$188 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 4/21. 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

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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Cheap Flights from Portland to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$436
Santo Domingo
Santo Domingo1 stop$557
Montego Bay
Montego Bay1 stop$512
Oranjestad
Oranjestad2 stops$558
Nassau
Nassau2 stops$523
Kingston
Kingston1 stop$824
Simpson Bay
Simpson Bay2 stops$555
Providenciales
Providenciales2 stops$571
Bridgetown
Bridgetown2 stops$637
George Town
George Town2 stops$487
Willemstad
Willemstad2 stops$640
St. John's
St. John's1 stop$840
Puerto Plata
Puerto Plata1 stop$589
Aguadilla
Aguadilla1 stop$459
Punta Cana
Punta Cana2 stops$436
Santo Domingo
Santo Domingo1 stop$557
Montego Bay
Montego Bay1 stop$512
Oranjestad
Oranjestad2 stops$558
Nassau
Nassau2 stops$523
Kingston
Kingston1 stop$824
Simpson Bay
Simpson Bay2 stops$555
Providenciales
Providenciales2 stops$571
Bridgetown
Bridgetown2 stops$637
George Town
George Town2 stops$487
Willemstad
Willemstad2 stops$640
St. John's
St. John's1 stop$840
Puerto Plata
Puerto Plata1 stop$589
Aguadilla
Aguadilla1 stop$459

Book Cheap Portland to Caribbean Islands 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 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Caribbean Islands

Sat, May 9 - Sat, May 16
Frontier Logo
12:27 pm - 10:37 am
PDX
-
PUJ
19h 10m
2 stops
Frontier Logo
11:07 am - 8:59 am
PUJ
-
PDX
24h 52m
2 stops
$436Frontier
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
11:35 pm - 3:01 pm
PDX
-
SJU
11h 26m
2 stops
American Airlines Logo
2:23 pm - 12:17 am
SJU
-
PDX
13h 54m
2 stops
$440American Airlines
Sun, May 24 - Fri, May 29
United Airlines Logo
10:00 am - 11:50 pm
PDX
-
SJU
10h 50m
1 stop
United Airlines Logo
1:00 am - 11:38 am
SJU
-
PDX
13h 38m
2 stops
$468United Airlines
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
8:40 am - 12:15 am
PDX
-
SJU
12h 35m
2 stops
Southwest Logo
10:10 am - 11:10 pm
SJU
-
PDX
16h 00m
2 stops
$470Southwest
Mon, Apr 20 - Sun, Apr 26
Southwest Logo
2:50 pm - 1:20 pm
PDX
-
STT
19h 30m
2 stops
Southwest Logo
3:20 pm - 1:25 am
STT
-
PDX
13h 05m
2 stops
$507Southwest
Tue, Mar 3 - Wed, Mar 11
Delta Logo
9:45 pm - 3:19 pm
PDX
-
MBJ
14h 34m
1 stop
Delta Logo
11:15 am - 7:00 pm
MBJ
-
PDX
9h 45m
1 stop
$512Delta
Tue, Mar 3 - Wed, Mar 11
Delta Logo
9:45 pm - 12:53 pm
PDX
-
MBJ
12h 08m
1 stop
Delta Logo
11:15 am - 10:23 pm
MBJ
-
PDX
13h 08m
2 stops
$517Delta
Thu, Feb 26 - Thu, Mar 5
United Airlines Logo
6:57 pm - 11:53 am
PDX
-
NAS
13h 56m
2 stops
United Airlines Logo
2:35 pm - 11:11 pm
NAS
-
PDX
11h 36m
1 stop
$554United Airlines
Mon, Mar 2 - Mon, Mar 9
Air Canada Logo
7:05 pm - 4:00 pm
PDX
-
SXM
16h 55m
2 stops
Air Canada Logo
4:00 pm - 2:40 pm
SXM
-
PDX
25h 40m
2 stops
$555Air Canada
Wed, Jun 3 - Wed, Jun 10
Air Canada Logo
3:25 pm - 5:30 pm
PDX
-
NAS
23h 05m
2 stops
Air Canada Logo
6:30 pm - 2:45 pm
NAS
-
PDX
23h 15m
2 stops
$556Air Canada
Booking Insights

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.

Can I save money by flying with a layover from Portland to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $357, prices are generally cheapest when you fly direct.

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 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 $781 and $690 respectively.

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 4 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$128
Best time to beat the crowds with an average 23% drop 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.

Reviews of the 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
SouthwestOverall score based on 4267 reviews
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

My flight to London from Philadelphia was cancelled due to weather.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

Flight was cancelled. But kayak thought it was still on time.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

The flight was delayed by 2 hours and we had no food or water or chargers

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Nothing everything cost money a bottle of water is 5 dollars and there wasn't even an outlet to plug 🔌 in my 📱 phone

You can’t beat Spirit’s prices on tickets, especially with the positive experience that comes with it! I appreciated the timeliness of Spirit airlines. The crew in the airport was very kind and wished you a good flight by name. The crew on the flight was attentive and friendly. Overall, I am very pleased with my experience with Spirit.

This was my best experience with spirit. I flew you guys 4 times and I must say this was the BEST

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports