HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$152+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
jul. 7 — jul. 141
lun. 7/7
lun. 7/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 julio 2, 2025.

Round-trip from

$367
(Mytrip)

One-way from

$152
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$555
From Portland to Caribbean
Search Deals
One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 julio 2, 2025.

This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/2910:23 amPDX - SJU
2 stops22h 09mSpirit Airlines
mar. 8/54:43 pmSJU - PDX
2 stops24h 32mSpirit Airlines
Deal found 7/1$367
This American Airlines deal was found by Cheapflights users on 7/2. 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.
jue. 7/2412:59 amPDX - SJU
1 stop19h 26mAmerican Airlines
lun. 7/2812:59 amSJU - PDX
2 stops12h 43mAmerican Airlines
Deal found 7/2$399
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/2410:34 amPDX - SJU
3 stops33h 26mMultiple Airlines
lun. 7/2811:59 pmSJU - PDX
2 stops17h 16mMultiple Airlines
Deal found 7/1$414
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/173:10 pmPDX - STT
2 stops18h 20mSpirit Airlines
lun. 7/2110:43 amSTT - PDX
2 stops25h 35mSpirit Airlines
Deal found 7/1$443
This United Airlines deal was found by Cheapflights users on 6/30. 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.
vie. 8/1510:55 pmPDX - SJU
1 stop12h 49mUnited Airlines
vie. 8/221:25 pmSJU - PDX
1 stop11h 03mUnited Airlines
Deal found 6/30$467
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/126:00 amPDX - SJU
2 stops13h 30mSouthwest
jue. 8/145:50 amSJU - PDX
2 stops13h 30mSouthwest
Deal found 7/1$481
This American Airlines deal was found by Cheapflights users on 6/29. 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.
sáb. 10/119:52 pmPDX - NAS
1 stop12h 33mAmerican Airlines
jue. 10/1611:00 amNAS - PDX
1 stop13h 02mAmerican Airlines
Deal found 6/29$489
This Delta deal was found by Cheapflights users on 7/2. 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.
mié. 10/2912:15 pmPDX - PUJ
1 stop21h 17mDelta
mié. 11/53:42 pmPUJ - PDX
1 stop10h 50mDelta
Deal found 7/2$491
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/133:10 pmPDX - PUJ
2 stops25h 44mMultiple Airlines
sáb. 7/193:25 pmPUJ - PDX
2 stops20h 53mMultiple Airlines
Deal found 7/2$492
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/217:52 pmPDX - STT
3 stops36h 21mMultiple Airlines
sáb. 9/610:49 amSTT - PDX
2 stops27h 23mMultiple Airlines
Deal found 7/2$498
This Delta deal was found by Cheapflights users on 7/2. 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.
mié. 9/31:30 pmPDX - MBJ
1 stop19h 53mDelta
mar. 9/92:30 pmMBJ - PDX
2 stops20h 42mDelta
Deal found 7/2$515
This Delta deal was found by Cheapflights users on 6/29. 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.
mar. 7/225:05 pmPDX - NAS
2 stops15h 28mDelta
mar. 7/293:00 pmNAS - PDX
2 stops11h 35mDelta
Deal found 6/29$515

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 julio 2, 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

mar. 7/29

10:23 am-11:32 am

2 stops22h 09m

San Juan Luis Munoz Marin Intl

mar. 8/5

4:43 pm-2:15 pm

2 stops24h 32m

$367

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

jue. 7/24

12:59 am-11:25 pm

1 stop19h 26m

San Juan Luis Munoz Marin Intl

lun. 7/28

12:59 am-10:42 am

2 stops12h 43m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

jue. 7/24

10:34 am-11:00 pm

3 stops33h 26m

San Juan Luis Munoz Marin Intl

lun. 7/28

11:59 pm-2:15 pm

2 stops17h 16m

$414

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

jue. 7/17

3:10 pm-12:30 pm

2 stops18h 20m

Saint Thomas Island Cyril E King

lun. 7/21

10:43 am-9:18 am

2 stops25h 35m

$443

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

vie. 8/15

10:55 pm-2:44 pm

1 stop12h 49m

San Juan Luis Munoz Marin Intl

vie. 8/22

1:25 pm-9:28 pm

1 stop11h 03m

$467

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 8/12

6:10 am-10:30 pm

2 stops13h 20m

San Juan Luis Munoz Marin Intl

jue. 8/14

5:50 am-4:00 pm

1 stop13h 10m

$481

PortlandNassau

PDX - NAS

PDXNAS

Portland

sáb. 10/11

9:52 pm-1:25 pm

1 stop12h 33m

Nassau Intl

jue. 10/16

11:00 am-9:02 pm

1 stop13h 02m

$489

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

jue. 8/14

10:55 pm-3:05 pm

1 stop13h 10m

Punta Cana

jue. 8/21

4:35 pm-8:51 am

2 stops19h 16m

$491

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

dom. 7/13

3:10 pm-7:54 pm

2 stops25h 44m

Punta Cana

sáb. 7/19

3:25 pm-9:18 am

2 stops20h 53m

$492

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

jue. 8/21

7:52 pm-11:13 am

3 stops36h 21m

Saint Thomas Island Cyril E King

sáb. 9/6

10:49 am-11:12 am

2 stops27h 23m

$498

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 54 results
1
2
3
...
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

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 June is currently the most expensive (average of $339). 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 julio 2, 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.

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 julio 2, 2025.
Read through reviews of airlines operating flights from Portland to Caribbean, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,272 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,983 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
JetBlue
7.3
Good
2,918 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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 $152. Users have also found prices from $172 and $190 on Frontier and JetBlue, 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 June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Los Angeles flights
Portland to O'Hare Intl flights
Portland to Denver flights
Portland to Las Vegas flights
Portland to Dallas/Fort Worth flights
Portland to Santa Ana flights
Portland to John F Kennedy Intl flights
Portland to Honolulu flights
Portland to Newark flights
Portland to San Francisco flights
Portland to Ontario flights
Portland to Sky Harbor Intl flights
Portland to San Diego flights
Boise to Seattle flights
Portland to Boston flights
Portland to Burbank flights
Portland to Kahului flights
Portland to Orlando flights
Portland to San Jose flights
Portland to Hobby flights
Portland to Heathrow flights
Portland to LaGuardia flights
Portland to Reagan-National flights
Portland to Narita flights
Portland to Minneapolis flights
Portland to Detroit flights
Portland to Salt Lake City flights
Portland to Nashville flights
Portland to Kailua-Kona flights
Portland to Cancún flights
Portland to Dulles Intl flights
Portland to Atlanta flights
Portland to Haneda flights
Portland to George Bush Intcntl flights
Portland to Mexico City flights
Portland to Austin flights
Boise to Las Vegas flights
Portland to Palm Springs flights
Portland to Baltimore flights
Portland to Miami flights
Redmond to Anchorage flights
Boise to Denver flights
Boise to Los Angeles flights
Boise to O'Hare Intl flights
Portland to Sacramento flights
Portland to Philadelphia flights
Portland to Vancouver Intl flights
Portland to Reno flights
Portland to Seattle flights
Eugene to Los Angeles flights

Top 8 airlines flying from Portland to Caribbean

Discover the top 8 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 julio 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$369FlexibilityNo cancel feeOn-time62%
DeltaCheapest$218Average$717FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$352FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$306Average$693FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$328Average$715FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$720FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$549FlexibilityNo cancel feeOn-time75%
Sun Country AirCheapest$475Average$771FlexibilityNo cancel feeOn-time83%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.