$110 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 23 - Wed, Oct 28
American Airlines Logo
7:30 am - 11:36 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
16h 06m1 stop Philadelphia
American Airlines Logo
5:37 pm - 9:46 amPWM  Portland-SJU San Juan Luis Munoz Marin Intl
16h 09m2 stops Washington, D.C. Reagan-National Miami
$225American Airlines
Sat, Oct 24 - Wed, Nov 11
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
6:00 am - 9:13 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 13m2 stops Philadelphia Charlotte Douglas
$303American Airlines
Fri, Oct 23 - Wed, Oct 28
American Airlines Logo
12:41 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
11h 18m2 stops Charlotte Douglas Washington, D.C. Reagan-National
American Airlines Logo
5:37 pm - 9:46 amPWM  Portland-SJU San Juan Luis Munoz Marin Intl
16h 09m2 stops Washington, D.C. Reagan-National Miami
$306American Airlines
Sat, Oct 24 - Wed, Nov 11
Delta Logo
6:45 am - 1:51 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
7h 06m1 stop New York John F Kennedy Intl
Delta Logo
2:05 pm - 11:15 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 10m1 stop Atlanta Hartsfield-Jackson
$316Delta
Sat, Oct 24 - Wed, Nov 11
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
6:00 am - 9:13 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 13m2 stops Philadelphia Charlotte Douglas
$321American Airlines
Mon, Sep 28 - Wed, Oct 7
United Airlines Logo
1:00 am - 10:02 amSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 02m2 stops Newark Washington, D.C. Dulles Intl
United Airlines Logo
6:00 am - 1:45 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
7h 45m1 stop Newark
$332United Airlines
Wed, Nov 4 - Mon, Nov 9
Southwest Logo
5:40 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
10h 05m2 stops Orlando Baltimore/Washington
Southwest Logo
5:20 am - 5:00 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
10h 40m2 stops Baltimore/Washington Tampa
$349Southwest
Sat, Oct 31 - Wed, Nov 4
American Airlines Logo
7:30 am - 4:29 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
8h 59m1 stop Philadelphia
American Airlines Logo
12:13 pm - 10:39 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
9h 26m2 stops Washington, D.C. Reagan-National Miami
$354American Airlines
Sat, Oct 24 - Wed, Nov 11
American Airlines Logo
12:21 pm - 11:36 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
11h 15m2 stops Miami Philadelphia
American Airlines Logo
6:00 am - 9:38 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 38m2 stops Philadelphia Miami
$356American Airlines
Mon, Sep 28 - Wed, Oct 7
United Airlines Logo
1:00 am - 10:02 amSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 02m2 stops Newark Washington, D.C. Dulles Intl
United Airlines Logo
6:00 am - 8:38 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 38m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$365United Airlines
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Cheapest flight

$110
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 12059 reviews
6.4Food
7.9Crew
6.8Entertainment
7.2Comfort
7.4Boarding
Airline reviews

It was good overall. On my transition from Philadelphia to Boston,the gate information wasn't correct. When I went to check the gate information; I found out that my flight was boarding clear across the airport at another gate. Fortunately I rushed over there and made it on time while they were in the middle of boarding.

10.0 ExcellentChristian, Sep 2026
Read more American Airlines reviews

It was good overall. On my transition from Philadelphia to Boston,the gate information wasn't correct. When I went to check the gate information; I found out that my flight was boarding clear across the airport at another gate. Fortunately I rushed over there and made it on time while they were in the middle of boarding.

For the first time in all my travels I found the arm rests very inadequate and painful. The arm rest between me and the passenger to my left was thin and didn’t support either of us. On the right side, (window side) the armrest was thin and short causing me pain mid-arm.

Not too much it was pretty good all the way around

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

The forward head smelled putrid and urine soaked, worse than any head in even transoceanic flights. The wifi stopped working after about an hour of flight.

Wifi was good on the flight from DCA to Dallas and terrible on the flight from Dallas to Tucson. The forward head in the flight from Dallas to Tucson was putrid smelling entirely urine soaked. The flight from DCA to Dallas was delayed by almost 30 min with a plane change.

As per usual for my flights with American Airlines, One flight was very delayed and caused me to miss my connection and they moved my flight to another day. I called customer support and was moved back to my original day but different flights. My layover flight was delayed by an additional 30 minutes while the flight crew confirmed that the plane was airworthy. Ultimately, it is less hassle to drive 10 hours than to fly 6 hours with American Airlines. I recommend my friends and family to hitch hike over taking this terrible transit.

On time departure was much appreciated. However, as a frequent flyer and American Advantage member, I was as disappointed not to get an aisle seat.

I've never seen such poor lack of information at a gate station in 69 years. The flight from COS was to depart at 12:37pm. At boarding time, the gate agent in the microphone mumbled something completely unintelligible. I understood one word. "mechanical". Nothing else. Absolutely nothing else was reported for the next 1-1/2 hours. Past the time for departure, at 12:37pm, the gate agent simply walked away and the station was left unattended, as all of the passengers waited expectantly. The board still said that the flight was ON TIME. That was hard to believe since it was then well past 12:37pm and we all were sitting at the gate and there was absolutely no gate agent anywhere in site. I stopped an employee who was standing somewhere else and said that we can use some information. Much later, the same gate agent said that he will have information for us about 5 minutes but he "doesn't know any more than you do." Of course, five minutes came and went and he did absolutely nothing. One and a half hours after 12:37pm, he opened the door and began boarding. No explanation, no apology. Once we were boarded, the same happened on the plane. We sat. No explanation, no apology, from any flight attendants. Finally, finally, a pilot apologized and explained that there would be a delay. WELL NO KIDDING !

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

Traveling to a place near Portland?

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