$192 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 9/1. 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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$565
Santo Domingo
Santo Domingo1 stop$668
Montego Bay
Montego Bay1 stop$432
Oranjestad
Oranjestad2 stops$674
Nassau
Nassau2 stops$572
Kingston
Kingston2 stops$694
Simpson Bay
Simpson Bay2 stops$589
Providenciales
Providenciales2 stops$676
Bridgetown
Bridgetown2 stops$667
George Town
George Town1 stop$675
Willemstad
Willemstad2 stops$715
Aguadilla
Aguadilla2 stops$538
Puerto Plata
Puerto Plata2 stops$715
St. John's
St. John's2 stops$716
Punta Cana
Punta Cana2 stops$565
Santo Domingo
Santo Domingo1 stop$668
Montego Bay
Montego Bay1 stop$432
Oranjestad
Oranjestad2 stops$674
Nassau
Nassau2 stops$572
Kingston
Kingston2 stops$694
Simpson Bay
Simpson Bay2 stops$589
Providenciales
Providenciales2 stops$676
Bridgetown
Bridgetown2 stops$667
George Town
George Town1 stop$675
Willemstad
Willemstad2 stops$715
Aguadilla
Aguadilla2 stops$538
Puerto Plata
Puerto Plata2 stops$715
St. John's
St. John's2 stops$716

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

Tue, Sep 22 - Wed, Sep 23
Southwest Logo
5:50 am - 9:05 pm
PDX
-
SJU
12h 15m
2 stops
Southwest Logo
5:15 am - 3:00 pm
SJU
-
PDX
12h 45m
2 stops
$431Southwest
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
11:34 pm - 1:12 pm
PDX
-
MBJ
11h 38m
1 stop
American Airlines Logo
2:12 pm - 11:59 pm
MBJ
-
PDX
11h 47m
1 stop
$432American Airlines
Mon, Nov 2 - Tue, Nov 10
Delta Logo
5:05 pm - 12:25 pm
PDX
-
MBJ
16h 20m
2 stops
Delta Logo
6:00 pm - 9:16 am
MBJ
-
PDX
18h 16m
2 stops
$437Delta
Tue, Sep 22 - Tue, Sep 22
United Airlines Logo
7:10 am - 8:38 pm
PDX
-
SJU
10h 28m
1 stop
United Airlines Logo
1:00 am - 3:56 pm
SJU
-
PDX
17h 56m
2 stops
$461United Airlines
Mon, Nov 9 - Tue, Nov 17
United Airlines Logo
5:00 am - 6:25 pm
PDX
-
SJU
9h 25m
1 stop
United Airlines Logo
2:21 pm - 9:08 pm
SJU
-
PDX
10h 47m
1 stop
$466United Airlines
Sat, Aug 29 - Thu, Sep 3
JetBlue Logo
11:27 pm - 2:11 pm
PDX
-
SJU
11h 44m
1 stop
JetBlue Logo
1:50 pm - 10:49 pm
SJU
-
PDX
11h 59m
1 stop
$479JetBlue
Tue, Nov 17 - Tue, Nov 24
Delta Logo
10:05 pm - 11:35 am
PDX
-
NAS
10h 30m
1 stop
Delta Logo
1:00 pm - 11:47 pm
NAS
-
PDX
13h 47m
2 stops
$594Delta
Wed, Sep 23 - Sun, Sep 27
Air Canada Logo
10:10 am - 5:30 pm
PDX
-
NAS
28h 20m
2 stops
Air Canada Logo
6:30 pm - 9:31 am
NAS
-
PDX
42h 01m
2 stops
$600Air Canada
Wed, Sep 23 - Sun, Sep 27
Air Canada Logo
10:10 am - 5:30 pm
PDX
-
NAS
28h 20m
2 stops
Air Canada Logo
6:30 pm - 9:31 am
NAS
-
PDX
42h 01m
2 stops
$640Air Canada
Mon, Aug 24 - Mon, Aug 31
JetBlue Logo
11:27 pm - 4:38 pm
PDX
-
AUA
14h 11m
2 stops
JetBlue Logo
2:25 pm - 1:01 pm
AUA
-
PDX
25h 36m
1 stop
$674JetBlue
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 March, when tickets cost $191 (return) on average. On the other hand, the most expensive months are May and January, when the average cost of round-trip tickets is $365 and $307 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 2 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$192
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 12% increase in price.
Flight from Portland to Montego Bay

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.
7.9
SouthwestOverall score based on 4246 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was really nice! I appreciate the gate attendant allowing families with small children to board early on in the process… that was very helpful! The internet service didn’t work with the app I was trying to use even though I paid the $8… other than that it was great! Oh and I should’ve asked for the whole cranberry cocktail can. That cup was about 2 sips…

I liked the boarding process with our loading group and numbers. I disliked that I couldn't guarantee our seats together. I didn't like that the Internet costs $8/ flight, but did love all the inflight options available through their app. I disliked no charging station at my seat for a 3+ hour flight.

Great! Although the flight was about 40 minutes delayed, the crew did a good job getting everything boarded quickly and efficiently.

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was old and thus the seats were not good. No cushion left whatsoever, and it all was a bit worn out.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

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!!!!

My seat had no padding, it was literally plywood with a plastic cover. I could not change seats on my 10 hour flight. My excitement for this trip helped me deal with the pain.

The flight was great. The crew were a little terse about the size of my bag. It fit fine.

The flights were on time- Great service Would have liked more options for food choices.

The brakes on the A220 are sensitive and uncomfortably grabby

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

We had a 90 minute delay due to equipment failure that was detected just before we took off. United rebooked my connecting flight.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.

Poor seating comfort, seat cushion too thin, very uncomfortable. My luggage didi not make the flight due to equipment change. At least. United had it delivered the next day. I was without my toilet items for one day.

Flight cancelled because of the grounded 737s. United was good about it and got us onto a later Alaska Airlines flight to Oakland (not San Francisco as originally intended). Had to go through security again and my wife dropped her MacBook Pro, which broke, a $2,500 whoopsie. But we made it home.

I liked being upgraded to first class. The flight was a redeye, so I did sleep most of it.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

DFW-LHR Toilets not kept clean Too cramped. Aisles so narrow crew were constantly banging into people on the aisle seats. Even then, the carts used are reduced width. Other than that it was a decent flight on both legs

Excellent customer service at check in at Austin flight to DFW and excellent customer service from Karren in terminal B at DFW.

The flight itself was fine, but between the man in front of me putting his chair back, and the gentleman next to me who took up 50% of my seat, my back and neck are destroyed from the flight. I’m hoping for a better outcome flying back.

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

We were told there would be no food/beverage service due to turbulence. There was very little turbulence on the 2+ hour flight. I was in First Class and thought they could have done a quick service after take off as they had a quite bit of time before we would be reaching the predicted turbulent area. They could have at least passed out a quick bag of pretzels.

Very disappointed with the crew and the lack of attention given to the passengers. On a 5 hour flight they never offered a snack. One time offered a beverage and didn’t pick up the used cups until the flight was on final approach. The two flight attendants in our section mentioned that they were best friends and compared their pre flight shoes. When paying for first/business class there is a level of service that should be expected. These two spent the majority of the flight in their seats playing on their phones and laughing with each other. Very frustrating!!!

I love the Kayak has keep on updating me about flight status as it was delayed for 30mins. as well notifications to book seat and if any change on booking. Tickets were also cheap compared to British Airways online website. No hidden charges or terms n conditions. Keep it up!!!

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

Domestic flights are good. Just stay away from international travel

Flight left 2 hours late with no explanation as to the delay

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports