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 ($420) and American Airlines ($452).

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 ($420) and American Airlines ($452).

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 Kingston , which takes 8h 27m , Montego Bay , which takes 9h 09m, and Nassau , which takes 9h 54m.

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 Kingston , which takes 8h 27m , Montego Bay , which takes 9h 09m, and Nassau , which takes 9h 54m.

$186 CHEAP FLIGHTS from Portland to Caribbean

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Flight Deals

One-wayRound-trip

Punta Cana2 stops$553

Santo Domingo2 stops$705

Montego Bay1 stop$452

Oranjestad2 stops$610

Santiago de los Caballeros2 stops$705

Nassau2 stops$450

Saint Thomas Island2 stops$420

Kingston2 stops$737

Simpson Bay2 stops$512

Providenciales2 stops$595

Bridgetown2 stops$622

George Town1 stop$628

Willemstad2 stops$631

Aguadilla2 stops$496

St. John's2 stops$668

Puerto Plata2 stops$715

Punta Cana2 stops$553

Santo Domingo2 stops$705

Montego Bay1 stop$452

Oranjestad2 stops$610

Santiago de los Caballeros2 stops$705

Nassau2 stops$450

Saint Thomas Island2 stops$420

Kingston2 stops$737

Simpson Bay2 stops$512

Providenciales2 stops$595

Bridgetown2 stops$622

George Town1 stop$628

Willemstad2 stops$631

Aguadilla2 stops$496

St. John's2 stops$668

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

Fri, Oct 30 - Sun, Nov 8

7:26 pm - 1:31 pmPDX Portland-STT Saint Thomas Island Cyril E King

15h 05m2 stops San Francisco Chicago O'Hare Intl

3:35 pm - 11:17 pmSTT Saint Thomas Island Cyril E King-PDX Portland

11h 42m1 stop Houston George Bush Intcntl

$420United Airlines

Fri, Oct 30 - Sun, Nov 8

11:30 pm - 1:31 pmPDX Portland-STT Saint Thomas Island Cyril E King

11h 01m1 stop Chicago O'Hare Intl

3:35 pm - 11:17 pmSTT Saint Thomas Island Cyril E King-PDX Portland

11h 42m1 stop Houston George Bush Intcntl

$420United Airlines

Tue, Jan 26 - Tue, Feb 2

10:59 pm - 5:05 pmPDX Portland-STT Saint Thomas Island Cyril E King

14h 06m1 stop Miami

6:39 pm - 1:21 pmSTT Saint Thomas Island Cyril E King-PDX Portland

22h 42m2 stops Miami Dallas/Fort Worth

$420American Airlines

Tue, Feb 2 - Sun, Feb 7

10:59 pm - 3:56 pmPDX Portland-STT Saint Thomas Island Cyril E King

12h 57m1 stop Miami

4:46 pm - 11:18 amSTT Saint Thomas Island Cyril E King-PDX Portland

22h 32m2 stops Miami Phoenix Sky Harbor Intl

$420American Airlines

Tue, Oct 20 - Tue, Oct 27

10:10 am - 1:35 pmPDX Portland-NAS Nassau Intl

24h 25m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

12:30 pm - 9:26 amNAS Nassau Intl-PDX Portland

23h 56m2 stops Toronto Pearson Intl Vancouver Intl

$450Air Canada

Tue, Oct 20 - Tue, Oct 27

10:10 am - 1:35 pmPDX Portland-NAS Nassau Intl

24h 25m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

12:30 pm - 9:26 amNAS Nassau Intl-PDX Portland

23h 56m2 stops Toronto Pearson Intl Vancouver Intl

$450Air Canada

Tue, Feb 2 - Tue, Feb 9

5:10 am - 10:00 pmPDX Portland-SJU San Juan Luis Munoz Marin Intl

12h 50m2 stops Las Vegas Harry Reid Intl Tampa

12:15 pm - 10:20 pmSJU San Juan Luis Munoz Marin Intl-PDX Portland

14h 05m2 stops Orlando Chicago Midway

$461Southwest

Tue, Oct 27 - Fri, Nov 6

10:15 pm - 11:30 amPDX Portland-MBJ Montego Bay Sangster Intl

11h 15m1 stop New York John F Kennedy Intl

5:44 pm - 10:42 amMBJ Montego Bay Sangster Intl-PDX Portland

19h 58m1 stop Atlanta Hartsfield-Jackson

$462Delta

Mon, Nov 2 - Mon, Nov 9

10:15 pm - 12:30 pmPDX Portland-MBJ Montego Bay Sangster Intl

11h 15m1 stop New York John F Kennedy Intl

