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$143+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$336
(FlightHub)

One-way from

$143
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$578
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. 11% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/12. 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.
Thu 7/1012:42 pmOAK - SJU
2 stops19h 50mSpirit Airlines
Wed 7/161:37 amSJU - OAK
2 stops24h 56mSpirit Airlines
Deal found 6/12$336
This Southwest deal was found by Cheapflights users on 6/12. 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.
Wed 9/108:30 pmOAK - SJU
2 stops10h 45mSouthwest
Wed 9/178:00 amSJU - OAK
2 stops12h 30mSouthwest
Deal found 6/12$369
This FlightHub deal was found by Cheapflights users on 6/10. 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.
Tue 7/85:30 amOAK - SDQ
2 stops25h 20mSpirit Airlines
Tue 7/1510:55 amSDQ - OAK
2 stops24h 33mSpirit Airlines
Deal found 6/10$378
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/227:30 amOAK - STT
2 stops22h 15mSpirit Airlines
Mon 8/259:40 amSTT - OAK
2 stops16h 59mSpirit Airlines
Deal found 6/10$394
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sun 7/69:38 pmOAK - MBJ
2 stops35h 24mSpirit Airlines
Wed 7/912:10 pmMBJ - OAK
2 stops25h 37mSpirit Airlines
Deal found 6/10$440
This FlightHub deal was found by Cheapflights users on 6/11. 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.
Fri 7/119:23 amOAK - PUJ
2 stops27h 32mSpirit Airlines
Thu 7/171:00 pmPUJ - OAK
2 stops22h 28mSpirit Airlines
Deal found 6/11$451
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Sun 8/35:39 pmOAK - SJU
2 stops26h 21mMultiple Airlines
Fri 8/81:37 amSJU - OAK
3 stops24h 56mMultiple Airlines
Deal found 6/11$467
This FlightHub deal was found by Cheapflights users on 6/11. 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.
Tue 7/89:38 pmOAK - KIN
2 stops35h 22mSpirit Airlines
Sat 7/128:47 amKIN - OAK
2 stops29h 00mSpirit Airlines
Deal found 6/11$523
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Thu 8/149:09 pmOAK - PUJ
2 stops34h 06mMultiple Airlines
Mon 8/181:01 pmPUJ - OAK
3 stops37h 38mMultiple Airlines
Deal found 6/10$573
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Wed 7/239:23 amOAK - MBJ
3 stops47h 07mMultiple Airlines
Tue 7/293:05 pmMBJ - OAK
2 stops19h 23mMultiple Airlines
Deal found 6/11$579
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 11/126:30 pmOAK - PUJ
2 stops16h 15mSouthwest
Thu 11/202:40 pmPUJ - OAK
2 stops20h 05mSouthwest
Deal found 6/10$583
This Southwest deal was found by Cheapflights users on 6/10. 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.
Sat 11/18:05 pmOAK - AUA
2 stops15h 55mSouthwest
Thu 11/64:00 pmAUA - OAK
2 stops18h 45mSouthwest
Deal found 6/10$584

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 June 12, 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

Thu 7/10

12:42 pm-11:32 am

2 stops19h 50m

San Juan Luis Munoz Marin Intl

Wed 7/16

1:37 am-11:33 pm

2 stops24h 56m

$336

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 9/10

5:25 pm-10:15 am

2 stops13h 50m

San Juan Luis Munoz Marin Intl

Wed 9/17

5:00 am-2:40 pm

2 stops12h 40m

$369

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Tue 7/8

5:30 am-9:50 am

2 stops25h 20m

Santo Domingo Las Americas

Tue 7/15

10:55 am-8:28 am

2 stops24h 33m

$378

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Fri 8/22

7:30 am-8:45 am

2 stops22h 15m

Saint Thomas Island Cyril E King

Mon 8/25

9:40 am-11:39 pm

2 stops16h 59m

$394

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sun 7/6

9:38 pm-11:02 am

2 stops35h 24m

Montego Bay Sangster Intl

Wed 7/9

12:10 pm-11:47 am

2 stops25h 37m

$440

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 7/11

9:23 am-3:55 pm

2 stops27h 32m

Punta Cana

Thu 7/17

1:00 pm-8:28 am

2 stops22h 28m

$451

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 8/3

5:39 pm-11:00 pm

2 stops26h 21m

San Juan Luis Munoz Marin Intl

Fri 8/8

1:37 am-11:33 pm

3 stops24h 56m

$467

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Tue 7/8

9:38 pm-11:00 am

2 stops35h 22m

Kingston Norman Manley

Sat 7/12

8:47 am-11:47 am

2 stops29h 00m

$523

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Thu 8/14

9:09 pm-10:15 am

2 stops34h 06m

Punta Cana

Mon 8/18

1:01 pm-11:39 pm

3 stops37h 38m

$573

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Wed 7/23

9:23 am-10:30 am

3 stops47h 07m

Montego Bay Sangster Intl

Tue 7/29

3:05 pm-8:28 am

2 stops19h 23m

$579

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 39 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 June is currently the most expensive (average of $339). 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 June 12, 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 June 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

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
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

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
8,052 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

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 $143. Users have also found prices from $278 and $371 on Southwest and Delta, 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 - Nassau 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 June is currently the most expensive (average of $339). 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$260Average$389FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$430Average$691FlexibilityNo cancel feeOn-time63%
DeltaCheapest$658Average$729FlexibilityNo cancel feeOn-timeN/A

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