Find Deals on Flights from Portland to Caribbean

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Portland to Caribbean

(Round-trip)
Depart: Sun Mar 5 2017 Return: Wed Mar 15 2017 Trip spans 10 days
American Airlines
American Airlines
PDX
STT
14h 14m
2 stops
STT
PDX
14h 30m
2 stops
Depart: Mon Jan 23 2017 Return: Tue Feb 7 2017 Trip spans 16 days
Delta
Delta
PDX
STT
10h 19m
1 stop
STT
PDX
12h 32m
1 stop
Depart: Mon Jan 23 2017 Return: Sun Jan 29 2017 Trip spans 7 days
Major Airline
Major Airline
PDX
STT
32h 48m
2 stops
STT
PDX
19h 18m
2 stops
Depart: Mon Jan 23 2017 Return: Thu Feb 2 2017 Trip spans 11 days
JetBlue
JetBlue
PDX
HAV
11h 59m
1 stop
HAV
PDX
12h 39m
1 stop
Depart: Fri Jan 20 2017 Return: Sat Jan 28 2017 Trip spans 9 days
United
United
PDX
PUJ
18h 35m
2 stops
PUJ
PDX
31h 50m
2 stops
Depart: Wed Feb 1 2017 Return: Mon Feb 6 2017 Trip spans 6 days
Alaska Airlines
Alaska Airlines
PDX
HAV
18h 00m
1 stop
HAV
PDX
17h 31m
1 stop
Depart: Tue Feb 7 2017 Return: Tue Feb 14 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
STT
11h 49m
2 stops
STT
PDX
14h 18m
2 stops
Depart: Wed Jan 11 2017 Return: Tue Jan 17 2017 Trip spans 7 days
Delta
Delta
PDX
AUA
21h 55m
2 stops
AUA
PDX
23h 52m
1 stop
Depart: Sun Jan 29 2017 Return: Tue Feb 7 2017 Trip spans 10 days
Major Airline
Major Airline
PDX
PUJ
21h 45m
2 stops
PUJ
PDX
31h 20m
2 stops
Depart: Sun Jan 8 2017 Return: Tue Feb 7 2017 Trip spans 31 days
Delta
Delta
PDX
UVF
22h 35m
2 stops
UVF
PDX
30h 48m
2 stops
Depart: Thu Feb 9 2017 Return: Thu Feb 16 2017 Trip spans 8 days
American Airlines
American Airlines
PDX
SJU
11h 35m
2 stops
SJU
PDX
11h 11m
1 stop
Depart: Tue Feb 14 2017 Return: Fri Feb 17 2017 Trip spans 4 days
Alaska Airlines
Alaska Airlines
PDX
HAV
18h 00m
1 stop
HAV
PDX
18h 31m
1 stop
Depart: Sat May 13 2017 Return: Sat May 20 2017 Trip spans 8 days
JetBlue
JetBlue
PDX
POP
11h 34m
1 stop
POP
PDX
13h 25m
1 stop
Depart: Thu Feb 2 2017 Return: Fri Feb 10 2017 Trip spans 9 days
Delta
Delta
PDX
SJU
17h 33m
2 stops
SJU
PDX
19h 07m
2 stops
Depart: Fri May 5 2017 Return: Sat May 13 2017 Trip spans 9 days
United
United
PDX
PUJ
15h 20m
2 stops
PUJ
PDX
11h 20m
1 stop
Depart: Wed Feb 22 2017 Return: Tue Feb 28 2017 Trip spans 7 days
American Airlines
American Airlines
PDX
GND
22h 06m
3 stops
GND
PDX
18h 17m
2 stops
Depart: Fri Feb 3 2017 Return: Thu Feb 9 2017 Trip spans 7 days
Major Airline
Major Airline
PDX
PUJ
9h 41m
1 stop
PUJ
PDX
32h 56m
1 stop
Depart: Wed Mar 1 2017 Return: Tue Mar 7 2017 Trip spans 7 days
Alaska Airlines
Alaska Airlines
PDX
HAV
18h 00m
1 stop
HAV
PDX
19h 30m
1 stop
Depart: Mon Jan 23 2017 Return: Mon Feb 6 2017 Trip spans 15 days
Delta
Delta
PDX
SJU
17h 33m
2 stops
SJU
PDX
21h 27m
2 stops
Depart: Tue Jan 3 2017 Return: Wed Jan 11 2017 Trip spans 9 days
United
United
PDX
POP
18h 53m
2 stops
POP
PDX
25h 06m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Portland
$330
Destination

Vieux Fort
$381
San Juan
$386
Saint Thomas Island
$330
San Felipe de Puerto Plata
$466
Oranjestad
$363
Punta Cana
$370
Havana
$415
Grenada
$442