$153 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, Mar 4 - Tue, Mar 9
American Airlines Logo
7:36 pm - 10:36 amSJU  San Juan Luis Munoz Marin Intl-PWM Portland
16h 00m1 stop Philadelphia
American Airlines Logo
6:07 am - 3:58 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Philadelphia
$294American Airlines
Tue, Dec 22 - Mon, Jan 11
Delta Logo
2:09 pm - 11:09 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
10h 00m1 stop Atlanta Hartsfield-Jackson
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
$306Delta
Tue, Dec 22 - Sun, Jan 10
Delta Logo
2:09 pm - 11:09 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
10h 00m1 stop Atlanta Hartsfield-Jackson
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
$363Delta
Tue, Dec 22 - Mon, Jan 11
American Airlines Logo
7:00 am - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
16h 59m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 9:11 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 11m2 stops Philadelphia Charlotte Douglas
$369American Airlines
Thu, Dec 17 - Thu, Dec 31
Delta Logo
7:00 am - 3:20 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 20m1 stop New York John F Kennedy Intl
Delta Logo
2:09 pm - 11:47 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 38m1 stop New York John F Kennedy Intl
$381Delta
Thu, Dec 3 - Mon, Dec 7
United Airlines Logo
1:00 pm - 8:42 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
8h 42m1 stop Newark
United Airlines Logo
6:00 am - 1:32 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
6h 32m1 stop Newark
$394United Airlines
Thu, Dec 17 - Thu, Dec 31
Delta Logo
7:00 am - 3:20 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 20m1 stop New York John F Kennedy Intl
Delta Logo
2:09 pm - 11:47 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
8h 38m1 stop New York John F Kennedy Intl
$397Delta
Thu, Dec 3 - Mon, Dec 7
United Airlines Logo
2:52 pm - 11:24 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 32m1 stop Newark
United Airlines Logo
7:00 am - 2:40 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
6h 40m1 stop Newark
$406United Airlines
Tue, Dec 1 - Thu, Dec 17
American Airlines Logo
7:05 am - 10:52 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
16h 47m1 stop Charlotte Douglas
American Airlines Logo
5:30 am - 9:16 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
14h 46m1 stop Charlotte Douglas
$415American Airlines
Tue, Dec 22 - Sun, Jan 10
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
6:00 am - 4:12 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
9h 12m1 stop Philadelphia
$428American Airlines
Useful Info

Good to know

Low season

February

Cheapest flight

$153
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.
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.
7.0
American AirlinesOverall score based on 12228 reviews
7.9Crew
6.8Entertainment
7.1Comfort
6.4Food
7.4Boarding
Airline reviews

All good. Flight crew was super friendly at the end of a long day

10.0 ExcellentToby, Nov 2026
Read more American Airlines reviews

All good. Flight crew was super friendly at the end of a long day

All good. Easy check in and boarding. Lovely flight crew

Friendly crew and pilot. And thank you to the pilot for his smooth landing technique where the wheels don't hit the ground hard - that should be table stakes but doesn't seem to be the case nowadays.

Four hour delay due to late plane arrival- second year in a row on MCO - DCA route. Pitiful service reliability from American. Will avoid in future

Flight was fine, food could have improved (Chicken Enchiladas) and so could the entertainment options on the seat rest (there was none).

I have generally had positive experiences with American Airlines (outside a handful of delayed flights), which is why I wanted to share this feedback constructively. On my recent flight, my travel experience was extremely uncomfortable because my seat mate significantly encroached into my assigned seat space for the duration of the flight. As a result, I was forced to sit partially sideways, with much of my shoulder and upper body extending into the aisle. Unfortunately, my back still hurts from maintaining that awkward position.I recognize that this is a sensitive and challenging issue for airlines and cabin crews to address. Everyone deserves to travel with dignity and respect, and I understand that individual circumstances can vary. However, fairness also requires that all passengers have reasonable access to the seat space they have paid for. When one passenger's use of space substantially impacts another passenger's ability to sit safely and comfortably, there should be a practical solution available.I appreciate the complexities involved, but I hope American Airlines will continue exploring ways to ensure that all passengers can travel comfortably and equitably. This experience detracted significantly from what should have been a routine flight.

The crew was great! The issue for me is the aircraft. The Airbus A32x is just not comfortable enough and the entertainment delivery via personal devices is problematic.

The crew was dis respectful even in business class. I will not recommend AA to anyone and will also fly only when there is no choice

Three aircraft in succession experienced maintenance issues, resulting in a six-hour delay. The original aircraft required replacement, and the substitute aircraft arrived more than two hours late. Passengers boarded that aircraft, only to be told later to deplane due to maintenance concerns. We then boarded a different aircraft that had arrived at the gate, only to be instructed to deplane once again because it, too, experienced maintenance issues. After hours of delays and two separate boarding and deplaning events, passengers were directed to a third aircraft departing from a different terminal and had to rush across the airport to make that flight. That was the only aircraft that ultimately departed without incident. Of course, passenger safety must come first, and I am grateful these issues were identified before takeoff. However, when three aircraft in succession require maintenance attention and passengers are repeatedly boarded before those issues are discovered, it raises legitimate concerns about American Airlines' preventive maintenance procedures and aircraft readiness checks. One aircraft with an unexpected issue can happen. Three aircraft in a row, combined with multiple boarding and deplaning events, suggests a pattern that warrants review. American Airlines needs to take a hard look at both its maintenance practices and its decision-making process for boarding passengers before determining that an aircraft is ready for service.

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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