$155 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 5/7. 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, 0 bags

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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

Wed, Apr 22 - Wed, Apr 29
United Airlines Logo
4:12 pm - 2:31 pm
MBJ
-
PDX
24h 19m
2 stops
United Airlines Logo
1:55 pm - 3:10 pm
PDX
-
MBJ
47h 15m
2 stops
$332United Airlines
Thu, Apr 23 - Thu, Apr 30
United Airlines Logo
4:12 pm - 12:44 am
MBJ
-
PDX
34h 32m
2 stops
United Airlines Logo
7:05 pm - 12:50 pm
PDX
-
MBJ
39h 45m
2 stops
$341United Airlines
Thu, Apr 23 - Thu, Apr 30
United Airlines Logo
4:12 pm - 10:34 pm
MBJ
-
PDX
32h 22m
2 stops
United Airlines Logo
3:59 pm - 1:30 pm
PDX
-
MBJ
43h 31m
3 stops
$357United Airlines
Tue, Apr 21 - Sat, Apr 25
American Airlines Logo
6:45 am - 10:49 pm
SJU
-
PDX
19h 04m
1 stop
American Airlines Logo
11:40 pm - 2:42 pm
PDX
-
SJU
12h 02m
1 stop
$436American Airlines
Thu, Jul 23 - Tue, Jul 28
Southwest Logo
6:30 am - 4:20 pm
SJU
-
PDX
12h 50m
2 stops
Southwest Logo
7:40 pm - 11:30 am
PDX
-
SJU
12h 50m
2 stops
$448Southwest
Tue, Apr 21 - Sat, Apr 25
American Airlines Logo
6:45 am - 10:49 pm
SJU
-
PDX
19h 04m
1 stop
American Airlines Logo
10:28 pm - 2:52 pm
PDX
-
SJU
13h 24m
1 stop
$456American Airlines
Sun, May 10 - Fri, May 15
Multiple Airlines Logo
3:08 am - 8:35 pm
SJU
-
PDX
44h 27m
2 stops
Multiple Airlines Logo
9:53 am - 2:01 am
PDX
-
SJU
37h 08m
3 stops
$492Multiple Airlines
Fri, Apr 24 - Sat, May 2
Delta Logo
6:05 am - 10:16 pm
SDQ
-
PDX
19h 11m
1 stop
Delta Logo
5:59 pm - 12:31 pm
PDX
-
SDQ
15h 32m
2 stops
$576Delta
Wed, Apr 1 - Sat, Apr 18
Multiple Airlines Logo
3:01 pm - 8:35 pm
SDQ
-
PDX
32h 34m
1 stop
Multiple Airlines Logo
10:03 am - 5:29 am
PDX
-
SDQ
16h 26m
1 stop
$594Multiple Airlines
Fri, Apr 24 - Sun, May 3
Delta Logo
6:05 am - 10:16 pm
SDQ
-
PDX
19h 11m
1 stop
Delta Logo
7:00 am - 12:17 am
PDX
-
SDQ
14h 17m
1 stop
$600Delta
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$155
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 5% 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 3 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.
7.9
DeltaOverall score based on 8278 reviews
7.9Comfort
8.1Boarding
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

8.0 ExcellentMary, Mar 2026
LGA - MKE
Read more Delta reviews

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

I wish the inflight entertainment system options were broader, but overall this was a fantastic crew and I can’t express how cheerful, welcoming, and attentive they were.

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

I paid $7,000 to fly round trip to Porto. I thought it was for business class. But on the leg from Miami to Newark, and again from Newark to Miami, i was in coach. One time in the middle seat of coach. From Newark to Porto I was in business class as expected, and it was fine. I fly to Portugal once per month, often paying $5,000 for business class. Usually i fly American Airlines. I'd be happy to fly more with United Airlines. But my experience was disappointing because i was put in the coach for almost half the flights.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It was okay, the food was good, but after the landing there was not enough time for luggage and security to catch a connection. It was crowded on board.

It’s always a great time flying with united airlines.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

It was amazing. I had several upgraded seats on my flight out. Everything went smooth with no delays.

They never clean the toilet, and the food is worse

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

An delay of almost 3 hours while passengers were already in the plane kept us very uncomfortable. The food was also very limited. A bad experience overall.

I guess if you don't run the AC it saves on fuel? Everyone complained the entire trip about how hot the cabin was. Also, extremely cramped. AA allows a little space per passenger as is legal. Not cheap, ticket prices were high.

The crew was excellent and overall the flight was good. No complaints.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

Never had such a lazy first class attendant. Literally spent 60%+ of the flight playing games on her personal phone making up excuses of why she was unavailable.

The flight attendants and the service is getting worse by the day.

Not to have gotten delayed by 2+ hours for the fourth straight American flight. They're the worst.

Like all of the flights I took to get down to Dallas. They were delayed

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