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Cheap flights from Oregon to Caribbean Islands from $153

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Caribbean Islands departing on 5/2. 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 Oregon to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:55 pm - 10:35 am
BOI
-
SJU
13h 40m
2 stops
Southwest Logo
10:00 am - 9:55 pm
SJU
-
BOI
13h 55m
2 stops
$416Southwest
Mon, May 4 - Sat, May 9
United Airlines Logo
10:38 pm - 2:40 pm
PDX
-
SJU
12h 02m
1 stop
United Airlines Logo
7:40 am - 6:55 pm
SJU
-
PDX
15h 15m
2 stops
$440United Airlines
Sat, Feb 28 - Wed, Mar 4
American Airlines Logo
11:47 pm - 3:35 pm
PDX
-
SJU
12h 48m
2 stops
American Airlines Logo
1:31 pm - 11:53 pm
SJU
-
PDX
13h 22m
1 stop
$449American Airlines
Tue, Apr 21 - Mon, May 4
American Airlines Logo
11:47 pm - 3:35 pm
PDX
-
SJU
12h 48m
2 stops
American Airlines Logo
11:59 pm - 12:58 pm
SJU
-
PDX
15h 59m
1 stop
$451American Airlines
Tue, Apr 21 - Mon, May 4
Delta Logo
9:45 pm - 12:53 pm
PDX
-
MBJ
12h 08m
1 stop
Delta Logo
11:15 am - 7:00 pm
MBJ
-
PDX
9h 45m
1 stop
$472Delta
Tue, Mar 3 - Wed, Mar 11
Delta Logo
3:59 pm - 12:32 pm
PDX
-
MBJ
17h 33m
2 stops
Delta Logo
11:15 am - 7:00 pm
MBJ
-
PDX
9h 45m
1 stop
$477Delta
Tue, Mar 3 - Wed, Mar 11
Multiple Airlines Logo
7:00 am - 12:30 pm
PDX
-
PUJ
25h 30m
1 stop
Multiple Airlines Logo
3:32 pm - 11:44 pm
PUJ
-
PDX
35h 12m
2 stops
$521Multiple Airlines
Sun, Mar 1 - Tue, Mar 10
Multiple Airlines Logo
7:00 am - 12:30 pm
PDX
-
PUJ
25h 30m
1 stop
Multiple Airlines Logo
5:39 pm - 4:50 pm
PUJ
-
PDX
26h 11m
1 stop
$523Multiple Airlines
Sun, Mar 1 - Tue, Mar 10
Air Canada Logo
7:05 pm - 3:00 pm
PDX
-
AUA
15h 55m
2 stops
Air Canada Logo
3:05 pm - 9:15 am
AUA
-
PDX
21h 10m
2 stops
$543Air Canada
Wed, Mar 4 - Wed, Mar 11
Air Canada Logo
9:50 am - 3:10 pm
PDX
-
AUA
26h 20m
2 stops
Air Canada Logo
4:05 pm - 2:40 pm
AUA
-
PDX
25h 35m
2 stops
$557Air Canada
Wed, Apr 15 - Tue, Apr 21

American Airlines flights from Oregon to Caribbean Islands

Our best American Airlines deals on Oregon to Caribbean Islands flight tickets
American Airlines
Apr 21
PDX11:47 pmPortland
12h 48m
2 stops
SJU3:35 pmSan Juan Luis Munoz Marin Intl
May 4
SJU1:31 pmSan Juan Luis Munoz Marin Intl
13h 22m
1 stop
PDX11:53 pmPortland
$449
American Airlines
Apr 21
PDX11:47 pmPortland
12h 48m
2 stops
SJU3:35 pmSan Juan Luis Munoz Marin Intl
May 4
SJU11:59 pmSan Juan Luis Munoz Marin Intl
15h 59m
1 stop
PDX12:58 pmPortland
$451
American Airlines
Mar 3
BOI7:00 amBoise Air Term. Gowen Fld
11h 34m
2 stops
SJU9:34 pmSan Juan Luis Munoz Marin Intl
Mar 10
SJU7:11 amSan Juan Luis Munoz Marin Intl
17h 12m
2 stops
BOI10:23 pmBoise Air Term. Gowen Fld
$452

