$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

Fri, Nov 13 - Sun, Nov 15
American Airlines Logo
1:40 pm - 11:54 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
11h 14m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
5:45 am - 1:39 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
6h 54m1 stop Charlotte Douglas
$316American Airlines
Tue, Dec 15 - Wed, Dec 30
Delta Logo
1:18 pm - 12:21 amNAS  Nassau Intl-PWM Portland
11h 03m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl
Delta Logo
5:35 am - 1:28 pmPWM  Portland-NAS Nassau Intl
7h 53m1 stop Atlanta Hartsfield-Jackson
$317Delta
Mon, Dec 14 - Thu, Dec 31
United Airlines Logo
12:55 pm - 11:24 pmNAS  Nassau Intl-PWM Portland
10h 29m1 stop Newark
United Airlines Logo
7:44 pm - 11:49 amPWM  Portland-NAS Nassau Intl
16h 05m1 stop Newark
$319United Airlines
Mon, Dec 14 - Sun, Jan 3
United Airlines Logo
2:55 pm - 9:05 amNAS  Nassau Intl-PWM Portland
18h 10m1 stop Newark
United Airlines Logo
6:00 am - 1:48 pmPWM  Portland-NAS Nassau Intl
7h 48m1 stop Newark
$329United Airlines
Fri, Nov 13 - Sun, Nov 15
American Airlines Logo
2:29 pm - 10:33 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 04m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 11:59 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
16h 59m1 stop Philadelphia
$336American Airlines
Wed, Dec 16 - Thu, Dec 31
United Airlines Logo
12:55 pm - 11:24 pmNAS  Nassau Intl-PWM Portland
10h 29m1 stop Newark
United Airlines Logo
7:44 pm - 11:49 amPWM  Portland-NAS Nassau Intl
16h 05m1 stop Newark
$348United Airlines
Wed, Dec 16 - Thu, Dec 31
United Airlines Logo
12:55 pm - 11:24 pmNAS  Nassau Intl-PWM Portland
10h 29m1 stop Newark
United Airlines Logo
7:44 pm - 11:49 amPWM  Portland-NAS Nassau Intl
16h 05m1 stop Newark
$349United Airlines
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
$353American Airlines
Thu, Nov 12 - Sun, Nov 15
American Airlines Logo
6:05 am - 3:21 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
10h 16m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
5:45 am - 1:39 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
6h 54m1 stop Charlotte Douglas
$356American Airlines
Mon, Dec 14 - Wed, Dec 30
Delta Logo
1:22 pm - 12:21 amNAS  Nassau Intl-PWM Portland
10h 59m1 stop New York John F Kennedy Intl
Delta Logo
5:35 am - 1:28 pmPWM  Portland-NAS Nassau Intl
7h 53m1 stop Atlanta Hartsfield-Jackson
$358Delta
Useful Info

Good to know

Low season

February

Cheapest flight

$182
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 15% 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 12193 reviews
7.1Comfort
6.4Food
7.4Boarding
6.8Entertainment
7.9Crew
Airline reviews

I didn't like anything about this flight. The only reason anyone drinks Jack is because you ran out of Woodford. You should know to stock more Woodford. When you wait of first class hand and foot from the minute they get on the plane 5 feet from me but then start service from the rear of the plane so main cabin plus gets the scraps, that's how you get people to stop flying your airline.

4.0 OkayGriffin, Oct 2026
Read more American Airlines reviews

I didn't like anything about this flight. The only reason anyone drinks Jack is because you ran out of Woodford. You should know to stock more Woodford. When you wait of first class hand and foot from the minute they get on the plane 5 feet from me but then start service from the rear of the plane so main cabin plus gets the scraps, that's how you get people to stop flying your airline.

American Airlines was horrible! The layover flight to DFW was delayed with no clear communication and for us having to stay the whole day which led to staying a night in Dallas was comped with 2 $12 dollar vouchers and a crappy hotel. We missed a whole day in Tokyo for our honeymoon and stressed the whole 24 hours. We were supposed to leave at the same time the following day, but that was delayed hours again. And instead of letting the delayed flight go first, they let the flight that was scheduled ahead of us. American should refund us the day wasted in Dallas that should have been in Tokyo! We had lost out on paid events that we can’t get refunded. When we finally did leave, it was a good flight. You would think that was the only issue with American but we from the LAX layover, we were delayed 6 hours and were given a $12 dollar voucher that covered a drink only. The only communication we were given then was that because they were delayed in a prior flight we were delayed again. I don’t understand why it was only with American that we had such a bad time with! They have definitely left a sour taste in our mouths for our honeymoon! And then they did send an email saying we could have 2K miles…. For what? To be delayed into another day and miss our flight again?

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

comfy and spacious seats for premium economy, nice flight attendants. only problem was the wifi did not work, and my entertainment screen was locked in Arabic language and all kids shows with no way of seemingly changing it. but the flight was fine and I arrived with no issues

extremely tight seats. seating next to a large person makes the space very uncomfortable. The crew is not very friendly either.

The flight was 3 hours and 40 minutes late. The communication around the delays was awful. I fly this route regularly and it is always late. I don't understand it. The flight attendants were not friendly and were generally loud. This was an overall bad look for American Airlines.

It was a late flight; crew was invisible. Zero air flow - the tiny plane was a sauna; the left the lights on for 1/2 of the flight; there was no water. Never again.

We were delayed a long time. We waited for “catering”. We didn’t get any food or accommodation for our wait. It made us land well after dinner time at our destination.

It was hot. Need more A/C blowing with more pressure from the overhead vents.

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
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