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: Fri Sep 15 2017 Return: Fri Sep 22 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
HAV
48h 29m
2 stops
HAV
PDX
20h 59m
2 stops
Depart: Sun Nov 12 2017 Return: Thu Nov 16 2017 Trip spans 5 days
American Airlines
American Airlines
PDX
HAV
10h 00m
1 stop
HAV
PDX
13h 12m
1 stop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
PDX
SJU
18h 10m
2 stops
SJU
PDX
13h 07m
2 stops
Depart: Sun Aug 27 2017 Return: Sat Sep 9 2017 Trip spans 14 days
United
United
PDX
SJU
23h 15m
1 stop
SJU
PDX
20h 05m
1 stop
Depart: Fri Jul 14 2017 Return: Sat Jul 22 2017 Trip spans 9 days
Delta
Delta
PDX
GND
12h 40m
1 stop
GND
PDX
32h 10m
1 stop
Depart: Sun Sep 17 2017 Return: Thu Sep 28 2017 Trip spans 12 days
Air Canada
Air Canada
PDX
POP
38h 25m
2 stops
POP
PDX
19h 43m
2 stops
Depart: Sat Dec 2 2017 Return: Sat Dec 9 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
HAV
16h 24m
2 stops
HAV
PDX
20h 59m
2 stops
Depart: Sat Oct 7 2017 Return: Mon Oct 9 2017 Trip spans 3 days
American Airlines
American Airlines
PDX
HAV
11h 15m
2 stops
HAV
PDX
18h 15m
2 stops
Depart: Thu Nov 9 2017 Return: Sun Nov 12 2017 Trip spans 4 days
JetBlue
JetBlue
PDX
POP
10h 48m
1 stop
POP
PDX
14h 31m
1 stop
Depart: Mon Nov 13 2017 Return: Wed Nov 15 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
PDX
SJU
15h 25m
2 stops
SJU
PDX
14h 07m
2 stops
Depart: Thu Aug 24 2017 Return: Tue Aug 29 2017 Trip spans 6 days
Delta
Delta
PDX
AUA
22h 40m
2 stops
AUA
PDX
23h 08m
2 stops
Depart: Fri Jun 23 2017 Return: Tue Jun 27 2017 Trip spans 5 days
Major Airline
Major Airline
PDX
SJU
4h 25m
nonstop
SJU
PDX
10h 25m
nonstop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
American Airlines
American Airlines
PDX
SJU
14h 49m
2 stops
SJU
PDX
15h 42m
2 stops
Depart: Fri Jul 21 2017 Return: Thu Jul 27 2017 Trip spans 7 days
United
United
PDX
SJU
15h 25m
1 stop
SJU
PDX
25h 47m
2 stops
Depart: Fri Nov 24 2017 Return: Sat Dec 2 2017 Trip spans 9 days
Major Airline
Major Airline
PDX
AUA
11h 58m
1 stop
AUA
PDX
22h 40m
1 stop
Depart: Fri Dec 29 2017 Return: Sat Jan 13 2018 Trip spans 16 days
Multiple Airlines
Multiple Airlines
PDX
NAS
22h 56m
1 stop
NAS
PDX
13h 49m
1 stop
Depart: Tue Oct 10 2017 Return: Thu Oct 19 2017 Trip spans 10 days
American Airlines
American Airlines
PDX
NAS
15h 25m
2 stops
NAS
PDX
10h 47m
1 stop
Depart: Fri Aug 25 2017 Return: Thu Aug 31 2017 Trip spans 7 days
United
United
PDX
MBJ
19h 15m
1 stop
MBJ
PDX
20h 51m
1 stop
Depart: Thu Sep 14 2017 Return: Tue Sep 19 2017 Trip spans 6 days
Major Airline
Major Airline
PDX
SJU
23h 07m
3 stops
SJU
PDX
17h 35m
3 stops
Depart: Wed Nov 22 2017 Return: Thu Nov 30 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
PDX
GCM
21h 20m
2 stops
GCM
PDX
9h 57m
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,
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Airports
Origin

Portland
$410
Destination

Nassau
$460
San Juan
$434
San Felipe de Puerto Plata
$713
Oranjestad
$435
Montego Bay
$519
George Town
$500
Havana
$410
Grenada
$456