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Cheap flights from Portland to Caribbean Islands from $144

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Caribbean Islands departing on 1/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:05 am - 8:55 pm
PDX
-
SJU
11h 50m2 stops
Southwest Logo
5:35 am - 1:45 pm
SJU
-
PDX
12h 10m2 stops
$369Southwest
Mon, Feb 2 - Thu, Feb 5
Southwest Logo
5:50 am - 12:40 am
PDX
-
SJU
14h 50m2 stops
Southwest Logo
5:40 am - 3:40 pm
SJU
-
PDX
14h 00m2 stops
$394Southwest
Sun, Jan 25 - Tue, Feb 3
Multiple Airlines Logo
7:10 am - 11:59 pm
PDX
-
SJU
36h 49m3 stops
Multiple Airlines Logo
3:55 am - 8:26 pm
SJU
-
PDX
20h 31m2 stops
$403Multiple Airlines
Tue, Feb 3 - Mon, Feb 9
American Airlines Logo
10:15 pm - 8:50 pm
PDX
-
SJU
18h 35m1 stop
American Airlines Logo
7:07 am - 10:11 pm
SJU
-
PDX
19h 04m1 stop
$414American Airlines
Tue, Jan 20 - Thu, Jan 22
United Airlines Logo
5:00 am - 5:38 pm
PDX
-
SJU
9h 38m1 stop
United Airlines Logo
7:40 am - 6:05 pm
SJU
-
PDX
13h 25m1 stop
$415United Airlines
Sat, Apr 25 - Thu, Apr 30
Delta Logo
9:45 pm - 2:31 pm
PDX
-
SJU
12h 46m1 stop
Delta Logo
7:00 am - 5:35 pm
SJU
-
PDX
14h 35m2 stops
$419Delta
Sun, Feb 1 - Tue, Feb 10
American Airlines Logo
11:01 pm - 12:30 pm
PDX
-
SJU
9h 29m1 stop
American Airlines Logo
8:20 am - 8:27 pm
SJU
-
PDX
16h 07m2 stops
$427American Airlines
Tue, Feb 3 - Tue, Feb 10
United Airlines Logo
3:54 pm - 1:50 pm
PDX
-
AUA
17h 56m2 stops
United Airlines Logo
3:00 pm - 10:32 pm
AUA
-
PDX
11h 32m1 stop
$496United Airlines
Mon, Jan 5 - Mon, Jan 12
Delta Logo
9:45 pm - 12:55 pm
PDX
-
AUA
11h 10m1 stop
Delta Logo
3:10 pm - 10:47 am
AUA
-
PDX
23h 37m2 stops
$530Delta
Thu, Jan 29 - Tue, Feb 3
Multiple Airlines Logo
7:05 am - 5:33 pm
PDX
-
PUJ
30h 28m2 stops
Multiple Airlines Logo
1:01 pm - 8:44 pm
PUJ
-
PDX
11h 43m1 stop
$549Multiple Airlines
Fri, Feb 27 - Fri, Mar 6

Southwest flights from Portland to Caribbean Islands

Our best Southwest deals on Portland to Caribbean Islands flight tickets
Southwest
Feb 2
PDX5:05 amPortland
11h 50m
2 stops
SJU8:55 pmSan Juan Luis Munoz Marin Intl
Feb 5
SJU5:35 amSan Juan Luis Munoz Marin Intl
12h 10m
2 stops
PDX1:45 pmPortland
$369
Find similar
Southwest
Jan 25
PDX5:50 amPortland
14h 50m
2 stops
SJU12:40 amSan Juan Luis Munoz Marin Intl
Feb 3
SJU5:40 amSan Juan Luis Munoz Marin Intl
14h 05m
2 stops
PDX3:45 pmPortland
$404
Find similar
Southwest
Jan 9
PDX6:20 amPortland
12h 50m
2 stops
SJU11:10 pmSan Juan Luis Munoz Marin Intl
Jan 16
SJU5:35 amSan Juan Luis Munoz Marin Intl
12h 10m
2 stops
PDX1:45 pmPortland
$467
Find similar

