$118 Find Cheap Flights from Caribbean Islands 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 2/15. 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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Everything you should know

Cheapest round-trip
$295
American Airlines
Wed 2/18Sat 2/21
SJU - PWM • 2 stops
Cheapest one-way
$118
Typical prices: $211-$218
American Airlines
Sun 2/15
SJU - PWM • 1 stop
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Flight Deals

Cheap Flights from Caribbean Islands to Portland

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

Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
4:37 pm - 12:12 pmSJU-PWM
20h 35m2 stops
American Airlines Logo
6:28 pm - 3:42 pmPWM-SJU
20h 14m2 stops
$295American Airlines
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Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
2:36 pm - 11:37 pmSJU-PWM
10h 01m2 stops
American Airlines Logo
5:17 pm - 10:09 amPWM-SJU
15h 52m2 stops
$378American Airlines
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Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
9:25 am - 6:03 pmSJU-PWM
9h 38m1 stop
American Airlines Logo
12:35 pm - 11:42 amPWM-SJU
22h 07m2 stops
$382American Airlines
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Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
11:00 am - 11:37 pmSJU-PWM
13h 37m2 stops
American Airlines Logo
7:02 am - 10:09 pmPWM-SJU
14h 07m1 stop
$434American Airlines
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Thu, Apr 23 - Sat, Apr 25
JetBlue Logo
1:59 am - 1:23 pmSJU-PWM
11h 24m1 stop
JetBlue Logo
2:20 pm - 10:47 pmPWM-SJU
8h 27m1 stop
$452JetBlue
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Fri, Apr 24 - Sat, Apr 25
Southwest Logo
5:35 am - 2:10 pmSJU-PWM
8h 35m1 stop
Southwest Logo
5:40 am - 2:50 pmPWM-SJU
9h 10m2 stops
$479Southwest
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Fri, Dec 12 - Mon, Dec 15
Delta Logo
6:35 pm - 11:59 pmSJU-PWM
6h 24m1 stop
Delta Logo
2:34 pm - 11:59 pmPWM-SJU
8h 25m1 stop
$490Delta
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Wed, Feb 18 - Sat, Feb 21
United Airlines Logo
8:10 am - 2:23 pmSJU-PWM
7h 13m1 stop
United Airlines Logo
3:05 pm - 12:36 amPWM-SJU
8h 31m1 stop
$502United Airlines
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Thu, Apr 23 - Sat, Apr 25
United Airlines Logo
1:05 am - 10:44 amSJU-PWM
9h 39m2 stops
United Airlines Logo
11:17 am - 9:24 pmPWM-SJU
10h 07m2 stops
$563United Airlines
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Fri, Apr 24 - Sat, Apr 25
Southwest Logo
6:50 am - 4:15 pmSJU-PWM
9h 25m2 stops
Southwest Logo
5:40 am - 2:50 pmPWM-SJU
9h 10m2 stops
$589Southwest
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Good to know

Low seasonFebruary
Cheapest flight$118
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 51% increase in price.
Flight from San Juan to Portland

FAQs for booking flights from Caribbean Islands to Portland

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Caribbean Islands 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 Islands 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 Islands with another airline.

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

 
Need help choosing which airline to fly with from Caribbean Islands 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 7998 reviews
8.2Boarding
7.9Comfort
8.5Crew
7.3Food
7.9Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, Oct 2025CDG - SEA
Read more Delta reviews

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.

Overall good experience; however, there was one flight attendant who was rather rough compared to everyone else. Everything else was good: entertainment, food. Delta keeps on delivering! Thank you!

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Flight left on time. Boarding was easy. Arrived to EWR 30 mins early. Luggage was deplaned in good time. Overall a very good experience.

Flight from Rome to SFO was excellent compared To our flight to Europe from SFO. The food was much tastier. You can see how UNITED is skimping, though. Instead of getting something mid flight you had to ask for it. It was not automatically served. There was a cookie at the end of the arrival meal, for example that tasted like it just came out of a box. They used to serve a little container of nuts, now … a tiny container of nuts, mixed with pretzels. This was business class that you really have to pay for! But this is minor complaints compared to the overall. My major complaint is the position of the even numbered seats by the windows. You have to turn around to see your window & the positioning as some other controls are harder to get at. This is compared to the odd number seat that are perfectly aligned.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

Excellent all round, first time flying United. App is very helpful.

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.

Nice comfortable flight from Barcelona back to the states. The premium economy offers the extra room we need for my husband. The food was good and our flight attendants were excellent.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

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