$148 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 4/23. 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

Thu, Apr 9 - Thu, Apr 16
United Airlines Logo
1:52 pm - 11:58 pm
MBJ
-
PDX
12h 06m
1 stop
United Airlines Logo
4:15 pm - 12:50 pm
PDX
-
MBJ
18h 35m
2 stops
$371United Airlines
Thu, May 7 - Tue, May 12
Southwest Logo
6:50 am - 8:10 pm
SJU
-
PDX
16h 20m
2 stops
Southwest Logo
6:30 am - 10:40 pm
PDX
-
SJU
13h 10m
2 stops
$406Southwest
Tue, Apr 21 - Sat, Apr 25
Delta Logo
12:55 pm - 10:02 pm
SJU
-
PDX
12h 07m
1 stop
Delta Logo
11:15 pm - 12:52 pm
PDX
-
SJU
10h 37m
1 stop
$416Delta
Fri, Aug 7 - Fri, Aug 14
Southwest Logo
5:30 am - 3:00 pm
SJU
-
PDX
12h 30m
1 stop
Southwest Logo
10:45 pm - 1:10 pm
PDX
-
SJU
11h 25m
1 stop
$438Southwest
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
3:00 pm - 9:24 am
SJU
-
PDX
21h 24m
1 stop
American Airlines Logo
7:00 am - 11:40 pm
PDX
-
SJU
13h 40m
2 stops
$450American Airlines
Wed, Apr 1 - Sun, Apr 5
Multiple Airlines Logo
10:00 am - 6:55 pm
SJU
-
PDX
35h 55m
2 stops
Multiple Airlines Logo
8:26 pm - 2:01 am
PDX
-
SJU
50h 35m
3 stops
$473Multiple Airlines
Thu, Apr 16 - Tue, Apr 21
Delta Logo
6:15 am - 5:10 pm
SJU
-
PDX
13h 55m
2 stops
Delta Logo
6:05 pm - 1:25 pm
PDX
-
SJU
16h 20m
2 stops
$486Delta
Wed, Apr 1 - Sun, Apr 5
Multiple Airlines Logo
1:11 pm - 6:55 pm
SJU
-
PDX
32h 44m
1 stop
Multiple Airlines Logo
8:26 pm - 2:01 am
PDX
-
SJU
50h 35m
3 stops
$487Multiple Airlines
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
1:35 pm - 11:22 pm
SJU
-
PDX
12h 47m
2 stops
American Airlines Logo
5:38 am - 11:40 pm
PDX
-
SJU
15h 02m
2 stops
$488American Airlines
Fri, Mar 20 - Sat, Mar 21
JetBlue Logo
2:35 pm - 10:08 pm
SDQ
-
PDX
10h 33m
1 stop
JetBlue Logo
10:30 pm - 1:10 pm
PDX
-
SDQ
11h 40m
1 stop
$783JetBlue
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$148
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 4% increase in price.
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 4299 reviews
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

10.0 ExcellentTy&Steph, Feb 2026
CLT - STL
Read more Southwest reviews

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Great plane, great attendants,great flight crew,on time. Wonderful flight home..

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

I couldn’t make my first flight due to weather delays trapping us in the town we were in. Then I had to buy a new ticket

Flight attendants had a little attitude. Food tastes no good.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

Overall we had a good experience during our flight from San Francisco to Houston.

Arrived early picked up my bag in a few minutes- great trip - thank you

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

I am an AA flyer for a very long time... AA has yet to disappoint.

Flight was delayed. Not much information on when the flight would take off. Eventually we were told it was maintenance. App was not giving updates.

We were delayed and due to lateness we were traveling from 11pm we were rerouted to FLL and couldnt deplane but stayed on the plane with no extra Service given (extra good options etc$ there Were so many things that could go wrong and did. This was not an enjoyable experience at all thoroughly exhausting

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