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
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 Apr 25 2017 Return: Wed May 3 2017 Trip spans 9 days
Major Airline
Major Airline
PDX
HAV
12h 45m
2 stops
HAV
PDX
22h 54m
2 stops
Depart: Mon Sep 11 2017 Return: Mon Sep 25 2017 Trip spans 15 days
Delta
Delta
PDX
HAV
10h 50m
1 stop
HAV
PDX
12h 16m
1 stop
Depart: Sat Aug 19 2017 Return: Wed Aug 30 2017 Trip spans 12 days
American Airlines
American Airlines
PDX
SJU
13h 25m
2 stops
SJU
PDX
14h 48m
2 stops
Depart: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
United
United
PDX
SJU
14h 50m
2 stops
SJU
PDX
11h 14m
1 stop
Depart: Mon Apr 17 2017 Return: Tue Apr 25 2017 Trip spans 9 days
Air Canada
Air Canada
PDX
BGI
15h 50m
2 stops
BGI
PDX
26h 30m
2 stops
Depart: Fri Jul 28 2017 Return: Sat Aug 5 2017 Trip spans 9 days
JetBlue
JetBlue
PDX
STT
9h 56m
1 stop
STT
PDX
25h 13m
2 stops
Depart: Thu May 4 2017 Return: Fri May 12 2017 Trip spans 9 days
Major Airline
Major Airline
PDX
HAV
12h 49m
2 stops
HAV
PDX
14h 42m
3 stops
Depart: Tue Apr 25 2017 Return: Wed May 3 2017 Trip spans 9 days
Delta
Delta
PDX
SJU
12h 43m
1 stop
SJU
PDX
13h 10m
1 stop
Depart: Sat Sep 16 2017 Return: Tue Sep 19 2017 Trip spans 4 days
American Airlines
American Airlines
PDX
SJU
12h 08m
1 stop
SJU
PDX
12h 06m
1 stop
Depart: Mon May 1 2017 Return: Sat May 13 2017 Trip spans 13 days
United
United
PDX
SJU
15h 02m
2 stops
SJU
PDX
15h 43m
2 stops
Depart: Tue May 2 2017 Return: Thu May 11 2017 Trip spans 10 days
Major Airline
Major Airline
PDX
HAV
8h 55m
1 stop
HAV
PDX
17h 29m
1 stop
Depart: Mon Jul 31 2017 Return: Wed Aug 9 2017 Trip spans 10 days
American Airlines
American Airlines
PDX
PLS
23h 57m
1 stop
PLS
PDX
21h 36m
1 stop
Depart: Tue Apr 18 2017 Return: Thu Apr 20 2017 Trip spans 3 days
United
United
PDX
NAS
28h 15m
2 stops
NAS
PDX
9h 34m
1 stop
Depart: Wed Aug 16 2017 Return: Wed Aug 23 2017 Trip spans 8 days
Delta
Delta
PDX
UVF
23h 00m
2 stops
UVF
PDX
20h 53m
2 stops
Depart: Fri Jun 9 2017 Return: Sat Jun 17 2017 Trip spans 9 days
Major Airline
Major Airline
PDX
HAV
10h 18m
1 stop
HAV
PDX
17h 24m
1 stop
Depart: Wed Aug 2 2017 Return: Wed Aug 9 2017 Trip spans 8 days
American Airlines
American Airlines
PDX
PLS
23h 57m
1 stop
PLS
PDX
21h 36m
1 stop
Depart: Fri Apr 21 2017 Return: Fri Apr 28 2017 Trip spans 8 days
United
United
PDX
PUJ
23h 55m
2 stops
PUJ
PDX
25h 14m
2 stops
Depart: Thu Sep 7 2017 Return: Mon Sep 11 2017 Trip spans 5 days
Delta
Delta
PDX
UVF
22h 21m
2 stops
UVF
PDX
27h 00m
2 stops
Depart: Thu Aug 24 2017 Return: Mon Aug 28 2017 Trip spans 5 days
Major Airline
Major Airline
PDX
HAV
10h 06m
1 stop
HAV
PDX
19h 39m
1 stop
Depart: Wed May 3 2017 Return: Thu May 11 2017 Trip spans 9 days
American Airlines
American Airlines
PDX
GCM
15h 16m
2 stops
GCM
PDX
13h 24m
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
$411
Destination

Bridgetown
$728
Nassau
$486
Vieux Fort
$496
Providenciales
$466
San Juan
$421
Saint Thomas Island
$734
George Town
$478
Punta Cana
$494
Havana
$411