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$173+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Dec 25 — Jan 11
Wed 12/25
Wed 1/1
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 December 20, 2024.

Round-trip from

$281
(Mytrip)

One-way from

$173
(FlightHub)
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 December 20, 2024.

This Mytrip deal was found by Cheapflights users on 12/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/279:25 pmOAK - SJU
2 stops24h 24mSpirit Airlines
Mon 12/304:30 amSJU - OAK
2 stops20h 00mSpirit Airlines
Deal found 12/20$682
This Mytrip deal was found by Cheapflights users on 12/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/272:04 pmOAK - SJU
3 stops31h 45mMultiple Airlines
Mon 12/302:45 amSJU - OAK
3 stops21h 45mMultiple Airlines
Deal found 12/20$845
This Delta deal was found by Cheapflights users on 12/20. 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.
Wed 12/255:30 amOAK - SJU
2 stops16h 48mDelta
Mon 1/62:11 pmSJU - OAK
2 stops13h 45mDelta
Deal found 12/20$884
This CheapOair deal was found by Cheapflights users on 12/19. 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 12/299:25 pmOAK - STT
2 stops33h 14mSpirit Airlines
Fri 1/35:45 pmSTT - OAK
2 stops43h 44mSpirit Airlines
Deal found 12/19$914
This Mytrip deal was found by Cheapflights users on 12/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/239:25 pmOAK - NAS
2 stops10h 35mMultiple Airlines
Fri 1/37:15 amNAS - OAK
3 stops30h 14mMultiple Airlines
Deal found 12/20$927
This Alaska Airlines deal was found by Cheapflights users on 12/19. 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.
Sun 12/297:32 pmOAK - NAS
2 stops43h 48mAlaska Airlines
Wed 1/19:00 amNAS - OAK
1 stop27h 21mAlaska Airlines
Deal found 12/19$960
This Mytrip deal was found by Cheapflights users on 12/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/243:55 pmOAK - SDQ
3 stops35h 30mMultiple Airlines
Tue 12/316:46 pmSDQ - OAK
3 stops32h 06mMultiple Airlines
Deal found 12/20$961
This Delta deal was found by Cheapflights users on 12/19. 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.
Wed 12/255:30 amOAK - SDQ
2 stops17h 19mDelta
Tue 12/313:54 pmSDQ - OAK
2 stops35h 19mDelta
Deal found 12/19$982
This Delta deal was found by Cheapflights users on 12/19. 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 12/285:08 pmOAK - PUJ
2 stops15h 32mDelta
Mon 12/302:05 pmPUJ - OAK
2 stops14h 09mDelta
Deal found 12/19$1,032
This Delta deal was found by Cheapflights users on 12/20. 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.
Tue 12/245:30 amOAK - NAS
2 stops13h 15mDelta
Thu 1/21:34 pmNAS - OAK
2 stops13h 40mDelta
Deal found 12/20$1,053
This Delta deal was found by Cheapflights users on 12/19. 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.
Wed 12/255:30 amOAK - MBJ
2 stops12h 21mDelta
Thu 1/212:36 pmMBJ - OAK
2 stops14h 38mDelta
Deal found 12/19$1,174
This Mytrip deal was found by Cheapflights users on 12/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:30 amOAK - SDQ
2 stops24h 27mSpirit Airlines
Tue 12/317:58 amSDQ - OAK
2 stops29h 45mSpirit Airlines
Deal found 12/20$1,210

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 December 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 1/14

7:42 am-9:21 am

3 stops21h 39m

San Juan Luis Munoz Marin Intl

Thu 1/23

6:55 pm-11:36 pm

2 stops32h 41m

$281

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Fri 2/7

5:45 am-10:46 am

2 stops25h 01m

Saint Thomas Island Cyril E King

Mon 2/10

11:51 am-11:36 pm

2 stops15h 45m

$302

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Tue 1/14

7:02 pm-12:55 pm

2 stops13h 53m

Santo Domingo Las Americas

Sat 1/18

1:55 pm-11:36 pm

2 stops13h 41m

$400

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 1/10

11:37 am-1:48 pm

2 stops23h 11m

Montego Bay Sangster Intl

Fri 1/17

1:16 pm-11:36 pm

2 stops13h 20m

$401

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 4/26

7:35 am-9:40 pm

2 stops11h 05m

San Juan Luis Munoz Marin Intl

Sat 5/3

6:20 am-5:35 pm

2 stops14h 15m

$444

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Fri 1/10

11:37 am-1:33 pm

2 stops22h 56m

Kingston Norman Manley

Fri 1/17

2:38 pm-11:36 pm

2 stops11h 58m

$453

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sun 2/2

11:37 am-3:45 pm

2 stops24h 08m

Punta Cana

Sun 2/9

4:50 pm-9:35 pm

3 stops32h 45m

$462

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sun 2/2

6:19 pm-3:45 pm

2 stops17h 26m

Punta Cana

Sun 2/9

7:05 am-6:47 am

2 stops27h 42m

$467

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Fri 2/28

7:32 pm-7:59 pm

1 stop21h 27m

Nassau Intl

Tue 3/4

11:00 am-7:52 pm

1 stop11h 52m

$484

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 1/7

9:25 pm-11:00 am

2 stops10h 35m

Nassau Intl

Tue 1/14

11:30 am-11:46 am

3 stops27h 16m

$521

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 30 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 $380). 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 December 20, 2024.

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 December 20, 2024.
Southwest
8.1
Very good
4,821 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
4,821 reviews
Southwest
8.1
Very good
4,821 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
9,545 reviews
Southwest
8.1
Very good
4,821 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
8,601 reviews
Southwest
8.1
Very good
4,821 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
8,120 reviews
Southwest
8.1
Very good
4,821 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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 $173. Users have also found prices from $352 and $535 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 - Saint Thomas Island Cyril E King or Oakland - Punta Cana 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 $380). 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 December 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$262Average$458FlexibilityNo cancel feeOn-time65%
DeltaCheapest$334Average$773FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$389Average$741FlexibilityNo cancel feeOn-time63%
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