$208 Find Cheap Flights from Caribbean to Portland - Compare and Save

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 8/11. 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, Sep 4 - Fri, Sep 11
United Airlines Logo
12:52 pm - 9:33 am
MBJ
-
PDX
46h 41m
2 stops
United Airlines Logo
10:50 am - 1:30 pm
PDX
-
MBJ
24h 40m
2 stops
$397United Airlines
Fri, Sep 4 - Fri, Sep 11
American Airlines Logo
2:12 pm - 11:59 pm
MBJ
-
PDX
11h 47m
1 stop
American Airlines Logo
6:00 am - 4:16 pm
PDX
-
MBJ
8h 16m
1 stop
$404American Airlines
Fri, Aug 28 - Sat, Sep 12
American Airlines Logo
2:52 pm - 10:54 am
MBJ
-
PDX
22h 02m
2 stops
American Airlines Logo
2:07 pm - 4:16 pm
PDX
-
MBJ
24h 09m
1 stop
$406American Airlines
Fri, Sep 4 - Fri, Sep 11
American Airlines Logo
5:08 pm - 11:33 am
MBJ
-
PDX
20h 25m
2 stops
American Airlines Logo
6:00 am - 4:16 pm
PDX
-
MBJ
8h 16m
1 stop
$409American Airlines
Thu, Sep 3 - Thu, Sep 10
American Airlines Logo
2:12 pm - 11:59 pm
MBJ
-
PDX
11h 47m
1 stop
American Airlines Logo
2:12 pm - 4:16 pm
PDX
-
MBJ
24h 04m
1 stop
$414American Airlines
Thu, Sep 3 - Thu, Sep 10
American Airlines Logo
5:08 pm - 11:34 am
MBJ
-
PDX
20h 26m
2 stops
American Airlines Logo
2:12 pm - 4:16 pm
PDX
-
MBJ
24h 04m
1 stop
$418American Airlines
Fri, Aug 28 - Tue, Sep 1
United Airlines Logo
12:15 am - 2:35 pm
BQN
-
PDX
17h 20m
2 stops
United Airlines Logo
5:00 am - 11:09 pm
PDX
-
BQN
15h 09m
2 stops
$586United Airlines
Sun, Sep 6 - Fri, Sep 11
Air Canada Logo
5:05 pm - 2:51 pm
PUJ
-
PDX
24h 46m
2 stops
Air Canada Logo
3:30 pm - 3:25 pm
PDX
-
PUJ
20h 55m
2 stops
$840Air Canada
Sat, Aug 8 - Sat, Aug 29
Delta Logo
9:13 am - 10:38 pm
KIN
-
PDX
15h 25m
2 stops
Delta Logo
6:45 am - 8:13 pm
PDX
-
KIN
11h 28m
1 stop
$1,052Delta
Sat, Aug 8 - Fri, Aug 28
Delta Logo
9:13 am - 6:55 pm
KIN
-
PDX
11h 42m
1 stop
Delta Logo
12:35 am - 8:13 pm
PDX
-
KIN
17h 38m
2 stops
$1,114Delta
Useful Info

Good to know

Low season

September

Cheapest flight

$208
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 5% 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 airlines flying 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.
7.4
United AirlinesOverall score based on 10020 reviews
7.3Comfort
7.7Boarding
8.1Crew
6.7Food
7.1Entertainment
Airline reviews

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

10.0 ExcellentAnonymous, May 2026
DEN - PDX
Read more United Airlines reviews

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Pilot Erika DeLong made us feel safe and at ease in a frankly scary time to be flying. Her warm smile and greeting and excellent command of the aircraft in foggy bumpy weather helped us all to calm our nerves and get us home safely.

Not enough room between rows and food was gross. $160 baggage charge?! Never again.

East Lounge in Denver was terrible. Turning away active military on orders? Really? Sad.

Clean and plenty of room for handbaggage. Leg room was cramped compared with the 777 from Frankfurt.

they made me check my carryon. There was space in the overhead bins.

Cramped and uncomfortable seats. Not enough room for 6’2” person such as myself.

Pretty turbulent, but not anyone’s fault. They got us there. Impressed that they carried on with a drink service.

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

It's very confusing because Kayak has it as American Airlines, but it was Hawaiian Airlines, but operated by Alaska Airlines. I had to go to the airport for my boarding pass because American said I didn't have any trips.

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

Packed commercial flight was as comfortable as can be expected

We were re routed due to a flight cancellation. We did not fly out of Miami. We originally booked first class and were moved to coach without being compensated.

2 gate changes, several announced delays, not enough room and seats at the gate. Many had to stand while waiting. The actual flight was fine.

Heathrow is a nightmare in general (crowded, etc). BA was great - having to take a bus between the gate and the plane is a bummer.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
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Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland