$160 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 9/3. 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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1 adult, Economy

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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 Cana2 stops$483
Santo Domingo
Santo Domingo2 stops$491
Montego Bay
Montego Bay2 stops$502
Oranjestad
Oranjestad2 stops$581
Nassau
Nassau2 stops$439
Simpson Bay
Simpson Bay2 stops$596
Kingston
Kingston2 stops$562
Providenciales
Providenciales2 stops$553
Bridgetown
Bridgetown2 stops$605
George Town
George Town2 stops$1,267
Willemstad
Willemstad2 stops$675
St. John's
St. John's1 stop$784
Puerto Plata
Puerto Plata1 stop$565
Aguadilla
Aguadilla1 stop$552
Punta Cana
Punta Cana2 stops$483
Santo Domingo
Santo Domingo2 stops$491
Montego Bay
Montego Bay2 stops$502
Oranjestad
Oranjestad2 stops$581
Nassau
Nassau2 stops$439
Simpson Bay
Simpson Bay2 stops$596
Kingston
Kingston2 stops$562
Providenciales
Providenciales2 stops$553
Bridgetown
Bridgetown2 stops$605
George Town
George Town2 stops$1,267
Willemstad
Willemstad2 stops$675
St. John's
St. John's1 stop$784
Puerto Plata
Puerto Plata1 stop$565
Aguadilla
Aguadilla1 stop$552
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 $437 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $765 and $762 respectively.

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

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

When flying from Portland to Caribbean, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Thursdays and the most expensive ones on Saturdays.

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 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$160
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 23% increase 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.

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

    The cheapest time of day to fly to Caribbean 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 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

 
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 4244 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

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.

10.0 ExcellentJoseph, Aug 2025SFO - BWI
Read more Southwest reviews

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.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Having to up charge for a seat assignment is not good. Delta can do better

I liked the friendliness of the staff. The cleanliness of all 3 planes.

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

De planning was an absolute mess. We were never told that we weren’t at the gate and that we had to go down unstable stairs and then hop on a bus. People were falling, we couldn’t tell who was in charge. Overall terrible communication that ended up leaving a bad impression at the very end of the experience.

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The service was good, the food could have been better.

Staff was rude. Didn’t give water for 2 hours. Worst service

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

This flight was perfect. No complaints and only the highest regard for the crew and ground staff and how they executed perfectly. I fly a lot with United and would request predictability and transparency in their operations instead of last minute changes.

This is for UA2274 from Houston to Sacramento. The flight was delayed arriving due to mechanical issues so we left about 3 hours later than scheduled. When boarding the plane the temperature inside was excessive - likely close to 100. Pilot apologized and said it was going to improve at altitude, which it did. But before that I honestly thought there might have been more delays removing passengers made ill from the heat. We were delayed leaving due to another mechanical issue. There was not water on the plane due to a panel that was not secured. They did that quickly, but the combination of mechanical issues was rather disturbing and did not reflect well on United.

1. when we went to check in, our 2 first class seats had been CANCELED and the flight was sold out. This was done without our prior knowledge. It was all we could do to restore one first class seat for my wife and I flew economy. 2, Our flight home was scheduled to leave at 10:30 pm. Due to tsunami warnings, the roads were closed and our flight status was uncertain as to whether it would leave as scheduled. It was announced that it would now leave at 11:20 pm and the roads were now open since the tsunami had come and gone. We made a mad dash to the airport and checked in. Delays were announced at 12:30 pm, 1:30 am, 2:30 am and at 3:30 am it was canceled. Since this was a flight due to natural (tsunami) causes, there was no compensation. We were told to return at 1:00 pm the next day and our baggage would be kept on the plane since the same plane was going to leave at 1:00 pm. We had to return to our hotel for the rest of the night. The same plane did not leave at 1:00 pm and our baggage was gone! All in all, it was a miserable performance by UA. Information was hard to obtain and no one knew what was going on and what was going to happen. Hundreds of passengers slept on the floor, chairs, etc. No food and no water was made available to the passengers. It was a situation where UA could care less what was going on. As a one million mile flyer, I had not experienced anything like this before and it was hugely disappointing!

Staff members were not helpful they ignored all calls for an attendant.

Flight was delayed and missed my connection Lufthansa didn’t respond.

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Crew should be nicer and emphatic with customers. Same cookies as the past 20 years. Seat are ok and the plane was clean though it was delayed.

Was not able to watch most shows on the entertainment site. They would not load

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

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

There is no room, no gluten free options, or any free internet/entertainment. You have to bring your own tablet or smartphone because there are no screens.

Plane was delayed for 6 hours, at first by weather, which is understandable, but was further delayed with NO given reason for 2 1/2 hours more. We had no clue when we were going to depart actually until they opened the ramp. VERY POOR to ZERO COMMUNICATION!!!

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

We had to turn around and head back to Manchester. Problem with a plane engine.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Very poor delay in dfw was really bad n long

I think the staff was nice. They took time to explain safety protocols. Boarding was great. They started early and our flight left a little early which was convenient. Having free games to play would have been better

I didn't order food. I requested a Tomato juice and was given a boody mary mix. The serve needs to warn the customer what their given. It wasn't a huge deal, but I wasted $4.50.

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

After 2 hrs the flight was canceled. The next flight wasn’t until 4 days away! They wouldn’t book us with other airlines. We ended up driving 15 hrs to get home

The flight was on time, boarding was efficient, staff was nice. Seats seem to have been upgraded on this model and were clean and tidy. I did not purchase in flight snacks.

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

First time on Spirit. Definitely a streamline flight but I would fly Spirit again.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Everything you need to know for your flight to Caribbean

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