$153 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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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

Fri, Apr 24 - Sun, May 3
United Airlines Logo
1:52 pm - 6:08 pm
MBJ
-
PDX
30h 16m
2 stops
United Airlines Logo
11:59 pm - 1:30 pm
PDX
-
MBJ
11h 31m
1 stop
$352United Airlines
Mon, May 4 - Mon, May 11
United Airlines Logo
2:40 pm - 6:46 pm
MBJ
-
PDX
30h 06m
2 stops
United Airlines Logo
7:15 am - 1:30 pm
PDX
-
MBJ
28h 15m
2 stops
$353United Airlines
Thu, Sep 10 - Wed, Sep 16
Southwest Logo
5:00 am - 3:00 pm
SJU
-
PDX
13h 00m
2 stops
Southwest Logo
10:45 pm - 2:30 pm
PDX
-
SJU
12h 45m
1 stop
$446Southwest
Tue, Apr 21 - Mon, Apr 27
American Airlines Logo
11:43 am - 10:56 pm
SJU
-
PDX
14h 13m
2 stops
American Airlines Logo
12:59 am - 6:10 pm
PDX
-
SJU
14h 11m
2 stops
$476American 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
10:28 pm - 12:29 pm
PDX
-
SJU
11h 01m
1 stop
$493American Airlines
Thu, May 7 - Tue, May 12
Delta Logo
2:35 pm - 11:44 pm
SJU
-
PDX
12h 09m
2 stops
Delta Logo
5:51 pm - 1:20 pm
PDX
-
SJU
16h 29m
2 stops
$510Delta
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
$600Delta
Tue, Aug 11 - Wed, Sep 30
Multiple Airlines Logo
3:35 pm - 12:22 am
SDQ
-
PDX
35h 47m
2 stops
Multiple Airlines Logo
2:50 pm - 5:29 am
PDX
-
SDQ
11h 39m
1 stop
$670Multiple Airlines
Tue, Apr 14 - Tue, Apr 28
Multiple Airlines Logo
3:35 pm - 8:35 pm
SDQ
-
PDX
32h 00m
1 stop
Multiple Airlines Logo
9:59 am - 5:29 am
PDX
-
SDQ
16h 30m
1 stop
$678Multiple Airlines
Mon, Jul 20 - Fri, Jul 24
Southwest Logo
12:45 pm - 1:20 am
GCM
-
PDX
14h 35m
2 stops
Southwest Logo
9:20 pm - 12:10 pm
PDX
-
GCM
12h 50m
2 stops
$682Southwest
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$153
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 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 8319 reviews
8.1Boarding
7.9Comfort
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

4.0 OkayAnonymous, Mar 2026
BHM - ATL
Read more Delta reviews

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

The head flight attendant made the trip excellent. He was very accommodating.

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Offered to check carry on to final destination. This is the most absurd thing in the world. I'm carrying on because I need what is in the carry-on. I'm okay with picking up at next stop but then I will be on much larger plane that can accommodate it. Also, if there is ever a change to your flight. Go to the airport and have the people there fix your ticket. Don't do it over the phone or online with United they screwed us up and ended up with flights for our last leg that took off before our first leg.

The economy seats on the 777 was not as cramped as I had feared, but the food was terrible.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Very poor food. Took more than 90 minutes for baggage to arrive at DFW

British Airways is an excellent airline. Comfort, food and airline personnel.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

It was great. Smooth flight, comfortable, left on time and landed on time.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

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