$135 Find Cheap Flights from Portland to Caribbean - Compare and Save

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Cheap Flights from Portland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$430
Montego Bay
Montego Bay1 stop$382
Oranjestad
Oranjestad2 stops$340
Nassau
Nassau1 stop$319
Kingston
Kingston2 stops$507
Simpson Bay
Simpson Bay2 stops$380
Providenciales
Providenciales1 stop$421
George Town
George Town2 stops$417
Puerto Plata
Puerto Plata2 stops$657
Punta Cana
Punta Cana1 stop$430
Montego Bay
Montego Bay1 stop$382
Oranjestad
Oranjestad2 stops$340
Nassau
Nassau1 stop$319
Kingston
Kingston2 stops$507
Simpson Bay
Simpson Bay2 stops$380
Providenciales
Providenciales1 stop$421
George Town
George Town2 stops$417
Puerto Plata
Puerto Plata2 stops$657
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?

The cheapest month for flights from Portland to Caribbean is January, when tickets cost $427 (return) on average. On the other hand, the most expensive months are April and July, when the average cost of round-trip tickets is $732 and $696 respectively.

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

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 4% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

September

Cheapest flight

$135
Best time to beat the crowds but there is an average 31% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Portland to Oranjestad

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.
8.0
SouthwestOverall score based on 4201 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Unfortunately, I left my headphone's case in the bag of the front seat. I was seating on 9C. Hopefully the found it and I can get it back. I have not been able to get in contact with Southwest. Other than that, everything went fine.

8.0 ExcellentSolon Leonel, Sep 2026
Read more Southwest reviews

Unfortunately, I left my headphone's case in the bag of the front seat. I was seating on 9C. Hopefully the found it and I can get it back. I have not been able to get in contact with Southwest. Other than that, everything went fine.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wifi was terrible. I couldn't get any work done on the long flight

It's a shame that SW was previously my preferred carrier until they started imposing all these fees (luggage, seats,etc) and pulling back on other perks. I only flew with them this time due to time frame I needed to be at destination. Wasn't provided gate info during check-in, Gate info wasn't displayed at airport until last minute, gate info didn't match what SW personnel announced at fate. Kind of a mess.

Flight was fine. Only thing was flight was delayed nearly 2 hours. Flight was originally scheduled to depart at 7:50pm but didn't depart until 9:50pm. I got home around midnight. It was later than desired and I had to get up early next day to take kids to practice. I have noticed that last flight of day on West Coast for Southwest always tend to have delays.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Trash experience on all my flights this week. Delay after delay. The flight I’m waiting for has been delayed 6 times and nearly 3 hours.

Southwest has been a nightmare. Delayed flights, missed connections, systems down. Never again am I flying southwest.

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

Late flight, screens not working and still had to pay for a drink

great! appreciated the last minute upgrade to Comfort+ exit row, as well

Crew completed ignored our aisle when giving snacks and coffee

The seats were great and the service was even better. Thank you!

The WiFi on the plane was out. I also thought movie options were lacking.

They changed my seat assignment from window to middle. I have a physical need to sit by the window because of spinal issues. I unboarded in pain, I also was placed between 2 very large men. I am very disappointed and now dealing with the physical aftermath.

These Delta 717 jets are ancient. No entertainment and you have to pay for WiFi that barely works and goes in and out the whole flight. Delta should be ashamed flying this garbage.

The crew were awesome and ready to help as much as possible. The gate agent in Atlanta was tremendously helpful. The delays were ridiculous. Getting home at 4am when I could have driven home faster was unimpressive. Being delayed for countless hours through the night wasn't a great travel experience.

The staff and crew were wonderful. The delays were atrocious. The missed connections problematic. Getting home at 4am and having to go to work at 8 am, not a great situation. The gate agent in Huntsville was amazing. She helped everyone efficiently and with excellent problem solving skills. Her communication was helpful, timely, and thoughtful.

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Price was crazy watch it if you Chan he your flight

The price. Omg $1100. Was crazy and it was not clear on the website.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

The united employees at the gate treated me very rudely and called me nefarious

The food was horrible. There was no. Wifi, and it was just terrible from bangkok to d. C

My flight got cancelled. Couldn’t get my luggage. It arrived at my destination ahead of me. I didn’t get my preordered meal. Had to spend the night in the airport.

The crew was good, the WiFi was amazing, but the plane was meh. Uncomfortable first class, not enough room for baggage. My stuff ended up being behind my seat, so I had to sit on the plane for 20 minutes before I could get to it after landing.

