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$132+ Cheap flights from Oakland, CA (OAK) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
janv. 27 — févr. 31
lun. 1/27
lun. 2/3
1 adult, Economy
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Cheap flight deals from Oakland to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated janvier 22, 2025.

Round-trip from

$243
(CheapOair)

One-way from

$132
(CheapOair)
From Oakland to Caribbean
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One-way flight from Oakland to Caribbean
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Find flight deals from Oakland to Caribbean

Cheapest flights from Oakland to Caribbean
Explore the most affordable flight options available from Oakland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on janvier 22, 2025.

This CheapOair deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/1812:40 pmOAK - SJU
2 stops20h 50mSpirit Airlines
mar. 2/255:56 pmSJU - OAK
2 stops21h 49mSpirit Airlines
Deal found 1/22$243
This FlightHub deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 2/75:45 amOAK - STT
2 stops25h 01mSpirit Airlines
lun. 2/1011:51 amSTT - OAK
2 stops15h 45mSpirit Airlines
Deal found 1/22$323
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/310:45 pmOAK - SJU
1 stop11h 55mDelta
ven. 10/102:53 pmSJU - OAK
1 stop9h 39mDelta
Deal found 1/20$375
This Priceline deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 3/24:14 pmOAK - PUJ
2 stops16h 28mSpirit Airlines
lun. 3/103:47 pmPUJ - OAK
2 stops20h 48mSpirit Airlines
Deal found 1/21$412
This Southwest deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/218:15 pmOAK - SJU
2 stops11h 00mSouthwest
mar. 8/268:00 amSJU - OAK
2 stops12h 30mSouthwest
Deal found 1/21$416
This CheapOair deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 3/55:52 pmOAK - MBJ
2 stops15h 10mSpirit Airlines
dim. 3/912:07 pmMBJ - OAK
2 stops23h 28mSpirit Airlines
Deal found 1/22$442
This Priceline deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 3/217:00 pmOAK - KIN
2 stops15h 28mSpirit Airlines
mer. 3/261:36 pmKIN - OAK
2 stops19h 15mSpirit Airlines
Deal found 1/22$501
This Alaska Airlines deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 3/96:49 amOAK - NAS
2 stops34h 10mAlaska Airlines
dim. 3/1610:00 amNAS - OAK
2 stops40h 43mAlaska Airlines
Deal found 1/22$509
This Mytrip deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 2/154:14 pmOAK - NAS
2 stops15h 46mMultiple Airlines
ven. 2/215:30 pmNAS - OAK
2 stops21h 15mMultiple Airlines
Deal found 1/22$514
This Mytrip deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 2/57:42 amOAK - UVF
2 stops27h 02mMultiple Airlines
mer. 2/124:45 pmUVF - OAK
3 stops33h 27mMultiple Airlines
Deal found 1/22$690
This Southwest deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/77:05 pmOAK - MBJ
2 stops13h 55mSouthwest
mer. 5/1412:00 pmMBJ - OAK
2 stops20h 50mSouthwest
Deal found 1/22$702
This Mytrip deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 1/265:59 pmOAK - PUJ
2 stops23h 46mMultiple Airlines
mar. 1/2810:50 pmPUJ - OAK
2 stops24h 35mMultiple Airlines
Deal found 1/22$738

Find flights from Oakland to Caribbean within your budget

Customize your flight search to find flights from Oakland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated janvier 22, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

mar. 2/18

12:40 pm-1:30 pm

2 stops20h 50m

San Juan Luis Munoz Marin Intl

mar. 2/25

5:56 pm-11:45 am

2 stops21h 49m

$243

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

ven. 2/7

5:45 am-10:46 am

2 stops25h 01m

Saint Thomas Island Cyril E King

lun. 2/10

11:51 am-11:36 pm

2 stops15h 45m

$323

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

dim. 3/2

4:14 pm-12:42 pm

2 stops16h 28m

Punta Cana

lun. 3/10

3:47 pm-9:35 am

2 stops20h 48m

$412

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

mer. 3/5

5:52 pm-12:02 pm

2 stops15h 10m

Montego Bay Sangster Intl

dim. 3/9

12:07 pm-9:35 am

2 stops23h 28m

$442

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

sam. 5/17

7:45 am-11:55 pm

2 stops13h 10m

San Juan Luis Munoz Marin Intl

sam. 5/24

6:20 am-5:35 pm

2 stops14h 15m

$467

OaklandKingston

OAK - KIN

OAKKIN

Oakland

ven. 3/21

7:00 pm-12:28 pm

2 stops15h 28m

Kingston Norman Manley

mer. 3/26

1:36 pm-6:51 am

2 stops19h 15m

$501

OaklandNassau

OAK - NAS

OAKNAS

Oakland

dim. 3/9

6:49 am-7:59 pm

2 stops34h 10m

Nassau Intl

dim. 3/16

10:00 am-11:43 pm

2 stops40h 43m

$509

OaklandNassau

OAK - NAS

OAKNAS

Oakland

sam. 2/15

4:14 pm-11:00 am

2 stops15h 46m

Nassau Intl

ven. 2/21

5:30 pm-11:45 am

2 stops21h 15m

$514

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

mer. 3/19

5:15 pm-10:20 am

2 stops14h 05m

San Juan Luis Munoz Marin Intl

mar. 4/1

7:45 am-11:59 pm

2 stops19h 14m

$578

OaklandCastries

OAK - UVF

OAKUVF

Oakland

mer. 2/5

7:42 am-2:44 pm

2 stops27h 02m

Castries Hewanorra

mer. 2/12

4:45 pm-10:12 pm

3 stops33h 27m

$690

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

Showing 1-10 of 28 results
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Best time to book a flight from Oakland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Oakland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Oakland to Caribbean

Get recent, data-driven insights about flights from Oakland to Caribbean including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Oakland, California to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $254). Flying from Oakland, California to Caribbean in March is currently the most expensive (average of $375). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OAK to CB?

Find hourly flight availability from Oakland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated janvier 22, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Caribbean as you normally would.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated janvier 22, 2025.
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.1
Very good
4,654 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.0
Very good
9,707 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
8,514 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Spirit Airlines
6.3
Okay
8,111 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Related info for your journey

Find useful and relevant information for your journey from Oakland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Oakland to Caribbean?

    Most people fly from Oakland (OAK) if they book a flight from Oakland to Caribbean. Oakland is conveniently located just 7.0 mi from Oakland’s city center.

  • What are the cheapest airlines to fly from Oakland, California to Caribbean one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $132. Users have also found prices from $333 and $684 on Delta and Alaska Airlines, respectively.

  • What are the most popular routes from Oakland, California to Caribbean?

    When deciding which route to take from Oakland, California to Caribbean consider Oakland - San Juan Luis Munoz Marin Intl, Oakland - Punta Cana or Oakland - Montego Bay Sangster Intl as they are the most popular.

  • Can I find deals for flights from Oakland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Oakland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Caribbean.

  • Can I find deals for business class flights from Oakland to Caribbean?

    Yes. Cheapflights offers flight deals from Oakland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oakland, California to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $254). Flying from Oakland, California to Caribbean in March is currently the most expensive (average of $375). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Oakland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Oakland to Caribbean

Discover the top 3 airlines that operate flights from Oakland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated janvier 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$262Average$458FlexibilityNo cancel feeOn-time65%
DeltaCheapest$334Average$802FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$389Average$725FlexibilityNo cancel feeOn-time63%
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