$178 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 1/10. 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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Everything you should know

Cheapest round-trip
$363
Overall average: $685
Frontier
Thu 11/13Sun 11/16
SJU - PDX • 2 stops
Cheapest one-way
$178
Typical prices: $261-$757
Frontier
Sat 1/10
SJU - PDX • 2 stops
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Flight Deals
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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

Thu, Nov 13 - Sun, Nov 16
Frontier Logo
2:11 am - 11:56 amSJU-PDX
13h 45m2 stops
Frontier Logo
3:26 pm - 4:10 pmPDX-SJU
20h 44m2 stops
$363Frontier
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Fri, Nov 14 - Sun, Nov 16
United Airlines Logo
3:46 pm - 10:45 pmSJU-PDX
10h 59m1 stop
United Airlines Logo
8:20 am - 10:22 pmPDX-SJU
10h 02m1 stop
$419United Airlines
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Tue, Nov 18 - Thu, Dec 4
Delta Logo
2:10 pm - 12:14 amSJU-PDX
14h 04m2 stops
Delta Logo
7:09 pm - 12:45 pmPDX-SJU
13h 36m2 stops
$457Delta
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Thu, Feb 26 - Sun, Mar 1
Delta Logo
6:15 am - 7:11 pmSJU-PDX
16h 56m2 stops
Delta Logo
12:55 am - 3:20 pmPDX-SJU
10h 25m1 stop
$472Delta
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Tue, Nov 18 - Thu, Dec 4
American Airlines Logo
2:47 pm - 11:31 pmSJU-PDX
12h 44m1 stop
American Airlines Logo
10:45 pm - 11:59 amPDX-SJU
9h 14m1 stop
$473American Airlines
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Sun, Dec 21 - Tue, Jan 6
Multiple Airlines Logo
3:55 am - 12:05 amSJU-PDX
24h 10m2 stops
Multiple Airlines Logo
1:51 pm - 4:08 pmPDX-SJU
22h 17m2 stops
$488Multiple Airlines
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Tue, Nov 18 - Thu, Dec 4
American Airlines Logo
3:56 pm - 11:26 pmSJU-PDX
11h 30m1 stop
American Airlines Logo
5:59 pm - 10:09 amPDX-SJU
12h 10m2 stops
$492American Airlines
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Mon, Dec 22 - Tue, Jan 6
Multiple Airlines Logo
5:22 pm - 9:10 pmSJU-PDX
31h 48m2 stops
Multiple Airlines Logo
1:51 pm - 4:08 pmPDX-SJU
22h 17m2 stops
$493Multiple Airlines
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Tue, Nov 4 - Thu, Nov 13
Southwest Logo
11:20 am - 9:25 pmSJU-PDX
14h 05m2 stops
Southwest Logo
7:10 pm - 11:00 amPDX-SJU
11h 50m2 stops
$545Southwest
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Sat, Nov 22 - Sat, Nov 29
Southwest Logo
1:55 pm - 12:40 amMBJ-PDX
13h 45m2 stops
Southwest Logo
6:20 pm - 12:50 pmPDX-MBJ
15h 30m2 stops
$657Southwest
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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$178
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 13% 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 4237 reviews
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

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

10.0 ExcellentStacy, Oct 2025SMF - DEN
Read more Southwest reviews

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.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

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 too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

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.

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

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

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

Typically flights with AA are good. The staff are pleasant, welcoming, and efficient.

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

The business class seats are dated and uncomfortable. The space is bare minimum and there is absolutely no privacy. For $4K, this is not what I expect.

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