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: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Major Airline
Major Airline
PDX
HAV
16h 24m
2 stops
HAV
PDX
16h 54m
2 stops
Depart: Mon Aug 28 2017 Return: Fri Sep 1 2017 Trip spans 5 days
Delta
Delta
PDX
HAV
10h 50m
1 stop
HAV
PDX
9h 58m
1 stop
Depart: Tue Sep 26 2017 Return: Mon Oct 2 2017 Trip spans 7 days
American Airlines
American Airlines
PDX
SJU
14h 49m
2 stops
SJU
PDX
10h 47m
1 stop
Depart: Fri Jun 2 2017 Return: Thu Jun 8 2017 Trip spans 7 days
United
United
PDX
SJU
12h 40m
2 stops
SJU
PDX
11h 45m
1 stop
Depart: Thu Jul 13 2017 Return: Mon Jul 31 2017 Trip spans 19 days
Alaska Airlines
Alaska Airlines
PDX
HAV
18h 00m
1 stop
HAV
PDX
11h 05m
1 stop
Depart: Fri May 19 2017 Return: Mon May 22 2017 Trip spans 4 days
Aeromexico
Aeromexico
PDX
SDQ
20h 56m
2 stops
SDQ
PDX
25h 44m
2 stops
Depart: Fri Oct 13 2017 Return: Fri Oct 20 2017 Trip spans 8 days
JetBlue
JetBlue
PDX
PUJ
32h 19m
2 stops
PUJ
PDX
13h 20m
1 stop
Depart: Mon Oct 2 2017 Return: Fri Oct 6 2017 Trip spans 5 days
Major Airline
Major Airline
PDX
HAV
12h 45m
2 stops
HAV
PDX
18h 44m
2 stops
Depart: Wed Aug 16 2017 Return: Thu Aug 24 2017 Trip spans 9 days
Delta
Delta
PDX
HAV
21h 09m
2 stops
HAV
PDX
21h 34m
2 stops
Depart: Fri Jun 16 2017 Return: Sun Jun 25 2017 Trip spans 10 days
Air Canada
Air Canada
PDX
PUJ
19h 15m
2 stops
PUJ
PDX
28h 50m
2 stops
Depart: Wed Sep 27 2017 Return: Wed Oct 11 2017 Trip spans 15 days
American Airlines
American Airlines
PDX
GCM
12h 11m
2 stops
GCM
PDX
17h 27m
2 stops
Depart: Sun Aug 27 2017 Return: Wed Sep 6 2017 Trip spans 11 days
Major Airline
Major Airline
PDX
AUA
22h 33m
2 stops
AUA
PDX
34h 23m
2 stops
Depart: Fri Jul 21 2017 Return: Mon Jul 31 2017 Trip spans 11 days
United
United
PDX
SJU
11h 20m
1 stop
SJU
PDX
13h 27m
2 stops
Depart: Wed Oct 4 2017 Return: Tue Oct 10 2017 Trip spans 7 days
American Airlines
American Airlines
PDX
GCM
11h 51m
2 stops
GCM
PDX
17h 27m
2 stops
Depart: Tue Oct 17 2017 Return: Wed Oct 25 2017 Trip spans 9 days
Delta
Delta
PDX
AUA
21h 59m
2 stops
AUA
PDX
21h 44m
2 stops
Depart: Tue Sep 12 2017 Return: Thu Sep 21 2017 Trip spans 10 days
Major Airline
Major Airline
PDX
AUA
22h 23m
2 stops
AUA
PDX
33h 16m
2 stops
Depart: Fri May 5 2017 Return: Wed May 10 2017 Trip spans 6 days
American Airlines
American Airlines
PDX
SJU
10h 21m
1 stop
SJU
PDX
14h 29m
2 stops
Depart: Sat Sep 16 2017 Return: Thu Sep 21 2017 Trip spans 6 days
United
United
PDX
PUJ
12h 05m
1 stop
PUJ
PDX
22h 41m
1 stop
Depart: Fri Oct 20 2017 Return: Sat Oct 28 2017 Trip spans 9 days
Major Airline
Major Airline
PDX
SJU
27h 53m
1 stop
SJU
PDX
10h 16m
1 stop
Depart: Sat Sep 16 2017 Return: Sat Sep 23 2017 Trip spans 8 days
Delta
Delta
PDX
PLS
24h 42m
2 stops
PLS
PDX
25h 30m
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.

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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
$389
Destination

Santo Domingo
$604
Providenciales
$480
San Juan
$434
Oranjestad
$429
George Town
$446
Punta Cana
$506
Havana
$389