$185 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 12/24. 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
$398
Typical prices: $481-$581
Multiple Airlines
Mon 12/22Tue 1/6
SJU - PDX • 3 stops
Cheapest one-way
$185
Typical prices: $255-$435
Southwest
Wed 12/24
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

Mon, Dec 22 - Tue, Jan 6
Multiple Airlines Logo
2:44 pm - 3:00 pmSJU-PDX
52h 16m3 stops
Multiple Airlines Logo
5:10 am - 4:13 pmPDX-SJU
31h 03m2 stops
$398Multiple Airlines
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Mon, Dec 22 - Tue, Jan 6
Multiple Airlines Logo
2:44 pm - 9:30 amSJU-PDX
46h 46m2 stops
Multiple Airlines Logo
5:10 am - 4:13 pmPDX-SJU
31h 03m2 stops
$408Multiple Airlines
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Thu, Jan 22 - Sat, Jan 31
Delta Logo
2:15 pm - 10:15 pmSJU-PDX
12h 00m1 stop
Delta Logo
7:00 am - 11:57 pmPDX-SJU
12h 57m1 stop
$419Delta
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Wed, Jan 21 - Thu, Jan 29
Delta Logo
3:55 pm - 10:15 pmSJU-PDX
10h 20m1 stop
Delta Logo
7:00 am - 11:57 pmPDX-SJU
12h 57m1 stop
$420Delta
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Wed, Dec 24 - Fri, Jan 2
American Airlines Logo
5:24 am - 5:11 pmSJU-PDX
15h 47m2 stops
American Airlines Logo
10:49 pm - 9:11 pmPDX-SJU
18h 22m1 stop
$428American Airlines
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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 - 12:30 pmPDX-SJU
9h 29m1 stop
$430American Airlines
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Tue, Jan 20 - Wed, Jan 28
Southwest Logo
5:40 am - 3:40 pmSJU-PDX
14h 00m2 stops
Southwest Logo
6:30 am - 11:10 pmPDX-SJU
12h 40m2 stops
$447Southwest
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Wed, Apr 1 - Sat, Apr 11
American Airlines Logo
1:30 am - 7:16 pmSJU-PDX
20h 46m1 stop
American Airlines Logo
11:07 pm - 11:00 amPDX-SJU
8h 53m1 stop
$457American Airlines
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Sun, Jan 11 - Sun, Jan 18
United Airlines Logo
3:20 pm - 10:53 pmMBJ-PDX
34h 33m2 stops
United Airlines Logo
11:05 pm - 2:00 pmPDX-MBJ
11h 55m1 stop
$498United Airlines
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Sun, Jan 11 - Sun, Jan 18
United Airlines Logo
3:20 pm - 11:57 amMBJ-PDX
23h 37m2 stops
United Airlines Logo
7:51 pm - 2:00 pmPDX-MBJ
15h 09m2 stops
$535United Airlines
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Good to know

Low seasonJanuary
Cheapest flight$185
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 11% 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 4255 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

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.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

One of the best airlines that I flew on, the flight attendants were very attentive and professional.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

We boarded late. The crew at the airport was dismissive. The seat cushion on the plane was uncomfortable.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

United has come a long way, it’s been a fantastic experience traveling with them.

Even though we were delayed, we were able to make our connection

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

Great crew, excellent landing, good food. Over all great experience. Thank you!

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

I like how the crew and pilot kept us updated Even though our flight was slightly delayed. We made up time for it in the air. I really did enjoy my seat and amenities and my trip and value overall.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

The inflight staff is never the issue always the extra and charges american charges! Literally 30 bucks for WiFi! Is insane and then it’s choppy and slow. If you pay for it once you don’t need to pay again for switching aircraft especially when there is flight delays

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

flight was good until we arrived at cmh ten minutes early but then sat on tarmac for twenty minutes because a plane was at our gate, so we had to wait despite the pilot tellling us that 3 other gates were open.

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