How does KAYAK find such low prices on flights from Portland to Caribbean?

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 Portland to Caribbean.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Caribbean?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to 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 Portland to Caribbean?

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 from Portland to Caribbean with an airline and back with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Caribbean?

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 from Portland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Which airlines provide the cheapest flights from Portland to Caribbean?

In the past 5 days, the cheapest round-trip tickets from Portland to Caribbean were found on American Airlines ($420) and United Airlines ($436).

Which airlines provide the cheapest flights from Portland to Caribbean?

In the past 5 days, the cheapest round-trip tickets from Portland to Caribbean were found on American Airlines ($420) and United Airlines ($436).

How long does a flight from Portland to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Portland are to Nassau , which takes 8h 14m , Kingston , which takes 9h 00m, and San Juan , which takes 10h 12m.

How long does a flight from Portland to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Portland are to Nassau , which takes 8h 14m , Kingston , which takes 9h 00m, and San Juan , which takes 10h 12m.

$194 CHEAP FLIGHTS from Portland to Caribbean

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Flight Deals

One-wayRound-trip

Punta Cana1 stop$560

Santo Domingo2 stops$703

Montego Bay2 stops$452

Oranjestad1 stop$639

Santiago de los Caballeros1 stop$700

Nassau2 stops$498

Saint Thomas Island2 stops$420

Kingston2 stops$765

Simpson Bay1 stop$498

Providenciales2 stops$649

Bridgetown2 stops$679

George Town2 stops$666

Willemstad2 stops$761

Aguadilla2 stops$586

St. John's2 stops$722

Puerto Plata2 stops$708

Punta Cana1 stop$560

Santo Domingo2 stops$703

Montego Bay2 stops$452

Oranjestad1 stop$639

Santiago de los Caballeros1 stop$700

Nassau2 stops$498

Saint Thomas Island2 stops$420

Kingston2 stops$765

Simpson Bay1 stop$498

Providenciales2 stops$649

Bridgetown2 stops$679

George Town2 stops$666

Willemstad2 stops$761

Aguadilla2 stops$586

St. John's2 stops$722

Puerto Plata2 stops$708

Book Cheap Portland to Caribbean Plane Tickets

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 Portland to Caribbean

Thu, Aug 20 - Fri, Aug 28

3:00 pm - 12:53 pm

PDX

STT

18h 53m

2 stops

4:42 pm - 10:54 am

STT

PDX

21h 12m

2 stops

$420American Airlines

Mon, Nov 9 - Tue, Nov 17

7:00 pm - 11:45 am

PDX

SJU

12h 45m

2 stops

5:45 am - 3:00 pm

SJU

PDX

13h 15m

2 stops

$436Southwest

Mon, Nov 2 - Wed, Nov 11

7:35 pm - 1:48 pm

PDX

MBJ

15h 13m

2 stops

2:54 pm - 11:12 pm

MBJ

PDX

11h 18m

1 stop

$452United Airlines

Fri, Oct 2 - Sat, Oct 10

5:00 am - 5:38 pm

PDX

SJU

9h 38m

1 stop

2:00 pm - 9:10 pm

SJU

PDX

10h 10m

1 stop

$456United Airlines

Mon, Nov 2 - Wed, Nov 11

5:34 pm - 12:25 pm

PDX

MBJ

15h 51m

2 stops

2:20 pm - 10:26 pm

MBJ

PDX

11h 06m

1 stop

$457Delta

Fri, Aug 21 - Thu, May 13

12:35 am - 3:02 pm

PDX

STT

11h 27m

2 stops

1:25 pm - 10:26 pm

STT

PDX

12h 01m

1 stop

$459Delta

Wed, Nov 18 - Tue, Dec 1

3:15 pm - 12:50 pm

PDX

MBJ

18h 35m

2 stops

1:50 pm - 9:26 am

MBJ

PDX

22h 36m

2 stops

$534Air Canada

Sun, Oct 25 - Sun, Nov 1

7:00 am - 12:45 pm

PDX

PUJ

26h 45m

2 stops

7:45 pm - 6:31 pm

PUJ

PDX

26h 46m

2 stops

$584Air Canada

Tue, Sep 1 - Sat, Sep 5

2:19 pm - 3:30 pm

PDX

AUA

22h 11m

1 stop

6:00 pm - 1:04 pm

AUA

PDX

22h 04m

1 stop

$639JetBlue

Thu, Aug 27 - Thu, Sep 3

2:15 pm - 3:30 pm

PDX

AUA

22h 15m

1 stop

1:55 pm - 10:49 pm

AUA

PDX

11h 54m

1 stop

$640JetBlue

Booking Insights

KAYAK's insights & trends for Portland to Caribbean flights

Get data-powered insights and trends into flights from Portland to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Prices

Airlines

What is the cheapest month to fly from Portland to Caribbean?

The cheapest month for flights from Portland to Caribbean is September, when tickets cost $624 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $791 and $791 respectively.

How far in advance should I book a flight from Portland to Caribbean?

To get a below average price on the flight from Portland to Caribbean, you should book around 2 weeks before departure, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Find deals

Low season	July
High season	March
Cheapest flight	$194

Best time to beat the crowds but there is an average 7% increase in price.

Most popular time to fly with an average 12% increase in price.

Flight from Portland to San Juan

How does KAYAK find such low prices on flights from Portland to Caribbean?
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 Portland to Caribbean.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Caribbean?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to 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 Portland to Caribbean?
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 from Portland to Caribbean with an airline and back with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Caribbean?
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 from Portland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Caribbean

Airports

Cabin class

Complete your trip

Flights to other cities

Origins

Popular routes

Return flight deals

Information on your arrival and departure airports

Portland (PDX)

$194 Find Cheap Flights from Portland to Caribbean - Compare and Save

Cheap Flights from Portland to Caribbean

Book Cheap Portland to Caribbean Plane Tickets

Recent round-trip flight deals from Portland to Caribbean

Recent one-way flight deals from Portland to Caribbean

Recent last minute flight deals from Portland to Caribbean

KAYAK's insights & trends for Portland to Caribbean flights

What is the cheapest month to fly from Portland to Caribbean?

How far in advance should I book a flight from Portland to Caribbean?

Which airlines provide the cheapest flights from Portland to Caribbean?

How long does a flight from Portland to Caribbean take?

Good to know

Low season

High season

Cheapest flight

FAQs - booking Caribbean flights

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Cabin class types available on flights to Portland

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

Flights to other popular destinations

Flights from domestic origins to Portland

Flights to popular destinations in Caribbean

Find deals for your return flight