American Airlines flights from Portland to Caribbean Islands

Our best American Airlines deals on Portland to Caribbean Islands flight tickets
American Airlines
Feb 3
PDX5:25 amPortland
12h 14m
2 stops
SJU9:39 pmSan Juan Luis Munoz Marin Intl
Feb 10
SJU8:20 amSan Juan Luis Munoz Marin Intl
15h 34m
2 stops
PDX7:54 pmPortland
$427
Find similar
American Airlines
Jan 9
PDX6:00 amPortland
11h 39m
1 stop
SJU9:39 pmSan Juan Luis Munoz Marin Intl
Jan 13
SJU8:20 amSan Juan Luis Munoz Marin Intl
16h 07m
2 stops
PDX8:27 pmPortland
$457
Find similar
American Airlines
Apr 1
PDX11:46 amPortland
13h 35m
1 stop
SJU4:21 amSan Juan Luis Munoz Marin Intl
Apr 15
SJU3:15 pmSan Juan Luis Munoz Marin Intl
11h 22m
1 stop
PDX11:37 pmPortland
$466
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Portland to Caribbean Islands 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, momondo users made 832,500 searches. Data last updated December 11, 2025.
Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 2/2

5:05 am-8:55 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Thu 2/5

5:35 am-1:45 pm

2 stops12h 10m

$369

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 1/25

5:50 am-12:40 am

2 stops14h 50m

San Juan Luis Munoz Marin Intl

Tue 2/3

5:40 am-3:40 pm

2 stops14h 00m

$394

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 2/3

7:10 am-11:59 pm

3 stops36h 49m

San Juan Luis Munoz Marin Intl

Mon 2/9

3:55 am-8:26 pm

2 stops20h 31m

$403

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/20

10:15 pm-8:50 pm

1 stop18h 35m

San Juan Luis Munoz Marin Intl

Thu 1/22

7:07 am-10:11 pm

1 stop19h 04m

$414

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 4/25

5:00 am-5:38 pm

1 stop9h 38m

San Juan Luis Munoz Marin Intl

Thu 4/30

7:40 am-6:05 pm

1 stop13h 25m

$415

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/1

9:45 pm-2:31 pm

1 stop12h 46m

San Juan Luis Munoz Marin Intl

Tue 2/10

7:00 am-5:35 pm

2 stops14h 35m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 2/3

11:01 pm-12:30 pm

1 stop9h 29m

San Juan Luis Munoz Marin Intl

Tue 2/10

8:20 am-8:27 pm

2 stops16h 07m

$427

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Mon 1/5

3:54 pm-1:50 pm

2 stops17h 56m

Oranjestad Reina Beatrix

Mon 1/12

3:00 pm-10:32 pm

1 stop11h 32m

$496

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Thu 1/29

9:45 pm-12:55 pm

1 stop11h 10m

Oranjestad Reina Beatrix

Tue 2/3

3:10 pm-10:47 am

2 stops23h 37m

$530

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Fri 2/27

7:05 am-5:33 pm

2 stops30h 28m

Punta Cana

Fri 3/6

1:01 pm-8:44 pm

1 stop11h 43m

$549

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Portland to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Portland, with most prices found around $445. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Portland averaging around $489.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Portland to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $454. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $655. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Portland to Caribbean Islands in the afternoon for as low as $428. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $602. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $578 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Portland for as low as $494 on momondo.

Can stopping save me money on Portland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Portland to Caribbean Islands.

Cheap Portland to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Caribbean Islands

Fastest flight time

9h 13m

Direct flights

None
The fastest flight from Portland to Caribbean Islands takes 9h 13m
There are no direct flights from Portland to Caribbean Islands. There are no popular flight routes from Portland to Caribbean Islands.
Search flight deals

  • When did momondo last update prices for flights from Portland Airport to Caribbean Islands?

    Prices for flights from Portland Airport to Caribbean Islands are updated daily.

  • How many operators does momondo search for flights from Portland Airport to Caribbean Islands?

  • How old do you have to be to fly from Portland Airport to Caribbean Islands?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Portland to Caribbean Islands?

Best airlines flying from Portland to Caribbean Islands

Compare and see reviews for airlines that fly from Portland to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $185Free CancellationRating
7.2
2,899 reviews
Search JetBlue flights
DeltaPriceFrom $190Free CancellationRating
7.9
8,005 reviews
Search Delta flights
Spirit AirlinesPriceFrom $243Free CancellationRating
6.3
8,177 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $347Free CancellationRating
7.2
11,049 reviews
Search American Airlines flights
United AirlinesPriceFrom $399Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
SouthwestPriceFrom $444Free CancellationRating
7.9
4,253 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Caribbean Islands?

It is quick and easy to find Portland to Caribbean Islands flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Caribbean Islands that suits you.

Can I find flights from Portland to Caribbean Islands with flexible booking policies on momondo?

All flight searches from Portland to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Portland to Caribbean Islands?

momondo helps you find the best flight between Portland and Caribbean Islands by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Portland to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Portland to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.

An easier way to manage your Caribbean Islands trip

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