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: Sat Jan 13 2018 Return: Sat Jan 20 2018 Trip spans 8 days
Alaska Airlines
Alaska Airlines
PDX
HAV
17h 15m
1 stop
HAV
PDX
10h 52m
1 stop
Depart: Fri Nov 10 2017 Return: Thu Nov 16 2017 Trip spans 7 days
Delta
Delta
PDX
HAV
10h 10m
1 stop
HAV
PDX
12h 10m
1 stop
Depart: Fri Oct 20 2017 Return: Mon Oct 23 2017 Trip spans 4 days
American Airlines
American Airlines
PDX
HAV
14h 55m
2 stops
HAV
PDX
13h 31m
1 stop
Depart: Wed Jan 3 2018 Return: Sat Jan 13 2018 Trip spans 11 days
Multiple Airlines
Multiple Airlines
PDX
HAV
16h 00m
1 stop
HAV
PDX
24h 10m
1 stop
Depart: Tue Dec 5 2017 Return: Mon Dec 11 2017 Trip spans 7 days
JetBlue
JetBlue
PDX
SJU
13h 20m
1 stop
SJU
PDX
12h 38m
1 stop
Depart: Fri Dec 1 2017 Return: Fri Dec 8 2017 Trip spans 8 days
United
United
PDX
PUJ
20h 20m
1 stop
PUJ
PDX
12h 25m
1 stop
Depart: Tue Jan 30 2018 Return: Sun Feb 4 2018 Trip spans 6 days
Alaska Airlines
Alaska Airlines
PDX
HAV
17h 15m
1 stop
HAV
PDX
17h 08m
1 stop
Depart: Fri Oct 27 2017 Return: Wed Nov 1 2017 Trip spans 6 days
American Airlines
American Airlines
PDX
HAV
14h 55m
2 stops
HAV
PDX
16h 31m
2 stops
Depart: Fri Feb 2 2018 Return: Sat Feb 10 2018 Trip spans 9 days
Alaska Airlines
Alaska Airlines
PDX
HAV
17h 15m
1 stop
HAV
PDX
17h 08m
1 stop
Depart: Wed Dec 6 2017 Return: Wed Dec 13 2017 Trip spans 8 days
JetBlue
JetBlue
PDX
SJU
13h 20m
1 stop
SJU
PDX
12h 38m
1 stop
Depart: Fri Oct 20 2017 Return: Wed Nov 8 2017 Trip spans 20 days
Multiple Airlines
Multiple Airlines
PDX
SJU
19h 05m
2 stops
SJU
PDX
13h 07m
1 stop
Depart: Sat Dec 2 2017 Return: Thu Dec 14 2017 Trip spans 13 days
American Airlines
American Airlines
PDX
HAV
15h 20m
2 stops
HAV
PDX
13h 02m
1 stop
Depart: Sun Nov 12 2017 Return: Fri Nov 17 2017 Trip spans 6 days
United
United
PDX
PUJ
26h 10m
2 stops
PUJ
PDX
32h 44m
2 stops
Depart: Fri Jan 19 2018 Return: Wed Jan 31 2018 Trip spans 13 days
Alaska Airlines
Alaska Airlines
PDX
HAV
9h 10m
1 stop
HAV
PDX
10h 52m
1 stop
Depart: Wed Jan 17 2018 Return: Wed Jan 24 2018 Trip spans 8 days
JetBlue
JetBlue
PDX
SJU
11h 44m
1 stop
SJU
PDX
12h 20m
1 stop
Depart: Mon Nov 13 2017 Return: Fri Nov 17 2017 Trip spans 5 days
United
United
PDX
PUJ
22h 55m
2 stops
PUJ
PDX
30h 25m
2 stops
Depart: Wed Feb 7 2018 Return: Tue Feb 13 2018 Trip spans 7 days
Delta
Delta
PDX
PUJ
19h 30m
2 stops
PUJ
PDX
16h 52m
2 stops
Depart: Sun Nov 12 2017 Return: Thu Nov 16 2017 Trip spans 5 days
American Airlines
American Airlines
PDX
PUJ
12h 00m
1 stop
PUJ
PDX
11h 12m
1 stop
Depart: Thu Jan 4 2018 Return: Sat Feb 3 2018 Trip spans 31 days
Alaska Airlines
Alaska Airlines
PDX
HAV
8h 55m
1 stop
HAV
PDX
10h 52m
1 stop
Depart: Tue Dec 5 2017 Return: Thu Jan 11 2018 Trip spans 38 days
United
United
PDX
AUA
28h 59m
1 stop
AUA
PDX
22h 53m
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.

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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
$371
Destination

San Juan
$410
Oranjestad
$435
Punta Cana
$425
Havana
$371