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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$147 CHEAP FLIGHTS from Caribbean to Portland

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

...and more

Travelers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals

Cheap Flights from Caribbean to Portland

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Caribbean to Portland

Thu, Jun 25 - Mon, Jun 29

5:15 pm - 12:05 am

SJU

PWM

6h 50m

1 stop

5:35 am - 12:25 pm

PWM

SJU

6h 50m

1 stop

$393Southwest

Thu, Jun 25 - Mon, Jun 29

1:15 pm - 12:05 am

SJU

PWM

10h 50m

2 stops

5:35 am - 12:25 pm

PWM

SJU

6h 50m

1 stop

$432Southwest

Thu, Apr 9 - Mon, Apr 13

6:50 am - 4:15 pm

SJU

PWM

9h 25m

2 stops

2:50 pm - 11:55 pm

PWM

SJU

9h 05m

2 stops

$440Southwest

Thu, Apr 9 - Mon, Apr 13

7:00 am - 9:07 am

SJU

PWM

26h 07m

1 stop

11:29 am - 12:25 am

PWM

SJU

12h 56m

1 stop

$447Multiple Airlines

Mon, May 4 - Wed, May 6

1:00 am - 10:18 am

SJU

PWM

9h 18m

2 stops

3:39 pm - 11:50 pm

PWM

SJU

8h 11m

1 stop

$455United Airlines

Fri, Apr 10 - Sun, Apr 12

5:05 am - 4:15 pm

SJU

PWM

11h 10m

2 stops

5:30 am - 4:30 pm

PWM

SJU

11h 00m

1 stop

$465Southwest

Mon, May 4 - Wed, May 6

1:00 am - 2:14 pm

SJU

PWM

13h 14m

2 stops

3:39 pm - 11:50 pm

PWM

SJU

8h 11m

1 stop

$476United Airlines

Mon, Apr 6 - Mon, Apr 13

6:00 am - 11:58 pm

SJU

PWM

17h 58m

1 stop

6:00 am - 10:49 pm

PWM

SJU

16h 49m

1 stop

$492JetBlue

Wed, Apr 1 - Sun, Apr 5

5:10 pm - 11:59 pm

SJU

PWM

6h 49m

1 stop

2:30 pm - 11:59 pm

PWM

SJU

9h 29m

1 stop

$496JetBlue

Thu, Jun 25 - Mon, Jun 29

1:15 pm - 12:05 am

SJU

PWM

10h 50m

2 stops

3:10 pm - 1:20 am

PWM

SJU

10h 10m

2 stops

$500Southwest

Useful Info

Cheapest flight	$147

Flight from San Juan 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.

7.1

American AirlinesOverall score based on 11403 reviews

7.2Comfort

7.5Boarding

8.0Crew

6.9Entertainment

6.4Food

Airline reviews

Never had such a lazy first class attendant. Literally spent 60%+ of the flight playing games on her personal phone making up excuses of why she was unavailable.

2.0 MediocreCody, Mar 2026

ORF - CLT

Read more American Airlines reviews

Never had such a lazy first class attendant. Literally spent 60%+ of the flight playing games on her personal phone making up excuses of why she was unavailable.

The flight attendants and the service is getting worse by the day.

Not to have gotten delayed by 2+ hours for the fourth straight American flight. They're the worst.

Like all of the flights I took to get down to Dallas. They were delayed

Other than nearly three hour delay for maintenance issues, everything went smooth

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

Meals were not so good. Snack between the meals was very bad. Like Japan Airlines, they could eliminate the snack and make the second meal much better.

The baggage claim experience was poor. The plane crew and the AA app said that checked baggage in CLT would be at carousel 7 but the sign at Baggage Claim said carousel 1. The carousel 1 sign had the correct flight # listed above the belt. But the luggage never came. I went to an AA baggage claim office after about 1 hour and the clerk directed me to another AA room that was poorly marked, with a closed door and no obvious way to know what to do. Finally someone opened the door and my bag was inside. The clerk was totally unable to explain why.

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Jackson

Freeport

Bartlett

Oxford

Windham

Intervale

Tamworth

Falmouth

Durham

Waterford

Everything you need to know for your flight to Portland

Airports

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Information on the airport you'll fly into in Portland

Portland (PWM)

$147 Find Cheap Flights from Caribbean to Portland

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

Cheap Flights from Caribbean to Portland

Recent round-trip flight deals from Caribbean to Portland

Recent one-way flight deals from Caribbean to Portland

Recent last minute flight deals from Caribbean to Portland

Good to know

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

Traveling to a place near Portland?

Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland

Cabin class types available on flights to Caribbean

Complete your trip to Portland with a hotel stay or car rental

Find direct flights for Portland

Flights to other popular destinations

Flights from domestic origins to Caribbean

Choose which airport to fly into in Portland

Find deals for your return flight