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$151+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Apr 30 — May 71
Wed 4/30
Wed 5/7
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 April 25, 2025.

Round-trip from

$359
(Mytrip)

One-way from

$151
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$479
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 April 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 April 25, 2025.

This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:45 amOAK - SJU
3 stops35h 17mSpirit Airlines
Fri 5/301:33 amSJU - OAK
2 stops23h 52mSpirit Airlines
Deal found 4/24$359
This Gotogate deal was found by Cheapflights users on 4/24. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/235:45 amOAK - STT
2 stops25h 12mSpirit Airlines
Mon 6/210:52 amSTT - OAK
2 stops27h 04mSpirit Airlines
Deal found 4/24$395
This Gotogate deal was found by Cheapflights users on 4/25. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2911:51 amOAK - SDQ
2 stops24h 54mSpirit Airlines
Mon 6/24:50 pmSDQ - OAK
2 stops21h 06mSpirit Airlines
Deal found 4/25$402
This CheapOair deal was found by Cheapflights users on 4/24. 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.
Sun 5/2511:51 amOAK - PUJ
2 stops23h 26mSpirit Airlines
Thu 5/293:22 pmPUJ - OAK
2 stops22h 34mSpirit Airlines
Deal found 4/24$407
This Southwest deal was found by Cheapflights users on 4/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/15:30 amOAK - SJU
2 stops14h 00mSouthwest
Wed 10/87:40 amSJU - OAK
2 stops15h 05mSouthwest
Deal found 4/24$434
This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:45 amOAK - SJU
3 stops35h 17mMultiple Airlines
Sat 5/318:12 pmSJU - OAK
3 stops27h 22mMultiple Airlines
Deal found 4/24$464
This CheapOair deal was found by Cheapflights users on 4/23. 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 5/2811:51 amOAK - MBJ
2 stops21h 11mSpirit Airlines
Mon 6/212:07 pmMBJ - OAK
2 stops24h 49mSpirit Airlines
Deal found 4/23$490
This Mytrip deal was found by Cheapflights users on 4/25. 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.
Thu 6/55:45 amOAK - KIN
2 stops28h 44mSpirit Airlines
Thu 6/121:34 pmKIN - OAK
2 stops33h 09mSpirit Airlines
Deal found 4/25$506
This Southwest deal was found by Cheapflights users on 4/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/307:00 pmOAK - MBJ
2 stops14h 55mSouthwest
Wed 6/113:55 pmMBJ - OAK
1 stop9h 30mSouthwest
Deal found 4/24$558
This Mytrip deal was found by Cheapflights users on 4/25. 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 5/2411:51 amOAK - PUJ
2 stops23h 26mMultiple Airlines
Mon 5/263:00 pmPUJ - OAK
2 stops34h 25mMultiple Airlines
Deal found 4/25$576
This Delta deal was found by Cheapflights users on 4/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:00 amOAK - SJU
2 stops13h 47mDelta
Thu 5/291:55 pmSJU - OAK
2 stops12h 54mDelta
Deal found 4/24$580
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/158:00 amOAK - NAS
2 stops32h 59mAlaska Airlines
Sun 5/189:00 amNAS - OAK
2 stops50h 45mAlaska Airlines
Deal found 4/24$591

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 April 25, 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

Sat 5/24

5:45 am-8:02 pm

3 stops35h 17m

San Juan Luis Munoz Marin Intl

Fri 5/30

1:33 am-10:25 pm

2 stops23h 52m

$359

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Fri 5/23

5:45 am-9:57 am

2 stops25h 12m

Saint Thomas Island Cyril E King

Mon 6/2

10:52 am-10:56 am

2 stops27h 04m

$395

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Thu 5/29

11:51 am-3:45 pm

2 stops24h 54m

Santo Domingo Las Americas

Mon 6/2

4:50 pm-10:56 am

2 stops21h 06m

$402

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sun 5/25

11:51 am-2:17 pm

2 stops23h 26m

Punta Cana

Thu 5/29

3:22 pm-10:56 am

2 stops22h 34m

$407

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 10/1

5:30 am-10:30 pm

2 stops14h 00m

San Juan Luis Munoz Marin Intl

Wed 10/8

7:40 am-7:45 pm

2 stops15h 05m

$434

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 5/24

5:45 am-8:02 pm

3 stops35h 17m

San Juan Luis Munoz Marin Intl

Sat 5/31

8:12 pm-8:34 pm

3 stops27h 22m

$464

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Wed 5/28

11:51 am-11:02 am

2 stops21h 11m

Montego Bay Sangster Intl

Mon 6/2

12:07 pm-10:56 am

2 stops24h 49m

$490

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Thu 6/5

5:45 am-12:29 pm

2 stops28h 44m

Kingston Norman Manley

Thu 6/12

1:34 pm-8:43 pm

2 stops33h 09m

$506

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 5/30

7:00 pm-11:55 am

2 stops14h 55m

Montego Bay Sangster Intl

Wed 6/11

3:55 pm-11:25 pm

1 stop9h 30m

$558

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sat 5/24

11:51 am-2:17 pm

2 stops23h 26m

Punta Cana

Mon 5/26

3:00 pm-10:25 pm

2 stops34h 25m

$576

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 33 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 April 25, 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 April 25, 2025.
Alaska Airlines
8.0
Very good
9,927 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,927 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,289 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Spirit Airlines
6.3
Okay
7,943 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $151. Users have also found prices from $276 and $290 on Southwest 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 - 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 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 April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$263Average$388FlexibilityNo cancel feeOn-time65%
DeltaCheapest$440Average$824FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$469Average$711FlexibilityNo cancel feeOn-time63%

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