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 United Airlines ($446) and Southwest ($461).

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 United Airlines ($446) and Southwest ($461).

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 Punta Cana , which takes 9h 03m , San Juan , which takes 9h 25m, and Nassau , which takes 9h 45m.

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 Punta Cana , which takes 9h 03m , San Juan , which takes 9h 25m, and Nassau , which takes 9h 45m.

$177 CHEAP FLIGHTS from Portland to Caribbean

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Flight Deals

One-wayRound-trip

Punta Cana1 stop$560

Santo Domingo2 stops$581

Montego Bay2 stops$452

Oranjestad2 stops$648

Santiago de los Caballeros1 stop$700

Nassau2 stops$554

Saint Thomas Island2 stops$420

Kingston2 stops$678

Simpson Bay1 stop$507

Providenciales2 stops$553

Bridgetown2 stops$617

George Town2 stops$579

Willemstad2 stops$529

Aguadilla2 stops$518

St. John's2 stops$702

Puerto Plata2 stops$715

Punta Cana1 stop$560

Santo Domingo2 stops$581

Montego Bay2 stops$452

Oranjestad2 stops$648

Santiago de los Caballeros1 stop$700

Nassau2 stops$554

Saint Thomas Island2 stops$420

Kingston2 stops$678

Simpson Bay1 stop$507

Providenciales2 stops$553

Bridgetown2 stops$617

George Town2 stops$579

Willemstad2 stops$529

Aguadilla2 stops$518

St. John's2 stops$702

Puerto Plata2 stops$715

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

Sat, Oct 24 - Sat, Oct 31

10:55 pm - 2:55 pm

PDX

STT

13h 00m

2 stops

3:46 pm - 1:33 pm

STT

PDX

24h 47m

2 stops

$420American Airlines

Tue, Nov 3 - Tue, Nov 10

11:03 pm - 12:17 pm

PDX

STT

9h 14m

1 stop

3:15 pm - 11:07 am

STT

PDX

23h 52m

2 stops

$420American Airlines

Tue, Aug 25 - Sun, Aug 30

7:10 am - 8:38 pm

PDX

SJU

10h 28m

1 stop

1:00 am - 9:50 am

SJU

PDX

11h 50m

1 stop

$446United Airlines

Tue, Jan 19 - Tue, Jan 26

7:00 am - 9:00 pm

PDX

SJU

10h 00m

1 stop

8:10 am - 7:07 pm

SJU

PDX

14h 57m

2 stops

$446United 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

$446Southwest

Tue, Jan 19 - Tue, Jan 26

5:10 am - 10:00 pm

PDX

SJU

12h 50m

2 stops

12:15 pm - 9:40 pm

SJU

PDX

13h 25m

2 stops

$446Southwest

Sun, Nov 8 - Sat, Nov 14

11:00 pm - 4:35 pm

PDX

MBJ

14h 35m

1 stop

4:00 pm - 11:59 pm

MBJ

PDX

10h 59m

1 stop

$462Delta

Sun, Nov 15 - Thu, Nov 19

11:10 pm - 2:20 pm

PDX

SJU

11h 10m

1 stop

3:35 pm - 9:52 pm

SJU

PDX

10h 17m

1 stop

$466Delta

Sat, Aug 29 - Thu, Sep 3

11:27 pm - 2:11 pm

PDX

SJU

11h 44m

1 stop

5:04 am - 1:01 pm

SJU

PDX

10h 57m

1 stop

$511JetBlue

Sat, Oct 31 - Sun, Nov 8

7:00 am - 1:25 pm

PDX

MBJ

28h 25m

2 stops

2:20 pm - 6:31 pm

MBJ

PDX

31h 11m

2 stops

$515Air Canada

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 March, when the average cost of round-trip tickets is $791 and $787 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	$177

Best time to beat the crowds but there is an average 8% increase in price.

Most popular time to fly with an average 11% increase in price.

Flight from Portland to Nassau

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)

$177 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