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$163+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$343
(FlightHub)

One-way from

$163
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$565
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. 10% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/1. 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 7/299:23 amOAK - SJU
2 stops23h 09mSpirit Airlines
Fri 8/11:37 amSJU - OAK
2 stops24h 56mSpirit Airlines
Deal found 7/1$343
This Southwest deal was found by Cheapflights users on 7/2. 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 8/307:55 pmOAK - SJU
2 stops11h 15mSouthwest
Wed 9/311:50 amSJU - OAK
2 stops11h 50mSouthwest
Deal found 7/2$429
This FlightHub deal was found by Cheapflights users on 7/1. 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 8/16:00 amOAK - STT
2 stops27h 30mSpirit Airlines
Thu 8/710:43 amSTT - OAK
2 stops24h 45mSpirit Airlines
Deal found 7/1$439
This CheapOair deal was found by Cheapflights users on 7/1. 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 7/2012:42 pmOAK - PUJ
2 stops22h 48mSpirit Airlines
Thu 7/2412:40 pmPUJ - OAK
2 stops22h 48mSpirit Airlines
Deal found 7/1$468
This Mytrip deal was found by Cheapflights users on 7/2. 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 8/166:00 amOAK - MBJ
3 stops25h 17mSpirit Airlines
Sat 8/2312:19 pmMBJ - OAK
2 stops13h 08mSpirit Airlines
Deal found 7/2$490
This Mytrip deal was found by Cheapflights users on 7/1. 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 7/229:23 amOAK - MBJ
2 stops25h 22mMultiple Airlines
Mon 7/2812:10 pmMBJ - OAK
2 stops22h 18mMultiple Airlines
Deal found 7/1$611
This Southwest deal was found by Cheapflights users on 7/1. 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 7/225:00 amOAK - MBJ
1 stop7h 55mSouthwest
Mon 7/282:55 pmMBJ - OAK
2 stops11h 25mSouthwest
Deal found 7/1$745
This Mytrip deal was found by Cheapflights users on 7/1. 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 7/89:38 pmOAK - PUJ
2 stops23h 04mMultiple Airlines
Sun 7/1312:40 pmPUJ - OAK
3 stops26h 47mMultiple Airlines
Deal found 7/1$751
This Mytrip deal was found by Cheapflights users on 7/2. 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 7/176:15 pmOAK - AUA
3 stops41h 25mMultiple Airlines
Thu 7/243:45 pmAUA - OAK
2 stops19h 43mMultiple Airlines
Deal found 7/2$760
This Southwest deal was found by Cheapflights users on 7/1. 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 7/227:05 pmOAK - GCM
2 stops14h 45mSouthwest
Sun 7/2712:45 pmGCM - OAK
2 stops23h 05mSouthwest
Deal found 7/1$780
This Southwest deal was found by Cheapflights users on 7/2. 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.
Thu 7/176:00 pmOAK - AUA
2 stops15h 35mSouthwest
Thu 7/241:30 pmAUA - OAK
2 stops13h 35mSouthwest
Deal found 7/2$787
This FlightHub deal was found by Cheapflights users on 7/1. 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 7/1$808

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 July 3, 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

Tue 7/29

9:23 am-11:32 am

2 stops23h 09m

San Juan Luis Munoz Marin Intl

Fri 8/1

1:37 am-11:33 pm

2 stops24h 56m

$343

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 8/30

7:55 pm-10:10 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Wed 9/3

11:50 am-8:40 pm

2 stops11h 50m

$429

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Fri 8/1

6:00 am-12:30 pm

2 stops27h 30m

Saint Thomas Island Cyril E King

Thu 8/7

10:43 am-8:28 am

2 stops24h 45m

$439

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sun 7/20

12:42 pm-2:30 pm

2 stops22h 48m

Punta Cana

Thu 7/24

12:40 pm-8:28 am

2 stops22h 48m

$468

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sat 8/16

6:00 am-9:17 am

3 stops25h 17m

Montego Bay Sangster Intl

Sat 8/23

12:19 pm-11:27 pm

2 stops13h 08m

$490

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 7/22

9:23 am-12:45 pm

2 stops25h 22m

Montego Bay Sangster Intl

Mon 7/28

12:10 pm-8:28 am

2 stops22h 18m

$611

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 7/22

5:00 am-2:55 pm

1 stop7h 55m

Montego Bay Sangster Intl

Mon 7/28

2:55 pm-12:20 am

2 stops11h 25m

$745

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

Thu 7/17

6:15 pm-2:40 pm

3 stops41h 25m

Oranjestad Reina Beatrix

Thu 7/24

3:45 pm-8:28 am

2 stops19h 43m

$760

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Tue 7/22

7:05 pm-11:50 am

2 stops14h 45m

George Town Owen Roberts Intl

Sun 7/27

12:45 pm-9:50 am

2 stops23h 05m

$780

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

Thu 7/17

6:00 pm-12:35 pm

2 stops15h 35m

Oranjestad Reina Beatrix

Thu 7/24

1:30 pm-12:05 am

2 stops13h 35m

$787

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 32 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 July 3, 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.

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 July 3, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Oakland to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

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

Crew

8.5

Food

7.1

Overall

8.0

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
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

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
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

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
8,086 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

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 $163. Users have also found prices from $198 and $305 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 - Kingston Norman Manley 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 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$260Average$397FlexibilityNo cancel feeOn-time65%
DeltaCheapest$380Average$730FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$430Average$684FlexibilityNo cancel feeOn-time63%

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