$188 Find Cheap Flights from Caribbean to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Portland departing on 1/27. 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 Portland

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

Save 24% or moreCompare multiple travel sites with one search.

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

Bundle and saveSave money when you bundle your flight + hotel.

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

Everything you should know

Cheapest round-trip
$417
Overall average: $557
Multiple Airlines
Mon 12/22Tue 1/6
SJU - PDX • 2 stops
Cheapest one-way
$188
Typical prices: $261-$749
Southwest
Tue 1/27
SJU - PDX • 2 stops
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Portland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Portland 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 Caribbean to Portland

Mon, Dec 22 - Tue, Jan 6
Multiple Airlines Logo
10:33 am - 9:10 pmSJU-PDX
38h 37m2 stops
Multiple Airlines Logo
7:07 am - 2:50 amPDX-SJU
39h 43m2 stops
$417Multiple Airlines
Find Deal
Mon, Dec 22 - Tue, Jan 6
Multiple Airlines Logo
10:33 am - 9:18 amSJU-PDX
26h 45m2 stops
Multiple Airlines Logo
6:14 am - 2:50 amPDX-SJU
40h 36m3 stops
$428Multiple Airlines
Find Deal
Mon, Dec 22 - Tue, Jan 6
American Airlines Logo
12:47 pm - 12:59 amSJU-PDX
16h 12m1 stop
American Airlines Logo
11:01 pm - 6:22 pmPDX-SJU
15h 21m1 stop
$429American Airlines
Find Deal
Mon, Dec 22 - Tue, Jan 6
Multiple Airlines Logo
7:25 am - 8:50 pmSJU-PDX
17h 25m1 stop
Multiple Airlines Logo
7:07 am - 2:50 amPDX-SJU
39h 43m2 stops
$445Multiple Airlines
Find Deal
Tue, Dec 23 - Wed, Dec 31
American Airlines Logo
10:25 am - 12:59 amSJU-PDX
18h 34m1 stop
American Airlines Logo
10:49 pm - 9:11 pmPDX-SJU
18h 22m1 stop
$457American Airlines
Find Deal
Tue, Dec 23 - Wed, Dec 31
Southwest Logo
11:35 am - 8:25 pmSJU-PDX
12h 50m2 stops
Southwest Logo
6:15 am - 12:35 amPDX-SJU
14h 20m2 stops
$504Southwest
Find Deal
Sat, Feb 28 - Mon, Mar 2
Delta Logo
8:00 am - 7:03 pmMBJ-PDX
14h 03m1 stop
Delta Logo
12:40 am - 2:40 pmPDX-MBJ
11h 00m1 stop
$506Delta
Find Deal
Wed, Feb 25 - Mon, Mar 2
United Airlines Logo
1:09 am - 2:48 pmBQN-PDX
17h 39m2 stops
United Airlines Logo
7:00 am - 11:57 pmPDX-BQN
12h 57m2 stops
$509United Airlines
Find Deal
Sat, Feb 28 - Mon, Mar 2
Delta Logo
4:40 pm - 9:29 amMBJ-PDX
19h 49m2 stops
Delta Logo
12:40 am - 2:40 pmPDX-MBJ
11h 00m1 stop
$510Delta
Find Deal
Wed, Feb 25 - Mon, Mar 2
United Airlines Logo
1:09 am - 2:48 pmBQN-PDX
17h 39m2 stops
United Airlines Logo
3:50 pm - 11:57 pmPDX-BQN
28h 07m3 stops
$541United Airlines
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$188
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from San Juan to Portland

FAQs for booking flights from Caribbean to Portland

  • How does KAYAK find such low prices on flights from Caribbean to Portland?

    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 Caribbean to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from 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 Caribbean to Portland?

    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 to Portland with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Portland?

    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 to Portland from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Caribbean to Portland

 
Need help choosing which airline to fly with from Caribbean to Portland? 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 4238 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

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

8.0 ExcellentTODD, Nov 2025DAL - CMH
Read more Southwest reviews

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.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

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

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

Seats comfortable, service and food very mediocre, staff not very attentive, worse than many other our flights with Delta.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

The flight attendants were very rude, beyond comprehension. I took a business class from London to SFO for the first time on United. When I asked for a second piece of bread during dinner, the serving attendant threw a 3rd bread on my plate and said, “here. You can have this one too”! I couldn’t believe the rudeness of the attendant. Most all attendants were very rude, unhelpful, sing the food was absolutely disgusting. Never fly United internationally in business class. My flight back to SFO was a nightmare!!

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

Very disappointed with food service. They ran out of entree selections- so for the last 10 rows only option was lentil stew. Not a fan. Then the morning service (pizza twist) was lukewarm at best- I exited my 12 hour flight having eaten a roll and dessert. They knew it was a full flight.

Premium Plus is a really good idea for longer flights

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Seaside
Vancouver
Salem
The Dalles
Lake Oswego
Clackamas
Stevenson
Government Camp
Carson
Kelso
Gleneden Beach
Gladstone
Oceanside
Dundee
Durham

Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland