$208 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 2/16. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$829
Santo Domingo
Santo Domingo2 stops$777
Montego Bay
Montego Bay2 stops$570
Oranjestad
Oranjestad2 stops$896
Nassau
Nassau2 stops$592
Saint Thomas Island
Saint Thomas Island2 stops$1,062
Kingston
Kingston2 stops$928
Simpson Bay
Simpson Bay2 stops$856
Bridgetown
Bridgetown2 stops$1,382
Willemstad
Willemstad2 stops$1,511
St. John's
St. John's2 stops$1,343
Punta Cana
Punta Cana2 stops$829
Santo Domingo
Santo Domingo2 stops$777
Montego Bay
Montego Bay2 stops$570
Oranjestad
Oranjestad2 stops$896
Nassau
Nassau2 stops$592
Saint Thomas Island
Saint Thomas Island2 stops$1,062
Kingston
Kingston2 stops$928
Simpson Bay
Simpson Bay2 stops$856
Bridgetown
Bridgetown2 stops$1,382
Willemstad
Willemstad2 stops$1,511
St. John's
St. John's2 stops$1,343

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

Sun, Dec 7 - Wed, Dec 17
Southwest Logo
7:45 pm - 10:25 amOAK-SJU
10h 40m2 stops
Southwest Logo
5:45 am - 2:05 pmSJU-OAK
12h 20m2 stops
$444Southwest
Find Deal
Wed, Dec 3 - Sat, Dec 13
Southwest Logo
9:00 am - 12:35 amOAK-SJU
11h 35m2 stops
Southwest Logo
5:40 am - 2:25 pmSJU-OAK
12h 45m2 stops
$489Southwest
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
7:10 pm - 11:35 amOAK-SJU
12h 25m2 stops
Southwest Logo
5:45 am - 2:05 pmSJU-OAK
12h 20m2 stops
$509Southwest
Find Deal
Mon, Dec 15 - Fri, Dec 19
Southwest Logo
7:10 pm - 10:25 amOAK-SJU
11h 15m2 stops
Southwest Logo
7:30 am - 5:35 pmSJU-OAK
14h 05m2 stops
$521Southwest
Find Deal
Fri, Feb 27 - Sat, Mar 7
Southwest Logo
7:50 pm - 10:00 amOAK-SJU
10h 10m2 stops
Southwest Logo
7:00 am - 4:40 pmSJU-OAK
13h 40m2 stops
$531Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
7:10 pm - 10:25 amOAK-SJU
11h 15m2 stops
Southwest Logo
5:45 am - 2:05 pmSJU-OAK
12h 20m2 stops
$541Southwest
Find Deal
Wed, Dec 17 - Wed, Dec 24
Delta Logo
5:55 am - 11:09 amOAK-MBJ
26h 14m2 stops
Delta Logo
2:23 pm - 11:54 amMBJ-OAK
24h 31m2 stops
$570Delta
Find Deal
Sun, Jan 11 - Thu, Jan 15
Delta Logo
12:38 pm - 1:31 pmOAK-NAS
21h 53m2 stops
Delta Logo
1:15 pm - 10:53 pmNAS-OAK
12h 38m2 stops
$592Delta
Find Deal
Tue, Dec 16 - Thu, Dec 25
Delta Logo
4:50 pm - 1:30 pmOAK-NAS
17h 40m2 stops
Delta Logo
1:31 pm - 10:47 pmNAS-OAK
12h 16m2 stops
$619Delta
Find Deal
Sat, Feb 14 - Sat, Feb 21
Multiple Airlines Logo
9:17 pm - 11:20 pmOAK-SDQ
22h 03m2 stops
Multiple Airlines Logo
4:37 pm - 6:56 pmSDQ-OAK
30h 19m3 stops
$777Multiple Airlines
Find Deal
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 $370, 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 January, when the average cost of round-trip tickets is $873 and $695 respectively.

Good to know

Low seasonOctober
Cheapest flight$208
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 4% increase in price.
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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $410 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $535.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports