$182 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

Thu, Dec 3 - Sun, Dec 6
American Airlines Logo
2:28 pm - 10:48 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 20m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 9:33 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 33m2 stops Philadelphia Charlotte Douglas
$316American Airlines
Tue, Dec 22 - Mon, Jan 11
American Airlines Logo
4:31 pm - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
7h 28m1 stop Charlotte Douglas
American Airlines Logo
10:52 am - 9:11 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
9h 19m2 stops Philadelphia Charlotte Douglas
$316American Airlines
Thu, Dec 3 - Sun, Dec 6
Southwest Logo
2:25 pm - 9:50 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
8h 25m1 stop Baltimore/Washington
Southwest Logo
1:40 pm - 1:10 amPWM  Portland-SJU San Juan Luis Munoz Marin Intl
10h 30m1 stop Baltimore/Washington
$316Southwest
Tue, Dec 22 - Mon, Jan 11
American Airlines Logo
8:08 am - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
15h 51m1 stop Philadelphia
American Airlines Logo
7:00 am - 4:57 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 57m1 stop Charlotte Douglas
$316American Airlines
Tue, Dec 22 - Mon, Jan 11
American Airlines Logo
4:31 pm - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
7h 28m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 9:30 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 30m2 stops Philadelphia Miami
$316American Airlines
Tue, Dec 22 - Mon, Jan 11
American Airlines Logo
6:00 am - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
17h 59m1 stop Philadelphia
American Airlines Logo
6:00 am - 9:30 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 30m2 stops Philadelphia Miami
$316American Airlines
Tue, Dec 22 - Mon, Jan 11
American Airlines Logo
4:31 pm - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
7h 28m1 stop Charlotte Douglas
American Airlines Logo
7:00 am - 4:57 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 57m1 stop Charlotte Douglas
$316American Airlines
Tue, Dec 22 - Mon, Jan 11
American Airlines Logo
11:41 am - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
12h 18m2 stops Miami Philadelphia
American Airlines Logo
10:52 am - 9:30 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
9h 38m2 stops Philadelphia Miami
$316American Airlines
Mon, Dec 21 - Sun, Jan 10
Delta Logo
4:00 am - 12:36 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 36m1 stop New York John F Kennedy Intl
Delta Logo
3:10 pm - 12:58 amPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 48m1 stop New York John F Kennedy Intl
$336Delta
Fri, Dec 25 - Thu, Dec 31
United Airlines Logo
8:05 am - 2:38 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
7h 33m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
6:00 am - 9:00 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 00m2 stops Newark Chicago O'Hare Intl
$336United Airlines
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Good to know

Low season

February
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 23% increase in price.

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.
7.0
American AirlinesOverall score based on 12233 reviews
6.4Food
7.4Boarding
6.8Entertainment
7.9Crew
7.2Comfort
Airline reviews

WiFi broken, very long wait for valet bags, and the typical long wait at O'Hare on a thursday to get clearance to take off and then again long taxi and wait for the gate.

6.0 GoodJulie, Nov 2026
Read more American Airlines reviews

WiFi broken, very long wait for valet bags, and the typical long wait at O'Hare on a thursday to get clearance to take off and then again long taxi and wait for the gate.

Got to gate late and they made me check my bag but when I got on flight there was lots of overheard bin space .

The gate agent in BNA got irritated with a lady for asking her about standby's and refused to hand out assigned standby tickets to ANYONE until Group 6 . She punished all standby passengers because of the one lady she did not like. When we boarded she said thank you to everyone as we scanned our boarding passes except the lady in front of me. Very petty and unprofessional

The old CRJ700's are rough, slightly larger regional jet would have been nice.

It was unfortunate that the plane had mechanical issues and delayed our flight, but I am glad we made it safely! On the first American flight from Charlotte to Phoenix, they changed the gate without getting a notification, and I had to make a mad dash!

Another American flight, another significant non weather related delay. Was delayed over 90 minutes on both legs of the round trip.

The flight was delayed several times as they didn't have pilots. Then we were boarded on the plane and again waited on the tarmac for over 30-40 minutes waiting for pilots to board. The in flight entertainment was confusing at best on how to use it. It took multiple attempts to get wifi to connect and by the time it worked the flight was almost over.

The flight was delayed and gate changed so that was not fun and the flight to Dallas from LAX was very delayed on Sunday. It was just not a great experience due to the delays both ways.

Fine. No announcement for Concierge Key to board. Not a big issue just pointing it out.

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

Traveling to a place near Portland?

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Jackson
Freeport
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Oxford
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