$161 Find Cheap Flights from Caribbean to Portland - Compare and Save

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Cheap Flights from Caribbean to Portland

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Portland

Fri, Oct 9 - Mon, Oct 19
American Airlines Logo
2:27 pm - 11:05 pmSJU  San Juan Luis Munoz Marin Intl-PDX Portland
11h 38m1 stop Philadelphia
American Airlines Logo
10:55 pm - 2:03 pmPDX  Portland-SJU San Juan Luis Munoz Marin Intl
12h 08m1 stop Chicago O'Hare Intl
$322American Airlines
Wed, Oct 21 - Thu, Oct 29
American Airlines Logo
10:36 am - 11:39 pmSJU  San Juan Luis Munoz Marin Intl-PDX Portland
16h 03m2 stops Miami Dallas/Fort Worth
American Airlines Logo
8:35 am - 10:57 pmPDX  Portland-SJU San Juan Luis Munoz Marin Intl
11h 22m1 stop Philadelphia
$322American Airlines
Wed, Oct 21 - Thu, Oct 29
American Airlines Logo
2:53 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-PDX Portland
12h 06m1 stop Chicago O'Hare Intl
American Airlines Logo
8:35 am - 10:57 pmPDX  Portland-SJU San Juan Luis Munoz Marin Intl
11h 22m1 stop Philadelphia
$322American Airlines
Thu, Nov 5 - Fri, Nov 13
American Airlines Logo
1:40 pm - 12:03 amSJU  San Juan Luis Munoz Marin Intl-PDX Portland
14h 23m2 stops Miami Dallas/Fort Worth
American Airlines Logo
11:09 pm - 3:03 pmPDX  Portland-SJU San Juan Luis Munoz Marin Intl
11h 54m2 stops Chicago O'Hare Intl Charlotte Douglas
$322American Airlines
Sat, Sep 19 - Sat, Sep 26
United Airlines Logo
12:52 pm - 9:29 amMBJ  Montego Bay Sangster Intl-PDX Portland
22h 37m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
4:07 pm - 11:43 amPDX  Portland-MBJ Montego Bay Sangster Intl
17h 36m2 stops Denver Intl Newark
$455United Airlines
Sat, Sep 19 - Sat, Sep 26
United Airlines Logo
12:52 pm - 9:50 amMBJ  Montego Bay Sangster Intl-PDX Portland
22h 58m1 stop Newark
United Airlines Logo
11:59 pm - 1:30 pmPDX  Portland-MBJ Montego Bay Sangster Intl
11h 31m1 stop Houston George Bush Intcntl
$470United Airlines
Sun, Sep 20 - Fri, Sep 25
Frontier Logo
7:00 am - 10:07 amSJU  San Juan Luis Munoz Marin Intl-PDX Portland
30h 07m2 stops Orlando Los Angeles
Frontier Logo
12:38 pm - 9:35 amPDX  Portland-SJU San Juan Luis Munoz Marin Intl
17h 57m2 stops Denver Intl Orlando
$482Frontier
Wed, Oct 14 - Mon, Oct 19
Delta Logo
2:59 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-PDX Portland
12h 00m2 stops Atlanta Hartsfield-Jackson Seattle/Tacoma Intl
Delta Logo
8:44 pm - 4:49 pmPDX  Portland-SJU San Juan Luis Munoz Marin Intl
17h 05m2 stops Seattle/Tacoma Intl Atlanta Hartsfield-Jackson
$506Delta
Tue, Nov 10 - Sun, Nov 15
Delta Logo
3:15 pm - 11:36 pmSJU  San Juan Luis Munoz Marin Intl-PDX Portland
12h 21m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
7:35 pm - 12:55 pmPDX  Portland-SJU San Juan Luis Munoz Marin Intl
13h 20m2 stops Seattle/Tacoma Intl New York John F Kennedy Intl
$506Delta
Wed, Oct 14 - Mon, Oct 19
United Airlines Logo
2:00 pm - 9:10 pmSJU  San Juan Luis Munoz Marin Intl-PDX Portland
10h 10m1 stop Denver Intl
United Airlines Logo
6:55 pm - 12:34 pmPDX  Portland-SJU San Juan Luis Munoz Marin Intl
14h 39m2 stops Denver Intl Washington, D.C. Dulles Intl
$506United Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$161
Best time to beat the crowds with an average 14% 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 10158 reviews
7.7Boarding
8.1Crew
6.6Food
7.3Comfort
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
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
Seaside
Vancouver
Salem
The Dalles
Clackamas
Stevenson
Lake Oswego
Carson
Government Camp
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