Both my flight where delayed Had 25min to make it to my transfer flight

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

Flight was delayed 3 hours. No food on plane besides snacks

Every thing went smooth. No complaints except deplaning could have been quicker

I was grossly overcharged to change my return flight. Had to do it through Kayak because it was booked that way and I was not given the fare price listed at the time on JetBlue or kayak. Was traveling with another couple that booked directly through JetBlue and they paid the $100 change fee and the difference between what they paid originally(same as me) and the displayed fares and it was less than $400 total for two tickets. I paid almost $700 to change the same fare tickets they purchased and had to pay again for upgraded seat selection that I previously paid for on top of the almost $700 increase. Difficult to talk to the kayak representative because of his accent. Told me I had to wait for confirmation to be sure it had been changed and that I could take up to a few hours. The call itself after the wait time took almost 30 minutes, which could’ve been done directly on JetBlue in 2 to 3 minutes.. My husband and I were given separate boarding zones. They would not let us board together. I had to board in the last zone. They made me check my bag even though my husband told me that he had a spot to put my carry-on. Since he boarded before me. The flight crew tried to accommodate, but the woman that was boarding in the terminal came down and would not let me take my carry-on. She was aggressive, rude and condescending to everybody in line and told them she was being audited. When I told her that my husband had secured a spot for me to put my carry-on with his backpack, that would then move to under the seat. She told me that she couldn’t play favorites, although I was second to last to board the plane since my boarding zone was changed. They told me because I forwarded my husband his ticket that’s what separated our boarding zones, but would not allow us to board together. The volume on my TV would not work, and my upgraded seat would not go into the fully upright position so I was told repeatedly during takeoff and landing to put my chair into the upright position which was embarrassing and uncomfortable to be told assertively so many times. I will not book through kayak again.

Nice plane, with TV, comfortable seats and leg room. Updated regularly on time changes

Overall, it was a fantastic experience had no movies up charge for everything haven’t flown in many many years. Crew is fantastic. Flight was good overall great experience.

My sons tv wasn’t working and they didn’t give him a kids meal I have to request it prior and no one told me!!! Then the 2nd flight they split us up. My two year old can’t sit alone on the plane hello?????

What's not to like? Value?definitely. Every JetBlue member was extremely friendly on this flight. Very very nice new-ish aircraft,plenty of room. GOOD coffee. Entertainment,I didn't need it,but I think its available. What to do better? Well,there's nothing we can do about the other people, unbelievable how some folks are operating. Just don't allow people to lug all their stuff onto the aircraft. 1 bag. That's it. Be easier for you too. I personally would enjoy more options in schedule. One flight in and out a day is warranted given the local,I understand, but the times are inconvenient. Again, I completely understand why it is that way,It would however be great to have different options.

Had to wait over an hour in line for a Jet Blue agent to appear at the the counter. Ended up a customer service agent from another airline lines helped to check us in, and boarding pass,

Thought the economy premium experience would match that of the Amsterdam to Boston flight. Aircraft was older: chair didn’t lean back. I had to buy a blanket, which on the flight over was complimentary. Flight crew seemed disinterested all around.

I propose enhancing the legroom across the entire cabin seating area and expanding the snack selection. The airline companies should prioritize customer needs over the extravagant and unjustified salaries of upper management.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The plane was delayed after we boarded - although they sent an email to my work email (which I did not get until later) there was no announcement from the PA about the delay in flight. Fortunately, they made up the time in the air and we landed around the original time.

I couldn’t get a beverage because my tray table was broken

Comfy and timely flight thanks to Cathay to all crew and the captain for our smooth landing.. above all thank You Lord for our Safe flight ❤️🙌🙏🏽

Flight took additional prep time since plane came from Mexico, which resultrd in boarding and plane prep being delayed for additional cleaning procedures. Once boarded, plane tire was identified as being low on air and needed to be replaced, which creared the need to deboard and further delays for what was already a late night flight. Would have expected a better scheduled turn around and prep buffer that would have not created that degree of delay and deboarding

Both directions of our trip were befuddled by massive delays, one of which led to our connecting flight being grounded mid air due to storms that we’d have missed if we were on time. The other our originating flight was delayed repeatedly until it arrived at our connecting airport later than our final leg was even supposed to have arrived. American cannot seem to manage rebooking s for a family party… both directions we had to come up with a plan to get to Boston stay overnight only one night each direction was covered by the airline -and take a bus to or from our destination. Missed an entire leg of our trip, hotel cancellation fees, expensive stay in Boston and bus ticket expenses are unlikely to be comped and the meal vouchers are worthless.

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental