$193 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 10/5. 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

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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Flight Deals

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 Cana1 stop$459
Santo Domingo
Santo Domingo1 stop$534
Montego Bay
Montego Bay1 stop$464
Oranjestad
Oranjestad1 stop$581
Nassau
Nassau1 stop$489
Simpson Bay
Simpson Bay2 stops$635
Kingston
Kingston1 stop$771
Providenciales
Providenciales1 stop$650
Bridgetown
Bridgetown1 stop$636
George Town
George Town1 stop$614
Willemstad
Willemstad1 stop$695
St. John's
St. John's1 stop$759
Puerto Plata
Puerto Plata1 stop$567
Aguadilla
Aguadilla2 stops$537
Punta Cana
Punta Cana1 stop$459
Santo Domingo
Santo Domingo1 stop$534
Montego Bay
Montego Bay1 stop$464
Oranjestad
Oranjestad1 stop$581
Nassau
Nassau1 stop$489
Simpson Bay
Simpson Bay2 stops$635
Kingston
Kingston1 stop$771
Providenciales
Providenciales1 stop$650
Bridgetown
Bridgetown1 stop$636
George Town
George Town1 stop$614
Willemstad
Willemstad1 stop$695
St. John's
St. John's1 stop$759
Puerto Plata
Puerto Plata1 stop$567
Aguadilla
Aguadilla2 stops$537

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

Thu, Nov 13 - Sun, Nov 16
Frontier Logo
12:52 pm - 4:10 pmPDX-SJU
23h 18m2 stops
Frontier Logo
2:11 am - 11:56 amSJU-PDX
13h 45m2 stops
$373Frontier
Find Deal
Thu, Oct 30 - Wed, Nov 5
Frontier Logo
12:52 pm - 4:10 pmPDX-SJU
24h 18m2 stops
Frontier Logo
1:59 am - 11:56 amSJU-PDX
13h 57m2 stops
$384Frontier
Find Deal
Fri, Oct 24 - Sat, Nov 8
Delta Logo
10:58 pm - 1:12 pmPDX-SJU
11h 14m1 stop
Delta Logo
7:00 am - 8:26 pmSJU-PDX
17h 26m2 stops
$419Delta
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Sun, Feb 15 - Sat, Feb 21
American Airlines Logo
2:10 pm - 4:55 amPDX-SJU
10h 45m1 stop
American Airlines Logo
7:20 am - 8:24 pmSJU-PDX
17h 04m1 stop
$444American Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
United Airlines Logo
8:30 am - 12:36 amPDX-SJU
12h 06m2 stops
United Airlines Logo
8:30 am - 5:52 pmSJU-PDX
13h 22m2 stops
$448United Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
Southwest Logo
6:15 am - 11:20 pmPDX-SJU
13h 05m2 stops
Southwest Logo
8:55 am - 6:15 pmSJU-PDX
13h 20m2 stops
$450Southwest
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Sat, Oct 11 - Sat, Oct 18
United Airlines Logo
5:15 pm - 12:34 pmPDX-SJU
16h 19m2 stops
United Airlines Logo
1:30 pm - 9:26 pmSJU-PDX
10h 56m1 stop
$451United Airlines
Find Deal
Sun, Oct 19 - Mon, Nov 24
American Airlines Logo
11:58 pm - 2:55 pmPDX-SJU
11h 57m2 stops
American Airlines Logo
12:02 pm - 11:31 pmSJU-PDX
15h 29m1 stop
$457American Airlines
Find Deal
Mon, Mar 9 - Wed, Mar 11
Delta Logo
7:00 am - 11:27 pmPDX-STI
13h 27m1 stop
Delta Logo
6:00 am - 9:35 pmSTI-PDX
18h 35m1 stop
$467Delta
Find Deal
Tue, Oct 28 - Mon, Nov 3
Southwest Logo
5:50 am - 10:45 pmPDX-SJU
13h 55m2 stops
Southwest Logo
11:20 am - 9:25 pmSJU-PDX
14h 05m2 stops
$508Southwest
Find Deal
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 $325, 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 January, when tickets cost $480 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $773 and $725 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, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$193
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 25% 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.

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
Alaska AirlinesOverall score based on 10000 reviews
8.1Boarding
7.8Comfort
7.1Food
7.0Entertainment
8.5Crew
Airline reviews

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

10.0 ExcellentAnonymous, Sep 2025PDX - MCI
Read more Alaska Airlines reviews

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

Website could be better with faster access to specific flight information and boarding pass once reservation is made. Not a fan of no seat selection on line. I had to consult gate agent each time to change seats on flights with lots of open seats. This cannot possibly be cost effective for airline. On plus side, Alaska seat legroom seemed larger than American. ns

Staff inside Portland terminal were rude, made us fell rushed and not at all accommodating to seniors. For this alone I will probably never booked from them again.

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

I booked a round trip. I ordered a lunch going and a lunch for the return but got both lunches going. Could have been my error. Both lunches were good.

Well the flight being delayed multiple time really was frustrating. But the crew and flight was good.

generally good. No snacks or drinks on the flight 3379 from Portland to San Jose, CA. Sad.

Everything except for the lack of a choice of the snack provided was great.

I like the friendliness of the staff. The food choices were OK. I wish there was more options. The entertainment through the movie portal was alright.

First time flying with Alaska, and it went great. Thank you for a great experience flying to PDX.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

We had to deboard 2 times due to maintenance issues. They changed the plane, and then we got deviated to LAX due to maibtenance issues on the other plane, had to sleep at LAX and los a full day.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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