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$137+ Cheap flights from Caribbean to Portland (PDX)

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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
1 adult, Economy
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Cheap flight deals from Caribbean to Portland

Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated March 3, 2025.

Round-trip from

$318
(Mytrip)

One-way from

$137
(Booking.com)

Popular in

November

Cheapest in

February

Average price

$570
From Caribbean to Portland
Search Deals
One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 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 Caribbean to Portland

Cheapest flights from Caribbean to Portland
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 3, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/216:15 pmSJU - PDX
2 stops24h 33mSpirit Airlines
Mon 3/316:50 pmPDX - SJU
2 stops26h 04mSpirit Airlines
Deal found 3/3$318
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.
Wed 11/57:25 amSJU - PDX
2 stops13h 24mAmerican Airlines
Tue 11/1112:17 pmPDX - SJU
2 stops12h 48mAmerican Airlines
Deal found 3/2$369
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.
Fri 9/191:05 amSJU - PDX
2 stops13h 30mUnited Airlines
Fri 10/310:56 pmPDX - SJU
1 stop10h 04mUnited Airlines
Deal found 3/3$459
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/202:15 pmSJU - PDX
1 stop10h 29mDelta
Fri 10/310:55 pmPDX - SJU
1 stop11h 15mDelta
Deal found 3/3$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.
Wed 4/162:25 pmMBJ - PDX
1 stop10h 37mAmerican Airlines
Wed 4/2310:34 pmPDX - MBJ
1 stop13h 46mAmerican Airlines
Deal found 3/2$538
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/17:40 amSJU - PDX
2 stops15h 25mSouthwest
Tue 4/86:35 pmPDX - SJU
2 stops12h 45mSouthwest
Deal found 3/2$539
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1312:35 pmSJU - PDX
1 stop12h 35mJetBlue
Tue 6/2411:35 pmPDX - SJU
1 stop14h 05mJetBlue
Deal found 3/2$551
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/163:05 pmMBJ - PDX
2 stops20h 07mMultiple Airlines
Wed 4/237:01 pmPDX - MBJ
2 stops21h 22mMultiple Airlines
Deal found 3/2$569
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/141:39 pmKIN - PDX
2 stops30h 26mMultiple Airlines
Mon 4/217:01 pmPDX - KIN
3 stops23h 34mMultiple Airlines
Deal found 3/2$582
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/272:09 amSJU - PDX
3 stops33h 03mMultiple Airlines
Sun 6/16:30 pmPDX - SJU
3 stops27h 34mMultiple Airlines
Deal found 3/2$596
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1112:09 amBQN - PDX
3 stops17h 46mUnited Airlines
Thu 3/135:00 amPDX - BQN
2 stops14h 57mUnited Airlines
Deal found 3/2$610
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/12:54 pmSDQ - PDX
1 stop11h 40mMultiple Airlines
Tue 4/227:01 pmPDX - SDQ
2 stops18h 28mMultiple Airlines
Deal found 3/1$620

Find flights from Caribbean to Portland within your budget

Customize your flight search to find flights from Caribbean to Portland 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

Caribbean

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 3/21

6:15 pm-3:48 pm

2 stops24h 33m

Portland

Mon 3/31

6:50 pm-11:54 pm

2 stops26h 04m

$318

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sat 4/26

6:05 am-10:47 pm

1 stop19h 42m

Portland

Sat 5/3

6:15 pm-10:50 am

2 stops13h 35m

$378

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/28

1:55 pm-10:01 pm

1 stop11h 06m

Portland

Wed 6/11

10:55 pm-1:10 pm

1 stop11h 15m

$465

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 4/30

1:05 am-2:58 pm

2 stops16h 53m

Portland

Fri 5/9

11:35 pm-12:34 pm

1 stop9h 59m

$507

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Wed 4/16

2:25 pm-11:02 pm

1 stop10h 37m

Portland

Wed 4/23

10:34 pm-2:20 pm

1 stop13h 46m

$538

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 4/1

7:40 am-8:05 pm

2 stops15h 25m

Portland

Tue 4/8

6:35 pm-10:20 am

2 stops12h 45m

$539

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 6/13

12:35 pm-10:10 pm

1 stop12h 35m

Portland

Tue 6/24

11:35 pm-4:40 pm

1 stop14h 05m

$551

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Wed 4/16

3:05 pm-9:12 am

2 stops20h 07m

Portland

Wed 4/23

7:01 pm-6:23 pm

2 stops21h 22m

$569

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Mon 4/14

1:39 pm-6:05 pm

2 stops30h 26m

Portland

Mon 4/21

7:01 pm-8:35 pm

3 stops23h 34m

$582

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 5/27

2:09 am-8:12 am

3 stops33h 03m

Portland

Sun 6/1

6:30 pm-1:04 am

3 stops27h 34m

$596

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/3

Showing 1-10 of 35 results
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Best time to book a flight from Caribbean to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Caribbean 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 Caribbean to Portland

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

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

Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $277). Flying from Caribbean to Portland in March is currently the most expensive (average of $376). 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 CB to PDX?

Find hourly flight availability from Caribbean to Portland. 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 Caribbean to Portland, 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 Portland by month

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

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated March 3, 2025.
Southwest
8.1
Very good
4,333 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

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

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

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

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

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

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

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

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

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.

JetBlue
7.4
Good
3,008 reviews
Southwest
8.1
Very good
4,333 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

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 Caribbean to Portland. 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 into for flights to Portland from Caribbean?

    Portland (PDX) is the airport you will fly into if you book a flight from Caribbean to Portland. It is only a 6.0 mi journey from Portland (PDX) to Portland’s city center.

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

    One-way options have recently been found by users for as low as $137 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $222 and Delta from $233 one-way.

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

    When deciding which route to take from Caribbean to Portland consider San Juan Luis Munoz Marin Intl - Portland, Santo Domingo Las Americas - Portland or Kingston Norman Manley - Portland as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean to Portland 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 Caribbean to Portland?

    Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $277). Flying from Caribbean to Portland in March is currently the most expensive (average of $376). 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

Traveling to a place near Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
Lincoln City
Beaverton
Seaside
McMinnville
Lake Oswego
Hillsboro
Vancouver
Gresham
Long Beach
Cannon Beach
Tigard
Hood River
Astoria
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Longview
Wilsonville

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Caribbean to Portland

Discover the top 6 airlines that operate flights from Caribbean to Portland. 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
JetBlueCheapest$288Average$517FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$308Average$597FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$310Average$385FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$342Average$562FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$432FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$424Average$570FlexibilityNo cancel feeOn-time63%
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