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.
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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: Tue Mar 14 2017 Trip spans 9 days
Delta
Delta
PDX
STT
10h 17m
1 stop
STT
PDX
12h 31m
1 stop
Depart: Tue Feb 21 2017 Return: Tue Mar 7 2017 Trip spans 15 days
Major Airline
Major Airline
PDX
STT
3h 31m
nonstop
STT
PDX
11h 31m
nonstop
Depart: Wed Feb 22 2017 Return: Thu Feb 23 2017 Trip spans 2 days
American Airlines
American Airlines
PDX
BGI
13h 31m
2 stops
BGI
PDX
19h 08m
2 stops
Depart: Mon Mar 20 2017 Return: Tue Apr 4 2017 Trip spans 16 days
JetBlue
JetBlue
PDX
UVF
11h 09m
1 stop
UVF
PDX
13h 04m
1 stop
Depart: Wed Mar 22 2017 Return: Tue Mar 28 2017 Trip spans 7 days
United
United
PDX
AUA
18h 10m
2 stops
AUA
PDX
32h 42m
1 stop
Depart: Tue Feb 7 2017 Return: Tue Feb 14 2017 Trip spans 8 days
Alaska Airlines
Alaska Airlines
PDX
HAV
18h 00m
1 stop
HAV
PDX
19h 35m
1 stop
Depart: Tue Feb 28 2017 Return: Wed Mar 8 2017 Trip spans 9 days
American Airlines
American Airlines
PDX
BGI
20h 06m
2 stops
BGI
PDX
19h 25m
2 stops
Depart: Sun Feb 12 2017 Return: Wed Feb 15 2017 Trip spans 4 days
Delta
Delta
PDX
PUJ
10h 57m
1 stop
PUJ
PDX
12h 29m
1 stop
Depart: Tue Apr 18 2017 Return: Wed Apr 26 2017 Trip spans 9 days
JetBlue
JetBlue
PDX
UVF
11h 09m
1 stop
UVF
PDX
13h 04m
1 stop
Depart: Mon Feb 13 2017 Return: Tue Feb 28 2017 Trip spans 16 days
Major Airline
Major Airline
PDX
SJU
35h 05m
2 stops
SJU
PDX
38h 50m
2 stops
Depart: Mon Mar 20 2017 Return: Thu Mar 23 2017 Trip spans 4 days
United
United
PDX
PUJ
14h 34m
2 stops
PUJ
PDX
22h 31m
1 stop
Depart: Wed Mar 1 2017 Return: Mon Mar 6 2017 Trip spans 6 days
Alaska Airlines
Alaska Airlines
PDX
HAV
18h 00m
1 stop
HAV
PDX
19h 35m
1 stop
Depart: Fri Jun 16 2017 Return: Mon Jun 19 2017 Trip spans 4 days
American Airlines
American Airlines
PDX
BGI
12h 24m
2 stops
BGI
PDX
17h 42m
2 stops
Depart: Fri Feb 10 2017 Return: Wed Feb 15 2017 Trip spans 6 days
Delta
Delta
PDX
UVF
20h 00m
1 stop
UVF
PDX
33h 37m
1 stop
Depart: Mon Mar 6 2017 Return: Sat Mar 18 2017 Trip spans 12 days
Major Airline
Major Airline
PDX
GND
11h 03m
1 stop
GND
PDX
34h 45m
1 stop
Depart: Thu Apr 13 2017 Return: Tue Apr 18 2017 Trip spans 6 days
Alaska Airlines
Alaska Airlines
PDX
HAV
8h 55m
1 stop
HAV
PDX
11h 09m
1 stop
Depart: Sun Feb 12 2017 Return: Wed Feb 15 2017 Trip spans 4 days
American Airlines
American Airlines
PDX
AUA
11h 55m
1 stop
AUA
PDX
33h 06m
1 stop
Depart: Mon Mar 20 2017 Return: Sun Mar 26 2017 Trip spans 7 days
United
United
PDX
PUJ
21h 01m
2 stops
PUJ
PDX
21h 11m
1 stop
Depart: Fri Jun 2 2017 Return: Thu Jun 8 2017 Trip spans 7 days
JetBlue
JetBlue
PDX
SJU
11h 47m
1 stop
SJU
PDX
13h 08m
1 stop
Depart: Wed Mar 1 2017 Return: Wed Mar 15 2017 Trip spans 14 days
Major Airline
Major Airline
PDX
SJU
20h 38m
2 stops
SJU
PDX
16h 29m
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
$404
Destination

Bridgetown
$421
Vieux Fort
$429
San Juan
$434
Saint Thomas Island
$404
Oranjestad
$426
Punta Cana
$428
Havana
$441
Grenada
$438