$135 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 7/21. 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

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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Flights Deals

Best Caribbean Islands Flight Deals from Oakland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$438
Santo Domingo
Santo Domingo2 stops$494
Montego Bay
Montego Bay2 stops$464
Oranjestad
Oranjestad2 stops$874
Nassau
Nassau2 stops$608
Kingston
Kingston2 stops$657
Bridgetown
Bridgetown2 stops$1,373
Punta Cana
Punta Cana2 stops$438
Santo Domingo
Santo Domingo2 stops$494
Montego Bay
Montego Bay2 stops$464
Oranjestad
Oranjestad2 stops$874
Nassau
Nassau2 stops$608
Kingston
Kingston2 stops$657
Bridgetown
Bridgetown2 stops$1,373

Cheap Flights from Oakland to Caribbean Islands

 
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, Jul 26 - 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
$326Spirit Airlines
Find Deal
Wed, Jul 16 - Tue, Jul 22
Spirit Airlines Logo
6:00 am - 11:32 amOAK-SJU
26h 32m2 stops
Spirit Airlines Logo
4:43 pm - 11:33 pmSJU-OAK
33h 50m2 stops
$327Spirit Airlines
Find Deal
Wed, Jul 16 - Tue, Jul 22
Southwest Logo
5:00 am - 10:25 pmOAK-SJU
14h 25m1 stop
Southwest Logo
1:25 pm - 11:15 pmSJU-OAK
12h 50m2 stops
$442Southwest
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Sun, Aug 3 - Thu, Aug 7
 Logo
5:39 pm - 2:45 pmOAK-SJU
42h 06m3 stops
 Logo
1:37 am - 11:33 pmSJU-OAK
24h 56m3 stops
Sun, Aug 3 - Fri, Aug 8
 Logo
5:39 pm - 2:45 pmOAK-SJU
42h 06m3 stops
 Logo
10:14 pm - 11:33 pmSJU-OAK
28h 19m3 stops
Tue, Jul 15 - Sun, Aug 17
Southwest Logo
5:00 am - 10:25 pmOAK-SJU
14h 25m1 stop
Southwest Logo
5:05 am - 2:30 pmSJU-OAK
12h 25m2 stops
$479Southwest
Find Deal
Tue, Nov 4 - Mon, Nov 10
Delta Logo
5:55 am - 11:21 pmOAK-SJU
13h 26m2 stops
Delta Logo
3:25 pm - 11:53 pmSJU-OAK
12h 28m2 stops
$715Delta
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Mon, Jul 21 - Wed, Jul 30
Delta Logo
4:55 pm - 12:35 pmOAK-PLS
16h 40m2 stops
Delta Logo
2:00 pm - 11:45 amPLS-OAK
24h 45m2 stops
$818Delta
Find Deal
Sat, Aug 16 - Sat, Aug 23
Alaska Airlines Logo
7:13 pm - 2:05 pmOAK-SJU
39h 52m2 stops
Alaska Airlines Logo
2:55 pm - 8:59 amSJU-OAK
45h 04m2 stops
$1,247Alaska Airlines
Find Deal
Tue, Aug 12 - Mon, Aug 18
Alaska Airlines Logo
8:00 am - 2:05 pmOAK-SJU
27h 05m2 stops
Alaska Airlines Logo
2:55 pm - 7:18 pmSJU-OAK
31h 23m2 stops
$1,265Alaska Airlines
Find Deal
Useful Info

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 $561, 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 $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$135
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 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.

Reviews of the top 3 airlines serving from Oakland to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Oakland to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Oakland to Caribbean Islands? 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 4278 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

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

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

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.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

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

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

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

It was fast but uncomfortable seats. Had to pay a bit extra not sure why? Maybe in selection of all my 4 tix together ? Just knew I had a balance before getting boarding pass online when departing from satx ? And flight was delayed..

Last minute 2-3 hr delay in flight schedule; no explanation Unexpected extra $52 charge What's the benefit of choosing a cheap airline if you trick people last minute and force them to pay extra last minute? Did not appreciate being cornered.

Seats are uncomfortable and too close together. Also, you missed my connection in Vegas on the way back and I ended up sleeping in the airport, flying back to Burbank instead of LAX and I got home 12 hours late.

Surprising everything went well. Nice attendants and fast getting on and off the plane. Overall, was happy with the experience.

Non-professional acting crew, Very uncomfortable seats…!! Very bad pricing with all the add-ons for seat choice, luggage fees, etc….soon you’ll charge extra for oxygen. The ticket price means Nothing because in the end, the actual amount i paid, i could have and will in the future continue to fly on a real airline…

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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