$196 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 3/10. 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

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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 Cana1 stop$527
Santo Domingo
Santo Domingo1 stop$536
Montego Bay
Montego Bay1 stop$553
Oranjestad
Oranjestad1 stop$500
Nassau
Nassau2 stops$516
Kingston
Kingston2 stops$628
Simpson Bay
Simpson Bay2 stops$597
Providenciales
Providenciales1 stop$650
Bridgetown
Bridgetown2 stops$566
George Town
George Town2 stops$558
Willemstad
Willemstad2 stops$558
St. John's
St. John's2 stops$656
Puerto Plata
Puerto Plata1 stop$568
Aguadilla
Aguadilla2 stops$627
Punta Cana
Punta Cana1 stop$527
Santo Domingo
Santo Domingo1 stop$536
Montego Bay
Montego Bay1 stop$553
Oranjestad
Oranjestad1 stop$500
Nassau
Nassau2 stops$516
Kingston
Kingston2 stops$628
Simpson Bay
Simpson Bay2 stops$597
Providenciales
Providenciales1 stop$650
Bridgetown
Bridgetown2 stops$566
George Town
George Town2 stops$558
Willemstad
Willemstad2 stops$558
St. John's
St. John's2 stops$656
Puerto Plata
Puerto Plata1 stop$568
Aguadilla
Aguadilla2 stops$627

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, Jan 20 - Wed, Jan 28
Southwest Logo
6:30 am - 11:10 pmPDX-SJU
12h 40m2 stops
Southwest Logo
12:10 pm - 10:05 pmSJU-PDX
13h 55m2 stops
$369Southwest
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Tue, Jan 20 - Wed, Jan 28
Southwest Logo
5:05 am - 8:55 pmPDX-SJU
11h 50m2 stops
Southwest Logo
12:10 pm - 10:05 pmSJU-PDX
13h 55m2 stops
$394Southwest
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Mon, May 4 - Mon, May 11
JetBlue Logo
11:40 pm - 4:05 pmPDX-SJU
13h 25m1 stop
JetBlue Logo
1:45 pm - 10:25 pmSJU-PDX
11h 40m1 stop
$396JetBlue
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Tue, Jan 20 - Thu, Jan 22
American Airlines Logo
10:15 pm - 8:50 pmPDX-SJU
18h 35m1 stop
American Airlines Logo
7:07 am - 6:51 pmSJU-PDX
15h 44m1 stop
$414American Airlines
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Sat, Apr 25 - Thu, Apr 30
United Airlines Logo
6:53 am - 8:38 pmPDX-SJU
10h 45m1 stop
United Airlines Logo
7:45 am - 6:05 pmSJU-PDX
13h 20m1 stop
$415United Airlines
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Mon, Jan 19 - Wed, Jan 28
Delta Logo
7:37 pm - 2:10 pmPDX-SJU
14h 33m2 stops
Delta Logo
3:55 pm - 10:15 pmSJU-PDX
10h 20m1 stop
$419Delta
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Tue, Jan 20 - Thu, Jan 29
Delta Logo
7:00 am - 11:57 pmPDX-SJU
12h 57m1 stop
Delta Logo
2:15 pm - 12:17 amSJU-PDX
14h 02m2 stops
$420Delta
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Sun, Jan 18 - Wed, Jan 28
Delta Logo
6:00 am - 11:45 pmPDX-SJU
13h 45m2 stops
Delta Logo
3:55 pm - 10:15 pmSJU-PDX
10h 20m1 stop
$421Delta
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Sun, Feb 1 - Tue, Feb 10
American Airlines Logo
7:38 am - 11:59 pmPDX-SJU
12h 21m2 stops
American Airlines Logo
8:20 am - 8:27 pmSJU-PDX
16h 07m2 stops
$426American Airlines
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Thu, Jan 29 - Tue, Feb 3
United Airlines Logo
11:05 pm - 4:50 pmPDX-AUA
13h 45m1 stop
United Airlines Logo
5:50 pm - 1:45 pmAUA-PDX
23h 55m2 stops
$500United Airlines
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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 $449 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $778 and $690 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 4 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$196
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Portland to Simpson 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.

  • 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 4254 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

from SFO-> FRA flight, AVML meal was significantly less compared to regular meal, especially no Desert, no Bread, no sides.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

This was an older airplane. The cabin was constantly warm to hot throughout the 10 hour flight and there were no vents to personalize air flow. Also since it was an older plane, the material and comfort of the chairs were very uncomfortable. I left my flight with major soreness on my tailbone.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Even though we were delayed, we were able to make our connection

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Uncomfortable seats and tiny tray table. Expensive snacks. Flight was on time and crew was pleasant but take me back to Southwest!

Boarding and unboarding processes were pretty smooth. I gave a low score for Boarding because of how my flight was missing from all the boards at the airport, and when I checked the flight status on the Spirit website, it said it would be departing from Terminal E, gate D15. There are no "D" gates in terminal E.

Speaker airport didn't work well, so we couldn't hear the boarding call but the plane was on time leaving and on time arriving took a while for them to open the door and there was a non-disruptive guy who was inebriated a few rows ahead of us. Overall the flight was good and we appreciate the on-time-ness

The plane was freezing and everyone had on their winter coats. I pulled out my sweaters out of my carryon to cover myself and put on an extra pair of socks. They offered NO FREE drinks or snacks on a 6 hour flight. The seats don’t have plugs or charges or any form of entertainment- so I just played my one downloaded game on my phone because I couldn’t sleep because I was too cold. Miserable flight though we landed safely.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

The flight was on time and the crew was very professional and accommodating. When other airlines are canceling flights Spirit is still flying with on time flights. I have no complaints and will continue to choose Spirit when it is the best option for me.

Very uncomfortable seat. Hard bar under cushion. Flight had no solution except to walk a around at times

Endless, trip oof my life, we still are in in plane waiting for getting off.after 3 hours delay. Not even a glass of water.

It was cheap. Spirit is what it is. I got to my destination and home safely. There was no food or entertainment without paying extra, which is fine. That’s why the flight was inexpensive.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports