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$152+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheap flight deals from Oakland to Caribbean

Keep the following information in mind while searching for Oakland to Caribbean flight deals. Data was last updated mayo 1, 2025.

Round-trip from

$324
(CheapOair)

One-way from

$152
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$497
From Oakland to Caribbean
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One-way flight from Oakland to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 mayo 1, 2025.

This CheapOair deal was found by Cheapflights users on 4/30. 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.
dom. 5/255:45 amOAK - SJU
2 stops26h 46mSpirit Airlines
sáb. 5/3112:36 pmSJU - OAK
2 stops12h 49mSpirit Airlines
Deal found 4/30$324
This CheapOair deal was found by Cheapflights users on 4/29. 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.
lun. 5/2611:51 amOAK - PUJ
2 stops23h 26mSpirit Airlines
dom. 6/13:22 pmPUJ - OAK
2 stops22h 34mSpirit Airlines
Deal found 4/29$395
This CheapOair deal was found by Cheapflights users on 4/29. 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.
lun. 5/1211:51 amOAK - MBJ
2 stops21h 11mSpirit Airlines
vie. 5/1612:07 pmMBJ - OAK
2 stops24h 49mSpirit Airlines
Deal found 4/29$403
This Southwest deal was found by Cheapflights users on 4/30. 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.
mar. 6/247:00 pmOAK - SJU
2 stops12h 40mSouthwest
sáb. 7/51:05 pmSJU - OAK
1 stop10h 15mSouthwest
Deal found 4/30$438
This Delta deal was found by Cheapflights users on 4/30. 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.
mar. 5/65:10 pmOAK - SJU
2 stops15h 30mDelta
sáb. 5/106:15 amSJU - OAK
2 stops19h 15mDelta
Deal found 4/30$442
This Mytrip deal was found by Cheapflights users on 4/29. 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.
jue. 6/52:07 pmOAK - AUA
3 stops45h 33mSpirit Airlines
dom. 6/83:45 pmAUA - OAK
2 stops31h 29mSpirit Airlines
Deal found 4/29$529
This Mytrip deal was found by Cheapflights users on 4/28. 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.
mié. 5/1411:51 amOAK - STT
3 stops24h 39mSpirit Airlines
dom. 5/184:35 pmSTT - OAK
3 stops20h 06mSpirit Airlines
Deal found 4/28$544
This Mytrip deal was found by Cheapflights users on 4/30. 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.
sáb. 6/145:30 amOAK - NAS
2 stops26h 30mMultiple Airlines
sáb. 6/214:00 pmNAS - OAK
3 stops27h 03mMultiple Airlines
Deal found 4/30$614
This Southwest deal was found by Cheapflights users on 5/1. 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.
mié. 5/287:15 pmOAK - MBJ
2 stops14h 20mSouthwest
mié. 6/412:00 pmMBJ - OAK
2 stops21h 10mSouthwest
Deal found 5/1$704
This Southwest deal was found by Cheapflights users on 4/29. 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.
jue. 6/56:55 pmOAK - AUA
2 stops16h 50mSouthwest
dom. 6/83:45 pmAUA - OAK
2 stops18h 25mSouthwest
Deal found 4/29$750
This Southwest deal was found by Cheapflights users on 4/29. 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.
mar. 6/37:00 pmOAK - PUJ
2 stops14h 40mSouthwest
mar. 6/104:05 pmPUJ - OAK
2 stops19h 35mSouthwest
Deal found 4/29$884
This Delta deal was found by Cheapflights users on 4/30. 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.
mié. 8/275:15 pmOAK - MBJ
2 stops17h 42mDelta
mar. 9/21:15 pmMBJ - OAK
2 stops12h 28mDelta
Deal found 4/30$945

Cheapflights Fare Finder

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 mayo 1, 2025.
Use the filters below to find and compare flights from Oakland to Caribbean that are best for you.

Fly from

Oakland

Fly to

Caribbean

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

dom. 5/25

5:45 am-11:31 am

2 stops26h 46m

San Juan Luis Munoz Marin Intl

sáb. 5/31

12:36 pm-10:25 pm

2 stops12h 49m

$324

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

lun. 5/26

11:51 am-2:17 pm

2 stops23h 26m

Punta Cana

dom. 6/1

3:22 pm-10:56 am

2 stops22h 34m

$395

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

lun. 5/12

11:51 am-11:02 am

2 stops21h 11m

Montego Bay Sangster Intl

vie. 5/16

12:07 pm-10:56 am

2 stops24h 49m

$403

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

mar. 6/24

7:00 pm-10:40 am

2 stops12h 40m

San Juan Luis Munoz Marin Intl

sáb. 7/5

1:05 pm-8:20 pm

1 stop10h 15m

$438

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

jue. 6/5

2:07 pm-2:40 pm

3 stops45h 33m

Oranjestad Reina Beatrix

dom. 6/8

3:45 pm-8:14 pm

2 stops31h 29m

$529

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

mié. 5/14

11:51 am-3:30 pm

3 stops24h 39m

Saint Thomas Island Cyril E King

dom. 5/18

4:35 pm-9:41 am

3 stops20h 06m

$544

OaklandNassau

OAK - NAS

OAKNAS

Oakland

sáb. 6/14

5:30 am-11:00 am

2 stops26h 30m

Nassau Intl

sáb. 6/21

4:00 pm-4:03 pm

3 stops27h 03m

$614

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

mié. 5/28

7:15 pm-11:35 am

2 stops14h 20m

Montego Bay Sangster Intl

mié. 6/4

12:00 pm-7:10 am

2 stops21h 10m

$704

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

jue. 6/5

6:55 pm-2:45 pm

2 stops16h 50m

Oranjestad Reina Beatrix

dom. 6/8

3:45 pm-7:10 am

2 stops18h 25m

$750

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

mar. 6/17

4:58 pm-1:25 pm

2 stops17h 27m

San Juan Luis Munoz Marin Intl

mar. 7/1

7:30 am-10:28 pm

2 stops17h 58m

$865

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 36 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.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Caribbean

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 December is currently the most expensive (average of $336). 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 mayo 1, 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 mayo 1, 2025.
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
British Airways
6.6
Okay
6,845 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
7,963 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $152. Users have also found prices from $371 and $700 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 December is currently the most expensive (average of $336). 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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$263Average$388FlexibilityNo cancel feeOn-time65%
DeltaCheapest$440Average$824FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$469Average$710FlexibilityNo cancel feeOn-time63%

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