Find Cheap 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
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: Wed Sep 6 2017 Return: Mon Oct 2 2017 Trip spans 27 days
American Airlines
American Airlines
PDX
HAV
9h 40m
1 stop
HAV
PDX
13h 51m
1 stop
Depart: Thu Nov 2 2017 Return: Tue Nov 7 2017 Trip spans 6 days
Delta
Delta
PDX
HAV
23h 14m
2 stops
HAV
PDX
21h 34m
2 stops
Depart: Mon Jan 22 2018 Return: Tue Jan 23 2018 Trip spans 2 days
United
United
PDX
SJU
20h 05m
1 stop
SJU
PDX
14h 29m
2 stops
Depart: Wed Feb 7 2018 Return: Wed Feb 14 2018 Trip spans 8 days
Major Airline
Major Airline
PDX
AUA
23h 18m
2 stops
AUA
PDX
17h 27m
2 stops
Depart: Fri Oct 27 2017 Return: Sun Nov 5 2017 Trip spans 10 days
JetBlue
JetBlue
PDX
PLS
14h 21m
1 stop
PLS
PDX
11h 37m
1 stop
Depart: Thu Feb 15 2018 Return: Sat Feb 24 2018 Trip spans 10 days
Aeromexico
Aeromexico
PDX
SDQ
28h 06m
1 stop
SDQ
PDX
33h 19m
2 stops
Depart: Thu Jan 11 2018 Return: Mon Jan 15 2018 Trip spans 5 days
Air Canada
Air Canada
PDX
PUJ
42h 10m
2 stops
PUJ
PDX
25h 00m
2 stops
Depart: Sun Oct 1 2017 Return: Sat Oct 7 2017 Trip spans 7 days
American Airlines
American Airlines
PDX
HAV
9h 40m
1 stop
HAV
PDX
13h 31m
1 stop
Depart: Tue Sep 26 2017 Return: Wed Oct 4 2017 Trip spans 9 days
United
United
PDX
SJU
14h 20m
2 stops
SJU
PDX
13h 15m
2 stops
Depart: Tue Oct 17 2017 Return: Wed Oct 25 2017 Trip spans 9 days
Delta
Delta
PDX
SJU
12h 00m
1 stop
SJU
PDX
11h 55m
1 stop
Depart: Sun Dec 3 2017 Return: Thu Dec 7 2017 Trip spans 5 days
American Airlines
American Airlines
PDX
HAV
10h 25m
1 stop
HAV
PDX
13h 02m
1 stop
Depart: Mon Oct 9 2017 Return: Tue Oct 17 2017 Trip spans 9 days
United
United
PDX
SJU
14h 40m
2 stops
SJU
PDX
12h 18m
1 stop
Depart: Sat Sep 9 2017 Return: Sat Sep 16 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
PLS
22h 39m
2 stops
PLS
PDX
10h 17m
1 stop
Depart: Tue Sep 26 2017 Return: Thu Oct 5 2017 Trip spans 10 days
Delta
Delta
PDX
PUJ
20h 15m
2 stops
PUJ
PDX
21h 29m
2 stops
Depart: Fri Jan 19 2018 Return: Wed Jan 31 2018 Trip spans 13 days
American Airlines
American Airlines
PDX
HAV
10h 45m
1 stop
HAV
PDX
12h 27m
1 stop
Depart: Mon Nov 13 2017 Return: Mon Nov 20 2017 Trip spans 8 days
United
United
PDX
SJU
14h 05m
2 stops
SJU
PDX
23h 29m
2 stops
Depart: Tue Feb 6 2018 Return: Tue Feb 13 2018 Trip spans 8 days
American Airlines
American Airlines
PDX
HAV
10h 45m
1 stop
HAV
PDX
12h 27m
1 stop
Depart: Wed Nov 8 2017 Return: Tue Nov 14 2017 Trip spans 7 days
Delta
Delta
PDX
NAS
18h 28m
2 stops
NAS
PDX
18h 26m
2 stops
Depart: Sun Dec 31 2017 Return: Mon Jan 15 2018 Trip spans 16 days
United
United
PDX
SJU
18h 05m
1 stop
SJU
PDX
12h 14m
1 stop
Depart: Wed Sep 27 2017 Return: Mon Oct 2 2017 Trip spans 6 days
American Airlines
American Airlines
PDX
HAV
16h 55m
2 stops
HAV
PDX
13h 51m
1 stop
* 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
$417
Destination

Santo Domingo
$679
Nassau
$472
Providenciales
$483
San Juan
$432
Oranjestad
$436
Punta Cana
$443
Havana
$417