$223 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 4/25. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
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

Sat, May 16 - Sat, May 23
United Airlines Logo
12:52 pm - 9:38 am
MBJ
-
PDX
22h 46m
1 stop
United Airlines Logo
10:40 pm - 3:10 pm
PDX
-
MBJ
14h 30m
2 stops
$351United Airlines
Sat, May 16 - Sat, May 23
United Airlines Logo
2:40 pm - 12:59 am
MBJ
-
PDX
36h 19m
2 stops
United Airlines Logo
11:40 pm - 3:10 pm
PDX
-
MBJ
13h 30m
2 stops
$366United Airlines
Fri, May 1 - Mon, May 4
Southwest Logo
6:50 am - 8:10 pm
SJU
-
PDX
16h 20m
2 stops
Southwest Logo
5:10 am - 8:00 pm
PDX
-
SJU
11h 50m
2 stops
$461Southwest
Tue, Apr 21 - Mon, Apr 27
Delta Logo
2:03 pm - 11:56 pm
SJU
-
PDX
12h 53m
2 stops
Delta Logo
7:32 pm - 11:45 am
PDX
-
SJU
13h 13m
2 stops
$476Delta
Tue, Apr 14 - Tue, May 5
Multiple Airlines Logo
3:26 pm - 11:50 am
SJU
-
PDX
47h 24m
3 stops
Multiple Airlines Logo
7:35 am - 5:26 pm
PDX
-
SJU
30h 51m
2 stops
$484Multiple Airlines
Tue, Apr 14 - Tue, May 5
American Airlines Logo
1:31 pm - 11:57 pm
SJU
-
PDX
13h 26m
2 stops
American Airlines Logo
11:40 pm - 2:52 pm
PDX
-
SJU
12h 12m
2 stops
$493American Airlines
Tue, Apr 14 - Tue, May 5
American Airlines Logo
1:31 pm - 11:57 pm
SJU
-
PDX
13h 26m
2 stops
American Airlines Logo
7:00 am - 11:02 pm
PDX
-
SJU
13h 02m
1 stop
$505American Airlines
Tue, Apr 14 - Tue, May 5
American Airlines Logo
5:45 am - 11:53 pm
SJU
-
PDX
21h 08m
1 stop
American Airlines Logo
7:00 am - 11:02 pm
PDX
-
SJU
13h 02m
1 stop
$506American Airlines
Tue, Apr 21 - Sat, Apr 25
Delta Logo
2:03 pm - 11:56 pm
SJU
-
PDX
12h 53m
2 stops
Delta Logo
5:30 am - 11:59 pm
PDX
-
SJU
15h 29m
2 stops
$526Delta
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
1:16 pm - 8:35 pm
MBJ
-
PDX
33h 19m
1 stop
Multiple Airlines Logo
7:35 am - 12:11 pm
PDX
-
MBJ
26h 36m
1 stop
$741Multiple Airlines
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$224
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 Montego Bay 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 8369 reviews
7.9Comfort
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

10.0 ExcellentViraj, Apr 2026
JFK - SFO
Read more Delta reviews

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Our recent international travel was from Newark, NJ to Grenada via Atlanta. During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta as it did not wait for arriving passengers. Consequently, we were delayed by 24 hours before the next available flight was provided. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for me as a resident of New Jersey.

This was my first flight with Delta, the overall experience was good. I would definitely consider them more with my future flights.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

It was perfect! I've never flown with United before, but I definitely will in the future

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

I liked that it was on time, however, the food was not good.

Fine. The issues I had were associated with luggage being delayed from Turkey to Tanzania

They were fast and I like how they used to entertainment system to play video about the safety.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

We purchase first class seats for the first time for multiples of standard economy ticket. There was no access to the club lounge and no priority boarding. The meal and the service once on the plane were superior and the seat was nicer, but not worth the price difference. I will be happy to seat in economy and spend the difference on more travel.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Delayed 24 hours. Should have called it much earlier They provided quality accommodations, food vouchers etc. FINALLY The issues started at 8 AM and they cancelled the flight at 11:30 PM, with no plans for a new flight.

Better snacks but flight and crew were amazing on this flight

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

It was the most un-special flight experience in my life.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

Flight was on-time, boarding was flawless and the crew was friendly.

The staff are very, very professional. It's what flying should feel like.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Seaside
Vancouver
Salem
The Dalles
Lake Oswego
Stevenson
Clackamas
Government Camp
Carson
Kelso
Gleneden Beach
Gladstone
Oceanside
Dundee
Durham

Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland