$213 Find Cheap Flights from Oakland to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to Caribbean Islands departing on 5/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Oakland to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$629
Santo Domingo
Santo Domingo2 stops$1,168
Montego Bay
Montego Bay2 stops$661
Oranjestad
Oranjestad2 stops$736
Nassau
Nassau2 stops$558
Saint Thomas Island
Saint Thomas Island2 stops$676
Kingston
Kingston3 stops$1,093
Simpson Bay
Simpson Bay2 stops$1,005
Bridgetown
Bridgetown2 stops$1,755
Willemstad
Willemstad2 stops$2,405
Punta Cana
Punta Cana2 stops$629
Santo Domingo
Santo Domingo2 stops$1,168
Montego Bay
Montego Bay2 stops$661
Oranjestad
Oranjestad2 stops$736
Nassau
Nassau2 stops$558
Saint Thomas Island
Saint Thomas Island2 stops$676
Kingston
Kingston3 stops$1,093
Simpson Bay
Simpson Bay2 stops$1,005
Bridgetown
Bridgetown2 stops$1,755
Willemstad
Willemstad2 stops$2,405

Book Cheap Oakland to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oakland to Caribbean Islands

Sat, Apr 25 - Thu, May 7
Delta Logo
5:55 am - 11:12 pm
OAK
-
SJU
14h 17m
2 stops
Delta Logo
2:48 pm - 11:57 pm
SJU
-
OAK
12h 09m
2 stops
$426Delta
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
7:45 pm - 10:55 am
OAK
-
SJU
12h 10m
2 stops
Southwest Logo
11:50 am - 9:20 pm
SJU
-
OAK
12h 30m
2 stops
$460Southwest
Sat, Apr 25 - Wed, May 6
Delta Logo
5:55 am - 11:12 pm
OAK
-
SJU
14h 17m
2 stops
Delta Logo
6:15 am - 4:24 pm
SJU
-
OAK
13h 09m
2 stops
$461Delta
Sat, Apr 25 - Tue, May 5
Delta Logo
5:55 pm - 11:45 am
OAK
-
SJU
14h 50m
2 stops
Delta Logo
6:15 am - 11:54 pm
SJU
-
OAK
20h 39m
2 stops
$508Delta
Tue, May 5 - Thu, May 28
Southwest Logo
9:05 pm - 10:35 am
OAK
-
SJU
10h 30m
2 stops
Southwest Logo
2:00 pm - 12:25 am
SJU
-
OAK
13h 25m
2 stops
$530Southwest
Sat, Aug 1 - Wed, Aug 5
Southwest Logo
5:40 am - 8:35 pm
OAK
-
SJU
11h 55m
1 stop
Southwest Logo
6:00 am - 8:00 pm
SJU
-
OAK
17h 00m
2 stops
$541Southwest
Fri, May 8 - Fri, May 15
Southwest Logo
11:55 pm - 1:20 pm
OAK
-
SJU
10h 25m
1 stop
Southwest Logo
2:00 pm - 12:25 am
SJU
-
OAK
13h 25m
2 stops
$550Southwest
Wed, Jul 29 - Tue, Aug 4
Southwest Logo
7:40 pm - 1:15 pm
OAK
-
NAS
14h 35m
2 stops
Southwest Logo
1:10 pm - 9:20 pm
NAS
-
OAK
11h 10m
2 stops
$558Southwest
Fri, Jun 26 - Thu, Jul 2
Southwest Logo
8:15 pm - 1:25 pm
OAK
-
NAS
14h 10m
2 stops
Southwest Logo
2:10 pm - 12:15 am
NAS
-
OAK
13h 05m
2 stops
$583Southwest
Sun, Sep 13 - Mon, Sep 21
Multiple Airlines Logo
8:22 pm - 11:15 pm
OAK
-
PUJ
23h 53m
2 stops
Multiple Airlines Logo
12:50 pm - 9:44 pm
PUJ
-
OAK
35h 54m
2 stops
$794Multiple Airlines
Booking Insights

KAYAK's insights & trends for Oakland to Caribbean Islands flights

Get data-powered insights and trends into flights from Oakland to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Oakland to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $368, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Oakland to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Oakland to Caribbean Islands is October, when tickets cost $382 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $925 and $672 respectively.

Find deals

Good to know

Low seasonOctober
Cheapest flight$213
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Oakland to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Oakland to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oakland to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oakland to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Oakland to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Oakland to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oakland to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Oakland to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Oakland (OAK)