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 Delta ($424).

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 Delta ($424).

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 Montego Bay , which takes 9h 55m , San Juan , which takes 10h 25m, and Santiago de los Caballeros , which takes 10h 55m.

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 Montego Bay , which takes 9h 55m , San Juan , which takes 10h 25m, and Santiago de los Caballeros , which takes 10h 55m.

$172 CHEAP FLIGHTS from Portland to Caribbean

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Flight Deals

One-wayRound-trip

Punta Cana1 stop$543

Santo Domingo1 stop$683

Montego Bay2 stops$424

Oranjestad2 stops$654

Santiago de los Caballeros1 stop$700

Nassau2 stops$568

Saint Thomas Island2 stops$420

Kingston2 stops$738

Simpson Bay2 stops$685

Providenciales1 stop$630

Bridgetown2 stops$652

George Town2 stops$618

Willemstad2 stops$704

Aguadilla2 stops$670

Puerto Plata2 stops$725

St. John's2 stops$666

Punta Cana1 stop$543

Santo Domingo1 stop$683

Montego Bay2 stops$424

Oranjestad2 stops$654

Santiago de los Caballeros1 stop$700

Nassau2 stops$568

Saint Thomas Island2 stops$420

Kingston2 stops$738

Simpson Bay2 stops$685

Providenciales1 stop$630

Bridgetown2 stops$652

George Town2 stops$618

Willemstad2 stops$704

Aguadilla2 stops$670

Puerto Plata2 stops$725

St. John's2 stops$666

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

11:34 pm - 3:52 pm

PDX

STT

13h 18m

2 stops

4:42 pm - 11:34 am

STT

PDX

21h 52m

2 stops

$420American Airlines

Fri, Aug 21 - Thu, Aug 27

5:35 pm - 3:34 pm

PDX

MBJ

19h 59m

2 stops

2:26 pm - 8:37 am

MBJ

PDX

20h 11m

2 stops

$424Delta

Mon, Nov 2 - Wed, Nov 11

10:05 pm - 12:25 pm

PDX

MBJ

11h 20m

1 stop

2:20 pm - 10:26 pm

MBJ

PDX

11h 06m

1 stop

$432Delta

Wed, Aug 19 - Thu, Aug 27

5:50 am - 9:05 pm

PDX

SJU

12h 15m

2 stops

10:00 am - 8:45 pm

SJU

PDX

13h 45m

2 stops

$436Southwest

Wed, Aug 26 - Wed, Sep 2

11:34 pm - 1:12 pm

PDX

MBJ

11h 38m

1 stop

12:38 pm - 11:59 pm

MBJ

PDX

13h 21m

2 stops

$442American Airlines

Mon, Sep 14 - Sat, Sep 19

10:45 pm - 12:50 pm

PDX

SJU

11h 05m

1 stop

10:25 am - 9:20 pm

SJU

PDX

13h 55m

2 stops

$451Southwest

Wed, Oct 28 - Wed, Nov 11

11:00 pm - 1:14 pm

PDX

MBJ

12h 14m

1 stop

2:54 pm - 11:12 pm

MBJ

PDX

11h 18m

1 stop

$462United Airlines

Sun, Oct 25 - Sun, Nov 8

11:00 pm - 11:13 am

PDX

MBJ

10h 13m

1 stop

3:45 pm - 11:13 pm

MBJ

PDX

10h 28m

1 stop

$474United Airlines

Sat, Aug 29 - Thu, Sep 3

11:27 pm - 2:11 pm

PDX

SJU

11h 44m

1 stop

1:50 pm - 10:49 pm

SJU

PDX

11h 59m

1 stop

$484JetBlue

Thu, Aug 20 - Fri, Aug 28

11:27 pm - 1:59 pm

PDX

STT

11h 32m

1 stop

2:49 pm - 10:29 pm

STT

PDX

34h 40m

2 stops

$583JetBlue

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 March, when tickets cost $191 (return) on average. On the other hand, the most expensive months are May and January, when the average cost of round-trip tickets is $365 and $307 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	$172

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 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)

$172 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

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