$168 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 4/16. 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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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, Apr 30 - Thu, May 7
United Airlines Logo
2:40 pm - 10:59 pm
MBJ
-
PDX
10h 19m
1 stop
United Airlines Logo
7:05 pm - 12:50 pm
PDX
-
MBJ
39h 45m
2 stops
$353United Airlines
Wed, Jun 10 - Thu, Jul 9
United Airlines Logo
2:40 pm - 11:53 pm
MBJ
-
PDX
35h 13m
2 stops
United Airlines Logo
11:59 pm - 1:30 pm
PDX
-
MBJ
11h 31m
1 stop
$362United Airlines
Wed, Jun 10 - Thu, Jul 9
United Airlines Logo
2:40 pm - 10:48 pm
MBJ
-
PDX
10h 08m
1 stop
United Airlines Logo
11:59 pm - 1:30 pm
PDX
-
MBJ
11h 31m
1 stop
$365United Airlines
Tue, Apr 21 - Sat, Apr 25
American Airlines Logo
11:43 am - 10:56 pm
SJU
-
PDX
14h 13m
2 stops
American Airlines Logo
6:00 am - 11:02 pm
PDX
-
SJU
14h 02m
1 stop
$456American Airlines
Fri, Aug 14 - Thu, Aug 20
Southwest Logo
5:30 am - 3:00 pm
SJU
-
PDX
12h 30m
1 stop
Southwest Logo
10:45 pm - 2:30 pm
PDX
-
SJU
12h 45m
1 stop
$468Southwest
Tue, May 19 - Thu, May 28
American Airlines Logo
1:15 pm - 10:47 pm
MBJ
-
PDX
11h 32m
1 stop
American Airlines Logo
9:47 pm - 11:19 am
PDX
-
MBJ
11h 32m
1 stop
$470American Airlines
Mon, May 11 - Sat, May 16
Multiple Airlines Logo
6:41 pm - 1:02 pm
SJU
-
PDX
45h 21m
3 stops
Multiple Airlines Logo
7:45 am - 2:08 am
PDX
-
SJU
15h 23m
2 stops
$497Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
3:35 pm - 8:35 pm
SDQ
-
PDX
32h 00m
1 stop
Multiple Airlines Logo
12:07 pm - 5:29 am
PDX
-
SDQ
14h 22m
2 stops
$590Multiple Airlines
Fri, Apr 24 - Sat, May 2
Delta Logo
6:05 am - 10:42 pm
SDQ
-
PDX
19h 37m
2 stops
Delta Logo
5:45 pm - 12:31 pm
PDX
-
SDQ
15h 46m
2 stops
$600Delta
Fri, Apr 24 - Sun, May 3
Delta Logo
6:05 am - 10:16 pm
SDQ
-
PDX
19h 11m
1 stop
Delta Logo
7:00 am - 12:17 am
PDX
-
SDQ
14h 17m
1 stop
$623Delta
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$168
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 6% lower on average.
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.
7.1
American AirlinesOverall score based on 11468 reviews
6.4Food
6.9Entertainment
7.9Crew
7.5Boarding
7.2Comfort
Airline reviews

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

2.0 Mediocresteven, Mar 2026
MIA - CLE
Read more American Airlines reviews

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Movie selections were very limited. Meals were not f So good.

Older airplane with worn out seats. No entertainment system at all. Connecting to Wi-Fi was problematic and hit and miss.

AA is flying sub par aging 787's to Tokyo. I fly other 787's long haul and these are at the bottom. Seats don't work well, tray tables don't work well and were dirty. The flight was great, the plane was not.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

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