$157 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 16 - Sun, Oct 18
American Airlines Logo
12:41 pm - 10:36 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 55m1 stop Charlotte Douglas
American Airlines Logo
7:24 pm - 11:20 amPWM  Portland-SJU San Juan Luis Munoz Marin Intl
15h 56m1 stop Charlotte Douglas
$278American Airlines
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
2:22 pm - 11:45 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 23m2 stops Philadelphia Washington, D.C. Reagan-National
American Airlines Logo
5:05 pm - 9:24 amPWM  Portland-SJU San Juan Luis Munoz Marin Intl
16h 19m2 stops Washington, D.C. Reagan-National Miami
$289American Airlines
Wed, Sep 2 - Wed, Sep 9
JetBlue Logo
5:50 pm - 12:59 amSJU  San Juan Luis Munoz Marin Intl-PWM Portland
7h 09m1 stop New York John F Kennedy Intl
JetBlue Logo
4:20 pm - 11:49 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
7h 29m1 stop New York John F Kennedy Intl
$292JetBlue
Wed, Sep 23 - Thu, Oct 1
JetBlue Logo
7:30 am - 3:39 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
8h 09m1 stop New York John F Kennedy Intl
JetBlue Logo
6:00 am - 4:49 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
10h 49m1 stop Atlanta Hartsfield-Jackson
$313JetBlue
Wed, Sep 23 - Wed, Sep 30
JetBlue Logo
7:30 am - 3:39 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
8h 09m1 stop New York John F Kennedy Intl
JetBlue Logo
6:00 am - 1:45 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
7h 45m1 stop Atlanta Hartsfield-Jackson
$353JetBlue
Sat, Aug 29 - Wed, Sep 2
JetBlue Logo
12:56 pm - 9:31 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
8h 35m1 stop Atlanta Hartsfield-Jackson
JetBlue Logo
2:53 pm - 11:52 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 59m1 stop New York John F Kennedy Intl
$361JetBlue
Mon, Sep 28 - Mon, Oct 5
United Airlines Logo
1:25 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
10h 34m2 stops Newark Washington, D.C. Dulles Intl
United Airlines Logo
5:15 am - 12:34 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
7h 19m1 stop Washington, D.C. Dulles Intl
$372United Airlines
Mon, Sep 14 - Mon, Sep 21
United Airlines Logo
7:00 am - 11:32 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
16h 32m2 stops Houston George Bush Intcntl Newark
United Airlines Logo
6:00 am - 2:44 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 44m1 stop Chicago O'Hare Intl
$395United Airlines
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
10:30 am - 10:05 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
11h 35m2 stops Orlando Chicago Midway
Southwest Logo
5:45 am - 4:25 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
10h 40m2 stops Baltimore/Washington Orlando
$402Southwest
Sun, Sep 13 - Mon, Sep 21
United Airlines Logo
1:00 am - 9:08 amSJU  San Juan Luis Munoz Marin Intl-PWM Portland
8h 08m1 stop Newark
United Airlines Logo
6:00 am - 2:44 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 44m1 stop Chicago O'Hare Intl
$409United Airlines
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Cheapest flight

$157
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 airline 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.
7.1
American AirlinesOverall score based on 11963 reviews
7.2Comfort
7.9Crew
7.5Boarding
6.8Entertainment
6.4Food
Airline reviews

The plane was late getting to Ontario by half an hour which makes it inconvenient when you have people waiting for you.

8.0 ExcellentRicardo, Aug 2026
Read more American Airlines reviews

The plane was late getting to Ontario by half an hour which makes it inconvenient when you have people waiting for you.

boarding sucked they lost my bag never flying Iberia again

Luggage handling and communication is extremely poor. I landed in india 15th and recived luggage today. Based on my itag the luggage was in Germany. They kept me in dark. Etihad num er in india was non operatuonal. Had to call USA etihad. It should not be so difficullt. I came for 1 week business trip everything was screwed . This is the first and also will be last for me

I wish I could've gotten a refund 😕 I never even got 😪 to go on my trip.

There was no service on the flight even though there was no turbulence or any other issues on the flight. Nobody greeted at the entry or leaving the airplane, staff crew looked annoyed and not helpful at all.

mechanical problem delayed more than 2 hours on the run way.

I paid extra for a seat up front and at last minute was moved to the 2nd to last row - which I could have had for free. No reason and no refund. Really great customer service American

You guys broke my bag so not good, and that was the cherry on top after a 4 hour delay, change of gates, etc.

Really good, premium economy is worth for a daytime flight coming back from europe

90 min delay for a food cart that needed to be fixed.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Jackson
Freeport
Bartlett
Oxford
Intervale
Windham
Tamworth
Falmouth
Waterford
Durham

Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland

Portland (PWM)