$139 Find Cheap Flights from Oakland to Caribbean

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 departing on 9/20. 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

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Cheap Flights from Oakland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$444
Santo Domingo
Santo Domingo2 stops$422
Montego Bay
Montego Bay2 stops$391
Oranjestad
Oranjestad2 stops$591
Nassau
Nassau3 stops$589
Kingston
Kingston3 stops$652
Port of Spain
Port of Spain3 stops$651
Puerto Plata
Puerto Plata2 stops$1,753
Punta Cana
Punta Cana2 stops$444
Santo Domingo
Santo Domingo2 stops$422
Montego Bay
Montego Bay2 stops$391
Oranjestad
Oranjestad2 stops$591
Nassau
Nassau3 stops$589
Kingston
Kingston3 stops$652
Port of Spain
Port of Spain3 stops$651
Puerto Plata
Puerto Plata2 stops$1,753

Book Cheap Oakland to Caribbean 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 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

Tue, Nov 18 - Sat, Nov 22
Southwest Logo
9:50 am - 12:35 amOAK-SJU
10h 45m2 stops
Southwest Logo
6:35 am - 8:45 pmSJU-OAK
18h 10m2 stops
$365Southwest
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Thu, Dec 4 - Mon, Dec 8
Spirit Airlines Logo
5:11 pm - 1:00 pmOAK-SJU
15h 49m2 stops
Spirit Airlines Logo
6:00 am - 4:16 pmSJU-OAK
38h 16m2 stops
$377Spirit Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
Spirit Airlines Logo
6:30 am - 12:54 amOAK-SJU
15h 24m2 stops
Spirit Airlines Logo
10:42 am - 11:32 pmSJU-OAK
15h 50m2 stops
$380Spirit Airlines
Find Deal
Wed, Oct 1 - Fri, Oct 17
Spirit Airlines Logo
2:39 pm - 9:44 amOAK-STT
16h 05m2 stops
Spirit Airlines Logo
11:01 am - 7:49 amSTT-OAK
23h 48m2 stops
$382Spirit Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
Spirit Airlines Logo
2:39 pm - 9:44 amOAK-STT
16h 05m2 stops
Spirit Airlines Logo
10:49 am - 11:32 pmSTT-OAK
15h 43m2 stops
$384Spirit Airlines
Find Deal
Sat, Nov 15 - Fri, Nov 21
Southwest Logo
7:40 am - 12:15 amOAK-SJU
12h 35m2 stops
Southwest Logo
5:40 am - 2:30 pmSJU-OAK
12h 50m2 stops
$389Southwest
Find Deal
Sat, Sep 6 - Sat, Sep 13
Spirit Airlines Logo
2:39 pm - 11:05 amOAK-MBJ
18h 26m2 stops
Spirit Airlines Logo
12:10 pm - 11:32 pmMBJ-OAK
13h 22m2 stops
$391Spirit Airlines
Find Deal
Sat, Sep 27 - Fri, Oct 3
Spirit Airlines Logo
2:39 pm - 9:44 amOAK-STT
16h 05m2 stops
Spirit Airlines Logo
10:49 am - 11:32 pmSTT-OAK
15h 43m2 stops
$396Spirit Airlines
Find Deal
Wed, Nov 26 - Tue, Dec 2
Delta Logo
5:55 am - 1:11 pmOAK-NAS
28h 16m2 stops
Delta Logo
4:50 pm - 12:24 pmNAS-OAK
22h 34m2 stops
$649Delta
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Fri, Nov 28 - Tue, Dec 2
Delta Logo
5:05 pm - 1:11 pmOAK-NAS
17h 06m2 stops
Delta Logo
1:21 pm - 12:24 pmNAS-OAK
26h 03m2 stops
$729Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Oakland to Caribbean flights

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Caribbean, 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 is October, when tickets cost $298 (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 $702 respectively.

Good to know

Low seasonJanuary
Cheapest flight$139
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Oakland to San Juan

FAQs - booking Caribbean flights

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland to Caribbean 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?

    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 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?

    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 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?

    The cheapest time of day to fly to Caribbean 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 is generally at night, which is peak travel time and where the average cost of a ticket is $535.

Reviews of the top airlines flying from Oakland to Caribbean

 
Need help choosing which airline to fly with from Oakland to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4246 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

10.0 ExcellentJoseph, Aug 2025SFO - BWI
Read more Southwest reviews

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

Unbelievable check in horrible. Asked to print tickets at the gate after a delay

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

Had a issue with catching flight due to airline, was unable to board flight

I liked how cheap it was but both my flights were delayed heavily

It was okay delay was long but I made it

I have never flown Spirit it was much better than anticipated!

Staff was very friendly. They attended to people nicely and reprimanded, in a professional way, to those who wouldn’t listen. AC wasn’t working on the flight waiting to depart in Burbank, so it was uncomfortable for a while since the flight was delayed but then better before take off.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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