$171 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 3/18. 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
$432
Typical prices: $446-$595
Southwest
Thu 2/26Sun 3/1
SJU - PDX • 2 stops
Cheapest one-way
$171
Typical prices: $233-$323
Frontier
Wed 3/18
SJU - PDX • 2 stops
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Flight Deals
Useful Info
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

Thu, Feb 26 - Sun, Mar 1
Southwest Logo
6:00 am - 2:55 pm
SJU
-
PDX
12h 55m
2 stops
Southwest Logo
6:50 pm - 10:30 am
PDX
-
SJU
11h 40m
2 stops
$432Southwest
Fri, Feb 27 - Sun, Mar 1
Delta Logo
6:15 am - 8:30 pm
SJU
-
PDX
18h 15m
2 stops
Delta Logo
7:00 am - 11:59 pm
PDX
-
SJU
12h 59m
1 stop
$440Delta
Thu, Jun 25 - Tue, Jun 30
JetBlue Logo
12:30 pm - 10:25 pm
SJU
-
PDX
12h 55m
1 stop
JetBlue Logo
11:40 pm - 4:05 pm
PDX
-
SJU
13h 25m
1 stop
$471JetBlue
Thu, Apr 30 - Tue, May 5
American Airlines Logo
11:38 am - 10:32 pm
SJU
-
PDX
13h 54m
2 stops
American Airlines Logo
11:59 pm - 2:52 pm
PDX
-
SJU
11h 53m
2 stops
$478American Airlines
Tue, Mar 31 - Tue, Apr 14
American Airlines Logo
7:11 am - 12:22 am
SJU
-
PDX
20h 11m
1 stop
American Airlines Logo
7:00 am - 11:01 pm
PDX
-
SJU
13h 01m
1 stop
$503American Airlines
Wed, May 27 - Wed, Jun 3
JetBlue Logo
1:45 pm - 10:25 pm
SJU
-
PDX
11h 40m
1 stop
JetBlue Logo
11:40 pm - 12:59 am
PDX
-
SJU
22h 19m
2 stops
$504JetBlue
Thu, May 21 - Sun, May 24
United Airlines Logo
1:40 pm - 10:55 pm
SJU
-
PDX
12h 15m
1 stop
United Airlines Logo
10:56 pm - 12:04 pm
PDX
-
SJU
10h 08m
1 stop
$512United Airlines
Fri, May 29 - Mon, Jun 1
United Airlines Logo
1:05 am - 9:21 am
SJU
-
PDX
11h 16m
1 stop
United Airlines Logo
10:56 pm - 1:45 pm
PDX
-
SJU
11h 49m
1 stop
$530United Airlines
Tue, Mar 3 - Sat, Mar 14
Multiple Airlines Logo
6:10 am - 8:33 pm
SDQ
-
PDX
18h 23m
1 stop
Multiple Airlines Logo
5:50 pm - 5:25 am
PDX
-
SDQ
32h 35m
2 stops
$572Multiple Airlines
Fri, Feb 20 - Sun, Mar 15
Multiple Airlines Logo
3:32 pm - 4:50 pm
SDQ
-
PDX
29h 18m
2 stops
Multiple Airlines Logo
7:00 am - 4:29 pm
PDX
-
SDQ
30h 29m
1 stop
$583Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$171
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 1% 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 airline flying 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.
7.2
American AirlinesOverall score based on 11189 reviews
7.5Boarding
6.4Food
7.2Comfort
8.0Crew
6.9Entertainment
Airline reviews

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

8.0 ExcellentAnonymous, Jan 2026
PHX - CMH
Read more American Airlines reviews

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

I think we deserve more than 25% refund for losing first class seats when having to reschedule flight due to weather.

The flight was completely full. Crew was not happy. Everyone was rude and brusque. Travelling with an arm in a cast and seating in the first row of economy cabin (in front of the separation) I needed help retrieving my tray for the meal. A staff member literally threw the tray on my lap, without helping to take out the tray. Boarding was messy, with 300 people waiting in an encloses space with low ceiling. I will try to avoid AA next time I have a long flight.

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

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Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland

Portland (PDX)