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$142+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
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 March 3, 2025.

Round-trip from

$214
(FlightHub)

One-way from

$142
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$834
From Portland to Caribbean
Search Deals
One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 3, 2025.

This FlightHub deal was found by Cheapflights users on 3/2. 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 3/261:51 pmPDX - STT
2 stops20h 09mSpirit Airlines
Tue 4/11:55 pmSTT - PDX
2 stops23h 25mSpirit Airlines
Deal found 3/2$214
This CheapOair deal was found by Cheapflights users on 3/3. 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.
Tue 4/16:13 pmPDX - SJU
2 stops12h 13mSpirit Airlines
Tue 4/86:25 pmSJU - PDX
2 stops22h 12mSpirit Airlines
Deal found 3/3$364
This Priceline deal was found by Cheapflights users on 3/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/67:01 pmPDX - SJU
2 stops15h 59mMultiple Airlines
Sat 5/104:15 pmSJU - PDX
1 stop28h 16mMultiple Airlines
Deal found 3/3$366
This American Airlines deal was found by Cheapflights users on 3/2. 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 4/1411:52 pmPDX - SJU
2 stops11h 43mAmerican Airlines
Thu 4/2411:50 amSJU - PDX
1 stop14h 38mAmerican Airlines
Deal found 3/2$369
This FlightHub deal was found by Cheapflights users on 3/2. 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.
Sat 5/32:33 pmPDX - MBJ
2 stops18h 22mSpirit Airlines
Sat 5/1012:11 pmMBJ - PDX
2 stops22h 01mSpirit Airlines
Deal found 3/2$383
This FlightHub deal was found by Cheapflights users on 3/2. 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.
Thu 3/276:50 pmPDX - PUJ
2 stops14h 27mSpirit Airlines
Wed 4/21:14 pmPUJ - PDX
2 stops24h 06mSpirit Airlines
Deal found 3/2$391
This Priceline deal was found by Cheapflights users on 3/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/167:01 pmPDX - AUA
2 stops16h 39mSpirit Airlines
Thu 4/243:45 pmAUA - PDX
2 stops20h 27mSpirit Airlines
Deal found 3/2$391
This United Airlines deal was found by Cheapflights users on 3/3. 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 4/2211:30 pmPDX - SJU
1 stop10h 04mUnited Airlines
Tue 4/291:40 pmSJU - PDX
1 stop10h 20mUnited Airlines
Deal found 3/3$394
This FlightHub deal was found by Cheapflights users on 3/2. 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 3/261:51 pmPDX - KIN
2 stops20h 37mSpirit Airlines
Wed 4/21:36 pmKIN - PDX
2 stops22h 44mSpirit Airlines
Deal found 3/2$460
This Delta deal was found by Cheapflights users on 3/2. 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 3/3112:59 amPDX - SJU
1 stop10h 06mDelta
Wed 4/96:15 amSJU - PDX
2 stops17h 34mDelta
Deal found 3/2$465
This American Airlines deal was found by Cheapflights users on 3/2. 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 11/36:46 pmPDX - STT
2 stops15h 14mAmerican Airlines
Wed 11/126:15 pmSTT - PDX
2 stops20h 03mAmerican Airlines
Deal found 3/2$499
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Wed 4/97:30 pmPDX - NAS
2 stops16h 29mUnited Airlines
Wed 4/162:53 pmNAS - PDX
1 stop11h 21mUnited Airlines
Deal found 3/1$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 March 3, 2025.

Fly from

Portland

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Wed 3/26

1:51 pm-1:00 pm

2 stops20h 09m

Saint Thomas Island Cyril E King

Tue 4/1

1:55 pm-10:20 am

2 stops23h 25m

$214

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/1

6:13 pm-9:26 am

2 stops12h 13m

San Juan Luis Munoz Marin Intl

Tue 4/8

6:25 pm-1:37 pm

2 stops22h 12m

$364

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 5/6

7:01 pm-2:00 pm

2 stops15h 59m

San Juan Luis Munoz Marin Intl

Sat 5/10

4:15 pm-5:31 pm

1 stop28h 16m

$366

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 4/14

11:52 pm-2:35 pm

2 stops11h 43m

San Juan Luis Munoz Marin Intl

Thu 4/24

11:50 am-11:28 pm

1 stop14h 38m

$369

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sat 5/3

2:33 pm-10:55 am

2 stops18h 22m

Montego Bay Sangster Intl

Sat 5/10

12:11 pm-8:12 am

2 stops22h 01m

$383

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Thu 3/27

6:50 pm-12:17 pm

2 stops14h 27m

Punta Cana

Wed 4/2

1:14 pm-10:20 am

2 stops24h 06m

$391

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Wed 4/16

7:01 pm-2:40 pm

2 stops16h 39m

Oranjestad Reina Beatrix

Thu 4/24

3:45 pm-9:12 am

2 stops20h 27m

$391

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/22

11:30 pm-12:34 pm

1 stop10h 04m

San Juan Luis Munoz Marin Intl

Tue 4/29

1:40 pm-9:00 pm

1 stop10h 20m

$394

PortlandKingston

PDX - KIN

PDXKIN

Portland

Wed 3/26

1:51 pm-12:28 pm

2 stops20h 37m

Kingston Norman Manley

Wed 4/2

1:36 pm-10:20 am

2 stops22h 44m

$460

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 3/31

12:59 am-2:05 pm

1 stop10h 06m

San Juan Luis Munoz Marin Intl

Wed 4/9

6:15 am-8:49 pm

2 stops17h 34m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 60 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 $353). 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 March 3, 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 March 3, 2025.
Southwest
8.1
Very good
4,333 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,333 reviews
Southwest
8.1
Very good
4,333 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Alaska Airlines
8.0
Very good
9,710 reviews
Southwest
8.1
Very good
4,333 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
8,068 reviews
Southwest
8.1
Very good
4,333 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

LATAM Airlines
7.5
Good
1,763 reviews
Southwest
8.1
Very good
4,333 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines
7.4
Good
8,679 reviews
Southwest
8.1
Very good
4,333 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $142. Users have also found prices from $185 and $214 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 $353). 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 March 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$352FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$213Average$371FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$242Average$524FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$281Average$675FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$288Average$509FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$328Average$714FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$692FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$425Average$681FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%
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