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$142+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 March 26, 2025.

Round-trip from

$278
(Mytrip)

One-way from

$142
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$529
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. 7% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 26, 2025.

This Mytrip deal was found by Cheapflights users on 3/25. 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.
Mon 5/58:37 pmOAK - SJU
2 stops24h 02mSpirit Airlines
Thu 5/81:59 amSJU - OAK
3 stops45h 15mSpirit Airlines
Deal found 3/25$278
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Fri 4/257:31 pmOAK - STT
3 stops35h 29mSpirit Airlines
Thu 5/111:05 amSTT - OAK
2 stops22h 44mSpirit Airlines
Deal found 3/25$343
This CheapOair deal was found by Cheapflights users on 3/25. 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.
Sun 5/46:40 pmOAK - MBJ
2 stops14h 15mSpirit Airlines
Fri 5/912:07 pmMBJ - OAK
2 stops24h 49mSpirit Airlines
Deal found 3/25$384
This FlightHub deal was found by Cheapflights users on 3/26. 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.
Wed 4/306:29 pmOAK - KIN
2 stops16h 02mSpirit Airlines
Wed 5/71:34 pmKIN - OAK
2 stops23h 22mSpirit Airlines
Deal found 3/26$384
This CheapOair deal was found by Cheapflights users on 3/24. 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.
Wed 4/236:29 pmOAK - PUJ
2 stops13h 37mSpirit Airlines
Wed 4/303:18 pmPUJ - OAK
2 stops18h 31mSpirit Airlines
Deal found 3/24$400
This Southwest deal was found by Cheapflights users on 3/25. 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.
Mon 9/18:15 pmOAK - SJU
2 stops11h 35mSouthwest
Sun 9/75:05 amSJU - OAK
2 stops12h 20mSouthwest
Deal found 3/25$493
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 3/255:15 pmOAK - SJU
2 stops15h 29mDelta
Tue 4/17:45 amSJU - OAK
2 stops19h 14mDelta
Deal found 3/25$577
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Tue 3/2512:11 pmOAK - SJU
2 stops24h 00mMultiple Airlines
Tue 4/19:51 pmSJU - OAK
3 stops35h 45mMultiple Airlines
Deal found 3/25$608
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 4/15:15 pmOAK - NAS
2 stops15h 20mDelta
Tue 4/81:01 pmNAS - OAK
2 stops13h 45mDelta
Deal found 3/25$625
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Sat 4/196:29 pmOAK - NAS
3 stops21h 46mMultiple Airlines
Wed 4/234:00 pmNAS - OAK
2 stops17h 49mMultiple Airlines
Deal found 3/25$658
This Southwest deal was found by Cheapflights users on 3/26. 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.
Tue 6/247:00 pmOAK - NAS
2 stops15h 15mSouthwest
Sat 6/282:20 pmNAS - OAK
2 stops20h 35mSouthwest
Deal found 3/26$705
This Southwest deal was found by Cheapflights users on 3/25. 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 6/117:05 pmOAK - PUJ
2 stops15h 40mSouthwest
Mon 6/164:25 pmPUJ - OAK
2 stops17h 05mSouthwest
Deal found 3/25$731

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 March 26, 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

Mon 5/5

8:37 pm-11:39 pm

2 stops24h 02m

San Juan Luis Munoz Marin Intl

Thu 5/8

1:59 am-8:14 pm

3 stops45h 15m

$278

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Fri 4/25

7:31 pm-10:00 am

3 stops35h 29m

Saint Thomas Island Cyril E King

Thu 5/1

11:05 am-6:49 am

2 stops22h 44m

$343

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sun 5/4

6:40 pm-10:55 am

2 stops14h 15m

Montego Bay Sangster Intl

Fri 5/9

12:07 pm-10:56 am

2 stops24h 49m

$384

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Wed 4/30

6:29 pm-12:31 pm

2 stops16h 02m

Kingston Norman Manley

Wed 5/7

1:34 pm-10:56 am

2 stops23h 22m

$384

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Wed 4/23

6:29 pm-11:06 am

2 stops13h 37m

Punta Cana

Wed 4/30

3:18 pm-6:49 am

2 stops18h 31m

$400

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 9/1

8:15 pm-10:50 am

2 stops11h 35m

San Juan Luis Munoz Marin Intl

Sun 9/7

5:05 am-2:25 pm

2 stops12h 20m

$493

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 4/19

6:29 pm-7:15 pm

3 stops21h 46m

Nassau Intl

Wed 4/23

4:00 pm-6:49 am

2 stops17h 49m

$658

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 6/24

7:00 pm-1:15 pm

2 stops15h 15m

Nassau Intl

Sat 6/28

2:20 pm-7:55 am

2 stops20h 35m

$705

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Wed 6/11

7:05 pm-1:45 pm

2 stops15h 40m

Punta Cana

Mon 6/16

4:25 pm-6:30 am

2 stops17h 05m

$731

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 4/8

5:15 pm-10:44 am

2 stops15h 29m

Montego Bay Sangster Intl

Wed 4/16

1:22 pm-11:43 pm

2 stops12h 21m

$749

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 29 results
1
2
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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 March 26, 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 March 26, 2025.
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Alaska Airlines
8.0
Very good
9,792 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,891 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Spirit Airlines
6.3
Okay
7,878 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Boarding

8.2

Overall

8.1

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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 $142. Users have also found prices from $389 and $483 on Alaska Airlines 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 - 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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$263Average$483FlexibilityNo cancel feeOn-time65%
DeltaCheapest$440Average$905FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$469Average$710FlexibilityNo cancel feeOn-time63%
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