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$116+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Round-trip from

$278
(FlightHub)

One-way from

$116
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$470
From Portland to Caribbean
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One-way flight from Portland to Caribbean
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Highest demand for flights based on searches. 7% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Find 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 January 30, 2025.

This FlightHub deal was found by Cheapflights users on 1/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/97:32 pmPDX - STT
2 stops14h 13mSpirit Airlines
Wed 3/1211:11 amSTT - PDX
2 stops29h 27mSpirit Airlines
Deal found 1/30$278
This Expedia deal was found by Cheapflights users on 1/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/117:32 pmPDX - PUJ
2 stops16h 10mSpirit Airlines
Tue 3/183:47 pmPUJ - PDX
2 stops21h 33mSpirit Airlines
Deal found 1/30$329
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/3011:02 amPDX - SJU
2 stops19h 30mSpirit Airlines
Wed 5/710:51 amSJU - PDX
2 stops24h 21mSpirit Airlines
Deal found 1/29$348
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Tue 9/166:45 pmPDX - SJU
2 stops13h 30mAmerican Airlines
Wed 10/18:30 amSJU - PDX
1 stop17h 30mAmerican Airlines
Deal found 1/30$359
This United Airlines deal was found by Cheapflights users on 1/28. 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 3/45:00 amPDX - SJU
1 stop9h 25mUnited Airlines
Tue 3/117:10 amSJU - PDX
2 stops14h 38mUnited Airlines
Deal found 1/28$376
This Delta deal was found by Cheapflights users on 1/28. 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.
Fri 2/2112:59 amPDX - SJU
1 stop10h 01mDelta
Wed 2/262:11 pmSJU - PDX
1 stop13h 18mDelta
Deal found 1/28$425
This FlightHub deal was found by Cheapflights users on 1/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/57:32 pmPDX - MBJ
2 stops13h 30mSpirit Airlines
Wed 3/1912:07 pmMBJ - PDX
2 stops24h 13mSpirit Airlines
Deal found 1/29$454
This American Airlines deal was found by Cheapflights users on 1/30. 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 4/2110:34 pmPDX - STT
1 stop15h 25mAmerican Airlines
Wed 4/304:50 pmSTT - PDX
2 stops20h 48mAmerican Airlines
Deal found 1/30$469
This Southwest deal was found by Cheapflights users on 1/30. 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.
Sun 9/149:05 pmPDX - SJU
1 stop12h 35mSouthwest
Tue 9/168:00 amSJU - PDX
2 stops13h 05mSouthwest
Deal found 1/30$480
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/17:15 amPDX - NAS
1 stop9h 44mAlaska Airlines
Sat 3/88:00 amNAS - PDX
1 stop16h 54mAlaska Airlines
Deal found 1/30$491
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/210:16 amPDX - SJU
3 stops43h 05mMultiple Airlines
Tue 2/48:40 pmSJU - PDX
2 stops23h 55mMultiple Airlines
Deal found 1/29$519
This United Airlines deal was found by Cheapflights users on 1/30. 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 3/17:46 pmPDX - NAS
2 stops16h 09mUnited Airlines
Sat 3/81:05 pmNAS - PDX
1 stop9h 55mUnited Airlines
Deal found 1/30$535

Find flights from Portland to Caribbean within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Sun 3/9

7:32 pm-12:45 pm

2 stops14h 13m

Saint Thomas Island Cyril E King

Wed 3/12

11:11 am-1:38 pm

2 stops29h 27m

$278

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Tue 3/11

7:32 pm-2:42 pm

2 stops16h 10m

Punta Cana

Tue 3/18

3:47 pm-10:20 am

2 stops21h 33m

$329

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 4/30

11:02 am-9:32 am

2 stops19h 30m

San Juan Luis Munoz Marin Intl

Wed 5/7

10:51 am-8:12 am

2 stops24h 21m

$348

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/23

10:55 pm-3:45 pm

1 stop12h 50m

San Juan Luis Munoz Marin Intl

Thu 2/27

7:45 am-11:58 pm

1 stop20h 13m

$359

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 3/4

5:00 am-6:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Tue 3/11

7:10 am-6:48 pm

2 stops14h 38m

$376

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Wed 3/5

7:32 pm-12:02 pm

2 stops13h 30m

Montego Bay Sangster Intl

Tue 3/25

12:07 pm-10:20 am

2 stops24h 13m

$389

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 2/21

12:59 am-3:00 pm

1 stop10h 01m

San Juan Luis Munoz Marin Intl

Wed 2/26

2:11 pm-11:29 pm

1 stop13h 18m

$425

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Wed 3/5

7:32 pm-12:02 pm

2 stops13h 30m

Montego Bay Sangster Intl

Tue 3/25

3:05 pm-5:18 pm

3 stops28h 13m

$434

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Mon 4/21

10:34 pm-4:59 pm

1 stop15h 25m

Saint Thomas Island Cyril E King

Wed 4/30

4:50 pm-10:38 am

2 stops20h 48m

$469

PortlandNassau

PDX - NAS

PDXNAS

Portland

Sat 3/1

7:15 am-7:59 pm

1 stop9h 44m

Nassau Intl

Sat 3/8

8:00 am-9:54 pm

1 stop16h 54m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 52 results
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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.

Travel insights for flights from Portland to Caribbean

Get recent, data-driven insights about flights from Portland to Caribbean including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $254). Flying from Portland to Caribbean in March is currently the most expensive (average of $372). 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.

What is the cheapest time of day to fly from PDX to CB?

Find hourly flight availability from Portland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 30, 2025.

When flying from Portland to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 January 30, 2025.
Southwest
8.1
Very good
4,585 reviews

Crew

8.7

Food

7.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Crew

8.7

Food

7.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,688 reviews
Southwest
8.1
Very good
4,585 reviews

Crew

8.7

Food

7.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Crew

8.7

Food

7.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.6
Good
1,617 reviews
Southwest
8.1
Very good
4,585 reviews

Crew

8.7

Food

7.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,156 reviews
Southwest
8.1
Very good
4,585 reviews

Crew

8.7

Food

7.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $116. Users have also found prices from $180 and $213 on American Airlines and Delta, respectively.

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

    The most popular flight routes from Portland to Caribbean are Portland - San Juan Luis Munoz Marin Intl, Portland - Punta Cana and Portland - Montego Bay Sangster Intl.

  • 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, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $254). Flying from Portland to Caribbean in March is currently the most expensive (average of $372). 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.

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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.
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Top 9 airlines flying from Portland to Caribbean

Discover the top 9 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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$357FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$225Average$365FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$242Average$1,014FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$281Average$661FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$288Average$509FlexibilityNo cancel feeOn-time62%
DeltaCheapest$305Average$690FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$695FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$421Average$638FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%
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