6:00 pm - 10:45 amMBJ Montego Bay Sangster Intl-PDX Portland

19h 45m1 stop Atlanta Hartsfield-Jackson

$462Delta

Tue, Dec 1 - Tue, Dec 8

11:40 am - 12:00 pmPDX Portland-MBJ Montego Bay Sangster Intl

21h 20m2 stops Denver Intl Baltimore/Washington

1:50 pm - 11:20 pmMBJ Montego Bay Sangster Intl-PDX Portland

12h 30m2 stops Orlando Chicago Midway

$462Southwest

Recent last minute flight deals from Portland to Caribbean

Sat, Aug 15 - Sat, Aug 22

1:38 pm - 4:08 pmPDX Portland-MBJ Montego Bay Sangster Intl

24h 30m1 stop Dallas/Fort Worth

5:08 pm - 11:34 amMBJ Montego Bay Sangster Intl-PDX Portland

20h 26m2 stops Miami Chicago O'Hare Intl

$605American Airlines

Sat, Aug 15 - Sat, Aug 22

11:34 pm - 1:34 pmPDX Portland-MBJ Montego Bay Sangster Intl

12h 00m2 stops Chicago O'Hare Intl Charlotte Douglas

5:08 pm - 11:34 amMBJ Montego Bay Sangster Intl-PDX Portland

20h 26m2 stops Miami Chicago O'Hare Intl

$613American Airlines

Sat, Aug 15 - Sat, Aug 22

10:50 am - 3:10 pmPDX Portland-MBJ Montego Bay Sangster Intl

26h 20m2 stops Denver Intl Washington, D.C. Dulles Intl

2:40 pm - 10:11 amMBJ Montego Bay Sangster Intl-PDX Portland

21h 31m3 stops Houston George Bush Intcntl Denver Intl San Francisco

$803United Airlines

Sat, Aug 15 - Sat, Aug 22

5:00 am - 3:10 pmPDX Portland-MBJ Montego Bay Sangster Intl

32h 10m2 stops Denver Intl Washington, D.C. Dulles Intl

2:40 pm - 10:11 amMBJ Montego Bay Sangster Intl-PDX Portland

21h 31m3 stops Houston George Bush Intcntl Denver Intl San Francisco

$827United Airlines

Thu, Aug 13 - Sat, Aug 15

6:05 am - 8:05 pmPDX Portland-SJU San Juan Luis Munoz Marin Intl

11h 00m2 stops Denver Intl Orlando

5:05 am - 4:50 pmSJU San Juan Luis Munoz Marin Intl-PDX Portland

14h 45m2 stops Orlando Phoenix Sky Harbor Intl

$896Southwest

Tue, Aug 11 - Thu, Aug 13

6:25 pm - 12:15 pmPDX Portland-NAS Nassau Intl

14h 50m2 stops Phoenix Sky Harbor Intl Orlando

1:10 pm - 11:40 pmNAS Nassau Intl-PDX Portland

13h 30m2 stops Orlando Denver Intl

$906Southwest

Thu, Aug 13 - Fri, Aug 28

6:45 am - 8:13 pmPDX Portland-KIN Kingston Norman Manley

11h 28m1 stop Atlanta Hartsfield-Jackson

9:13 am - 6:55 pmKIN Kingston Norman Manley-PDX Portland

11h 42m1 stop Atlanta Hartsfield-Jackson

$1,069Delta

Thu, Aug 13 - Tue, Aug 25

6:45 am - 8:13 pmPDX Portland-KIN Kingston Norman Manley

11h 28m1 stop Atlanta Hartsfield-Jackson

9:13 am - 9:44 pmKIN Kingston Norman Manley-PDX Portland

14h 31m1 stop Atlanta Hartsfield-Jackson

$1,069Delta

Sat, Aug 15 - Sat, Aug 22

7:45 pm - 6:30 pmPDX Portland-MBJ Montego Bay Sangster Intl

20h 45m3 stops Vancouver Intl Calgary Toronto Pearson Intl

7:30 pm - 7:11 pmMBJ Montego Bay Sangster Intl-PDX Portland

25h 41m3 stops Toronto Pearson Intl Calgary Vancouver Intl

$1,949Multiple Airlines

Sat, Aug 15 - Thu, Aug 20

7:59 pm - 11:15 pmPDX Portland-SJU San Juan Luis Munoz Marin Intl

24h 16m2 stops Santa Ana J. Wayne/Orange Cnty Chicago O'Hare Intl

12:55 am - 4:46 pmSJU San Juan Luis Munoz Marin Intl-PDX Portland

18h 51m3 stops Chicago O'Hare Intl Santa Ana J. Wayne/Orange Cnty Boise Air Term. Gowen Fld

$2,338Alaska Airlines

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 $610 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $815 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 4 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Find deals

Low season	July
High season	March
Cheapest flight	$186

Best time to beat the crowds but there is an average 9% increase in price.

Most popular time to fly with an average 14% 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)

$186 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