$167 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 5/18. 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$486
Santo Domingo
Santo Domingo2 stops$580
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad1 stop$646
Nassau
Nassau2 stops$614
Kingston
Kingston2 stops$668
Simpson Bay
Simpson Bay2 stops$735
Providenciales
Providenciales2 stops$686
Bridgetown
Bridgetown2 stops$587
George Town
George Town2 stops$587
Willemstad
Willemstad2 stops$777
Aguadilla
Aguadilla2 stops$733
Puerto Plata
Puerto Plata2 stops$705
St. John's
St. John's2 stops$855
Punta Cana
Punta Cana1 stop$486
Santo Domingo
Santo Domingo2 stops$580
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad1 stop$646
Nassau
Nassau2 stops$614
Kingston
Kingston2 stops$668
Simpson Bay
Simpson Bay2 stops$735
Providenciales
Providenciales2 stops$686
Bridgetown
Bridgetown2 stops$587
George Town
George Town2 stops$587
Willemstad
Willemstad2 stops$777
Aguadilla
Aguadilla2 stops$733
Puerto Plata
Puerto Plata2 stops$705
St. John's
St. John's2 stops$855

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

Sun, Aug 16 - Sat, Aug 29
American Airlines Logo
11:20 pm - 1:17 pm
PDX
-
MBJ
11h 57m
1 stop
American Airlines Logo
12:47 pm - 9:36 pm
MBJ
-
PDX
10h 49m
1 stop
$392American Airlines
Sun, Aug 16 - Sat, Aug 29
American Airlines Logo
11:20 pm - 1:28 pm
PDX
-
MBJ
12h 08m
2 stops
American Airlines Logo
2:20 pm - 11:56 pm
MBJ
-
PDX
11h 36m
1 stop
$397American Airlines
Tue, Sep 22 - Sat, Sep 26
United Airlines Logo
12:50 pm - 11:43 am
PDX
-
MBJ
20h 53m
2 stops
United Airlines Logo
12:52 pm - 9:05 pm
MBJ
-
PDX
10h 13m
1 stop
$407United Airlines
Tue, Sep 22 - Sat, Sep 26
United Airlines Logo
4:07 pm - 11:43 am
PDX
-
MBJ
17h 36m
2 stops
United Airlines Logo
2:40 pm - 12:59 am
MBJ
-
PDX
12h 19m
2 stops
$412United Airlines
Sun, Aug 23 - Tue, Aug 25
Delta Logo
7:14 pm - 3:34 pm
PDX
-
MBJ
18h 20m
2 stops
Delta Logo
4:59 pm - 9:25 am
MBJ
-
PDX
18h 26m
2 stops
$427Delta
Fri, Aug 14 - Sun, Aug 23
Southwest Logo
6:05 am - 10:15 pm
PDX
-
SJU
13h 10m
2 stops
Southwest Logo
5:30 am - 12:45 pm
SJU
-
PDX
10h 15m
1 stop
$466Southwest
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
10:45 pm - 1:10 pm
PDX
-
SJU
11h 25m
1 stop
Southwest Logo
5:30 am - 3:00 pm
SJU
-
PDX
12h 30m
1 stop
$481Southwest
Fri, May 29 - Thu, Jun 4
Delta Logo
5:51 pm - 1:20 pm
PDX
-
SJU
16h 29m
2 stops
Delta Logo
1:16 pm - 11:44 pm
SJU
-
PDX
13h 28m
2 stops
$530Delta
Sat, May 23 - Wed, May 27
JetBlue Logo
2:30 pm - 1:44 am
PDX
-
SDQ
32h 14m
1 stop
JetBlue Logo
3:10 am - 1:10 pm
SDQ
-
PDX
13h 00m
1 stop
$610JetBlue
Thu, May 28 - Mon, Jun 1
JetBlue Logo
2:30 pm - 1:44 am
PDX
-
SDQ
32h 14m
1 stop
JetBlue Logo
3:10 am - 1:10 pm
SDQ
-
PDX
13h 00m
1 stop
$630JetBlue
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 May, when tickets cost $179 (return) on average. On the other hand, the most expensive months are February and December, when the average cost of round-trip tickets is $279 and $253 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 4 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$167
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 10% 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.

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 4314 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

On time departure and early arrival. Flight attendant very nice.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports