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$106+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/103:00 pmOAK - SJU
2 stops22h 43mSpirit Airlines
Tue 12/178:31 pmSJU - OAK
2 stops25h 10mSpirit Airlines
Deal found 11/19$230
This CheapOair deal was found by Cheapflights users on 11/21. 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 12/185:30 amOAK - STT
2 stops25h 09mSpirit Airlines
Wed 12/2511:44 amSTT - OAK
2 stops15h 08mSpirit Airlines
Deal found 11/21$338
This CheapOair deal was found by Cheapflights users on 11/21. 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.
Tue 12/319:25 pmOAK - MBJ
2 stops13h 20mSpirit Airlines
Sat 1/112:49 pmMBJ - OAK
2 stops11h 46mSpirit Airlines
Deal found 11/21$422
This Mytrip deal was found by Cheapflights users on 11/21. 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 12/73:00 pmOAK - STX
3 stops22h 03mMultiple Airlines
Wed 12/119:30 amSTX - OAK
3 stops27h 55mMultiple Airlines
Deal found 11/21$595
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/167:06 pmOAK - SDQ
2 stops18h 28mSpirit Airlines
Mon 12/2311:04 amSDQ - OAK
2 stops13h 26mSpirit Airlines
Deal found 11/20$751
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Sun 12/229:25 pmOAK - SJU
3 stops32h 22mMultiple Airlines
Thu 1/24:30 amSJU - OAK
3 stops33h 13mMultiple Airlines
Deal found 11/20$913
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/245:16 pmOAK - KIN
2 stops15h 53mSpirit Airlines
Sat 11/301:14 pmKIN - OAK
2 stops22h 58mSpirit Airlines
Deal found 11/20$1,088
This Alaska Airlines deal was found by Cheapflights users on 11/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/46:00 amOAK - SJU
2 stops29h 15mAlaska Airlines
Wed 12/116:25 amSJU - OAK
2 stops29h 45mAlaska Airlines
Deal found 11/20$1,307
This CheapOair deal was found by Cheapflights users on 11/21. 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.
Thu 12/269:25 pmOAK - AUA
2 stops38h 15mSpirit Airlines
Thu 1/24:40 pmAUA - OAK
2 stops31h 50mSpirit Airlines
Deal found 11/21$1,319
This Southwest deal was found by Cheapflights users on 11/21. 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 12/217:30 amOAK - SJU
1 stop13h 00mSouthwest
Sat 1/45:35 amSJU - OAK
2 stops13h 45mSouthwest
Deal found 11/21$1,514
This Delta deal was found by Cheapflights users on 11/20. 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 12/185:14 pmOAK - NAS
2 stops15h 42mDelta
Mon 12/231:34 pmNAS - OAK
2 stops13h 40mDelta
Deal found 11/20$1,516
This Delta deal was found by Cheapflights users on 11/19. 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 12/186:00 amOAK - KIN
2 stops12h 10mDelta
Tue 1/79:00 amKIN - OAK
2 stops17h 56mDelta
Deal found 11/19$1,898

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 12/10

3:00 pm-5:43 pm

2 stops22h 43m

San Juan Luis Munoz Marin Intl

Tue 12/17

8:31 pm-5:41 pm

2 stops25h 10m

$230

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Mon 1/6

5:30 am-10:39 am

2 stops25h 09m

Saint Thomas Island Cyril E King

Sun 1/12

11:46 am-6:47 am

2 stops23h 01m

$325

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 3/1

7:20 am-11:20 pm

1 stop12h 00m

San Juan Luis Munoz Marin Intl

Wed 3/5

9:05 am-6:05 pm

2 stops13h 00m

$384

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Thu 1/16

5:34 pm-1:37 pm

2 stops17h 03m

Montego Bay Sangster Intl

Thu 1/23

2:42 pm-11:35 pm

2 stops11h 53m

$412

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 1/7

5:06 pm-2:20 pm

2 stops17h 14m

San Juan Luis Munoz Marin Intl

Tue 1/14

7:00 am-4:26 pm

2 stops13h 26m

$423

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sun 1/12

5:34 pm-3:49 pm

2 stops18h 15m

Punta Cana

Thu 1/16

4:54 pm-10:03 pm

3 stops33h 09m

$453

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sun 1/12

5:34 pm-3:49 pm

2 stops18h 15m

Punta Cana

Thu 1/16

8:35 pm-10:03 pm

2 stops29h 28m

$577

OaklandChristiansted

OAK - STX

OAKSTX

Oakland

Sat 12/7

3:00 pm-5:03 pm

3 stops22h 03m

Christiansted Henry Rohlsen

Wed 12/11

9:30 am-9:25 am

3 stops27h 55m

$595

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Sat 2/1

7:42 am-5:13 pm

2 stops29h 31m

Santo Domingo Las Americas

Tue 2/4

4:59 pm-6:47 am

2 stops41h 48m

$613

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Thu 3/27

8:25 pm-1:50 pm

2 stops15h 25m

Montego Bay Sangster Intl

Sun 3/30

2:05 pm-11:15 pm

2 stops11h 10m

$695

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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.

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 $335). 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 November 21, 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 November 21, 2024.
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

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
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

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
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

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
8,169 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

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 $106. Users have also found prices from $256 and $497 on Delta and Southwest, 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 March is currently the most expensive (average of $335). 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.

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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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$262Average$469FlexibilityNo cancel feeOn-time65%
DeltaCheapest$334Average$770FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$478Average$689FlexibilityNo cancel feeOn-time63%
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