Caribbean

$167+ Cheap flights from Portland (PDX) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
May 27 — Jun 31
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Cheap flight deals from Portland to Caribbean

Cheapest flights from Portland to Caribbean
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.

This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:45 pm
PDX
-
MBJ
1 stop11h 10m
American Airlines
Wed 11/1111:09 am
MBJ
-
PDX
1 stop13h 06m
American Airlines
Deal found 4/27$392
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:59 pm
PDX
-
MBJ
1 stop11h 47m
United Airlines
Wed 11/112:48 pm
MBJ
-
PDX
2 stops21h 52m
United Airlines
Deal found 4/26$397
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:15 am
PDX
-
MBJ
1 stop8h 35m
United Airlines
Sun 11/222:48 pm
MBJ
-
PDX
1 stop21h 42m
United Airlines
Deal found 4/22$401
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:50 pm
PDX
-
MBJ
2 stops20h 53m
United Airlines
Sat 9/2612:52 pm
MBJ
-
PDX
1 stop10h 13m
United Airlines
Deal found 4/23$407
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:15 pm
PDX
-
STT
1 stop11h 53m
United Airlines
Thu 5/141:22 pm
STT
-
PDX
1 stop12h 37m
United Airlines
Deal found 4/25$420
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:45 pm
PDX
-
MBJ
2 stops15h 40m
Delta
Tue 11/106:00 pm
MBJ
-
PDX
2 stops18h 31m
Delta
Deal found 4/23$427
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:59 pm
PDX
-
STT
1 stop12h 44m
United Airlines
Tue 5/121:22 pm
STT
-
PDX
1 stop12h 37m
United Airlines
Deal found 4/26$445
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2811:30 pm
PDX
-
MBJ
1 stop13h 40m
United Airlines
Sun 8/92:40 pm
MBJ
-
PDX
1 stop10h 08m
United Airlines
Deal found 4/25$448
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:45 pm
PDX
-
SJU
1 stop11h 15m
Southwest
Thu 9/245:30 am
SJU
-
PDX
1 stop12h 30m
Southwest
Deal found 4/25$466
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/310:40 pm
PDX
-
MBJ
2 stops12h 50m
United Airlines
Mon 8/174:12 pm
MBJ
-
PDX
2 stops19h 09m
United Airlines
Deal found 4/22$470
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:42 pm
PDX
-
MBJ
2 stops13h 33m
American Airlines
Sun 11/224:05 pm
MBJ
-
PDX
2 stops22h 05m
American Airlines
Deal found 4/22$472
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1810:45 pm
PDX
-
SJU
1 stop11h 25m
Southwest
Mon 9/215:30 am
SJU
-
PDX
1 stop12h 30m
Southwest
Deal found 4/24$481

Find flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated April 27, 2026.

Round-trip from

$392
(American Airlines)

One-way from

$167
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$555
From Portland to Caribbean
One-way flight from Portland to Caribbean
Highest demand for flights based on searches. 10% potential increase in price ($66 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Average for round-trip flights in April 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 27, 2026.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Sun 5/10

10:15 pm-1:08 pm

1 stop11h 53m

Saint Thomas Island Cyril E King

Thu 5/14

1:22 pm-10:59 pm

1 stop12h 37m

$420

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Tue 10/13

11:58 pm-1:05 pm

2 stops11h 07m

Montego Bay Sangster Intl

Tue 10/20

10:50 am-10:59 pm

2 stops14h 09m

$517

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Fri 9/18

11:15 pm-1:30 pm

2 stops12h 15m

Montego Bay Sangster Intl

Sat 9/26

12:52 pm-10:52 pm

1 stop12h 00m

$517

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 5/29

5:05 pm-12:01 pm

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Thu 6/4

1:16 pm-11:44 pm

2 stops13h 28m

$530

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/25

11:30 pm-12:34 pm

1 stop10h 04m

San Juan Luis Munoz Marin Intl

Sun 5/31

1:00 am-9:25 am

1 stop11h 25m

$530

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 10/6

6:56 am-8:38 pm

1 stop10h 42m

San Juan Luis Munoz Marin Intl

Thu 10/8

2:00 pm-10:52 pm

1 stop11h 52m

$530

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Wed 7/29

6:50 pm-3:10 pm

2 stops18h 20m

Montego Bay Sangster Intl

Mon 8/3

2:40 pm-9:47 am

2 stops21h 07m

$547

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sat 10/17

10:59 pm-3:00 pm

1 stop13h 01m

Punta Cana

Sat 10/24

1:25 pm-9:05 pm

1 stop10h 40m

$556
Quickest round-trip

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 7/22

10:52 pm-12:04 pm

1 stop10h 12m

San Juan Luis Munoz Marin Intl

Wed 8/5

3:56 pm-12:02 am

1 stop11h 06m

$564

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 7/31

11:30 pm-1:45 pm

1 stop11h 15m

San Juan Luis Munoz Marin Intl

Fri 8/7

6:30 am-4:35 pm

2 stops13h 05m

$568

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Portland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Caribbean

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

The best time to book flights from Portland to Caribbean is 46 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Portland to Caribbean?

Currently, May is the cheapest month in which you can book a flight from Portland to Caribbean (average of $179). Flying from Portland to Caribbean in February is currently the most expensive (average of $279). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 27, 2026.
Read through reviews of airlines operating flights from Portland to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Portland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly from for flights from Portland to Caribbean?

    For a flight from Portland to Caribbean, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city.

  • How long is the flight from Portland to Caribbean?

    Airlines like United Airlines, American Airlines, and Delta fly from Portland to Caribbean in about 11h 07m. The time it takes to get you to your destination can typically vary by up to 4h 49m. Portland and Caribbean are separated by a distance of 3155 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Portland to Caribbean one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $172. Users have also found prices from $185 and $190 on JetBlue and Southwest, respectively.

  • What are the most popular routes from Portland to Caribbean?

  • Can I find deals for flights from Portland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Portland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Caribbean.

  • Can I find deals for business class flights from Portland to Caribbean?

    Yes. Cheapflights offers flight deals from Portland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland to Caribbean?

    Currently, May is the cheapest month in which you can book a flight from Portland to Caribbean (average of $179). Flying from Portland to Caribbean in February is currently the most expensive (average of $279). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Portland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Portland to Caribbean

Discover the top 5 airlines that operate flights from Portland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$446FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$662FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$224Average$663FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$396Average$730FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$408Average$682FlexibilityNo cancel feeOn-time63%

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