$163 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 10/17. 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.
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1 adult, Economy

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Best Caribbean Flight Deals from Oakland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$468
Montego Bay
Montego Bay3 stops$490
Oranjestad
Oranjestad3 stops$760
Nassau
Nassau2 stops$1,510
Kingston
Kingston2 stops$1,111
Simpson Bay
Simpson Bay3 stops$679
Bridgetown
Bridgetown3 stops$1,070
Punta Cana
Punta Cana2 stops$468
Montego Bay
Montego Bay3 stops$490
Oranjestad
Oranjestad3 stops$760
Nassau
Nassau2 stops$1,510
Kingston
Kingston2 stops$1,111
Simpson Bay
Simpson Bay3 stops$679
Bridgetown
Bridgetown3 stops$1,070

Cheap Flights from Oakland to Caribbean

 
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, Jul 29 - Fri, Aug 1
Spirit Airlines Logo
9:23 am - 11:32 amOAK-SJU
23h 09m2 stops
Spirit Airlines Logo
1:37 am - 11:33 pmSJU-OAK
24h 56m2 stops
$343Spirit Airlines
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Fri, Jul 25 - Tue, Jul 29
Spirit Airlines Logo
6:00 am - 11:32 amOAK-SJU
26h 32m2 stops
Spirit Airlines Logo
1:37 am - 11:33 pmSJU-OAK
24h 56m2 stops
$389Spirit Airlines
Find Deal
Thu, Oct 16 - Sun, Oct 19
Spirit Airlines Logo
7:48 pm - 4:46 pmOAK-SJU
17h 58m2 stops
Spirit Airlines Logo
10:51 am - 11:39 pmSJU-OAK
15h 48m2 stops
$396Spirit Airlines
Find Deal
Sun, Jul 27 - Tue, Jul 29
Spirit Airlines Logo
6:00 am - 12:06 amOAK-SJU
15h 06m2 stops
Spirit Airlines Logo
1:37 am - 11:33 pmSJU-OAK
24h 56m2 stops
$398Spirit Airlines
Find Deal
Sat, Aug 30 - Wed, Sep 3
Southwest Logo
7:55 pm - 10:10 amOAK-SJU
11h 15m2 stops
Southwest Logo
11:50 am - 8:40 pmSJU-OAK
11h 50m2 stops
$429Southwest
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Tue, Jul 15 - Tue, Jul 22
Southwest Logo
5:00 am - 10:25 pmOAK-SJU
14h 25m1 stop
Southwest Logo
7:30 am - 7:20 pmSJU-OAK
14h 50m2 stops
$442Southwest
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Sat, Sep 13 - Sat, Sep 20
Delta Logo
5:05 pm - 11:48 amOAK-SJU
15h 43m2 stops
Delta Logo
12:58 pm - 10:48 pmSJU-OAK
12h 50m2 stops
$492Delta
Find Deal
Tue, Jul 22 - Mon, Jul 28
 Logo
9:23 am - 12:45 pmOAK-MBJ
25h 22m2 stops
 Logo
12:10 pm - 8:28 amMBJ-OAK
22h 18m2 stops
Tue, Jul 22 - Mon, Jul 28
 Logo
9:23 am - 12:45 pmOAK-MBJ
25h 22m3 stops
 Logo
12:10 pm - 8:28 amMBJ-OAK
22h 18m2 stops
Sat, Oct 18 - Tue, Oct 21
Delta Logo
5:05 pm - 11:48 amOAK-MBJ
16h 43m2 stops
Delta Logo
1:13 pm - 11:53 pmMBJ-OAK
12h 40m2 stops
$880Delta
Find Deal
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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 November, when the average cost of round-trip tickets is $873 and $735 respectively.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$163
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly and prices are also 10% lower on average.
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 3 airlines serving 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 4266 reviews
8.0Comfort
7.0Food
8.6Crew
8.2Boarding
7.6Entertainment
Airline reviews

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.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

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.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

737-800 in first class was pretty dumpy. Seat had an uncomfortable angle, storage under the seat was blocked so even my very modest backpack didn't fit, power outlet was flaky. Weird tiny seat pockets that couldn't hold a gallon ziploc bag, emesis bag missing, etc. etc. No in-flight service due to turbulence. Crew was excellent, boarding was smooth despite a full flight.

Delta flight was on time, seats were comfortable, and crew was nice.

Bathrooms dirty sinks clogged. No one seemed to clean them. Plane very old

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.

Good on that leg. When I arrived in Detroit I had to wait over an hour for luggage.

First off, i received an e-mail to allow me to check in for our flight. I folllowed the link, when it came to the seat selection, I was unable to select any "free" seats ( meaning without any additional charge) because everything was " unavailable". My Husband and I were ttavelling with our 3 children hence, i wanted to be assured that we were all seated next to each other. I tried 3 times and everytime I click the selection it said " error loading". What the system wants is for me to buy the seats ( anywhere from $25 to $50 dollars each passenger) like I did on our flight bound to L.A. I called customer service and the guy was unhelpful all he kept repeating was to come really early at the airport and we will be assigned seats there. Imagine my anxiety!!! Spirit says they are a budget airline but they are actually the opposite!! And just before our flight, the flight attendant KEPT announcing/ selling the seats that were not purchased for a cheaper price!! Like it was a bidding/ bargaining game! This was our first and last time to fly Spirit.

The crew was very nice. I would like to see them offer basic refreshments just like a soda and pretzels, etc. for free.

Good experience except for the drunk woman who was with a child. Sad

Too many time late and postponed No electrical power for my electric devices

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

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