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Caribbean Islands

$152+ Cheap flights from Oakland, CA (OAK) to Caribbean Islands

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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Oakland to Caribbean Islands

Keep the following information in mind while searching for Oakland to Caribbean Islands flight deals. Data was last updated May 1, 2025.

Round-trip from

$324
(CheapOair)

One-way from

$152
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$497
From Oakland to Caribbean Islands
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One-way flight from Oakland to Caribbean Islands
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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 May 2025
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Find flight deals from Oakland to Caribbean Islands

Cheapest flights from Oakland to Caribbean Islands
Explore the most affordable flight options available from Oakland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This CheapOair deal was found by Cheapflights users on 4/30. 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 5/255:45 amOAK - SJU
2 stops26h 46mSpirit Airlines
Sat 5/3112:36 pmSJU - OAK
2 stops12h 49mSpirit Airlines
Deal found 4/30$324
This CheapOair deal was found by Cheapflights users on 5/1. 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.
Sat 5/1711:51 amOAK - PUJ
2 stops23h 26mSpirit Airlines
Fri 5/233:22 pmPUJ - OAK
2 stops22h 34mSpirit Airlines
Deal found 5/1$385
This CheapOair deal was found by Cheapflights users on 4/29. 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 5/1211:51 amOAK - MBJ
2 stops21h 11mSpirit Airlines
Fri 5/1612:07 pmMBJ - OAK
2 stops24h 49mSpirit Airlines
Deal found 4/29$403
This Southwest deal was found by Cheapflights users on 4/30. 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 - SJU
2 stops12h 40mSouthwest
Sat 7/51:05 pmSJU - OAK
1 stop10h 15mSouthwest
Deal found 4/30$438
This Delta deal was found by Cheapflights users on 4/30. 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 5/65:10 pmOAK - SJU
2 stops15h 30mDelta
Sat 5/106:15 amSJU - OAK
2 stops19h 15mDelta
Deal found 4/30$442
This Mytrip deal was found by Cheapflights users on 4/30. 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 - NAS
2 stops30h 00mMultiple Airlines
Thu 5/295:30 pmNAS - OAK
2 stops31h 55mMultiple Airlines
Deal found 4/30$557
This Southwest deal was found by Cheapflights users on 4/30. 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 7/256:00 pmOAK - PUJ
2 stops13h 50mSouthwest
Wed 7/303:45 pmPUJ - OAK
2 stops19h 55mSouthwest
Deal found 4/30$598
This Mytrip deal was found by Cheapflights users on 5/1. 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.
Wed 5/75:36 pmOAK - STT
3 stops37h 21mSpirit Airlines
Mon 5/122:41 pmSTT - OAK
2 stops23h 15mSpirit Airlines
Deal found 5/1$617
This Mytrip deal was found by Cheapflights users on 5/1. 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.
Thu 6/269:38 pmOAK - SJU
3 stops38h 38mMultiple Airlines
Mon 6/3011:44 amSJU - OAK
3 stops31h 42mMultiple Airlines
Deal found 5/1$641
This Delta deal was found by Cheapflights users on 4/30. 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 9/105:15 pmOAK - PLS
2 stops16h 30mDelta
Tue 9/162:05 pmPLS - OAK
2 stops12h 48mDelta
Deal found 4/30$690
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 5/147:55 pmOAK - NAS
2 stops45h 04mAlaska Airlines
Sat 5/179:00 amNAS - OAK
2 stops13h 14mAlaska Airlines
Deal found 4/30$700
This Southwest deal was found by Cheapflights users on 5/1. 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.
Wed 5/287:15 pmOAK - MBJ
2 stops14h 20mSouthwest
Wed 6/412:00 pmMBJ - OAK
2 stops21h 10mSouthwest
Deal found 5/1$704

Cheapflights Fare Finder

Customize your flight search to find flights from Oakland to Caribbean Islands 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 May 1, 2025.
Use the filters below to find and compare flights from Oakland to Caribbean Islands that are best for you.

Fly from

Oakland

Fly to

Caribbean Islands

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 5/25

5:45 am-11:31 am

2 stops26h 46m

San Juan Luis Munoz Marin Intl

Sat 5/31

12:36 pm-10:25 pm

2 stops12h 49m

$324

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sat 5/17

11:51 am-2:17 pm

2 stops23h 26m

Punta Cana

Fri 5/23

3:22 pm-10:56 am

2 stops22h 34m

$385

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Mon 5/12

11:51 am-11:02 am

2 stops21h 11m

Montego Bay Sangster Intl

Fri 5/16

12:07 pm-10:56 am

2 stops24h 49m

$403

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 6/24

7:00 pm-10:40 am

2 stops12h 40m

San Juan Luis Munoz Marin Intl

Sat 7/5

1:05 pm-8:20 pm

1 stop10h 15m

$438

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 5/24

5:45 am-2:45 pm

2 stops30h 00m

Nassau Intl

Thu 5/29

5:30 pm-10:25 pm

2 stops31h 55m

$557

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 7/25

6:00 pm-10:50 am

2 stops13h 50m

Punta Cana

Wed 7/30

3:45 pm-8:40 am

2 stops19h 55m

$598

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 6/26

9:38 pm-3:16 pm

3 stops38h 38m

San Juan Luis Munoz Marin Intl

Mon 6/30

11:44 am-4:26 pm

3 stops31h 42m

$641

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Wed 9/10

5:15 pm-12:45 pm

2 stops16h 30m

Providenciales

Tue 9/16

2:05 pm-11:53 pm

2 stops12h 48m

$690

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Wed 5/14

7:55 pm-7:59 pm

2 stops45h 04m

Nassau Intl

Sat 5/17

9:00 am-7:14 pm

2 stops13h 14m

$700

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Wed 5/28

7:15 pm-11:35 am

2 stops14h 20m

Montego Bay Sangster Intl

Wed 6/4

12:00 pm-7:10 am

2 stops21h 10m

$704

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 34 results
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Best time to book a flight from Oakland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

What is the cheapest month to book a flight from Oakland, California to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $254). Flying from Oakland, California to Caribbean Islands 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 EPX?

Find hourly flight availability from Oakland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 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 Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated May 1, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Oakland to Caribbean Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

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
4,293 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
British Airways
6.6
Okay
6,845 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

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
7,963 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

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 Islands. 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 Islands?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oakland to Caribbean Islands.

  • What are the cheapest airlines to fly from Oakland, California to Caribbean Islands one-way?

    The cheapest airlines for a one-way flight from Oakland, California to Caribbean Islands are Spirit Airlines ($152), Southwest ($285), and Delta ($387).

  • What are the most popular routes from Oakland, California to Caribbean Islands?

    The most popular route from Oakland, California to Caribbean Islands is Oakland - San Juan Luis Munoz Marin Intl. You may also consider Oakland - Punta Cana or Oakland - Montego Bay Sangster Intl.

  • Can I find deals for flights from Oakland to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Oakland to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Caribbean Islands.

  • Can I find deals for business class flights from Oakland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Oakland to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $254). Flying from Oakland, California to Caribbean Islands 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.

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Alternative routes for Oakland to Caribbean Islands

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 Islands

Discover the top 3 airlines that operate flights from Oakland to Caribbean Islands. 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$263Average$388FlexibilityNo cancel feeOn-time65%
DeltaCheapest$440Average$824FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$469Average$710FlexibilityNo cancel feeOn-time63%

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