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$161+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheap 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 30, 2025.

Round-trip from

$369
(Delta)

One-way from

$161
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$515
From Portland to Caribbean
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One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This Delta deal was found by Cheapflights users on 4/28. 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.
Mon 6/27:14 amPDX - SJU
1 stop13h 28mDelta
Mon 6/91:31 pmSJU - PDX
2 stops13h 58mDelta
Deal found 4/28$369
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Tue 5/135:40 pmPDX - SJU
3 stops38h 51mSpirit Airlines
Thu 5/151:59 amSJU - PDX
3 stops37h 43mSpirit Airlines
Deal found 4/29$384
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Sun 9/1410:45 pmPDX - SJU
1 stop10h 15mUnited Airlines
Mon 9/227:00 amSJU - PDX
2 stops16h 37mUnited Airlines
Deal found 4/28$387
This JetBlue deal was found by Cheapflights users on 4/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1211:35 pmPDX - SJU
1 stop13h 14mJetBlue
Mon 6/1612:55 pmSJU - PDX
1 stop12h 20mJetBlue
Deal found 4/28$412
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/276:07 pmPDX - SJU
2 stops13h 52mAmerican Airlines
Tue 6/36:30 amSJU - PDX
2 stops13h 34mAmerican Airlines
Deal found 4/28$432
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Fri 6/134:35 pmPDX - SJU
3 stops39h 04mMultiple Airlines
Thu 6/191:44 pmSJU - PDX
2 stops31h 00mMultiple Airlines
Deal found 4/29$440
This FlightHub deal was found by Cheapflights users on 4/29. 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 5/75:40 pmPDX - PUJ
2 stops17h 37mSpirit Airlines
Fri 5/163:22 pmPUJ - PDX
2 stops24h 20mSpirit Airlines
Deal found 4/29$442
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1110:47 pmPDX - NAS
1 stop11h 44mUnited Airlines
Sat 5/173:10 pmNAS - PDX
1 stop8h 56mUnited Airlines
Deal found 4/29$465
This FlightHub deal was found by Cheapflights users on 4/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/261:37 pmPDX - STT
2 stops17h 20mSpirit Airlines
Sun 6/110:52 amSTT - PDX
2 stops28h 50mSpirit Airlines
Deal found 4/28$469
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1012:40 amPDX - NAS
2 stops10h 15mDelta
Sat 5/171:13 pmNAS - PDX
2 stops12h 28mDelta
Deal found 4/29$479
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2510:24 pmPDX - NAS
1 stop17h 51mAmerican Airlines
Wed 5/284:10 pmNAS - PDX
1 stop9h 29mAmerican Airlines
Deal found 4/29$500
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Sat 6/75:40 pmPDX - PUJ
2 stops17h 37mMultiple Airlines
Fri 6/136:00 amPUJ - PDX
3 stops38h 44mMultiple Airlines
Deal found 4/29$512

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 30, 2025.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.

Fly from

Portland

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 6/2

7:14 am-11:42 pm

1 stop13h 28m

San Juan Luis Munoz Marin Intl

Mon 6/9

1:31 pm-12:29 am

2 stops13h 58m

$369

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 5/13

5:40 pm-11:31 am

3 stops38h 51m

San Juan Luis Munoz Marin Intl

Thu 5/15

1:59 am-12:42 pm

3 stops37h 43m

$384

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 6/12

11:35 pm-3:49 pm

1 stop13h 14m

San Juan Luis Munoz Marin Intl

Mon 6/16

12:55 pm-10:15 pm

1 stop12h 20m

$412

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 5/27

6:07 pm-10:59 am

2 stops13h 52m

San Juan Luis Munoz Marin Intl

Tue 6/3

6:30 am-5:04 pm

2 stops13h 34m

$432

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 6/13

4:35 pm-10:39 am

3 stops39h 04m

San Juan Luis Munoz Marin Intl

Thu 6/19

1:44 pm-5:44 pm

2 stops31h 00m

$440

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Wed 5/7

5:40 pm-2:17 pm

2 stops17h 37m

Punta Cana

Fri 5/16

3:22 pm-12:42 pm

2 stops24h 20m

$442

PortlandNassau

PDX - NAS

PDXNAS

Portland

Sun 5/11

10:47 pm-1:31 pm

1 stop11h 44m

Nassau Intl

Sat 5/17

4:01 pm-10:57 pm

1 stop9h 56m

$465

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Mon 5/26

1:37 pm-9:57 am

2 stops17h 20m

Saint Thomas Island Cyril E King

Sun 6/1

10:52 am-12:42 pm

2 stops28h 50m

$469

PortlandNassau

PDX - NAS

PDXNAS

Portland

Sat 5/10

12:40 am-1:55 pm

2 stops10h 15m

Nassau Intl

Sat 5/17

1:13 pm-10:15 pm

2 stops12h 02m

$479

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 5/27

8:30 am-11:54 pm

1 stop12h 24m

San Juan Luis Munoz Marin Intl

Mon 6/2

1:05 am-12:22 pm

2 stops14h 17m

$496

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 50 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.

Cheapflights Insights

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

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 December is currently the most expensive (average of $336). 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 April 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 April 30, 2025.
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $161. Users have also found prices from $185 and $214 on Delta and American Airlines, 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 December is currently the most expensive (average of $336). 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.
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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$223Average$306FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$245Average$373FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$250Average$534FlexibilityNo cancel feeOn-time75%
JetBlueCheapest$288Average$380FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$298Average$686FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$728FlexibilityNo cancel feeOn-time71%
DeltaCheapest$366Average$704FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$450Average$701FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%

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