Southwest flights from Oregon to Caribbean Islands

Our best Southwest deals on Oregon to Caribbean Islands flight tickets
Southwest
May 4
BOI6:55 pmBoise Air Term. Gowen Fld
13h 40m
2 stops
SJU10:35 amSan Juan Luis Munoz Marin Intl
May 9
SJU10:00 amSan Juan Luis Munoz Marin Intl
13h 55m
2 stops
BOI9:55 pmBoise Air Term. Gowen Fld
$416
Southwest
Apr 1
BOI5:40 amBoise Air Term. Gowen Fld
11h 50m
2 stops
SJU7:30 pmSan Juan Luis Munoz Marin Intl
Apr 8
SJU8:10 amSan Juan Luis Munoz Marin Intl
16h 00m
2 stops
BOI10:10 pmBoise Air Term. Gowen Fld
$481
Southwest
Apr 1
PDX11:55 pmPortland
15h 35m
2 stops
NAS6:30 pmNassau Intl
Apr 22
NAS2:10 pmNassau Intl
12h 00m
2 stops
PDX11:10 pmPortland
$485

momondo Fare Finder

 
Customize your flight search to find flights from Oregon 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 February 7, 2026.
Use the filters below to find and compare flights from Oregon to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 5/4

6:55 pm-10:35 am

2 stops13h 40m

San Juan Luis Munoz Marin Intl

Sat 5/9

10:00 am-9:55 pm

2 stops13h 55m

$416

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 2/28

10:38 pm-2:40 pm

1 stop12h 02m

San Juan Luis Munoz Marin Intl

Wed 3/4

7:40 am-6:55 pm

2 stops15h 15m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/21

11:47 pm-3:35 pm

2 stops12h 48m

San Juan Luis Munoz Marin Intl

Mon 5/4

1:31 pm-11:53 pm

1 stop13h 22m

$449

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/21

11:47 pm-3:35 pm

2 stops12h 48m

San Juan Luis Munoz Marin Intl

Mon 5/4

11:59 pm-12:58 pm

1 stop15h 59m

$451

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Tue 3/3

9:45 pm-12:53 pm

1 stop12h 08m

Montego Bay Sangster Intl

Wed 3/11

11:15 am-7:00 pm

1 stop9h 45m

$472

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Tue 3/3

3:59 pm-12:32 pm

2 stops17h 33m

Montego Bay Sangster Intl

Wed 3/11

11:15 am-7:00 pm

1 stop9h 45m

$477

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sun 3/1

7:00 am-12:30 pm

1 stop25h 30m

Punta Cana

Tue 3/10

3:32 pm-11:44 pm

2 stops35h 12m

$521

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sun 3/1

7:00 am-12:30 pm

1 stop25h 30m

Punta Cana

Tue 3/10

5:39 pm-4:50 pm

1 stop26h 11m

$523

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Wed 3/4

7:05 pm-3:00 pm

2 stops15h 55m

Oranjestad Reina Beatrix

Wed 3/11

3:05 pm-9:15 am

2 stops21h 10m

$543

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Wed 4/15

9:50 am-3:10 pm

2 stops26h 20m

Oranjestad Reina Beatrix

Tue 4/21

4:05 pm-2:40 pm

2 stops25h 35m

$557

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 Oregon 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 Oregon, with most prices found around $468. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Oregon averaging around $498.

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

You are more likely to see cheaper flights to Caribbean Islands from Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $580 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Oregon for as low as $504 on momondo.

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

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

Cheap Oregon to Caribbean Islands flight deals and tips

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

Fastest flight time

7h 40m

Direct flights

None
The fastest flight from Oregon to Caribbean Islands takes 7h 40m
There are no direct flights from Oregon to Caribbean Islands. There are no popular flight routes from Oregon to Caribbean Islands.
Search flight deals

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

    Prices for flights from Oregon to Caribbean Islands were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oregon to Caribbean Islands.

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

    The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Oregon to Caribbean Islands

Compare and see reviews for airlines that fly from Oregon to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $184Free CancellationRating
7.9
8,172 reviews
Search Delta flights
JetBluePriceFrom $185Free CancellationRating
7.2
2,896 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $241Free CancellationRating
6.3
8,430 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $327Free CancellationRating
7.4
9,254 reviews
Search United Airlines flights
American AirlinesPriceFrom $364Free CancellationRating
7.2
11,249 reviews
Search American Airlines flights
SouthwestPriceFrom $438Free CancellationRating
8.0
4,280 reviews
Search Southwest flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean Islands from Oregon.

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

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

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Oregon to Caribbean Islands.

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

Price alerts on flights to Caribbean Islands from Oregon are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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