Airlines Logo
2:55 pm - 10:23 pmSJU-PDX
10h 28m1 stop
$397United Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
 Logo
4:35 pm - 10:39 amPDX-SJU
39h 04m3 stops
 Logo
1:44 pm - 5:44 pmSJU-PDX
31h 00m2 stops
Fri, Jun 13 - Thu, Jun 19
American Airlines Logo
11:49 pm - 3:00 pmPDX-SJU
12h 11m2 stops
American Airlines Logo
1:10 pm - 11:59 pmSJU-PDX
13h 49m2 stops
$442American Airlines
Find Deal
Fri, May 30 - Wed, Jun 4
 Logo
4:35 pm - 7:19 pmPDX-SJU
23h 44m2 stops
 Logo
1:44 pm - 5:44 pmSJU-PDX
31h 00m2 stops
Fri, Jun 13 - Thu, Jun 19
American Airlines Logo
10:24 pm - 2:40 pmPDX-SJU
13h 16m1 stop
American Airlines Logo
6:10 am - 11:07 pmSJU-PDX
19h 57m1 stop
$452American Airlines
Find Deal
Mon, May 19 - Mon, Jun 2
United Airlines Logo
10:47 pm - 1:31 pmPDX-NAS
11h 44m1 stop
United Airlines Logo
3:10 pm - 9:06 pmNAS-PDX
8h 56m1 stop
$465United Airlines
Find Deal
Sun, May 11 - Sat, May 17
Southwest Logo
7:40 pm - 10:25 amPDX-SJU
11h 45m2 stops
Southwest Logo
1:05 pm - 11:35 pmSJU-PDX
13h 30m1 stop
$619Southwest
Find Deal
Sun, Jun 29 - Sat, Jul 5
Southwest Logo
9:15 pm - 12:35 pmPDX-SJU
12h 20m1 stop
Southwest Logo
5:30 am - 3:40 pmSJU-PDX
13h 10m1 stop
$629Southwest
Find Deal
Sun, Jun 29 - Sat, Jul 5
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KAYAK's insights & trends for Portland to Caribbean Islands flights

Get data-powered insights and trends into flights from Portland to Caribbean Islands 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 Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Caribbean Islands, 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 Islands is September, when tickets cost $392 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $795 and $717 respectively.

What’s the cheapest day of the week to fly from Portland to Caribbean Islands?

The average price of all round-trip flights from Portland to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Tuesday and more expensive on a Thursday. On your return trip to Portland, you should consider flying back on a Thursday, and avoid Saturdays for better deals.

How far in advance should I book a flight from Portland to Caribbean Islands?

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 Islands, 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 Islands, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.


Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$144
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Portland to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

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

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $428 on average. Morning departures are around 41% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $602.

Top 5 airlines serving from Portland to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Portland to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Caribbean Islands? 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
Alaska AirlinesOverall score based on 9968 reviews
7.9Comfort
8.2Boarding
7.1Entertainment
7.1Food
8.5Crew
Airline reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

8.0 ExcellentAnonymous, Apr 2025PDX - PHX
Read more Alaska Airlines reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

It was alright other than the changes in the Alaska Lounge. That and the migraine I had were disappointing. Other then that everything went well.

It was a short flight so no refreshments or entertainment which was fine.

Flying in both directions across country the gate designated on my boarding pass was wrong. From w to e across the country the passenger next to me coughed the entire way.

Although both planes (flights) had mechanical issue delaying both of my flights, the crew members handled everything with ease. Both flights had the smoothest take off and landing. I opted to upgrade my seat to first class and really lucked out getting the seat at the very front of the plane. Awesome treat to myself. I really enjoyed my flight.

The staff from check-in counter to the flight crew were great. Flight was right on schedule. 10/10

Changed flight from San Fran to Seattle Then with a Delayed takeoff barely made my connection Waited over an hour for luggage 😜

It was good. There was a mistake made in Seattle. Somehow we were bumped out of our seats as if we weren't on the flight anymore. The woman at the gate caught it and announced our name to come up and she fixed it.

I wouldn’t fly with Alaska again if you paid me.

I appreciated Alaska Airlines very much, they are expanding traveling locations globally as they partnered with another company and am excited and looking forward to our next traveling adventure with this great Airline. Thank you kindly

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

Electric plugs didn't work. Entertainment system wasn't working

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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