$180 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 10/16. 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

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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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$444
Santo Domingo
Santo Domingo2 stops$422
Montego Bay
Montego Bay2 stops$524
Oranjestad
Oranjestad2 stops$604
Nassau
Nassau2 stops$649
Kingston
Kingston3 stops$652
St. John's
St. John's2 stops$1,707
Punta Cana
Punta Cana2 stops$444
Santo Domingo
Santo Domingo2 stops$422
Montego Bay
Montego Bay2 stops$524
Oranjestad
Oranjestad2 stops$604
Nassau
Nassau2 stops$649
Kingston
Kingston3 stops$652
St. John's
St. John's2 stops$1,707

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, Nov 8 - Mon, Nov 10
Spirit Airlines Logo
12:15 pm - 8:44 pmOAK-SJU
28h 29m2 stops
Spirit Airlines Logo
6:00 am - 4:15 pmSJU-OAK
14h 15m2 stops
$365Spirit Airlines
Find Deal
Thu, Nov 6 - Mon, Nov 10
Spirit Airlines Logo
12:15 pm - 4:23 pmOAK-SJU
24h 08m2 stops
Spirit Airlines Logo
6:00 am - 4:15 pmSJU-OAK
14h 15m2 stops
$371Spirit Airlines
Find Deal
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
Tue, Sep 16 - Tue, Sep 23
Southwest Logo
7:10 pm - 10:50 amOAK-SJU
12h 40m2 stops
Southwest Logo
7:20 am - 5:40 pmSJU-OAK
13h 20m2 stops
$390Southwest
Find Deal
Sun, Oct 26 - Sun, Nov 2
Southwest Logo
4:30 pm - 9:05 amOAK-SJU
13h 35m2 stops
Southwest Logo
5:40 am - 2:30 pmSJU-OAK
12h 50m2 stops
$465Southwest
Find Deal
Tue, Sep 2 - Sat, Sep 6
 Logo
6:00 am - 11:28 pmOAK-SJU
38h 28m3 stops
 Logo
6:44 am - 11:32 pmSJU-OAK
19h 48m2 stops
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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Thu, Oct 2 - Thu, Oct 9
 Logo
6:30 am - 10:30 amOAK-NAS
25h 00m3 stops
 Logo
11:30 am - 7:49 amNAS-OAK
23h 19m3 stops
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
Fri, Dec 12 - Wed, Dec 17
Alaska Airlines Logo
2:31 pm - 2:53 pmOAK-SJU
20h 22m2 stops
Alaska Airlines Logo
8:09 am - 11:59 pmSJU-OAK
19h 50m2 stops
$1,530Alaska 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 $569, 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 January, when the average cost of round-trip tickets is $873 and $702 respectively.

Good to know

Low seasonJanuary
Cheapest flight$180
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 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 airlines flying 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 4246 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
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.

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.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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