$106 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 5/1. 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
$313
JetBlue
Mon 5/11Thu 5/14
SJU - PWM • 1 stop
Cheapest one-way
$106
Typical prices: $192-$226
United Airlines
Fri 5/1
SJU - PWM • 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, May 11 - Thu, May 14
JetBlue Logo
3:00 pm - 11:36 pm
SJU
-
PWM
8h 36m
1 stop
JetBlue Logo
6:00 am - 1:29 pm
PWM
-
SJU
7h 29m
1 stop
$313JetBlue
Sun, Mar 15 - Wed, Mar 18
Southwest Logo
9:50 pm - 11:55 am
SJU
-
PWM
14h 05m
2 stops
Southwest Logo
4:30 pm - 11:00 pm
PWM
-
SJU
6h 30m
1 stop
$379Southwest
Thu, Mar 5 - Thu, Mar 12
United Airlines Logo
8:30 am - 10:51 pm
SJU
-
PWM
15h 21m
2 stops
United Airlines Logo
6:00 am - 1:40 pm
PWM
-
SJU
7h 40m
1 stop
$404United Airlines
Mon, May 11 - Thu, May 14
Southwest Logo
2:00 pm - 11:25 pm
SJU
-
PWM
9h 25m
2 stops
Southwest Logo
2:50 pm - 11:55 pm
PWM
-
SJU
9h 05m
2 stops
$406Southwest
Fri, Jul 10 - Mon, Jul 13
Southwest Logo
5:30 am - 12:20 pm
SJU
-
PWM
6h 50m
1 stop
Southwest Logo
5:35 am - 12:25 pm
PWM
-
SJU
6h 50m
1 stop
$424Southwest
Wed, Mar 4 - Thu, Mar 12
United Airlines Logo
2:05 am - 10:49 am
SJU
-
PWM
9h 44m
1 stop
United Airlines Logo
6:00 am - 1:40 pm
PWM
-
SJU
7h 40m
1 stop
$438United Airlines
Thu, Mar 5 - Thu, Mar 12
Southwest Logo
6:30 am - 4:45 pm
SJU
-
PWM
11h 15m
2 stops
Southwest Logo
12:35 pm - 11:35 pm
PWM
-
SJU
11h 00m
2 stops
$444Southwest
Fri, Jul 10 - Mon, Jul 13
Southwest Logo
5:30 am - 12:20 pm
SJU
-
PWM
6h 50m
1 stop
Southwest Logo
1:00 pm - 11:35 pm
PWM
-
SJU
10h 35m
2 stops
$465Southwest
Fri, Jul 10 - Sun, Jul 12
Southwest Logo
5:30 am - 12:20 pm
SJU
-
PWM
6h 50m
1 stop
Southwest Logo
5:30 am - 12:25 pm
PWM
-
SJU
6h 55m
1 stop
$486Southwest
Sun, Mar 15 - Wed, Mar 18
Southwest Logo
9:50 pm - 11:55 am
SJU
-
PWM
14h 05m
2 stops
Southwest Logo
12:30 pm - 10:15 pm
PWM
-
SJU
9h 45m
2 stops
$495Southwest
Useful Info

Good to know

Cheapest flight$106
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 8157 reviews
7.9Comfort
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
Airline reviews

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

10.0 ExcellentG, Feb 2026
FLL - ATL
Read more Delta reviews

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

Great other than a couple very drunk guys that for a while kept bumping my seat from behind. The staff did their best to control them. Even refused serving them alcohol and allowed the gal sitting next to them to move.

The attendant on board was amazing. She should be doing business/first international long haul.

The boarding was cumbersome. The staff was not aligned. They called group 1 but then the agent said no. Then they called group 1 again but still would not board us. Then they called group 2 and they all came up and still hadn’t started boarding. Then someone came from the plane and said why is no one coming? And the agent said bc i thought not yet and she said I said over the walkie talkie to send the passengers down? What was not clear about that? Also, onboard, the crew gave announcements very ironic/authoritative, and in first class they gave us a cheesebox. My expectations based on competition airlines, is a warm meal. A little underwhelming.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They are always late and seats was also not having working charger

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

did not have enough meal for first class passengers so offer us snack

Arrived 40 min early which was great - sat in runway for 35 min so no gain. Then waited for luggage 45 min. They need to staff accordingly knowing its one of the busiest week in Phx

My flight got rerouted due to crew rest. I was sent to Dallas customer service was not very polite. Was given a $40 room voucher for Motel 6 and $12 to eat with. It delayed me by a day. Where if I would have just stuck with my original flight Arizona was delayed to Cleveland and I could have made it home. They put me on a 9:00 flight out of Dallas to Cleveland without my knowledge or consent. When originally I was told it would be 8:45 a.m. on February 1st. I told them I could not take the 9:00 flight because I did not have anybody to pick me up from the airport at that time. I'm extremely disappointed in how I was treated. And I will not fly American Airlines again.

I am very appreciative of the help provided to me by Dennis and Whitney. I had lost my phone at EWR airport and they were very kind in assisting me. This included advice on how to file a report and also helping me connect with family. The pilot was also great about keeping passengers updated on the flight progress with regular communications over the system.

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

Old equipment, needs upgrade and seat comfort. Internet didn't work 75% or the time.

The screens were inoperable for movies and such, but everything else was just fine

For a 5 1/2 hour flite i considered the "business class" to be subpar. The seats were just ok, no amenities, really nothing more than a long domestic flight. Frankly disappointed.

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